Definely's new product chief on keeping lawyers in charge in the AI age
Former Meta product executive John Connolly believes legal AI should help lawyers make more confident decisions.
Contents
Since leaving Meta last year, John Connolly has swapped the world of big tech infrastructure for something a little more nascent: legal AI.
“You want to work on a really hard problem,” he says. “There are two at the moment. The bleeding edge of the foundation models - and then the other one is: how do you actually keep humans on top?”
That second question is what drew him to Definely, the fast-growing legal tech company best known for its Microsoft Word add-in for lawyers, where he joined earlier this year.
As chief product officer, Connolly is focused on improving the offering and figuring out what comes next. His bet is that legal AI won’t replace lawyers, but it will make their role harder.
We sat down with Connolly to talk about why he made the jump, and what it says about where legal AI is heading.
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From Meta scale to legal nuance
At Meta, Connolly worked in the company’s trust and safety division, tackling problems that sit where policy, engineering and human judgment meet.
It was his team’s responsibility to stop bad actors infiltrating the tech giant’s advertising system - the engine behind around $200 billion in revenue at the last count.
“You’ve got to set policy and then try to police it,” he says. “When you’re doing anything at the scale of four billion people, edge cases end up being tens of millions.”
The experience influenced how he thinks about decision-making and is something that translates surprisingly well to law.
“Things you think might never happen always happen when you’re at that kind of scale,” he says. “The key was not to try to never catch good people in the net, but to have a good way to fix it when you do.”
The problem: helping lawyers say no
At Definely, Connolly sees the central challenge as helping lawyers make confident decisions in a space where counterparties and AI tools are generating more legal content than ever.
“The lawyer needs to make the call: this is not acceptable,” he says. “To do that, they have to fully understand it.”
The lawyer needs to make the call: this is not acceptable - to do that, they have to fully understand it.
Rather than replacing that judgment, Definely is designed to support it.
“Give me all the scaffolding to confidently accept or reject something in that moment - don’t make the decision for me,” Connolly says. “That’s just not the role.”
It’s a different approach from many in the market, where AI tools promise end-to-end automation.
“There’s a lot of law that will get automated - and rightly so,” he says. “But that’s not what interests me. Multi-hundred-million-pound transactions with 100-page documents - that’s super hard. That’s the bit I find attractive.”
Why more AI may mean more legal work
Connolly pushes back on the idea that AI will reduce demand for lawyers. If anything, he thinks it will increase it.
“There’s going to be more and more intelligence,” he says. “But human accountability is going to persist.”
He points to early signs of this in everyday life. “Schools say now that they get 40-page letters in incredible legalese from parents,” he says. “This is what ChatGPT has done to the world.”
As more people generate quasi-legal content, someone still needs to review and validate it.
“I don’t see the need for a lawyer to actually say yes or no going away,” he says. “There’ll just be more for lawyers to get on top of.”
The need for a lawyer to actually say yes or no is not going away - there’ll just be more for lawyers to get on top of.
Definely’s role, he says, is to stop that becoming unmanageable.
Law Firm | Trainee First Year | Trainee Second Year | Newly Qualified (NQ) |
|---|---|---|---|
| Addleshaw Goddard | £52,000 | £56,000 | £100,000 |
| Akin | £60,000 | £65,000 | £174,418 |
| A&O Shearman | £56,000 | £61,000 | £150,000 |
| Ashurst | £57,000 | £62,000 | £140,000 |
| Baker McKenzie | £56,000 | £61,000 | £145,000 |
| Bird & Bird | £48,500 | £53,500 | £102,000 |
| Bristows | £48,000 | £52,000 | £95,000 |
| Bryan Cave Leighton Paisner | £55,000 | £58,000 | £125,000 |
| Burges Salmon | £49,500 | £51,500 | £76,000 |
| Charles Russell Speechlys | £52,000 | £55,000 | £93,000 |
| Cleary Gottlieb | £62,500 | £67,500 | £164,500 |
| Clifford Chance | £56,000 | £61,000 | £150,000 |
| Clyde & Co | £48,500 | £51,000 | £85,000 |
| CMS | £50,000 | £55,000 | £120,000 |
| Cooley | £55,000 | £60,000 | £157,000 |
| Davis Polk | £65,000 | £70,000 | £180,000 |
| Debevoise | £55,000 | £60,000 | £173,000 |
| Dechert | £55,000 | £61,000 | £165,000 |
| Dentons | £52,000 | £56,000 | £104,000 |
| DLA Piper | £52,000 | £57,000 | £130,000 |
| Eversheds Sutherland | £50,000 | £55,000 | £110,000 |
| Farrer & Co | £48,500 | £51,000 | £89,000 |
| Fieldfisher | £48,500 | £52,000 | £100,000 |
| Freshfields | £56,000 | £61,000 | £150,000 |
| Fried Frank | £55,000 | £60,000 | £175,000 |
| Gibson Dunn | £60,000 | £65,000 | £180,000 |
| Goodwin Procter | £55,000 | £60,000 | £175,000 |
| Gowling WLG | £48,500 | £53,500 | £105,000 |
| Herbert Smith Freehills Kramer | £56,000 | £61,000 | £145,000 |
| HFW | £52,000 | £56,000 | £103,500 |
| Hill Dickinson | £44,000 | £45,000 | £80,000 |
| Hogan Lovells | £56,000 | £61,000 | £140,000 |
| Irwin Mitchell | £43,500 | £45,500 | £78,000 |
| Jones Day | £60,000 | £68,000 | £165,000 |
| K&L Gates | £50,000 | £55,000 | £115,000 |
| Kennedys | £43,000 | £46,000 | £85,000 |
| King & Spalding | £62,000 | £67,000 | £175,000 |
| Kirkland & Ellis | £60,000 | £65,000 | £174,418 |
| Latham & Watkins | £60,000 | £65,000 | £174,418 |
| Linklaters | £56,000 | £61,000 | £150,000 |
| Macfarlanes | £56,000 | £61,000 | £140,000 |
| Mayer Brown | £55,000 | £60,000 | £150,000 |
| McDermott Will & Schulte | £65,000 | £70,000 | £174,418 |
| Milbank | £65,000 | £70,000 | £174,418 |
| Mills & Reeve | £46,800 | £47,000 | £84,000 |
| Mishcon de Reya | £50,000 | £55,000 | £100,000 |
| Norton Rose Fulbright | £56,000 | £61,000 | £140,000 |
| Orrick | £60,000 | £65,000 | £160,000 |
| Osborne Clarke | £55,500 | £57,500 | £97,000 |
| Paul Hastings | £60,000 | £68,000 | £173,000 |
| Paul Weiss | £60,000 | £65,000 | £180,000 |
| Penningtons Manches Cooper | £48,000 | £50,000 | £83,000 |
| Pinsent Masons | £52,000 | £57,000 | £105,000 |
| Quinn Emanuel | n/a | n/a | £180,000 |
| Reed Smith | £53,000 | £58,000 | £125,000 |
| Ropes & Gray | £62,000 | £67,000 | £170,000 |
| RPC | £48,000 | £52,000 | £95,000 |
| Shoosmiths | £45,000 | £47,000 | £105,000 |
| Sidley Austin | £60,000 | £65,000 | £175,000 |
| Simmons & Simmons | £54,000 | £59,000 | £120,000 |
| Simpson Thacher | n/a | n/a | £178,000 |
| Skadden | £58,000 | £63,000 | £177,000 |
| Slaughter and May | £56,000 | £61,000 | £150,000 |
| Squire Patton Boggs | £50,000 | £55,000 | £110,000 |
| Stephenson Harwood | £50,000 | £55,000 | £105,000 |
| Sullivan & Cromwell | £65,000 | £70,000 | £174,418 |
| Taylor Wessing | £52,000 | £57,000 | £115,000 |
| TLT | £44,000 | £47,500 | £85,000 |
| Travers Smith | £55,000 | £60,000 | £130,000 |
| Trowers & Hamlins | £47,000 | £51,000 | £85,000 |
| Vinson & Elkins | £60,000 | £65,000 | £173,077 |
| Watson Farley & Williams | £51,500 | £56,000 | £107,000 |
| Weightmans | £36,000 | £38,000 | £70,000 |
| Weil | £60,000 | £65,000 | £170,000 |
| White & Case | £62,000 | £67,000 | £175,000 |
| Willkie Farr & Gallagher | £60,000 | £65,000 | £180,000 |
| Withers | £47,000 | £52,000 | £95,000 |
| Womble Bond Dickinson | £43,000 | £45,000 | £83,000 |
Rank | Law Firm | Revenue | Profit per Equity Partner (PEP) |
|---|---|---|---|
| 1 | DLA Piper* | £3,130,000,000 | £2,500,000 |
| 2 | A&O Shearman | £2,900,000,000 | £2,000,000 |
| 3 | Clifford Chance | £2,400,000,000 | £2,100,000 |
| 4 | Hogan Lovells | £2,320,000,000 | £2,400,000 |
| 5 | Linklaters | £2,320,000,000 | £2,200,000 |
| 6 | Freshfields | £2,250,000,000 | Not disclosed |
| 7 | CMS** | £1,800,000,000 | Not disclosed |
| 8 | Norton Rose Fulbright* | £1,800,000,000 | Not disclosed |
| 9 | HSF Kramer | £1,360,000,000 | £1,400,000 |
| 10 | Ashurst | £1,030,000,000 | £1,390,000 |
| 11 | Clyde & Co | £854,000,000 | Not disclosed |
| 12 | Eversheds Sutherland | £769,000,000 | £1,400,000 |
| 13 | Pinsent Masons | £680,000,000 | £790,000 |
| 14 | Slaughter and May*** | £650,000,000 | Not disclosed |
| 15 | BCLP* | £640,000,000 | £790,000 |
| 16 | Simmons & Simmons | £615,000,000 | £1,120,000 |
| 17 | Bird & Bird** | £580,000,000 | £720,000 |
| 18 | Addleshaw Goddard | £550,000,000 | £1,000,000 |
| 19 | Taylor Wessing | £526,000,000 | £1,100,000 |
| 20 | Osborne Clarke** | £476,000,000 | £800,000 |
| 21 | DWF | £466,000,000 | Not disclosed |
| 22 | Womble Bond Dickinson | £450,000,000 | Not disclosed |
| 23 | Kennedys | £428,000,000 | Not disclosed |
| 24 | Fieldfisher | £385,000,000 | £1,000,000 |
| 25 | Macfarlanes | £371,000,000 | £3,100,000 |
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Competing in a crowded market
Connolly joins Definely at a time when competition in legal AI continues to heat up. Well-funded players like Harvey and Legora are expanding rapidly, bundling multiple capabilities into broader platforms - including their own Word integrations.
Definely is not trying to follow them.
“We believe in a best-of-breed stack,” Connolly says. “We’re not going to try to be everything for everyone.”
Instead, Definely is going narrow: helping lawyers understand, assess and decide on documents, in real time.
“We are experts at helping you understand, assess, and then decide whether you want to say yes or no,” he says.
Why Word is a feature, not a limitation
One of Definely’s defining characteristics is its deep integration with Microsoft Word - the software lawyers continue to rely on and that underpins most legal documents.
Connolly sees that choice as a key strength for the company. Rather than pulling lawyers into new interfaces, Definely meets them where they already work.
“Be quick, be bright, be gone,” he says. “The lack of space forces that.”
This contrasts with some competitors building standalone platforms or dashboards. For Connolly, the key is keeping the lawyer’s work product, and accountability, front and centre.
Big tech and the future of legal AI
Connolly is realistic about the role of big tech in legal AI. Having worked inside one, he understands both their strengths and limits.
“You’d be a fool to ignore other people,” he says. But he doesn’t believe they will dominate every layer of the stack.
Instead, he expects an ecosystem to emerge, with general-purpose AI platforms coexisting alongside specialised tools.
“There will be a battle between the general enterprise AI platform and the legal-specific platforms,” he says. “But we’ll play nicely with others.”
There will be a battle between the general enterprise AI platform and the legal-specific platforms - but we’ll play nicely with others.
Definely’s approach is to complement rather than compete head-on.
Building a product lawyers love
One surprise since joining has been how Definely is received by users.
“It’s a product that is loved, but underpromoted,” he says.
He recalls testing sentiment among lawyers by seeding a sceptical question in a WhatsApp group. The response was unexpectedly strong.
“Once you’ve seen it, it’s painful to live without,” Connolly says. “It’s like once you’ve flown business class.”
The next phase
Looking ahead, Connolly’s aim is for Definely to become part of how lawyers make decisions - inside Word and beyond.
“We’ll be right next to them as they’re deciding yes, no, do I accept this,” he says.
At the same time, the company will integrate more with other tools and workflows. Part of that strategy is Definely’s recently launched Model Context Protocol (MCP) - effectively an API that connects AI models to Definely’s contract review tools.
Connolly says the aim is for Definely’s MCP to become “the essential anchor for accuracy”. The broader pitch is that lawyers will increasingly need systems that can verify where information comes from as AI-driven drafting becomes the norm.
In a market chasing ever-bigger ambitions, Definely’s strategy is one of focus and, for Connolly, that’s the point.
“I could take ten times the people I have and still niche down on this area,” he says.
The bet is that in a future where AI is very accomplished at coming up with answers, the hardest problem will be deciding which ones to trust.
| Firm | London office since | Known for in London |
|---|---|---|
| Akin | 1997 | Restructuring, funds |
| Baker McKenzie | 1961 | Finance, capital markets, TMT |
| Davis Polk | 1972 | Leveraged finance, corporate/M&A |
| Gibson Dunn | 1979 | Private equity, arbitration, energy, resources and infrastructure |
| Goodwin | 2008 | Private equity, funds, life sciences |
| Kirkland & Ellis | 1994 | Private equity, funds, restructuring |
| Latham & Watkins | 1990 | Finance, private equity, capital markets |
| McDermott Will & Schulte | 1998 | Finance, funds, healthcare |
| Milbank | 1979 | Finance, capital markets, energy, resources and infrastructure |
| Paul Hastings | 1997 | Leveraged finance, structured finance, infrastructure |
| Paul Weiss | 2001 | Private equity, leveraged finance |
| Quinn Emanuel | 2008 | Litigation |
| Sidley Austin | 1974 | Leveraged finance, capital markets, corporate/M&A |
| Simpson Thacher | 1978 | Leveraged finance, private equity, funds |
| Skadden | 1988 | Finance, corporate/M&A, arbitration |
| Sullivan & Cromwell | 1972 | Corporate/M&A, restructuring, capital markets |
| Weil | 1996 | Restructuring, private equity, leverage finance |
| White & Case | 1971 | Capital markets, arbitration, energy, resources and infrastructure |
| Law firm | Type | First-year salary |
|---|---|---|
| White & Case | US firm | £32,000 |
| Stephenson Harwood | International | £30,000 |
| A&O Shearman | Magic Circle | £28,000 |
| Charles Russell Speechlys | International | £28,000 |
| Freshfields | Magic Circle | £28,000 |
| Herbert Smith Freehills | Silver Circle | £28,000 |
| Hogan Lovells | International | £28,000 |
| Linklaters | Magic Circle | £28,000 |
| Mishcon de Reya | International | £28,000 |
| Norton Rose Fulbright | International | £28,000 |
Law Firm | Trainee First Year | Trainee Second Year | Newly Qualified (NQ) |
|---|---|---|---|
| A&O Shearman | £56,000 | £61,000 | £150,000 |
| Clifford Chance | £56,000 | £61,000 | £150,000 |
| Freshfields Bruckhaus Deringer | £56,000 | £61,000 | £150,000 |
| Linklaters | £56,000 | £61,000 | £150,000 |
| Slaughter and May | £56,000 | £61,000 | £150,000 |
Law Firm | Trainee First Year | Trainee Second Year | Newly Qualified (NQ) |
|---|---|---|---|
| A&O Shearman | £56,000 | £61,000 | £150,000 |
| Clifford Chance | £56,000 | £61,000 | £150,000 |
| Freshfields Bruckhaus Deringer | £56,000 | £61,000 | £150,000 |
| Linklaters | £56,000 | £61,000 | £150,000 |
| Slaughter and May | £56,000 | £61,000 | £150,000 |
Law Firm | Trainee First Year | Trainee Second Year | Newly Qualified (NQ) |
|---|---|---|---|
| Ashurst | £57,000 | £62,000 | £140,000 |
| Bryan Cave Leighton Paisner | £55,000 | £58,000 | £125,000 |
| Herbert Smith Freehills | £56,000 | £61,000 | £145,000 |
| Macfarlanes | £56,000 | £61,000 | £140,000 |
| Travers Smith | £55,000 | £60,000 | £130,000 |
| Firm | Merger year | Known for in London |
|---|---|---|
| BCLP | 2018 | Real estate, corporate/M&A, litigation |
| DLA Piper | 2005 | Corporate/M&A, real estate, energy, resources and infrastructure |
| Eversheds Sutherland | 2017 | Corporate/M&A, finance |
| Hogan Lovells | 2011 | Litigation, regulation, finance |
| Mayer Brown | 2002 | Finance, capital markets, real estate |
| Norton Rose Fulbright | 2013 | Energy, resources and infrastructure, insurance, finance |
| Reed Smith | 2007 | Shipping, finance, TMT |
| Squire Patton Boggs | 2011 | Corporate/M&A, pensions, TMT |
Law Firm | Trainee First Year | Trainee Second Year | Newly Qualified (NQ) |
|---|---|---|---|
| Ashurst | £57,000 | £62,000 | £140,000 |
| Bryan Cave Leighton Paisner | £55,000 | £58,000 | £125,000 |
| Herbert Smith Freehills Kramer | £56,000 | £61,000 | £145,000 |
| Macfarlanes | £56,000 | £61,000 | £140,000 |
| Travers Smith | £55,000 | £60,000 | £130,000 |
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