Holly Hogan is an IP litigator who has become one of the most business-forward legal leaders in tech. She spent nearly a decade at Automattic, the platform behind WordPress (which powers 40% of the web), and led the team through global litigation, privacy, AI strategy, and a lot of scaling in between.
Most recently, Holly was GC in residence at Mayer Brown, the first law firm to model the concept after the VC world. And in Q4 2025, she stepped in as General Counsel at Deepgram, a frontier voice AI company.
Holly and GC AI founder Cecilia Ziniti have known each other for a decade through the L-Suite community, and in this conversation, they discuss moving through uncertainty with a clear head, navigating novel legal challenges, and introducing legal AI to your department strategically.
“Every legal team thinks they're special, but my team really is super business forward,” Holly said. “We get lots of comments that we were the best legal team folks ever worked with, and that they felt like we were thought partners and not just lawyers.”
A Day in the Life of a GC in Residence
As Mayer Brown’s GC in residence, Holly ran sessions with practice groups on how to position themselves for what clients genuinely need, proctored one-on-one sessions with partners and associates, and managed AI initiatives across the firm.
She also helped launch Mayer Brown’s Technology General Counsel in Residence program in 2023. Holly describes the program as “immersive knowledge sharing.” For her, teaching is a rare opportunity to step back from the velocity of in-house work and think carefully about how law firms and in-house teams serve each other, rather than just getting the work done.
The course’s biggest value for prospective GCs is learning what it feels like to bounce between employment law, a product launch, a media inquiry, an HR issue, and a regulatory matter all before lunch.
"What they wanted was to talk a lot about the unique challenges that we face as tech companies,” said Holly. “They're trying to be and are very AI forward, and very innovative in how they approach legal services. How can they become not just a subject matter expert, but actually a trusted advisor?"
Note from CZ: I had a version of this experience as a young associate at Morrison and Foerster when the firm brought in GCs for a day. It was one of the most inspiring things I saw early in my career. What Holly did is the inverse: she gave the firm associates a window into the in-house experience that most partners never get up close.
Holly’s Proudest Moment from a Decade-Long Legal Battle
Holly joined Automattic as the second lawyer in the building when the company had a few hundred people. By the time she left, it had grown to nearly 2,000. WordPress currently powers around 40 percent of the internet, which means the legal challenges that came with that scale were genuinely novel. Holly’s day-to-day involved payments law, messaging law, global privacy, AI strategy, and acquisitions, often all at the same time.
Her decade-long tenure held a lot of great moments, but her proudest was during a case that started before she even arrived: a nine-year fight to protect a user in Turkey who had published content critical of the government. The Turkish government had ordered the content be removed, but Automattic refused.
“It was nine years of really just standing there, continuing to press, continuing to ask,” she said. “We eventually got a victory, a really big victory, but being able to have success against all odds, I think that's something that's really unique from a legal perspective.”
The grit to fight for the right thing for nine years, no matter how difficult, is a testament to the kind of company Automattic is, and the kind of leader Holly is. Holly came from IP litigation knowing almost nothing about payments law. When Automattic moved into that space, she hired someone who had a fintech background, and she built a team philosophy around that same idea. Hire for expertise, but hire for curiosity too. A fast-growing company will always need both.
“Of course we want to hire lawyers who know a lot about the vertical, but I also look for curiosity and agility and the desire to learn and grow into different things,” said Holly. “I think that's the key, especially at a fast paced company, is you're gonna need to hire people that are willing to grow and jump into things that they don't know.”
Great GCs Turn Lawyers into Business Partners
Holly's philosophy for building excellent in-house legal teams comes down to two principles:
Pair lawyers with the business units they serve and make them feel as much a part of those teams as they do the legal department.
Be deliberate about the language the team uses to describe its own work, because words build culture faster than almost anything else.
“For example, don't say 'the business,' we are the business,” said Holly. “We didn't clear legal disclosures for this product launch, we helped launch the product. We didn't do legal review for XYZ contracts, we helped close XYZ deals."
Using deliberate language to describe her team’s achievements helped the company reframe what the legal team was there to do. Holly reinforced Legal’s critical contributions at every opportunity until the mindset shift stuck.
The second key to success is autonomy. Holly gave her team real room to explore within their assigned departments, with guardrails when needed but without the kind of second-guessing that teaches lawyers to play it safe rather than add value.
"Give people a lot of autonomy and experience to be able to do things with the right amount of guidance,” Holly said. “You got a safety net there if needed, but really letting people move in that space is crucial."
Note from CZ: I had a stakeholder once describe Legal as “doing the paperwork on a multi-million dollar deal.” I pulled them aside immediately to reiterate: we're helping you close this deal. Holly built that mindset into Automattic’s culture intentionally.
Moving Forward When You Don’t Know All the Rules
Two years ago, Holly was watching other GCs telling their teams not to use AI out of uncertainty. They were waiting for rules that didn't exist yet. She decided to do the opposite.
"The worst risk here is standing still,” Holly said. “I think it’s important to be open about saying ‘we don't know what the rules are,’ and then making the best judgments we have based on what we know. We have to shift, and that's fine."
At Automattic, Holly responded to the flood of AI questions by building clear guidance documents for each functional team that gave people permission to move forward without needing to escalate every decision to legal.
Engineering got a two-page coding guide developed in partnership with the engineering leads. Marketing got practical permissions framed around what was genuinely different from existing IP rules. Consumer-facing teams got a disclosure framework built on consumer protection law: what does the user need to know to make a good decision here?
Next, she ran a proactive internal campaign to ensure everyone at the company was on the same page. This helped the entire organization move forward on AI while the rest of the industry was still in shock.
Her view on AI for lawyers specifically is equally direct. The Socratic method, the interrogatory mindset, the litigator's instinct to ask layered questions and iterate on the answers, all of it maps directly to good AI prompting.
"Clear writing reflects clear thinking,” Holly said. “I would venture to say that clear prompting reflects clear thinking too. Lawyers should be some of the best adopters of AI because of that skill."
Holly is currently in the most AI-forward role of her career yet as GC at Deepgram. She’s building the legal infrastructure for a company racing toward the moment when voice AI passes the five-minute Turing test. The rules are still being written, and that’s Holly’s favorite part.
Her advice for in house-lawyers is this: don't run a generic legal team, and don’t try to be anyone but yourself.
"Be an original,” said Holly. “Think about what makes you you, and lead into the best parts of yourself. And from a company level, what's unique and different about your company. Reflect those values in what you do for your legal team."
For in-house lawyers who are ready to do their best thinking and most audacious building, GC AI gives you the leverage to move faster, think bigger, and show up as the business partner your company needs. Try it for free!
