For five years, Mandell was a partner and global head of Withers' practice group focused on advising company founders. But in February, he took a gamble — along with a 50% pay cut — and joined Inflection AI, which was established in 2022 and offers a large language model, or LLM, called Pi.
As general counsel, Mandell has seen firsthand how AI is evolving and has impacted work generally — and how lawyers are utilizing the technology to be more efficient, he said.
"My change was strongly driven by my desire to go back into AI at this time," said Mandell, whose resume includes working in-house at another AI company, Nauto, which is in the autonomous vehicle space. "I do think this is a really unique time to be part of what's happening in AI, and I don't think that that's going to last forever."
But his recent career decision didn't come without trepidation. Mandell said it was "a really big deal" to leave his lucrative practice at an international law firm. During his five years at Withers, he maintained a practice representing more than 700 clients.
Mandell is among the seasoned lawyers leading the legal departments at AI companies who are embracing the challenge of helping build AI tools and of being involved in emerging law related to the technology.
That emerging law includes the European Union's introduction in August 2024 of the world's first comprehensive regulation of AI tools, which placed restrictions on the development and use of the technology across all member states. And in just a few months, Colorado will join several other jurisdictions around the U.S., including Tennessee and New York City, to regulate AI tools.
"I have the most fun when I'm learning, so staying on the cutting-edge of the effort to figure out how the law adapts to technology, which is always out ahead of the law, is always challenging and interesting for me," said Andy Hepburn, general counsel at SafeGuard Privacy, a compliance privacy platform used by in-house counsel and other corporate teams.
But there are challenges, too. General counsel at AI companies need to understand what is required from an in-house perspective as they work with both their internal clients and outside counsel, Mandell said.
He underscored that to be a general counsel at an AI company, a lawyer must truly want to understand and be interested in the technology. And top corporate lawyers often are working with limited resources in a nonstop, fast-paced startup environment — with work at varying hours — while they wear multiple hats and have a number of responsibilities.
"You need to be ready for the unexpected," said John Lee, general counsel at legal operations startup Ruli Inc. "You need to be ready to roll up your sleeves to do anything ... to get our product refined and released, take in the feedback of our customers, and any other tasks that may be required to help the company succeed."
Hepburn acknowledged that it can be scary to join an AI startup because of the uncertainties. Where will the company be in a year? Five years? Will it be successful?
"But because I'm a big fan and a big believer in lifelong learning, I find that that's the environment where I have the most opportunity to learn and grow, both personally and professionally," he said. "Those benefits have always outweighed the fear and risk."
Hepburn previously worked in-house at well-known organizations including Georgia-Pacific, Sony Mobile and Meta Group Inc., which merged with technology research and consulting firm Gartner Inc. Most recently, he was general counsel at advertising technology company Sizmek, which was acquired in part by Amazon in 2019 before it shuttered in 2024.
"The fun thing for me, and it's why I joined SafeGuard, is helping a small company — whose mission I believe in deeply — grow and build their offerings and their presence in the marketplace," he said. "I'm at the point where doing interesting, fun things with good people is my primary motivator."
Mandell, too, said he was enthused at the idea of joining several of his friends and former colleagues who worked at Inflection.
"They knew me and trusted me," he said about Inflection's leadership team. "I was able to come in, be part of the executive leadership team and have a certain amount of credibility, which was really valuable."
This isn't the first such foray for Mandell. Earlier in his career, he left his role as a senior associate at Orrick Herrington & Sutcliffe LLP to join one of the first online photo-sharing platforms, eMemories, as general counsel in 2000. He also was the first lawyer — and later the first acting general counsel — at LinkedIn during its early years.
Now at Inflection, Mandell works with outside counsel to determine how to integrate in-house AI tools so that his legal team and their outside counsel can collaborate more efficiently.
And as a member of the company's executive leadership team, Mandell is focused on working with other senior executives and engineers to further enhance the company's AI models and build AI products.
For Mandell and other general counsel at AI companies, they see the businesses as places to apply their experiences as seasoned lawyers. Over the summer, California attorney Jeff Bleich, who served as special counsel to former President Barack Obama, started as chief legal officer at the multibillion-dollar AI startup Anthropic.
In his post on LinkedIn about taking the job, Bleich said, "I'm inspired by both the mission and our team at Anthropic for their commitment to building safe AI systems and deploying them responsibly to help people solve humanity's greatest challenges."
Similarly, Lee had been elsewhere in the legal industry before he entered the AI space. He was an in-house attorney at Alphabet Inc.'s venture fund CapitalG and in private practice at several firms, including White & Case LLP, WilmerHale and Morgan Lewis & Bockius LLP.
After about three years at CapitalG, he began searching for an opportunity as a senior lawyer "to have a greater impact," he said. That led him to legal AI startups, first at software developer Ivo AI Inc. last year, and then at Ruli in March.
Lee said he was drawn in part to the startup aspect of Ruli, which last year went public with a $2.2 million pre-seed funding round led by venture capital firm SignalFire.
Lee's perspective and experience also played roles in his career decision, he said, and he appreciates the chance to be involved in the changes happening to how lawyers work.
For example, he currently helps Ruli's engineers develop new products that apply AI to assist in-house legal teams across a broad spectrum of legal, contractual and knowledge management tasks.
"Being more experienced, a lot of folks I know are also on the more senior level," Lee said. "I'm getting more of that knowledgeable feedback, as opposed to somebody who might be younger in their career and might not be able to give that type of thought-through feedback."
And he can't ignore the significance of AI for lawyers.
"The impact of AI on legal is going to be huge," Lee said. "Legal is one of the primary use cases."
--Additional reporting by Matt Perez, Alex Baldwin and Sue Reisinger. Editing by Marygrace Anderson.
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