FlexFest: Legal Work, Unbundled. Presented by Priori. Eight sessions exploring the new models reshaping legal teams and careers. Available on demand.

Event Sessions

Welcome in. Every session from the day is here, each with its recording and a written recap. Pick a card to start.

Opening Remarks

Basha RubinCEO + Co-Founder at Priori
Mirra LevittCo-Founder at Priori
The Big Picture

Priori co-founders Basha Rubin and Mirra Levitt open the company's inaugural virtual conference, welcoming legal leaders who are building and reimagining what the future of legal work looks like, before a brief industry overview leads into the day's sessions.

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Session 1

Welcome + The State of Flexible Legal Work

Basha RubinCEO + Co-Founder at Priori
The Big Picture

Basha Rubin argues that the legal industry is living through two separate unbundlings at once, and that confusing them is why conversations about AI in legal keep going in circles. The first unbundling is happening to the work itself: AI is splitting legal services into an execution layer, which is repricing sharply down, and a judgment layer, which is repricing up. That one is technology-driven and effectively inevitable. The second unbundling follows from it and hits the institutions built around bundled work - the law firm pyramid, the outside counsel panel, the full-time hire as the default answer to every capacity problem. That second one is not inevitable. It is a design problem, and the people in the room are the ones who will either design it deliberately or let it be designed for them by litigation, regulation and the AI companies. Everything else on the FlexFest agenda sits somewhere on that map.

Top 7 Breakthroughs

1. Two Unbundlings, Not One: Separating what is happening to us from what is ours to design

Key Insight:

Priori was founded in 2013 on a single question about unbundling, and generative AI has finally made it operative. Two distinct unbundlings are now underway. The work is coming apart into an execution layer and a judgment layer, driven by technology and carrying a feeling of inevitability. Then the institutions built around bundled work come apart and reconstitute into something new. Keeping the two separate is what makes the rest of the industry conversation tractable.

Core Question:

If you hire the lawyer and not the firm, why does so much work still go to big law? That was the founding question behind Priori in 2013, and it is the same question AI is now forcing on the whole market.

2. Rising Demand and Rising Automation Are Both True: Why efficiency expands the market instead of shrinking it

Key Insight:

Every demand indicator is up - 97% of general counsel report rising work volume, alongside rises in pro se cases, cases filed, global M&A and law school applicants. At the same time, Anthropic's labor market research estimates AI could theoretically perform 89% of legal tasks, which is not the same as 89% of jobs. These look contradictory but point to the same shift: when the cost of execution falls, demand does not disappear, it grows. Work that could never be justified before can now be done, and AI generates legal demand of its own through governance, verification and regulatory disputes, while also raising the speed of business that legal has to support.

The Jevons paradox. When steam engines got more efficient, Britain did not burn less coal, it burned more.

Core Question:

How can rising work volume and rising automation both be true at once? Because falling execution costs move the economic threshold of what work is worth doing at all.

3. Execution Down, Judgment Up: The two halves of the old bundle are repricing in opposite directions

Key Insight:

Legal has always sold execution and judgment as a single product priced by the hour, and the pyramid was how a client bought both at once. AI is pulling them apart. On the execution side - search, extraction, document review, summaries, first drafts - estimates already show 40% to 90% reductions in time for review and diligence, and first-year classes at law firms are starting to shrink. On the judgment side - deal structure, risk calls, difficult interpersonal situations, negotiation, strategy - rates rose 7.3% last year, top partners are reaching $4,000 an hour, AI-skilled lawyers command roughly a 56% salary premium, and postings for AI specialization are up 182%.

Core Question:

Where do final advice, representation and ownership of risk actually live once execution is unbundled? Rubin flags accountability as a vital and still unresolved part of the story.

4. The Billable Hour May Break From the Supply Side: Firms could need the change more than clients do

Key Insight:

Rates, not volume, have carried the pyramid forward - AmLaw 100 revenue has nearly doubled since 2008 on basically flat demand growth. Despite near-universal dissatisfaction, alternative fees still represent barely 6% of outside counsel spend, while 61% of chief legal officers are pushing to change how outside services are priced and 80% say they plan to reallocate work away from traditional providers. The twist is that the pressure may not come from the buyer at all. With fewer hours underneath the pyramid, a firm cannot bill its way to growth, and has to price what is left, which is judgment.

Core Question:

Is this the death of the billable hour? Rubin's answer is no, but a significant repricing is expected.

5. In-House Becomes the Router: Scaling judgment with demand turns into a design requirement

Key Insight:

64% of in-house legal teams plan to insource more work on flat headcount, because they can now absorb the execution layer. That makes the in-house function the router of work - the place where decisions get made about what goes where. It also creates the pressure point: the team is being asked to absorb more work without growing, and while demand fluctuates, headcount does not fluctuate as easily. Scaling judgment up and down in step with demand stops being a staffing nicety and becomes a design requirement of the department.

6. Flexible Talent Is the Judgment Layer: Expertise, not availability, is what prices flexible work

Key Insight:

The data cuts directly against treating flexible talent as a commodity bench. 83% of flexible lawyers say demand for their skill set meets or exceeds available supply, only 15% saw any pushback on their rate in the last 12 months, and half never negotiate at all. Looking forward, 41% expect compensation to rise against 9% who expect it to fall. Asked what most strengthens pricing power, the answer was expertise - practice area, industry, or a prior in-house seat - which together account for 88% of pricing. A typical flex talent lawyer grosses around $300,000 and takes home around $270,000. Critically, the variable is hours, not rates, which makes closing the gap between engagements an infrastructure problem the market is actively building.

7. The Second Unbundling Is a Design Choice: Default architecture is still architecture

Key Insight:

The first unbundling, the work, is happening whether the profession participates or not. The second, the institutions, is genuinely open. Rubin's warning is that declining to design it is not neutral - it hands the design to litigation, regulation, and the AI companies and their financiers, who are content to let the value of legal work accrue to them. Department leaders, legal ops professionals, flexible lawyers and builders all have a hand in that architecture, and pricing runs through all of it, because when execution and judgment reprice in opposite directions, how you price is the strategy.

Prompts for Deeper Reflection
  • If AI can theoretically perform a large share of legal tasks in your department, which of those tasks are actually load-bearing for your team's judgment, and which are just habit?
  • Where does accountability for final advice sit in your organization today, and would that answer survive an engagement where the execution layer was handled somewhere else entirely?
  • Your headcount is unlikely to move as fast as your demand does. What would it take for your team to scale judgment up and down deliberately rather than reactively?
  • If 88% of flexible talent pricing power comes down to expertise, are you buying flexible lawyers for their availability or for what they specifically know? Which one are you actually paying for?
  • When execution and judgment reprice in opposite directions, how you price becomes the strategy. Does your current pricing model reflect a decision you made, or one you inherited?
Share-Worthy Moments
“When steam engines got more efficient, Britain didn't burn less coal, it burned more. Efficiency expands consumption.”
— Basha Rubin
“We will work differently, and there will be more work to do.”
— Basha Rubin
“The unit of legal value is moving away from producing the answer and toward deciding, contextualizing, and owning it.”
— Basha Rubin
“Everyone assumes the billable hour will change because clients finally demand it. It may change because the firms need it to.”
— Basha Rubin
“If we don't design it, it gets designed by default, by litigation, regulation, the AI companies and their financiers, who are perfectly happy to let the value of legal work accrue to them.”
— Basha Rubin
About the Speaker
  • Basha Rubin, CEO + Co-Founder at Priori - Rubin co-founded Priori with Mirra Levitt in 2013, starting as a small business marketplace built on the premise that clients should be able to hire the lawyer rather than the firm. Priori has since grown into a flexible talent marketplace and an AI-empowered outside counsel selection platform, and Rubin hosted FlexFest, Priori's inaugural virtual conference, as well as moderating four of its sessions.

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Session 2

The Legal Department of the Future: Smaller Teams, Smarter Systems

Mark SmolikChief Legal Officer at DHL
Mike HavenGlobal Head of Legal Ops at Meta
Rishi VarmaChief Legal and Ethics, Compliance Officer, and Corporate Secretary at Cargill
Basha Rubin (moderator)CEO & Co-Founder at Priori
The Big Picture

The headline is not that legal departments are shrinking. All three leaders predict roughly flat headcount, and the interesting change is in composition: fewer roles organized around manually moving information, more organized around designing systems, supervising outputs and translating legal risk into operational logic. What makes that shift possible is not buying AI, it is owning your data - and the panel is blunt that most of the industry has this backwards. Mark Smolik's fifteen-year data project at DHL is the precondition for the AI initiatives DHL runs today, not a side effect of them. Rishi Varma's contract intelligence work at Cargill only produced value once it could answer questions about Cargill's own risk tolerance. Mike Haven names the gap between what the technology can do and what departments actually do with it, and lists its real causes, including one nobody likes to say out loud: people are being asked to replace themselves. Meanwhile all three are quietly rewiring the routing decision so that "send it to outside counsel" stops being the reflex.

Top 7 Breakthroughs

1. Flat Headcount, Different People: The pyramid of lawyers is not what replaces the pyramid of lawyers

Key Insight:

Asked to predict five years out, all three leaders said headcount stays broadly flat, but the mix changes substantially. Mark Smolik's team of 91 will ebb and flow with a fast-growing business while adding more data-driven roles; DHL hired its first data scientist three years ago. Rishi Varma expects a shift away from the traditional lawyer and legal professional mix toward data scientists, product builders and AI agents, with Cargill hiring its first legal ops data scientist this year. Mike Haven pushes back on the premise itself: resource needs are unknowable without knowing business demand, and if demand keeps growing, technology absorbs the increment rather than shrinking the team. The through-line is fewer jobs organized around manually moving information and more organized around designing systems, supervising outputs, and translating legal risk into operational logic - including a new class of talent that feels half lawyer, half technologist.

Core Question:

Five years from now, is your legal department's headcount bigger or smaller, and is your outside counsel budget higher or lower? On budget, the panel expects flattening rather than growth, with outside counsel concentrated on bet-the-company litigation and M&A while routine questions get answered internally first.

2. Data Before Tools: DHL's AI capability rests on a filing system started fifteen years ago

Key Insight:

Smolik's AI journey began long before anyone was talking about AI. Joining DHL with a five-person team, Smolik asked where the company's information lived and found most of it sat with external counsel - which meant paying outside counsel not just to handle matters but to report on them. The team built its own library, initially paper, then a document management system, and spent eighteen months deciding how information should be segregated across M&A, corporate and secretarial work. In retrospect they were tagging and structuring data without knowing that was what they were doing. As the database matured across the Western Hemisphere, layering AI tools on top was straightforward, and two of DHL's AI initiatives have now been running a full two years and paying real dividends. Smolik's warning is that plenty of departments are buying tools under peer and board pressure and then discovering they have no knowledge bank to point them at.

Action Step:

If you do not know where to start, do not start with a tool. Take a breath, find out where your data actually is, then work with your people to organize, aggregate and structure it so it is ready when you want to layer AI on top.

3. The Capability-Adoption Chasm Has Five Causes, Not One: Everyone blames the technology; the blockers are mostly human

Key Insight:

Haven identifies a significant gap between what agents can already do and what people are actually doing with them, and breaks the causes down: data foundations, governance concerns, choosing the right tool from a crowded stack, the shortage of legal engineers with capacity to build, and finally self-preservation - real fear that AI will absorb the tasks that constitute someone's job. Smolik adds a market-structure cause: technologists, private equity and venture capital identified a sleepy $1.4 trillion global legal industry running on a business model from the 1980s and 1990s, and built tools faster than buyers could evaluate them. The result is that supply has outrun demand-side literacy, and cautious buyers wait, aware that anything they spend six or seven figures on may be superseded before IT finishes evaluating it.

Imagine walking into a Home Depot technology store for legal. The shelves are full, you are the head of legal operations, and you have no idea what to begin to buy.

Action Step:

For anyone genuinely afraid of being replaced, reskill rather than wait. Haven's worked example is the paralegal who moves into a legal agentic engineer role - identifying where agentic workflows can be inserted, securing the data those workflows need, and building them out.

4. Read the Bills, Not the Press Release: How buyers separate real AI transformation from a purchased license

Key Insight:

Smolik has watched firms extol AI initiatives with no visible evidence behind them, and the test applied is arithmetic: DHL now has cost data on every matter, and those costs are not falling. Commodity work that took ten hours two years ago can take an hour today, yet the bill has not moved - suggesting firms are capturing the efficiency as margin rather than passing it through. Haven's test is behavioral: firms making genuine progress are eager to show it, inviting clients in to brainstorm about solutions they have built, while firms that are dodgy about their AI use tell you what you need to know. Varma sees firms responding differently again, marketing their judgment, regulator relationships and a partner's thirty-plus years of experience as the thing a repeatable platform cannot replace. All three confirm this now factors into outside counsel selection, and increasingly so.

Core Question:

A contract that took ten hours two years ago takes an hour today. So why is the bill still for ten hours?

5. Build a Brain Around Your Own Risk Tolerance: The knowledge outside counsel cannot have

Key Insight:

Varma's goal at Cargill was not document search, it was building something that could learn how the company actually tolerates risk - which varies by product, region, and whether the counterparty is a global giant or a small regional customer. Incoming lawyers cannot know that and normally absorb it from colleagues over years. The proof case: a customer's general counsel called about an agreement that had been stuck for twelve months, and Cargill's own team explained the customer was asking them to accept risk the company never accepts. Interrogating the contract intelligence tool showed that across a 161-year history Cargill had in fact accepted comparable risk in comparable circumstances; those particular lawyers had simply never seen it. Once the team confirmed its operations, controls and governance could support that level of risk, it negotiated a deal. Varma is also deliberate about scope, working in bite-sized chunks - litigation profile, M&A profile - rather than trying to ingest everything the company has ever done, and Varma flags that the real operational detail often lives in purchase orders, invoices and statements of work rather than the thirty-page master agreement.

Action Step:

Force your teams to access your own data and ask their own questions about your risk tolerance, rather than routing the question outward by default.

6. Rewiring the Routing Reflex: "Does this have to go outside at all?" becomes the first question

Key Insight:

All three departments delegate real routing autonomy, but each has engineered the default. DHL centralized everything when the team was small and external spend was out of control; now senior leaders route within a vetted panel that gets annual performance reviews, most work arrives through an intake tool built over ten years, and only genuinely novel matters requiring a new firm need Smolik's sign-off. Varma pressure-tests the reflex directly - the instinct to go outside because a question is new or complex - and incentivized it out of the direct reports by requiring each of them to find their own "AI dividend" as a quarterly objective. Varma deliberately did not tell them where to look. Cargill's IP team went furthest, layering AI on their patent database to file office actions faster, draft patents and review inventions in the queue, eliminating their need for outside counsel altogether and creating competitive pressure across other teams. Haven instills a sequence: can we handle this internally, and if not, what risk and complexity level is this, and what type of firm actually matches it.

Core Question:

Does it have to go to a white shoe firm in New York? If the matter is not high risk and high complexity, maybe not.

7. Onboarding Cost Is the Real Constraint on Flexible Talent: Kill the ramp-up penalty and the whole resourcing calculus changes

Key Insight:

Haven tracks a metric called timekeepers per full-time employee - how many distinct timekeepers a firm burned to deliver the equivalent of one person's year. A high ratio signals inefficiency, because every additional timekeeper has to spin up on the business and the matter. The same anxiety is what makes teams hesitant about new firms and flexible talent. If AI can compress that ramp-up, the metric stops mattering as much and the reluctance goes with it. Smolik describes the foundation that makes this work in practice at DHL, where five flexible professionals handle commercial customer contracts against a playbook of board-approved commercial expectations and an alternative clause library, with AI moving that from something a person has to remember to something a new contract is automatically vetted against. As Smolik frames it, capturing a brain is really just capturing how you do what you do and the four corners within which you operate.

Prompts for Deeper Reflection
  • If you layered an AI tool on your department's data tomorrow, would it have anything structured enough to work with? Be honest about which answer you would get.
  • Your team's assumptions about what risk your company "never accepts" - are those documented anywhere, or are they inherited from whoever trained the current lawyers?
  • What is your equivalent of the AI dividend? If you asked each of your direct reports to find one and refused to tell them where to look, what would come back?
  • When a matter arrives, what is the actual first question your lawyers ask? Not the one in the policy - the one they ask.
  • If ramp-up time on new resources stopped being a penalty, which work would you move, and to whom?
Share-Worthy Moments
“The future is not a pyramid of lawyers with that support wrapped around them.”
— Rishi Varma
“A contract two years ago would take 10 hours. Today it could take an hour. Why am I getting a bill for 10 hours?”
— Mark Smolik
“That model allows your lawyers to become the architects of judgment and not just the producers of answers.”
— Rishi Varma
“Asking people to replace themselves with a tool is not an easy thing to do.”
— Mike Haven
“The clients own the workflow, the data, and the operating environment.”
— Mark Smolik
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw firm collapse or merge out of existence primarily because of AI?

A: Unanimous yes. Smolik was most specific, expecting it especially below the AmLaw 25. Varma and Haven both agreed without qualification.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: The panel split. Smolik said yes, with more support personnel such as data scientists taking their place. Varma agreed, describing a mix shift toward newer professionals including legal engineers and data scientists. Haven declined to agree, expecting the number to stay roughly flat while the responsibilities of practicing lawyers change dramatically. Rubin went further than any of them, predicting the number of practicing lawyers rises as the overall size and speed of business increases, and offered to settle it over a drink in five years.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Varma said yes, mostly on volume: there are so many firms, and so many clients at varying stages of the journey toward answering questions internally, that default demand keeps the model in place. Haven said no, and grounded it in supply-side economics - firms simply cannot bill as much time for certain tasks as they used to, and those tasks have been their bread and butter, so they will need pricing structures that reduce overall matter costs for clients while increasing their own margins. Smolik also said no, expecting CEOs and CFOs to put enough pressure on general counsel and chief legal officers to force alternative arrangements.

Q: Lightning round - in the next five years, will legal departments expect outside counsel to plug into their systems rather than the other way around?

A: Unanimous yes, and all three said it is already happening. Haven expects a move toward shared systems in the cloud - shared vaults and spaces where both sides can put documents and query them - and is not convinced it matters much who owns them. Smolik was the most emphatic: the clients own the workflow, the data and the operating environment. Varma agreed and noted that the data firms hold on Cargill is Cargill's data, pointing to a collaboration hub the company has been running with two of its largest firms for three years.

About the Speakers
  • Mark Smolik, Chief Legal Officer at DHL - Smolik has been with DHL a little over seventeen years, leading a legal department of 91 people with responsibility spanning the company's Western Hemisphere operations. Smolik began the data-centralization work that underpins DHL's current AI initiatives roughly fifteen years ago, starting with a five-person team and a paper filing system.
  • Mike Haven, Global Head of Legal Ops at Meta - Haven leads legal operations at Meta, where the work centers on agentic workflows, the emerging legal agentic engineer role, and operational metrics such as timekeepers per full-time employee that expose inefficiency in outside counsel staffing.
  • Rishi Varma, Chief Legal and Ethics, Compliance Officer, and Corporate Secretary at Cargill - Varma leads legal at Cargill, a 161-year-old global business, where Varma hired the department's first legal ops data scientist this year, built a contract intelligence capability designed to learn the company's own risk tolerance, and runs an "AI dividend" program requiring each direct report to find their own efficiency gains.
  • Basha Rubin (moderator), CEO & Co-Founder at Priori - Rubin co-founded Priori in 2013 and hosted FlexFest, Priori's inaugural virtual conference.

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Session 3

Unbundling Legal Work: From Concept to Operating Model

Ava GuoAVP - Senior Legal Counsel at AT&T
Brendan McMurrerVP, Associate General Counsel - LegalEdge at AT&T
Mirra Levitt (moderator)Chief Product Officer & Co-Founder at Priori
The Big Picture

Legal Edge is AT&T's answer to unbundling built from the inside: an in-house law firm with an AI-first mentality, launched six months ago at 24 people and already at 35. What makes the conversation unusual is how little of it is about technology. Brendan McMurrer and Ava Guo describe an initiative whose hardest work is human - deciding to start big because pilots cannot move a company of AT&T's size, giving lawyers explicit permission to fail because a firm associate never could, pairing legal ops process expertise with substantive legal expertise, and refusing to become fluent in any one tool because that tool will be a different tool within a year. Their sharpest correction is aimed at the industry's expectations of AI itself: there is no pixie dust, and the value shows up only after somebody sits down and breaks a process into its actual constituent parts. The payoff they point to is not automation. It is that a team of twenty to thirty attorneys can handle work that used to need a firm of hundreds, and can spend its time on the judgment everyone went to law school for.

Top 8 Breakthroughs

1. An In-House Law Firm With an AI-First Mentality: What Legal Edge actually is

Key Insight:

Legal Edge is a technology-driven center of expertise inside the AT&T legal department, dedicated to delivering legal services using advanced technologies and generative AI in partnership with departmental colleagues, the business, and trusted outside counsel. The starting scope was chosen on a clear logic: litigation, investigations and regulatory matters are where an in-house team sits closest to the clients and closest to the documents, which means it can conduct factual development faster and at lower cost than sending the work out. The team is a deliberate mix of attorneys, paralegals, legal operations professionals and e-discovery professionals - the e-discovery group Guo previously led moved across intact.

2. Start Big on Purpose: At AT&T's scale, a pilot is indistinguishable from doing nothing

Key Insight:

AT&T did try the conventional route. A few years ago there was a small pilot phase testing a handful of use cases, and it produced some small successes. But as the pace of technology development accelerated, the team concluded it needed to move faster and grow much larger to build its own muscle and keep pace. In the second half of last year they explored how to build an AI-first in-house legal practice, became convinced it could work, and launched at scale in January. Six months in, the team has grown from 24 people to about 35, roughly 50% growth.

Core Question:

Did you consider starting with something smaller? They did, and rejected it - because in a company of AT&T's size, small pilots do not move the needle, and driving real change required starting at scale.

3. AI-First, Not AI-Native: The human is at both ends of the workflow

Key Insight:

McMurrer is deliberate about not adopting the "AI-native" label that many new law firm ventures are using. Legal Edge values the human relationships on its teams - with departmental peers, business colleagues and outside counsel - and does not rely solely on its AI tools. The operating principle is simple and structural: a human asks the question, a human validates the output, and the AI machine sits in the middle. Teams are encouraged to use AI to build more efficient processes, but the people stay in the loop by design rather than by exception.

4. There Is No AI Pixie Dust: AI-first does not mean AI can do everything

Key Insight:

Guo's counter to the prevailing news coverage is that reading about AI produces a belief that you can sprinkle it over an existing process and get magic. The reality is that the tools still get things wrong or misinterpret - not necessarily the blatant hallucinations of a few years ago, but errors that require human validation nonetheless. The more you actually work with the tools, the more obvious that becomes, and the more apparent the volume of effort required to get a tool to do precisely what you need.

AI pixie dust - the idea that you come in, sprinkle some over everything, and it all suddenly becomes magical.

Action Step:

Take your whole process, break it down into its many small constituent pieces, and work out how to rebuild it with an AI-first mentality. Educate, then educate again on how much effort that actually takes.

5. Permission to Fail Is the Competitive Advantage: And it is one that billing lawyers structurally cannot have

Key Insight:

From the January boot camp onward, Legal Edge told its people they had freedom to experiment: build, test, iterate, test again, and do not be afraid to fail. New hires arriving from law firms find this genuinely refreshing, because at their firms they were expected to bill, and nobody can bill for a failure - so even lawyers curious about AI had only explored it on a personal basis. Legal Edge measures its impact quantitatively on cost savings, time savings and efficiencies per matter as work moves into the model, but explicitly does not measure the experimentation itself, treating it instead as on-the-job training that abstract tool training cannot substitute for.

Core Question:

Does it matter whether an attorney needed twenty prompt iterations instead of five? Not if the work is still finished at a fraction of the time and cost that outside counsel would have charged.

6. The Playbook Is the Asset: Tens of hours of clause-level work buys back hundreds of hours of negotiation

Key Insight:

Contracting looked like the obvious AI win and turned out to be the opposite, because every contract, every clause, every fallback provision and every business interaction is different. What made it work was pairing a Legal Edge person with one of AT&T's contracting experts and sitting down to break the thing apart clause by clause - what is accepted on clause A, B and C, and if not accepted, what fallbacks X, Y and Z apply - then drafting a playbook from scratch and rethinking the whole process. That exercise is what makes the AI behave the way it is supposed to. McMurrer's parallel point is that there is no one-size-fits-all solution either; their best results come from meeting people at their level, finding their individual pain points, and building for those.

Action Step:

Pair substantive expertise with process expertise and go clause by clause. In their example a legal ops professional with program and project management skills worked alongside a contract expert who knew the significance of each provision - neither could have produced the playbook alone.

7. Master Adaptability, Not a Tool: Tool A may be tool Z inside two years

Key Insight:

Guo's position is not disinterest in technology - quite the opposite, self-described as interested to a nerdy extent. You should understand what sits behind your tools, how they are trained, how they are leveraged and which tool suits which type of work. What you should not do is become wedded to a particular product, because things are changing fast enough that today's favorite may not exist in two years or may have morphed into something else. The higher-value skill is a deep working understanding of what AI is genuinely good at and genuinely bad at, because that is what lets you choose tools at all. Being a master of one thing is worth less when that one thing can be five different things within a year.

8. What It Takes to Thrive Here: Curiosity, perseverance, and treating colleagues like colleagues

Key Insight:

Asked what qualities the model demands, McMurrer leads with a curious mind - a willingness to learn, to solve problems, to experiment, to challenge the status quo, and to fail and persist. Above all, believing there is a better way to do things. Guo adds perseverance and something more specific about the change management: shifting people off years of practice is genuinely hard, and what you used to do was not wrong, there are simply now better ways. That means talking to colleagues as colleagues, explaining things so they resonate, and showing the benefit rather than mandating the change. Role diversity helps here too, because lawyers are trained and inclined to be risk averse, while a legal ops professional will look at what a lawyer considers one step and correctly identify it as ten. The team culture is captured in an adage from AT&T's general counsel that Legal Edge has adopted: two is one and one is none.

Prompts for Deeper Reflection
  • Is your innovation effort sized to actually change anything in your organization, or is it sized to be safe?
  • Your lawyers cannot bill for a failure. Where in your operating model have you created space where failure costs nothing?
  • Which of your processes have you genuinely broken into its constituent steps, and which have you simply pointed a tool at?
  • If a legal ops professional walked your team through a routine task, how many steps would they find where you currently see one?
  • Are you building expertise in a particular tool, or building the ability to judge what AI is good and bad at? Which of those survives the next product cycle?
Share-Worthy Moments
“Small pilots really just don't move the needle.”
— Brendan McMurrer
“You're going to come in, sprinkle some AI pixie dust on everything, and it's all of a sudden going to become magical and fantastic. And that's just not the way AI works.”
— Ava Guo
“They were always expected to bill, and they couldn't bill for a failure. We just have the exact opposite mentality.”
— Brendan McMurrer
“I don't care that it takes you 100 tries. I care that at the end of the day, we are still coming out on top.”
— Ava Guo
“The tens of hours that went into developing this playbook is going to save you hundreds of hours of negotiation and back and forth with the other party down the line.”
— Ava Guo
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Guo said no. McMurrer said yes, reasoning that AI reduces the reliance of companies like AT&T on outside counsel for certain tasks, which pressures firm profits and pushes firms to merge in order to hold onto scale. Guo added a caveat worth keeping: a firm could collapse or merge and cite AI as the reason without AI being the actual reason.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: Both said no. McMurrer expects a dawn of new AI-first lawyers supporting an increasing number of matters, driven by technology development, increased regulatory scrutiny, and the rise of AI-drafted complaints in litigation - all of which generate more legal work rather than less.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Guo said no, and has said so publicly before: the billable hour model is coming to an end sooner rather than later, and firms are already exploring other ways to bill. McMurrer distinguished existence from dominance - the billable hour has proved remarkably hard to kill and will still exist, but expects it to disappear from more commoditized work while remaining the model for the strategic expertise and judgment AT&T relies on outside counsel for.

Q: Lightning round - in the next five years, will every major legal department have some version of an AI-enabled center of expertise?

A: McMurrer said absolutely, because given the pace of change over the last twelve months, the opportunity cost of not building internal AI legal expertise will be too great to ignore. Guo agreed, and added a message for any listening law firms: they would be shocked at the pace some of their clients are moving.

Q: Lightning round - in the next five years, will the most successful legal teams be defined more by the quality of their individual lawyers or by the quality of the systems they build around legal expertise?

A: Guo said both, on the grounds that you cannot build a high-quality system around legal expertise without individual legal expertise to build it from. McMurrer leaned toward process, expecting it to be what determines success from an efficiency standpoint in five years, while still requiring strategic judgment.

About the Speakers
  • Brendan McMurrer, VP, Associate General Counsel - LegalEdge at AT&T - McMurrer leads the AT&T Legal Edge team, which launched six months ago and has grown from 24 to roughly 35 people. McMurrer describes the team as very much in startup mode, with a stated focus on supporting the team and making sure they have what they need to succeed.
  • Ava Guo, AVP - Senior Legal Counsel at AT&T - Guo came from the law firm side and joined AT&T about four years ago to lead its e-discovery and legal technology groups, moving that team into Legal Edge when it launched six months ago. Guo's focus is technology and process, with a particular emphasis on upskilling attorneys, paralegals and legal ops professionals across the organization.
  • Mirra Levitt (moderator), Chief Product Officer & Co-Founder at Priori - Levitt co-founded Priori with Basha Rubin in 2013 and leads product.

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Session 4

Case Study: How Organizations Can Build a More Intentional Legal Resourcing Model

Aaron BoersmaSpend Innovation Lead, Policy & Legal Ops+ at Ford
Matthew Wheatley (moderator)Chief Commercial Officer at Priori
The Big Picture

Plenty of legal departments use flexible talent. Far fewer have built a framework around it, and this session is a working account of one that has. Aaron Boersma's starting move is to refuse the resourcing question until the "why" is answered - why you hold internal headcount, why you engage outside counsel, why an alternative provider, why flexible talent - because each instrument does something structurally different. Flexible talent's specific advantages are speed of deployment and proximity to the business, which is precisely what a discrete outside counsel engagement cannot offer. From there the session becomes a clinic in what legal operations is actually for. Ford centralized its flexible talent relationships while deliberately leaving the hiring decision with the hiring manager, on the principle that operations exists to make frontline decisions easier and better informed rather than to make them. And the posture Boersma credits for the program's success is not sophistication but humility: admitting where the team is out of its depth, asking providers the supposedly dumb question about what information they actually need, and treating honesty in both directions as the thing that makes a partnership durable.

Top 8 Breakthroughs

1. Start With Why You Are Buying: Resourcing decisions are unanswerable until the purpose is named

Key Insight:

Boersma's title, Spend Innovation Lead, effectively means that money going out the door to resource the legal team falls in that purview - and the framework starts a step before the sourcing decision. Before you can put the best people in the right place, in any industry, you have to understand the why of what you are buying in the first place. Each resourcing channel exists to do something different, and treating them as interchangeable capacity is what produces incoherent programs.

Core Question:

Why do we have headcount internally? Why do we engage outside counsel? Why do we engage an alternative legal service provider? And why do we leverage flexible talent? Answer those separately and the insourcing, outsourcing and near-sourcing decisions largely resolve themselves.

2. Speed and Proximity Are the Two Real Advantages: What flexible talent gives you that a discrete engagement cannot

Key Insight:

The first advantage is flexibility in the literal sense - as needs arise, a flexible resource can be deployed very fast. The second matters more and gets discussed less: proximity to the business. Outside counsel engagements are typically discrete, with hyper-discrete subject matter expertise, and those individuals do not sit with stakeholders inside the company. They are not positioned to understand how the business makes money, what actually matters, or what will culturally move the needle. Flexible resources can get embedded with teams far faster, often inside the company's own systems - laptop, email address, chat - and Boersma frames the design question accordingly: where in the business do we need resources that sit close to our stakeholders and genuinely understand the matters? Boersma is also careful that this is not only about lawyers, but legal professionals of all shapes and sizes.

3. Secondments and Flexible Talent Are Different Instruments: One is the firm's investment, the other is your sourcing decision

Key Insight:

Drawing on prior experience inside law firms on pricing and economics, Boersma explains that firms treat secondments as an investment - a way to deepen themselves in the operations of a business and learn its inner workings, aimed at long-term work and long-term return. But secondees are there for a short period, and the expertise is extracted quickly when they leave. Flexible talent inverts the logic: the company is sourcing a very specific resource for a very specific need it has identified. That difference in who owns the objective is why Boersma sees considerably more room for creativity in a flexible talent ecosystem. Secondments also require a scale of relationship that most engagements do not have, which makes matching the right secondee to the right moment a real operational problem.

4. Centralize the Relationship, Not the Decision: Ford's model, and the line it deliberately does not cross

Key Insight:

In a legal department of Ford's size, the pre-centralization picture was a provider making contact with as many people as there are lawyers in the department, hoping to be top of mind whenever a need arose - inefficient for everyone, including Ford. Centralizing those relationships through legal ops means a provider talks to one person instead of fifteen or twenty. The critical constraint is what stayed decentralized: who gets hired sits with the hiring manager, full stop, because no third party should be telling a lawyer who they can and cannot work with. What centralization contributes instead is a better decision environment - all relevant CVs visible on an equal playing field, easy to access, with the bias of arrival order stripped out. The same logic extends to outside counsel: give a managing counsel enough data that the choice rests on more than "I know them, this is my gut." As Boersma frames it, operations is not there to replace frontline judgment; it exists to make that judgment easier to exercise and better informed. A concrete win is removing administrative load - a frontline lawyer scheduling interviews and combing resumes is time not spent with stakeholders.

Core Question:

Why is centralization actually helpful, and where would it hurt? Boersma insists on answering both before building anything, treating legal ops almost as an internal consultancy that has to make the case rather than issue the mandate.

5. Earn the Right to Advise: Go and sit with the people whose decisions you are trying to improve

Key Insight:

Getting involved in whether work goes to flexible talent, an AmLaw 100 firm, or another provider starts with having earned stakeholder trust, and Boersma notes some teams welcome that involvement and some do not, often for good reasons on both sides. Being principled about which resource types work well and why cannot come from pontificating in the abstract - transactions, litigation and appellate work are genuinely different ecosystems with different practices, different decision-making and different people. Boersma's measure of success in serving stakeholders is simply how well those stakeholders and their business are understood, because without that there is nothing to deliver.

Action Step:

Go to gemba, a saying Boersma cites from Ford. Go sit with your stakeholders, be with them, watch how they work, and use that to verify whether you are actually giving them the right information to make the right decisions.

6. Humility as an Operating Principle: The dumb question is the one that improves the talent you get

Key Insight:

Boersma's team operates on an explicit premise: there are things they will be the experts on, and a larger share of things they will not be, and being honest about which is which is the point. Applied to vendors, this produced a genuinely useful discovery - flexible talent providers source talent in materially different ways, which means the information one provider needs to find the right person differs from what the next one needs. Rather than assume a single intake format works, the team asks providers directly what they are missing, which in turn helps those providers find better talent. Boersma credits much of the program's placement success across a range of vendors to that posture, plus a continuous improvement mindset Boersma calls the real game changer.

A marriage. Boersma draws the comparison directly from one, describing what makes a great partner as both people being honest about where things are going well and where they are not. Partnerships without that honesty do not last, in either setting.

Action Step:

Ask your providers the dumb question - are we actually giving you everything you need to provide us with the best talent? Then act on the answer.

7. Lean Into What You Are Genuinely Great At: Advice for practitioners, and the end of the "does flex work?" era

Key Insight:

Asked what distinguishes successful flexible practitioners, Boersma's answer is knowing what you are excellent at and leaning into it with confidence, rather than presenting as a universal fit. Paired with that, and just as important, is honesty about the edges - saying openly that a particular requirement is not where you are strongest but you are willing to lean in. In Boersma's experience across organizations that honesty is admired far more than a seemingly perfect cookie-cutter match. The same openness applies to logistics: where you are in your own practice, what else you have going on, and what a part-time engagement realistically looks like. Boersma also marks a shift in the market. Seven or eight years ago the industry was still debating where flexible talent could help; that question now sits firmly in the past, and the live question is simply how to find good people.

Unicorns - which, as Boersma notes, is Priori's own mascot. Companies engaging flexible talent are not looking for them. They are looking for people who are really good at what they do and willing to put in the work.

Action Step:

Be transparent about where you are good, where you are great, and what else you have going on. Boersma has never seen that degree of openness fail to land well with a hiring manager.

8. AI Uncertainty Is Why Demand Is Spiking Now: Flexible talent is how organizations move while the line keeps shifting

Key Insight:

Boersma's theory for the current surge is that AI has introduced uncertainty across a wide range of work streams. Boersma pushes back on the framing first: forty years of AI research has not been about machines replacing humans, whatever the headlines say, but about optimizing machines for tasks they are good at so that humans can concentrate where they are best equipped to advise and counsel. What has changed is that the boundary between the two is now moving constantly. Companies are uncertain what AI will do to their business, their sales velocity, their contracting. Flexible talent is valuable precisely in that gap, because it is a resource type that can be put in place quickly to support the organization through the change - and Boersma expects that dynamic to keep accelerating adoption across the ecosystem. Wheatley adds a supporting data point from a decade in the space: conversations have moved from skepticism that anyone would choose to practice this way to five customers in a single week asking how to do it.

Prompts for Deeper Reflection
  • Can you articulate, channel by channel, why your organization uses internal headcount, outside counsel, alternative providers and flexible talent? If two of those answers are the same, one of them is probably wrong.
  • Which of your resourcing needs genuinely require proximity to the business rather than subject matter expertise? Are you currently buying the wrong one for those?
  • In your program, has centralization been used to improve frontline decisions or to take them over? Which would your lawyers say?
  • Where is your team out of its depth right now, and when did you last say so out loud to a partner or vendor?
  • If you practice flexibly, what are you actually excellent at - and is your positioning built on that, or on trying to look like a fit for everything?
Share-Worthy Moments
“Operations isn't there to replace the decision making of the frontline lawyer. Operations exists to make those decisions much easier to make, and much more informed along the way.”
— Aaron Boersma
“Humility should really rule here. Let's admit when we're out of our depth, let's ask questions to get better and then continue from there.”
— Aaron Boersma
“We're not all looking for unicorns, even though that is the mascot for Priori. We're looking for just people who are really good at what they do and that are willing to put in the work.”
— Aaron Boersma
“Where can flex talent really help? That feels like a question that sits in the past very much now.”
— Aaron Boersma
“I think we are only at the starting line for what legal demand growth is going to look like because of AI.”
— Aaron Boersma
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Yes. Boersma has no doubt AI will change how firms operate, and expects the gap between early and late adopters to become a meaningful difference in profitability and sustainability. Boersma softened the wording slightly - "collapse" may be aggressive - but expects merger and acquisition activity to jump from what is already an active baseline.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: Absolutely not. Boersma expects demand for legal services to grow at an extraordinary pace and believes the industry is only at the starting line for AI-driven demand growth. Wheatley named the mechanism as the Jevons paradox and agreed for the record, adding that this is what makes it an exciting moment for anyone exploring alternative practice options.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Yes, and Boersma is direct that this holds whether or not anyone likes it. While uncertainty persists about what AI does to efficiency, companies are still building panels around hourly rates, and by that estimate it takes more than five years to build out service lines capable of sustaining pricing at a unit cost level.

About the Speakers
  • Aaron Boersma, Spend Innovation Lead, Policy & Legal Ops+ at Ford - Boersma leads spend innovation on Ford's legal ops team, with responsibility spanning how the legal team is resourced and where that money goes. Boersma previously held a range of pricing and finance roles at Google and at a global law firm, experience drawn on when explaining how firms think about secondment economics, and is a co-founder of the legal AI company White Shoe.
  • Matthew Wheatley (moderator), Chief Commercial Officer at Priori - Wheatley has worked in the flexible legal talent space for ten years and moderated two FlexFest sessions.

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Session 5

Leading in the Age of Agentic Legal

David LatFounder at Original Jurisdiction
Sabastian NilesPresident, Chief Legal Officer & Corporate Secretary at Salesforce
Basha Rubin (moderator)CEO & Co-Founder at Priori
The Big Picture

Sabastian Niles has argued publicly that the era of the AI pilot is over, and this conversation is the operational version of that claim. The recurring move throughout is to refuse the technology framing. Asked what real adoption looks like, Niles talks about the firm-client relationship becoming a shared operating system. Asked how to spot a firm whose AI story is marketing, the answer is transparency and a willingness to co-innovate, and the warning is that failing that test does not merely mark a firm as a laggard, it damages trust. Asked how Salesforce sequenced its own build-out, the answer starts not with a tech stack but with the executive thesis for what a legal and compliance function is supposed to deliver. From there the session gets genuinely novel: every individual contributor should have an agentic span of control, agent managers are a real job, and the hardest question - if agents absorb the routine work junior lawyers learned judgment on, where does the next generation's judgment come from - gets an answer most lawyers will find uncomfortable. Judgment, Niles argues, has building blocks. It can be unpacked. And if it can be unpacked, the floor can be raised at scale.

Top 8 Breakthroughs

1. Real Adoption Is a Relationship Change, Not a Tool Purchase: How a buyer tests an AI story

Key Insight:

Asked for the most concrete thing a firm has actually shown - a changed way of delivering work rather than a license announcement - Niles points to firms accepting that the firm-client relationship itself has to evolve into something closer to a shared operating system spanning internal and outside counsel teams. The firms doing this are unpacking workflows and engaging on outcomes, on how risk and judgment are being handled, and on the guardrails and oversight that keep AI's risks managed while its benefits accrue to the client. Some are building genuine agentic trust models, and notably the mature ones distribute that mandate rather than confining it to the managing partner or executive committee, letting associates, paralegals and practice group teams engage with it. Niles's evaluation criteria as a buyer are concrete: whether AI and process automation hold up against traditional client expectations on confidentiality, privilege and security; enterprise-scale delivery; jurisdiction-specific and subject matter expertise; measurable client outcomes; and how automation translates into competitive pricing and fee structures. A firm that cannot be transparent about where it sits on that maturity curve, or about its own roadmap, or that will not commit to co-innovating, lands in a worse place than the laggard bucket - it undermines the trust the industry runs on.

Core Question:

As a buyer of legal services, how do you separate real integration from marketing language? Look for transparency about the journey rather than claims about the destination, and for a firm willing to be honest about what is still on its roadmap.

2. Start From the Executive Thesis, Not the Tech Stack: What is this function actually supposed to deliver?

Key Insight:

Niles deliberately steps away from tech stack questions, because the clarity that unlocked Salesforce's acceleration came from a different direction. The operating principle is that this is not AI for AI's sake, or agentic transformation for its own sake, which means you have to be able to state what the function exists to do. Niles names three things for legal, compliance and trust functions: first, being a genuine enterprise business asset that accelerates growth while protecting trust and license to operate; second, operating leverage, meaning expanded capacity without proportional cost; third, translating that into operating structures and talent capabilities that can actually deliver it. The leverage piece resolves into a resourcing question - right work, right time, right service level, and the right person or function providing it. Having that thesis is what let the team connect AI work to real business value rather than to activity.

Core Question:

What is the executive thesis for what your function is supposed to deliver? Without an answer, transformation work has nothing to be measured against.

3. Customer Zero: Legal is the heaviest internal user, and legal becomes an API

Key Insight:

Salesforce Legal handles hundreds of thousands of requests a year, and the design question was how much of that volume could be automated or moved into a self-serve model - what many businesses call deflection - with AI embedded at every step including contract drafting, reviews and compliance checks. The detail Niles highlights is cultural rather than technical: because the company runs on Slack, it built a tool called Slackbot, and the legal team is the top user of Slackbot across the entire company. Legal is not merely consuming it either; the team is training and grounding the agents in its own expertise, playbooks and learnings, and calibrating what responsible AI means for the wider enterprise. Niles calls the result a force multiplier, and frames the destination for a technical audience as legal as an API - legal insights and even execution made directly accessible to the functions that need them.

4. Agentic Span of Control: Every individual contributor should be managing agents

Key Insight:

Span of control is a private-sector management concept that Niles observes professional service firms do not naturally reach for. Applied to agents, it inverts what an individual contributor is: the traditional definition is someone who does not manage people, but Niles argues that in the future every individual contributor ought to be orchestrating agents - including, eventually, agents at their law firms across that shared operating system, and supervisory agents that check other agents' work. The appeal is not only capacity; it builds AI fluency and opens genuinely new career and development paths. The necessary counterpart is a new human role. Salesforce was, Niles is told, among the first companies to create agent managers - dedicated people at the intersection of legal expertise and agentic risk, who proactively mitigate legal and reputational risk without becoming a bottleneck, through risk scoring systems, user acceptance testing frameworks, standardized guardrails and governance checkpoints. Niles's argument for why the legal industry specifically should lead here is blunt: adoption will be a function of trust.

Managerial span of control. A leader's is measured in direct reports, and some executives famously carry forty or sixty. An individual contributor's should now be measured in agents.

Action Step:

Give every individual contributor an agentic span of control - agents to manage, orchestrate and supervise - rather than treating agent oversight as something only managers do.

5. Make Everyone a Builder: The change management that Niles would have done deeper and faster

Key Insight:

Salesforce created a joint innovation group that put legal innovation and legal ops under one roof, and the point of it was not to centralize building but to distribute it - to make everyone a builder and surface what the teams already know. Niles describes the ideal as a beginner's mind blended with expertise, on the grounds that the people doing the work know what needs unlocking, what needs simplifying, and where friction actually arises, and those insights should determine both what gets built and what gets scaled. The most striking result is who became the advocates: people who were not technologists, and candidly people who had been fairly oppositional about where these tools could be relevant, are now among the strongest champions and ambassadors. Asked what they would do differently, Niles's answer is to have done exactly this more deeply and faster, with more champions across the teams.

Action Step:

Go and ask the least senior people in the building how they are actually using the tools, where they find friction, and what could be simplified - Niles does this with Salesforce's Future Force interns - then pair those insights with the people who have been there for years. That pairing is where the value is.

6. Where Agents Are Not Ready, the Answer Is Hybrid: And the trust architecture does not exist yet

Key Insight:

Niles starts with the obvious failure case - firms of all sizes and reputations submitting hallucinations to courts - and notes that trust is earned and can be broken. But the answer is not simply more human review, because humans are fallible, tired and overwhelmed too; it is a hybrid of human accountability and oversight with agents and AI participating in the checking. The deeper gap is structural. In a piece written with Salesforce's chief AI scientist, Niles argues there is not yet a developed trusted agentic architecture, because every existing standard, rule and dynamic is fundamentally built around humans. That also requires clarity about when a workflow needs deterministic approaches and when probabilistic ones are acceptable, and it maps onto the classic distinction between rules and standards, where standards are looser and lean on judgment. Niles holds strong conviction, while expecting dispute, that AI agents are not ready at scale to complete negotiations on matters of importance, nor to adjudicate or arbitrate matters between themselves, and that humans are not ready either. Other named gaps include translation quality, where more progress would bring parties genuinely closer together. Cost discipline belongs here too: alongside client pricing there is token management and optimization, which turns triage into a question of what the right agent for the task is - or in the framing Niles was given, when you actually need the Ferrari.

The old London clearinghouse. Centuries ago, banks had to get in a room together and negotiate standards from scratch, because there were no rules yet governing whether you could trust the other side. Agentic legal work is at the same stage.

7. Judgment Has Building Blocks: The session's most contrarian claim

Key Insight:

Asked the hardest question in the profession right now - if agents absorb the routine work junior lawyers learned on, how does the next generation develop the judgment clients are actually paying for - Niles gives a two-part answer. Part one is that AI literacy, or what Niles calls agentic workflow competence, has to be treated as a core professional skill at every level, from equity and non-equity partners through counsel, associates, paralegals and broader staff, with real programming behind it rather than tone at the top. Because so much legal learning has historically come through apprenticeship and hands-on work, developing this competence means using the tools and building hybrid workflows for yourself and your teams, not watching a video. Niles also anticipates more roles around strategic auditing, where the discipline is not only checking the first pass but improving it in ways that build judgment. Part two is the contrarian half: judgment has building blocks, has context, and is grounded in knowledge, which means it can in part be unpacked - and the goal of unpacking it is either superior judgment or, at minimum, raising the floor of the judgment delivered at scale. Lat offers a personal test case, having drafted a response to a note from a child's teacher, run it past ChatGPT, been told the draft was overreacting and over-disclosing, and found on reflection that the machine was right and that a second human reader preferred the machine's version.

Core Question:

Have we overstated that judgment is deeply intangible, qualitative, something you only know when you see it?

Action Step:

Be deliberate about building AI literacy, and use the technology as a challenger rather than an oracle. Niles explicitly designs multi-stakeholder councils inside these tools - assigning personas across customers, levels of sophistication, industries or authors - because bringing a genuine range of perspectives to bear is a component of what people recognize as great judgment.

8. What Happens to the Hourly Rate: The billable hour was always being tested

Key Insight:

Niles's position is that the billable hour has always been problematized, because even under it the client is assessing the firm on outcomes delivered, relationships deepened, benefits shared, efficiencies found and who is actually doing the work. The only question was whether those criteria were explicit or whether everything got unduly simplified into hours in equals value out. On that reading, Niles does not object to an hourly model that has fixed, measurable elements - provided it embraces the expectation that considerably more gets done inside each of those hours. The prediction is that clients move beyond pure hourly rates en masse, with more alternative fee arrangements and continuing debate about capped structures for particular unpacked workflows. Niles then floats a genuinely different incentive design: rather than a firm billing hours and expecting payment, give the firm a specified budget, ask it to deliver what the client needs within that budget, and let it absorb the gain from doing better - which pushes the firm to decide its own team composition, delivery model and use of AI and agents.

Core Question:

Is agentic delivery going to break the model of the billable hour? Niles's answer is that it forces creativity, variation and flexibility, and that firms and clients who refuse that face a serious existential threat.

Prompts for Deeper Reflection
  • When your firms pitch their AI capability, are you testing it against confidentiality, privilege, security, enterprise-scale delivery and measurable outcomes - or against how convincing the deck is?
  • Can you state the executive thesis for your own function in three sentences? If not, what exactly is your AI work being measured against?
  • Which of your individual contributors currently manage nothing? What would change if each of them was orchestrating agents instead?
  • Which people in your organization were most resistant to these tools, and have you tried making any of them a builder?
  • If judgment really does have building blocks, which of yours could you actually articulate - and what would it take to raise the floor for everyone on your team rather than relying on your own ceiling?
Share-Worthy Moments
“This is not solely or even primarily a technology challenge. For service providers, it ultimately becomes and is often right now a relationship challenge.”
— Sabastian Niles
“Every individual contributor ought to have an agentic span of control.”
— Sabastian Niles
“Trust is earned, trust can be broken.”
— Sabastian Niles
“Judgment itself has building blocks, has contexts, is grounded, say, on broad or narrow knowledge.”
— Sabastian Niles
“Maybe we have overstated the magic of judgment.”
— David Lat
From the Q&A

Q: Lightning round - in the next five years, will every lawyer be expected to manage AI agents as part of their day-to-day work?

A: Yes, with a correction to the question: broaden "lawyer" to every legal professional, all of whom will be expected to manage and orchestrate these teams. Niles then adds the inverse, flagged as potentially controversial - legal professionals will also use AI agents to help allocate and distribute work. Humans stay at the top, but the arrangement becomes a much more shared operating system than a hierarchy.

Q: Lightning round - in the next five years, will clients stop hiring law firms that cannot show how AI has changed their actual service delivery model?

A: Yes, without qualification.

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Certainly increased mergers. Niles frames it through Clayton Christensen's innovator's dilemma: AI will push firms to change, adapt and innovate, and possibly to become more grounded in their core mission, while firms unable to evolve will create a host of problems for themselves. On collapse specifically, Niles adds a second path that has nothing to do with refusing AI - a firm that uses AI in ways that destroy trust is also heading toward existential issues. But that risk cannot become an excuse to avoid innovating and evolving responsibly.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: No. Niles argues that the risks, opportunities and ambiguity every participant in society now faces are exactly where legal professionals can deliver differentiated value, and that value is increasing exponentially, with AI as a force multiplier. The caveat is pointed: the nature of the work and the expertise will have to evolve, and for practicing lawyers who do not bring curiosity and evolution to it, that is a career-limiting approach.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: No.

About the Speakers
  • Sabastian Niles, President, Chief Legal Officer & Corporate Secretary at Salesforce - Niles leads legal at Salesforce and has argued publicly, including in an open letter to the legal industry, that the era of the AI pilot is over. Salesforce Legal operates as customer zero for the company's own agentic tools, embedding agents into the triage and routing of hundreds of thousands of requests a year. Niles co-wrote a piece with Salesforce's chief AI scientist on the current absence of an agentic trust architecture, and came up at Wachtell Lipton.
  • David Lat, Founder at Original Jurisdiction - Lat founded Original Jurisdiction and hosts its podcast, and was described in the introduction as the original legal content creator, from Above the Law, before that was a profession. Lat also came up at Wachtell Lipton and led this conversation as a continuation of an earlier podcast interview with Niles.
  • Basha Rubin (moderator), CEO & Co-Founder at Priori - Rubin introduced the session and framed its two lenses, what the moment means for in-house teams and what it means for the firms and providers serving them, before handing the conversation to Lat.

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Session 6

What It Takes to Build a Thriving Flex Legal Career

Anjali SareenFlexible Legal Professional at Uncommon Counsel
Odini GogoFlexible Legal Professional at Gogo & Moore
Matthew Wheatley (moderator)Chief Commercial Officer at Priori
The Big Picture

This session is the practitioner's-eye view of everything the rest of FlexFest discussed structurally, and its most useful quality is that neither speaker romanticizes the work. Anjali Sareen and Odini Gogo have five and ten-plus years in flexible practice respectively, and both push back on the fear that most keeps lawyers from trying it: neither has experienced a moment of wanting work and not finding it. What they replace that fear with is a more accurate set of requirements. In-house experience matters more than law firm training here, because the job is to arrive inside a business and get it to yes rather than to say no with authority. Every new engagement means proving yourself again to a business that assumes legal exists to block it. And the trait that actually determines whether someone thrives is not comfort with uncertainty but the absence of ego - you are an integrated member of a team whose internal politics are not yours to have opinions about. Gogo's framing is the one to keep: work is available, but it will not simply come to you, and if the motivation is only a paycheck there are easier ways to earn one.

Top 7 Breakthroughs

1. Control, and the Break as the Actual Product: More control does not mean less work or lesser work

Key Insight:

Gogo came to the model wanting greater control over career, over which work to accept, over which people to work with, and over how time gets structured - and stayed for the quality and variety of the work, plus the room to build a separate company alongside practice. Sareen's route was different: after firm environments including a traditional solo practice, the appeal was doing sophisticated, high-level, complex legal work without the business development and without clients new to working with an attorney at all. What both describe as the real deliverable is the break. Sareen can work extremely long hours for a client they value across a three or six month engagement, then take a full month off in which the inbox genuinely is not filling up and there is no accumulating backlog waiting - which is not possible in-house and not possible in traditional firm practice. Wheatley's observation is the one worth holding onto: more control has not meant working less or working on less sophisticated matters.

2. Demand Is Not the Risk People Think It Is: And AI is expanding it, not shrinking it

Key Insight:

The fear that stops lawyers from trying flexible practice is whether the work will be there, and both speakers answer flatly that it has been. Their practice areas are the ones under the most pressure - technology transactions, commercial contracts, data privacy, and increasingly AI counseling, which Sareen now treats as roughly half the practice alongside data privacy. Gogo's point is that AI has increased demand rather than reduced it, because AI deals bring their own issues about what data is being transmitted and how it gets protected, and because growing companies, AI companies included, still need commercial transaction lawyers to get deals closed. Sareen adds a sharper version: two or three years ago pure data privacy experience was the differentiator, and now the lawyers who evolve alongside AI are the ones who get to have this experience of work being available whenever they want it. Gogo also names the real constraint honestly - the worry is not finding work, it is managing it all.

Core Question:

Will there be enough demand to sustain a flexible practice? In these practice areas, both say yes without hesitation, with the caveat that the answer is tied to evolving with where the work is going.

3. In-House Experience Beats Big Law Training Here: Because the job is getting to yes

Key Insight:

Both reject the assumption that law firm training is the critical credential. Gogo is generous about what it does teach - rigor, precision, responsiveness, managing complex matters under pressure - but both identify in-house experience as what makes a flexible lawyer effective, because the core skill is arriving inside an organization and understanding within weeks how it operates, how to navigate its people and internal politics, and how to answer legal questions in a form the business can digest. Sareen puts the distinction in one line: on the law firm side you have some leeway to say no, and on the in-house side that does not exist. Gogo extends it into what good advice looks like - not "here is the risk, full stop," but here is the risk, here is how we get to yes, and if we do these specific things we can get to what you are trying to do.

Core Question:

Is big law experience required to work this way? Definitely not - both are helpful in their own regard, but in-house experience is the more important preparation.

4. You Are In-House, After You Prove It Again: The first weeks of every engagement are an audition

Key Insight:

Asked whether business stakeholders treat a flexible lawyer as inside or outside the team, both describe the same arc. You arrive as an unknown, into a relationship where the business already assumes legal exists to stop it doing things, and you have to prove yourself. Gogo is matter-of-fact that this is universal rather than a slight against flexible practitioners - you get in, you prove yourself, they get comfortable. Once past that point, Sareen describes it as feeling entirely in-house while an engagement runs: no line between you and the business, frequently no line between you and the in-house legal team, and genuine reliance on you as a member of an integrated team. Gogo notes that good clients bring flexible counsel in as a partner and route sophisticated, problem-solving work to them, and that a real engagement always exists because of a real and immediate need - you are never simply parked.

5. No Ego Is the Underrated Requirement: And uncertainty is a smaller factor than people assume

Key Insight:

Sareen dismantles the uncertainty worry first - the picture of going months without work has not matched reality, and would not for most lawyers genuinely dedicated to it. The honest version of that concern is narrower: if you need a predictable paycheck every two weeks and want to know exactly what each day holds, this is not for you. The trait that actually matters is the one nobody anticipates. Sareen's formulation is taking nothing seriously except practicing law, which in this context means having no ego about anything else. You are an integrated member of a team while simultaneously not being embedded enough in the corporate environment to hold opinions about how that team is run, how its meetings go, or how someone interacts with you. Something bothering you has to roll off, because the engagement exists for one or two discrete things and will end. Sareen is clear this coexists with taking the legal work itself completely seriously and wanting to make genuine connections.

6. Intention Is the Gate: Nobody here is romanticizing this

Key Insight:

Gogo draws a distinction that reframes the whole session. Many lawyers want out of the practice of law and are looking for the shortest possible route through it to something else. Both speakers have built full lives outside practice and still actively want to practice - Gogo describes being a lawyer as a privilege, and remembers hoping to get into law school at all, something many people never get to do. That makes flexible practice a conscious choice rather than an exit. The warning attached is specific: work is available everywhere but it will not simply arrive, and it takes the same personality and drive that produce success anywhere else. Engagements can also be genuinely all-consuming, with a deal closing that depends on your availability, because by then you are part of an in-house team and that is how the business sees you.

Core Question:

What is your intention, and why do you want to do this? Gogo's counsel is that it should not just be a paycheck, because if money is the goal there are other things you can do.

7. It Is Not Sales, It Is Fit: The honest trade-off of working through a platform

Key Insight:

Sareen rejects the premise of being a natural salesperson and uses that to explain why platforms work. The genuine downside is stated plainly: solo practitioners doing their own business development generally charge more per hour because they work with clients one-off, whereas an engagement guaranteeing twenty, thirty or forty hours pays less than a standalone hourly rate - a real consideration, not a footnote. The upside is that the work never becomes salesy. Sareen is not doing business development, but meeting potential clients and assessing fit, which means the part of the brain that dreads selling never has to switch on - and for a lawyer who believes they would be terrible at sales, that makes this a viable path rather than a compromised one. Gogo's version emphasizes being pre-vetted: because clients trust the platform to send good lawyers, an introduction becomes a conversation rather than a pitch, which is also why sophisticated work arrives. Gogo also names the unglamorous benefit that matters in practice - not having to chase invoices or work out when payment is coming, because somebody else owns that.

Prompts for Deeper Reflection
  • If your honest fear about flexible practice is demand, is that fear grounded in your practice area, or in the general story you have absorbed about the model?
  • Which of your existing experience actually transfers - the firm training you were told mattered, or the in-house instinct for getting a business to yes?
  • Could you walk into an organization and be genuinely useful inside a few weeks without needing anyone to acknowledge your seniority?
  • Sareen takes nothing seriously except practicing law. Which of the things you currently take seriously at work would you have to let go of?
  • What is your actual intention here - a different way to practice, or a way out of practicing? Gogo's point is that the answer determines whether this works for you.
Share-Worthy Moments
“There's never been a moment where I felt like I wanted to do more work and it wasn't available.”
— Anjali Sareen
“The best advice as an in-house counsel is you don't just say, here's the risk. You say, here's the risk, and this is how we can get to yes.”
— Odini Gogo
“I don't take anything seriously, except practicing law.”
— Anjali Sareen
“It will not just come to you. You have to have the personality, you have to have the drive. It's all the same things that make you successful in school and in life.”
— Odini Gogo
“I'm not actually doing sales. I'm not actually doing the business development. It's more that I'm meeting with potential clients and seeing if we're a fit.”
— Anjali Sareen
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Gogo said no - firms will still be here, in a changed form, because everything changes. Sareen said maybe, but attributed the driver to something other than AI: attorneys and clients wanting a different model for how work is done and services are received, which Sareen expects to matter more than the technology itself.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: Probably not. Sareen's reasoning is that the field is so academic and intellectual that people will keep being drawn to it in large numbers for the same reasons the two of them were. Gogo agreed.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Yes, from both, and Gogo's answer is the most pointed in the session. Predictions of the hourly model's death have been circulating for ten and twenty years; it is how lawyers are paid, and lawyers are also the people writing the laws. Gogo is personally open to a different structure and would welcome the conversation, but sees too many people making too much money under the current one for it to change within a lifetime, citing having read about a lawyer who made $40 million - not in personal injury but at a law firm, through structural bonuses, all of it hourly. Sareen agreed, expecting alternative fee arrangements to be more demanded, more offered and more accepted, while noting that legal is not the only industry that exchanges a rate for a measure of time, which makes it hard to move away from.

About the Speakers
  • Anjali Sareen, Flexible Legal Professional at Uncommon Counsel - Sareen has practiced for about fourteen years and worked flexibly for over five. A career that began in intellectual property now centers on technology transactions, split roughly evenly between data privacy and AI, the latter having grown substantially over the past two years. Sareen previously worked in several firm environments including a traditional solo practice, and sits on Priori's advisory board.
  • Odini Gogo, Flexible Legal Professional at Gogo & Moore - Gogo has worked flexibly for over ten years, making them one of the earliest practitioners in the space, with a practice in technology transactions, commercial contracts and AI-related counseling. Previous roles include King & Spalding and Cisco, and Gogo is simultaneously building a separate company alongside legal practice. Gogo also sits on Priori's advisory board.
  • Matthew Wheatley (moderator), Chief Commercial Officer at Priori - Wheatley has worked with both speakers across more than thirty engagements at dozens of Fortune 500 and high-growth companies, and describes both as trusted advisors to the Priori team.

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Session 7

Is Legal Demand Actually Changing?

Eric Dodson GreenbergEVP, General Counsel & Corporate Secretary at Cox Media Group
Keir GumbsChief Legal Officer at Edward Jones
Basha Rubin (moderator)CEO & Co-Founder at Priori
The Big Picture

This session answers its own title with specifics rather than sentiment. Keir Gumbs's evidence is that the urgency to backfill a departing lawyer has quietly disappeared, because AI and other levers now absorb the gap. Eric Dodson Greenberg's is that the Cox Media Group department has started allocating work differently, toward a wider set of choices. From there the conversation becomes an unusually candid account of what buyers are actually doing: Edward Jones cut its outside firm count by at least half and locked rates for two years, and both leaders now treat turnaround speed as a selection criterion rather than a nicety. The most useful argument is Greenberg's warning to firms that their healthy financials are a rear-view mirror, and the most useful advice is what both would tell a managing partner - stipulate that quality must be spectacular, then compete on knowing the client's business, because generic advice has become almost free and specific advice is where the remaining value sits. Both end optimistic, and for the same reason: what clients ultimately buy is a trusted relationship that tells them what to do, and that is the one thing the tools do not supply.

Top 8 Breakthroughs

1. The Evidence Is in the Hiring: The urgency to backfill a departure has quietly gone

Key Insight:

Gumbs offers the most concrete signal of the session. Historically, when someone left the legal function the message from the team was that they had to be replaced immediately - there was real urgency attached. Over the last six months, as more AI tools have come into use, Gumbs has observed more delay in bringing in new talent and, more tellingly, more acceptable delay, because teams are using AI and other levers to cover the gap that departure created. Greenberg's evidence points the same direction from a different angle: the department is starting to allocate work differently than before, and Greenberg expects that to keep shifting toward a multiplicity of choices rather than a default channel, evolving slowly rather than all at once.

Core Question:

From a chief legal officer's vantage point, what is one piece of evidence that AI is actually changing demand? Not projections - what has visibly changed in how the department behaves.

2. A Preferred Counsel Program as the Lever: Half the firms, work moved down-market, rates frozen

Key Insight:

Edward Jones launched a new preferred counsel program this year, an eight or nine month effort that reduced the number of outside firms used by at least half. The substance was not merely consolidation - the team looked hard at what work was actually going out and thought strategically about what smaller and regional firms could do versus the AmLaw 50 tier. The result is a much smaller cohort of large-firm preferred counsel and considerably more work going to smaller regional and local firms. The pricing terms are the part other departments can copy directly: every firm entering the new arrangement locked its hourly rates for at least two years, and agreed that no further rate increases would happen without pre-approval from the Edward Jones team. Gumbs is careful to credit a shared services team rather than taking the credit, noting that "we" is being used extraordinarily royally.

3. Healthy Financials Are a Rear-View Mirror: What should a firm be managing to?

Key Insight:

Greenberg accepts the premise that big law looks fine - rates holding, demand steady, profits strong - and argues that this is simply not predictive. Firms should be managing to the future, because the metrics describe what is already behind them. What changes the picture is structural: AI-native firms, a proliferation of boutiques, and above all collapsed barriers to entry, since AI supplies research and resource capacity that previously required a firm around you. Greenberg expects this to start visibly playing out in 2027, and expects big law to continue existing - but for different reasons and on a different model. The firms that anticipate the shift will be very much in the mix and very successful; the ones that look at excellent numbers and conclude nothing needs to change will not, in Greenberg's view, exist. Greenberg illustrates the gap with an exchange relayed second-hand, in which someone in the legal AI space reviewed a firm's AI strategy and told them they would be out of business in five to six years - and when they expressed shock, offered that maybe it would be seven.

In 2007 the economy looked great. There was a point when Blockbuster looked great and BlackBerry looked unstoppable. Empirically strong performance is not the same as a sustainable position.

Core Question:

If the financials look healthy, what convinces a firm that the ground is actually shifting? Greenberg's answer is that nothing in the current metrics will, which is exactly the problem.

4. Speed Became a Selection Criterion, and New Services Appeared: Two different changes, often conflated

Key Insight:

Gumbs describes a live comparison across litigation firms. Some deliver an AI-prepared deposition summary within an hour or two of the deposition ending, alongside the lead litigator's own read of how it went. Others take days or a week, which was entirely normal years ago and now reads as slow. The firms delivering near-real-time deposition and hearing summaries are getting more work, and Gumbs is direct that satisfaction as a consumer rises accordingly, out of an unwillingness to wait a week for something that can demonstrably be produced in thirty minutes. Greenberg adds that this is only half the change. A decision relevant to the industry now arrives with an AI-generated summary from a young partner or senior associate within five minutes of issuance - which Greenberg forwards to the CEO a minute later, explicitly labeled as AI-generated, not as a criticism but out of delight at the delivery. The other half is services that did not previously exist at all: the team recently fed a body of material into a database and used AI to produce a strategic take on their negotiation approach.

Core Question:

How long would that have taken before? Greenberg's answer to a legal ops colleague was that it is not a thing - it would not have been done at all, at any cost in time or resources.

5. Insourcing Buys Institutional Knowledge, Not Just Savings: The cost case is the smaller half

Key Insight:

Edward Jones has been insourcing for a decade, beginning under Gumbs's predecessor. Ten years ago the legal function was literally a handful of lawyers alongside a few hundred compliance staff, with roughly 70 to 80 percent of legal work done outside; today it is a legal team of around 160 within a legal, compliance and risk organization of about a thousand. The cost logic is straightforward - sustainable, predictable work done internally costs materially less, and the discipline is identifying work you know you will need in future so you can bring that talent in rather than paying a premium later. But Gumbs rates the second benefit higher: with outside counsel, the firm becomes the expert in your business, whereas what Gumbs actually wants is a division full of people who know both the law and Edward Jones. Looking forward, the firm's "future of work" initiative runs on four levers applied across every organization, not only legal: AI and automation; outsourcing, split between offshore work and contractors including flexible talent; upskilling and reskilling people into different kinds of work; and process optimization, on the recognition that many processes were designed twenty years ago and may no longer make sense. Greenberg's parallel example is a digital twin - an area of law that lost its dedicated lawyer and was absorbed by a colleague with deep expertise for whom it is not the highest and best use of time. Rather than hand the area to an agent, they are building a twin that learns it from the department's own institutional knowledge, which both reduces outside counsel dependence and frees that lawyer for work where the expertise matters more. Greenberg's read across peer conversations is that departments are largely not shrinking deliberately but letting attrition do it, using the technology to absorb each lost role - a slow decline in headcount while the department's output grows.

6. Tyranny of Choice or Tyranny of Pitches: Two CLOs disagree, and legal ops is the answer either way

Key Insight:

Greenberg has written about a tyranny of choice paralyzing in-house teams, now that work no longer simply defaults to big law and the options include AI-native firms, various kinds of alternative providers, new technologies and boutiques. Greenberg's approach is to place a lot of small bets, with a legal ops lead curating the choices so the team is not sitting through endless demos - which is why Greenberg considers the anthropology of the in-house team so important, because a legal ops professional who understands both the technology and how the business and legal team actually work is uniquely positioned to filter. Greenberg sees alternative providers as similarly well placed to guide clients given their exposure across many clients and tools, and identifies an opportunity law firms are largely not taking: coming to a client with what they are seeing elsewhere and offering to help implement it. Gumbs reframes the problem entirely - it feels to Gumbs less like a tyranny of choice than a tyranny of pitches, a constant stream of firms in every bucket. Gumbs is not especially torn about selection, because each provider type has a natural niche: a six-month vacancy suggests flexible talent, a highly specialized need suggests a boutique that does only that. Greenberg adds a category worth naming, off-label AI - a tool marketed for one purpose that solves a different one after adaptation. Greenberg's team took an M&A tool and applied it to a process carrying revenue and legal risk, after a team member recognized the analogy, with the legal ops person acting as liaison to the platform.

Legal ops as the skeleton key - what opens the door to a new opportunity, though Greenberg is clear the door does not open automatically, and implementation does not always go as planned.

7. Knowledge Management Is a Verb: And curiosity is the skill that does not get automated

Key Insight:

Greenberg names two things that change and one that does not. The first change is that knowledge management stops being a noun. It used to be a compilation, a thing that existed; now it is an ongoing process of finding data, adding to it and making it accessible, and it seeps into the architecture of the whole team. The second is that legal ops becomes more important still, partly for the reasons already discussed but also because the legal team is becoming a gateway for enterprise AI - these tools are not like downloading a new version of a word processor, they require understanding how people work, what problem they are solving and where friction sits, which is a vantage point legal uniquely has. The thing that does not change is curiosity. Prompt engineering is real and important, but what makes it effective is being curious, thinking by analogy and spotting gaps - the things lawyers were trained to do. That shifts hiring away from "have you done these filings, have you done these deals" toward lawyers who are ambidextrous, curious and agile with AI, and Greenberg expects the liberal arts capacity of a lawyer to matter more than before. Greenberg also expects emotional intelligence to become more valuable, not less: as more is turned over to machines, the ability to empathize and to be trusted is what big law's moat is actually made of. Gumbs's parallel from Edward Jones is a shared services function across legal, compliance and risk containing a dedicated data team, built because regulatory reporting, discovery and compliance constantly require data that is neither easy to find nor in one place - alongside a target of over 60% average daily AI tool use across the legal division, higher than the rest of the firm.

8. Movie Theater Economics, and What a Firm Must Now Do: Where the money actually comes from

Key Insight:

Greenberg's model of the traditional firm is a cinema. A blockbuster film commands a handsome ticket price, but the theater makes its money on popcorn and soda. A firm charges a lot for a partner - that is the blockbuster - while the economics run on the sixth-year associate, the third-year and the five second-years staffed to the matter. Boutiques, AI-native firms, alternative providers and flexible talent all disrupt that, because once buyers can disaggregate partner-level judgment from commoditizable work and price the latter separately, general counsel start assembling an a la carte menu instead of eating off the prix fixe one. Notably, Greenberg says they may pay more than today for genuinely unlevered access to a specific partner's expertise, paired with a provider handling diligence and document review. The scale gap is still enormous - Rubin cites the AmLaw 200 at roughly $190 billion in revenue growing 13% year on year, against alternative providers at around $30 billion growing 18%, faster but not fast enough to catch up. Asked directly what a firm should do to keep the work, Gumbs starts by stipulating what everyone skips: the quality has to be spectacular. Then, deliver more value through speed, and above all know the client's organization. Generic advice is Gumbs's biggest pet peeve and has nothing to do with money, and that criticism includes even AmLaw 25 firms among those with wonderful lawyers who are poor at customizing advice to the specific business receiving it - a narrowing margin for error, because the ability to get generic advice has grown while the value of specific advice has risen. Greenberg wants a conversation about value rather than price, and more sophistication in pricing than the era when it was an older partner with a legal pad deciding that 10% seemed right. Greenberg's most instructive example is a firm that ran a joint AI experiment with the Cox Media Group team, came back and said they had learned as much as the client had, and took an amount off the rate - which Greenberg could not verify as mathematically correct but which felt fair and felt like it was getting at value. Both leaders end on the same note about why optimism is warranted: Edward Jones is itself an advice business facing the same automation, and what clients want is not the data but a trusted relationship that tells them what to do about it.

Action Step:

For firms who want to keep the relationship - stipulate spectacular quality, compete on turnaround, learn the client's business well enough to stop giving generic advice, bring a sophisticated conversation about value rather than a rate letter, and offer the client access to your own knowledge base so they benefit from what you have seen across the industry.

Prompts for Deeper Reflection
  • When someone leaves your team, has the urgency to backfill changed? That single observation may be the most honest measure of whether AI has actually changed your demand.
  • Could your department lock outside counsel rates for two years and require pre-approval for increases? If not, what specifically is stopping you?
  • Which of your firms would look better and which would look worse if turnaround speed became an explicit selection criterion?
  • Are you insourcing to save money or to own the expertise? The second one is harder to reverse and worth more.
  • If generic advice is now nearly free, what does your team or your firm provide that could not be produced by someone who does not know your business?
Share-Worthy Moments
“The metrics are telling them what's behind them.”
— Eric Dodson Greenberg
“It's very easy to get used to getting a deposition summary in an hour.”
— Keir Gumbs
“Knowledge management is no longer a thing. It's a verb. It's an ongoing action.”
— Eric Dodson Greenberg
“Some of the biggest firms, and I'm going to include AmLaw 25, wonderful lawyers, horrible at customizing their advice to the actual business or person to whom that advice is being delivered.”
— Keir Gumbs
“The billable hour is like the Twinkie of the legal world. It's going to survive nuclear winters.”
— Eric Dodson Greenberg
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Yes from both, with Greenberg adding an exclamation point. Rubin noted at this point that every single FlexFest speaker had answered yes to this question.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: No from both, though for a reason that complicates the question. Greenberg's answer is that lawyers will be doing different things rather than that there will be fewer of them. Gumbs agreed, framing it as the same general number of practicing lawyers doing wildly different work.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Yes from both, with careful qualifications. Gumbs said yes; Greenberg said yes but not overwhelmingly dominant, and offered the session's most quotable line about the billable hour surviving nuclear winters. Greenberg also named a dirty secret - general counsel like the billable hour, because it is the least bad option and they are comfortable with it - while expecting its share to fall well below today's level. Gumbs drew the sharper distinction: it may end up the prevailing model rather than the dominant one.

About the Speakers
  • Eric Dodson Greenberg, EVP, General Counsel & Corporate Secretary at Cox Media Group - Greenberg leads legal at Cox Media Group, a multi-platform media company based in Atlanta. Greenberg writes about the changing legal market and is credited in the session with coining several of its framings, including the golden era of the alternative legal service provider and the bionic boutique, and previously practiced at a law firm alongside Keir Gumbs.
  • Keir Gumbs, Chief Legal Officer at Edward Jones - Gumbs leads a legal, compliance and risk organization of roughly a thousand people, including a legal team of about 160, at a financial services firm with around 20,000 financial advisors and, as Gumbs notes, more branches than Starbucks. Recent initiatives include a new preferred counsel program, a shared services function spanning legal, compliance and risk with its own dedicated data team, and a firm-wide future of work program built on four resourcing levers.
  • Basha Rubin (moderator), CEO & Co-Founder at Priori - Rubin co-founded Priori in 2013 and moderated four FlexFest sessions.

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Session 8

AI-Native Services and the End of Scale as an Advantage

Mark PikeAssociate General Counsel at Anthropic
Zack ShapiroFounder/Managing Partner at Rains Law
Basha Rubin (moderator)CEO & Co-Founder at Priori
The Big Picture

This session gets closer than any other at FlexFest to the mechanics of the shift, because both speakers are hands-on. Zack Shapiro's central diagnosis is that technologists and lawyers are talking past each other: one group projects forward from capability without accounting for institutional friction, the other tries a short prompt, gets a decent but unusable answer, and concludes the whole thing is overhyped. What bridges that gap is what Shapiro calls the input layer - the skill of explaining to a model what you want, which has to come from lawyers rather than vendors. From there the economics reframe sharply. Clients were never buying junior associate hours; the leverage model was simply how services got delivered. So AI does not erode big law's value, it improves big law's margins - and the problem is that the pricing model was built to sell the part that is disappearing. Mark Pike's counterweight is the demand nobody is serving: 80% of civil litigants appear without a lawyer. And the session's sharpest warning has nothing to do with hallucinations. Because these models will produce a plausible answer to almost anything, the real risk is the temptation to hand over your thinking, when practicing well means doing the thinking and using it as the input.

Top 8 Breakthroughs

1. The Diffusion Gap, and the Input Layer That Closes It: Why capability and adoption keep missing each other

Key Insight:

Shapiro describes the gap between frontier capability and enterprise adoption as one of the most important facts in the economy right now, and is even-handed about who is at fault. Technology companies see genuinely transformative capability, and skip forward to a world where the transformation has already happened, without fully reckoning with the slow bureaucratic work of getting there - which makes their timelines optimistic. Meanwhile lawyers hear that AI will rewrite their profession, try the tools with a brief prompt about a work product they know well, receive a predictably decent but not-ready-for-primetime response, and conclude the technology is overhyped and can be deferred. Both sides need this resolved: technology companies must eventually show real enterprise efficiency and revenue to justify their valuations, and Shapiro does not yet see numbers indicating that is happening, while firms face client questions about where the AI efficiency has gone and pressure from AI-native upstarts raising very large venture rounds specifically to outflank them. What closes the gap is the input layer - lawyers learning how to talk to the models in order to hand off execution and automate legal process. Crucially, Shapiro argues this has to come largely from legal professionals themselves, and frames the work of the next decade as helping lawyers who already have the judgment and experience translate that into handing off execution.

A genie. What is remarkable about the technology is how elaborate a wish you can cast, and what is dangerous is the classic genie failure mode of literalism - wish for a billion dollars and it falls out of the sky onto your head, wish to be the smartest person on earth and everyone else disappears. Precision in the asking is the whole skill. Rubin called it the best analogy for prompt engineering yet heard.

Core Question:

Why are these two groups still talking past each other? Because each is generalizing from a partial experience - one from what the technology can do, the other from what a thirty-second attempt produced.

Action Step:

Two levers, per Shapiro. First, prompting - write or speak considerably longer prompts than you think you need, and be narrow enough that you cannot be misunderstood. Second, custom skill creation, which mostly means having the model do it for you: feed it Anthropic's guide to creating custom skills, point it at your own history of chats, and ask it to pitch you the skills it could build. Pike's version is to simply try things, borrow the skills and plugins other people are publishing rather than building from scratch, and point the model at your team's ticket history to ask where it could help.

2. In-House Is Adopting Faster Than Firms: And the usage data shows who is actually doing the work

Key Insight:

Pike attributes the split to incentives rather than aptitude. In-house lawyers are told to do more with less, are measured on business outcomes, and are actively trying not to be seen as bottlenecks. Law firms have real incentives to preserve the billable hour and a reputation for conservatism about new technology. The usage evidence is striking: stack-ranked against other knowledge workers, lawyers are the number one power users of the Cowork function - the agentic capability that lets the model operate a desktop computer and work autonomously for hours or days on large projects, which knowledge workers have only had access to for around six months. In-house teams are further ahead partly for a mundane reason: where a company already has the tool deployed, there is no procurement cycle to clear, which a firm starting from scratch has to work through. What Pike is most enthusiastic about is that the ecosystem is open, with builders creating and sharing skills and workflows that others remix.

3. Big Law's Value Is Not Eroding, Its Margins Are Improving: The problem is that the pricing model sells the wrong half

Key Insight:

Shapiro's reframe is the most important economic point in the session. The value big law delivers is perversely different from what its invoices describe. High partner rates matter less to profits per partner than the leverage model does - very large teams of associates doing document review in litigation, due diligence in transactional work, and sometimes checking typos or formatting signature pages. That is work it is hard to imagine a smart Fortune 500 general counsel paying for in five years. The bad news is that the economic engine has to change. The good news is that this was never what clients were trying to buy, which means the value proposition is intact and the margins are simply getting better - something almost any other industry would celebrate. Law's difficulty is that it is one of the last industries running a cost-plus model, which was a poor incentive structure to begin with. The move required is from cost-plus leveraged billable hours to value-based pricing, whether flat fees, success fees, contingency fees or subscriptions. Big law disproportionately holds the best lawyers in the world and the institutions that carry the largest matters, and clients genuinely want that judgment for bet-the-company litigation and front-page M&A. The task is capturing that value as judgment rather than as hours. Rubin notes the irony surfaced earlier in the day: for years in-house teams argued firms should leave the billable hour for the clients' sake, and now firms may need to leave it for their own.

4. Jevons in Law, and What Actually Changes for Junior Lawyers: 50% of each job, not 50% of jobs

Key Insight:

Both speakers reach for the Jevons paradox, and Shapiro applies it precisely: legal supply is severely constrained relative to demand, and there are many things people should use lawyers for and do not, because it is expensive, the cost is unpredictable, and finding a lawyer you trust is a baroque process. Cheaper delivery therefore means more legal services consumed, not fewer - largely good for access to justice, potentially bad in that anyone can now generate a plausible-sounding demand letter, which may simply mean more litigation. Pike's parallel is that personal computers and spreadsheets were expected to end accounting and instead expanded it, possibly moving it down-market, which suggests real mid-market opportunity in legal. The distinction Shapiro insists on is the one most commentary misses: AI automating 50% of legal jobs, which Shapiro thinks is wrong, versus AI automating 50% of each legal job, which is what Shapiro observes among genuine power users. And those power users are not working fewer hours - to a person they are working more, on higher-value work. For junior lawyers the implication is that value-add stops being billable hours of menial work, which is good for the juniors who exist, but it also means law school is a poor choice if the motive is a low-risk upper-middle-class trajectory rather than wanting to practice. Associate development has to change accordingly: the premium is judgment and client service, and the way to build judgment is to be in the room when the partner is making the difficult calls.

Jiro Dreams of Sushi - the apprenticeship model where you make rice for years before you are allowed to touch the fish. Shapiro's point is that armies of associates doing grunt work is not how judgment gets built from here.

Core Question:

Is law school a rational choice for a new graduate today? Shapiro's answer depends entirely on motive - if you want to be a lawyer this is as good a time as ever, and Shapiro would have been a far better law student with these tools; if you are deferring the job market and are agnostic about the job itself, it is a bad time.

5. Access to Justice Is the Latent Demand: 80% of civil litigants have no lawyer

Key Insight:

Pike connects the surge in law school applications to something other than economics - people are applying because they want to help and to be counselors, and the unmet need is enormous: immigration cases where people cannot find a lawyer or know their rights, landlord-tenant disputes, and a large volume of public service work that goes undone. The structural blocker is not desire but debt, and the career treadmill that law school debt and career services pipelines create. Pike sees AI changing that arithmetic, both because it is easier than ever to start your own practice as costs fall, and because tools can reach people directly. Pike's illustration is a JD-MBA student at UNLV who teaches continuing legal education and runs change management for lawyers in Nevada while still in school, held up as the model for taking charge of a career path. Quoting Sonia Ebron of Courtroom 5 after launching Claude for Legal plugins with them, Pike frames the mission plainly, and is also honest about the counterweight: the explosion in pro se claims includes people who do not understand the technology is hallucinating, which strengthens rather than weakens the case for lawyers being involved.

6. Probabilistic and Deterministic Both, and the Real Risk Is Ceding Your Thinking

Key Insight:

Rubin raises a genuine tension: these tools are probabilistic, so five identical questions can produce five different answers, and that is a feature rather than a defect - which pulls directly against a decade and a half of legal tech pushing toward standardization through the NVCA forms and the oneNDA project. Pike's answer is candid about limits: Anthropic was founded as a research lab, publishes what it finds on interpretability, and is transparent that the field does not fully understand why models do what they do, which for legal work is a useful disclaimer rather than an embarrassment. What has improved is grounding - giving models the same authoritative sources and tools a lawyer would use makes outputs more repeatable and reduces the confident fabrication of three years ago. Pike also offers a deeper possibility: perhaps there is not always a correct answer in law, the gray area is real, and that ambiguity is precisely where human judgment earns its place. Shapiro agrees the mature system is hybrid, with deterministic code where there is an objective answer - share counts and per-share math in Shapiro's deal tooling, or verifying that case names in a brief correspond to real cases - and generative models where the work is qualitative, taking a lawyer's intent and expressing it in language. On that view the variation does not matter, because different valid phrasings can capture the same logic. Shapiro is impatient with how much of the public conversation fixates on hallucination: submitting fabricated case names to a federal judge is a failure of judgment, not of technology, and it is not too much to ask that an associate read the case names before filing. There are also techniques for having a model check its own work, and for having models from different labs check each other. The deeper hazard is subtler - because these systems produce a plausible response to almost any input, there is real temptation to treat them as permission to stop thinking. Shapiro's own practice is the inverse: do the hard cognitive work first and use it as the input, which now means walking outside and free-associating into a phone for minutes at a time and coming home to a good draft, working harder rather than less.

Giving the model a calculator to do math. Grounding it in the tools and primary sources lawyers actually use is what makes the output repeatable, rather than asking it to produce the answer from memory.

7. How to Spot Real Sophistication Versus AI Theater: Two signals, both visible from the client's side

Key Insight:

Shapiro is blunt that there is a great deal of theater, and that genuinely skilled practitioners remain a small percentage of the profession - but argues the difference is not subtle once you know what to look for. The first signal is efficiency, which buyers are already watching. Shapiro's example: on a venture deal where the term sheet required the early-stage client to cover the investor's legal fees up to $35,000, Shapiro asked opposing counsel at a large firm to produce the first draft of the industry-standard documents given the client was paying anyway, and was told the $35,000 would not cover drafting them. Weeks later, working with Claude Code over a weekend, Shapiro built a deal engine - a non-AI tool that connects to the model through an MCP server - which takes a pre-round cap table and a term sheet and produces solid drafts of all the documents with the math, per-share prices and preferred series correct. Firms with that capability will price differently. The second signal is subtler and more telling: the things that used to be too expensive in human effort and are now nearly free, delivered as extras. Clients in a priced round always want to know how far along the deal is, how long until close, and what the last round of edits was actually about - and no lawyer previously had time to write that memo, nor would a client pay for it. Working inside Cowork, Shapiro can point the model at revisions it already has and ask for a memo with full detail and nuance, pitched for a non-lawyer. It is one prompt, it costs nothing to produce, no extra charge is passed to the client, and clients love it.

Action Step:

As a buyer, look for both signals rather than one. Efficiency tells you a firm has adopted the tools; new services that nobody used to offer tell you a firm has actually changed how it works.

8. Judgment Is Decision-Making Under Uncertainty: Not taste, and not pattern matching

Key Insight:

Rubin sets the frame that gives the session its stakes: the technology is arriving whether the profession likes it or not, but the shape of the industry is genuinely within its control, and nobody has to accept the future being sold to them on where accountability lives or what it means to be a lawyer. Just because a technology could stand up in court does not make that the future anyone should want - it has to serve the profession's ends. Shapiro takes up the phrase and applies it to what Shapiro calls the human kernel left at the end, and is deliberately dismissive of the Silicon Valley preference for "taste," because the word blurs together judgment and pattern matching, and pattern matching is something models are very good at. What Shapiro believes is uniquely human, and will increasingly define what practicing law means, is decision-making in the face of uncertainty. That is what lawyers actually do, transactional and litigation alike: helping clients make difficult decisions about legal challenges. Models are strong at execution once you have explained what you want, and genuinely weak at making the decision for you, which is precisely where people get into trouble by expecting otherwise. The practical conclusion is a training prescription: get comfortable making difficult decisions when it is unclear what to do, because building that muscle is the most valuable thing a lawyer can do now.

Core Question:

What is the human kernel that is left at the end of all of this? Shapiro's answer is judgment, defined narrowly enough to be useful - deciding under uncertainty, not recognizing patterns.

Prompts for Deeper Reflection
  • When you last concluded a tool was overhyped, how much did you actually put into the prompt? Shapiro's argument is that most of the profession has tested its own input layer, not the technology.
  • If your firm's leveraged associate work disappeared from the invoice, would your value proposition to clients change or would only your pricing model have to?
  • Which parts of your work are genuinely qualitative and which have an objectively correct answer? Those two need different tools, and mixing them up is where the failures come from.
  • Is there anything you could deliver to clients tomorrow that used to be too expensive in human effort to be worth offering? That is the signal buyers are watching for.
  • Are you using these tools to think harder, or to think less? Be honest, because Shapiro's point is that the output looks similar in both cases and only one of them compounds.
Share-Worthy Moments
“It's not that big law's value is being eroded. It's that their margins are getting better.”
— Zack Shapiro
“There is a big difference between AI automating 50% of legal jobs, which I think is wrong, and AI automating 50% of each legal job, which is what I am seeing.”
— Zack Shapiro
“Most people don't know they have legal rights until it's too late to use them. Claude can now meet them where they are.”
— Sonia Ebron of Courtroom 5, quoted by Mark Pike
“There is a real temptation to use AI as an invitation to turn your brain off and cede your cognition. Practicing law with AI the right way is the exact opposite.”
— Zack Shapiro
“You won't know what spells work until you try them, and it's cheap to try.”
— Mark Pike
From the Q&A

Q: Lightning round - in the next five years, will an AmLaw 100 firm collapse or merge out of existence primarily because of AI?

A: Yes from both speakers, without elaboration.

Q: Lightning round - in the next five years, will there be fewer practicing lawyers in the United States than there are today?

A: No from both. Shapiro reasoned that the increase in people going to law school will largely translate into people practicing. Pike also said no, while flagging the counter-signal that certain law schools are reportedly shrinking their class sizes, and landed on there being enough work to be done that the profession will find a way.

Q: Lightning round - in the next five years, will hourly billing still be the dominant model?

A: Pike said no. Shapiro split the question on timing, which is the more precise answer: during the next five years, yes; five years from now, no - with the transition expected to take about that long.

About the Speakers
  • Mark Pike, Associate General Counsel at Anthropic - Pike is a product lawyer who has been at Anthropic for almost three years and has spent recent months working on Claude for Legal, including plugin launches with access-to-justice organizations. Pike is non-technical and does not code, and describes building the internal tooling their product legal team runs on directly with the company's own tools.
  • Zack Shapiro, Founder/Managing Partner at Rains Law - Shapiro leads a startup-focused legal boutique that runs more or less end to end on Anthropic's products, and wrote the widely circulated article on the AI-native law firm earlier this year, along with the essays "Two Clocks" and "The Input Layer." Shapiro now spends significant time advising some of the largest law firms in the country on what it means to diffuse AI into a law practice.
  • Basha Rubin (moderator), CEO & Co-Founder at Priori - Rubin co-founded Priori in 2013 and moderated four FlexFest sessions, closing this one on the argument that the industry's future is within its own control.

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Session 9

Closing Remarks

The Big Picture

Basha Rubin and Mirra Levitt close the day by naming the thread that ran through it: the widening gap between what AI models can now do and what adoption actually looks like inside law firms and in-house teams. Rather than treat that gap as a lag to be closed, they hold it open as a real question, because law is fundamentally a human profession of humans advising humans through complex problems. Levitt's reframe is the sharpest note to end on: "adoption" is too thin a lens, and the harder work is designing the human systems, not just the technology, that let teams keep reaching excellence for clients.

Top 3 Breakthroughs

1. The Capability-Adoption Chasm Is the Through-Line: The day's recurring theme was the gap between what the models can do and what teams actually adopt

Key Insight:

Asked what stood out, Basha Rubin points to the chasm that recurred across the day's conversations, between the models' capability and what adoption actually looks like at law firms and in-house teams right now. It was less any single session's topic than the current running underneath all of them.

2. Hold the Gap Open as a Question, Not a Lag to Close: Some of the gulf may be structural because law is humans advising humans

Key Insight:

Rather than assume the gap simply narrows over time, Rubin leaves it genuinely open. Law is fundamentally a human profession, humans advising other humans through complex challenges, so part of the distance between capability and adoption may be structural rather than a temporary lag, and worth designing around rather than waiting out.

Core Question:

As we architect the future of the profession together, will that gulf between what the models can do and how humans actually practice remain, and how much of it is structural?

3. Human Systems, Not Just Technology Systems: "Adoption" is too thin a frame for what comes next

Key Insight:

Mirra Levitt reframes the whole conversation: legal keeps talking about adoption and its challenges, but that is too thin a way to think about the moment. The real question is what human systems need to be built, alongside the technology, for teams to take advantage of it and keep achieving excellence for clients and firms alike.

Prompts for Deeper Reflection
  • Which parts of the gap between what AI can do and what your team actually does are a temporary lag, and which are structural to a human profession?
  • If "adoption" is too thin a frame, what human systems, roles, incentives, review, and training, would your team need to build to genuinely take advantage of the technology?
  • Where in your own practice is the model already capable but the workflow, trust, or accountability is not ready, and what would it take to close that specific gap?
Share-Worthy Moments
“Law is fundamentally a human profession of humans advising other humans about how to solve complex challenges.”
— Basha Rubin
“So much in legal we talk about adoption and the challenges around adoption, and I think that's too thin a way to think about the future of legal right now.”
— Mirra Levitt

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