Legal Leaders

We're officially 3L's!After finishing our 2L year at Berkeley Law, I sat down with classmates Riya Dhanjal, James Courser, and Rameses Neale to reflect on law school, Big Law recruiting, AI, burnout, networking, and student life.We discuss Berkeley Law’s culture and grading system, the realities of accelerated Big Law recruiting, the growing role of AI in legal practice, and what we wish we knew before starting law school.Topics include:• Big Law recruiting and networking advice• AI in legal education and practice• Berkeley Law culture and student life• Practice area selection and firm differences• Journals, externships, and extracurriculars• Burnout, balance, and imposter syndrome

Dina Segal is the Chief Legal Officer at Gusto, where she leads legal, compliance, and government affairs for a platform serving over 400,000 small businesses across the United States. In this episode, Dina shares her journey from growing up in Ukraine—where she was inspired by her grandfather’s work as a lawyer advocating for his community—to building a diverse legal career across BigLaw, fintech, and high-growth technology companies.We dive into her path through tax, litigation, and FCPA work during the 2008 financial crisis, her transition into corporate law, and her move in-house—where she ultimately rose into executive leadership roles at companies like Intuit before becoming CLO at Gusto.This conversation covers:- How to successfully transition from BigLaw to in-house- What it takes to grow into a Chief Legal Officer role- Why understanding the business is critical for in-house lawyers- How to approach career pivots with a “learning mindset” -Building and scaling legal, compliance, and government affairs teams- How AI is transforming legal workflows, decision-making, and team capacityDina also shares practical advice on promotions, leadership, and why the best lawyers today are not just advisors—but builders embedded within the business.If you’re a law student, practicing attorney, or operator working closely with legal teams, this episode offers a clear look at how modern legal careers are evolving—and what it takes to stay ahead.“Every change is a combination of intentionality and a leap of faith.”A great reminder that careers aren’t planned—they’re built.

Lisa Gorman is one of the most accomplished legal executives in tech. She spent nearly nine years at Eventbrite, rising from employment counsel to General Counsel and Chief Legal Officer. During her tenure, she helped lead Eventbrite's legal strategy through its IPO, global expansion, the pandemic's devastation of the live events industry, and ultimately a $500 million acquisition by Bending Spoons.In this episode, we discuss her unconventional path from English literature major to tech CLO, how she transitioned from law firm partner to in-house counsel by organically becoming part of her client's team, and what it takes to expand beyond your core expertise. Lisa shares how she went from employment law to leading litigation, content moderation, product, privacy, regulatory, and the entire legal function. We explore the value of building trust and tenure at a single company, the role of legal AI tools like GCAI in modern practice, and her experience leading Eventbrite's content moderation program and DSA compliance. Lisa also addresses what the future holds for junior lawyers in an AI-driven world and reflects on her biggest career highlight of leading the $500M sale to Bending Spoons.Lisa offers candid advice for law students and early-career lawyers about finding work that doesn't feel like a grind, the value of staying when you find the right fit, and keeping an open mind about where your legal career might take you.#Eventbrite #ContentModeration #TrustAndSafety #DSACompliance #LegalTechnology #GCAI #LegalOperations #MergersAndAcquisitions #BerkeleyLaw #LawSchool

In this episode, I sit down with Dennis Adsit, an executive coach with over a decade of experience helping leaders navigate transitions and build high-performing teams. Dennis holds a PhD in industrial psychology and has coached everyone from startup founders at Techstars to C-suite executives, with prior experience leading Six Sigma implementation and global call centers at Intuit.Dennis reveals why most lawyers' resumes fail: they focus on credentials and responsibilities instead of business impact. He introduces his WAS-DID-IS framework, which structures your story around the situation you faced, the actions you took, and the measurable results you delivered. We explore his four-pillar model of executive effectiveness: setting strategic context, executing efficiently, building talent, and managing yourself. Dennis explains how AI is changing leadership priorities, making the "generosity gene"—your ability to celebrate your team and create connection—more critical than ever for retaining talent and maintaining productivity.For lawyers transitioning from firms to in-house roles or moving into general counsel positions, Dennis breaks down the specific mindset shift required: from individual contributor solving legal problems to leader building platforms for others to succeed. He also offers tactical advice for early-career professionals on saying yes to diverse opportunities and becoming known as reliable problem-solvers.About Adsum Insights:  www.adsuminsights.comhttps://medium.com/@dennis_adsit/lawyers-and-the-mystery-of-the-missing-case-efffd3106814

I spoke with Dan Haley, Chief Legal Officer of Flock Safety, to walk through a career that spans nearly a decade in Big Law and senior legal leadership roles at some of the fastest-growing technology companies in the country. Dan shares what it’s really like to make the transition from law firms to in-house, including the tradeoffs, surprises, and lessons he learned along the way.We talk about navigating high-stakes moments such as major acquisitions, IPOs, and scaling legal teams through periods of rapid growth and uncertainty. Dan also discusses his current role at Flock Safety, the legal and constitutional questions surrounding public safety technology, and how he thinks about privacy, the Fourth Amendment, and responsible innovation from the CLO seat.Throughout the conversation, Dan reflects on career decision-making, leadership, and why focusing on doing excellent work, staying open to unexpected opportunities, and building genuine professional relationships can matter more than rigid long-term planning. This episode is relevant for law students, associates, and in-house lawyers interested in high-growth tech, legal leadership, and building a meaningful career over time.