Building Legal as the Company's Air Traffic Control with Ekumene Lysonge, NerdWallet CLO

Building Legal as the Company's Air Traffic Control with Ekumene Lysonge, NerdWallet CLO

Ekumene Lysonge is the Chief Legal Officer and Corporate Secretary at NerdWallet, where he leads a combined Trust and Safety organization of 34 people spanning legal, security, compliance, and privacy across a public fintech platform that serves 25 million+ customers a month.  With operational experience across corporate America before legal leadership, he credits that time as a business operator with shaping his approach: business-centric first, risk-centric second. His team is three-quarters of the way through automating their routine legal workflows with agentic AI solutions. Ekumene says legal should function like air traffic control: making sure ideas take off, land safely, and never crash. That's why he merged legal, security, compliance, and privacy into one Trust and Safety org at NerdWallet.  He and Cecilia talk about what it looks like to say yes first and make it durable, how his team evaluates AI chatbots in the sandbox before they ship, and why he's comfortable operating at 70-75% accuracy in an AI-powered legal function. Ekumene also shares the reflecting-pool conversation with a mentor that reoriented his entire approach to problem-solving: stop over-engineering; start with common sense. Follow Ekumene: @Ekumene Lysonge [https://www.linkedin.com/in/ekumenelysonge/] on LinkedIn Show notes: - Trust and Safety as a unified org: Ekumene broke down the silos between legal, security, compliance, and privacy at NerdWallet, rebranding them under one umbrella where legal protects customer trust and security protects customer safety. - Business-centric risk tolerance: Ekumene approaches every conversation as business-centric first, not risk-centric. His philosophy: you need to always be in a position to say yes, but the yes has to be durable enough to stand up to scrutiny. - Eyes wide open decision-making: How Ekumene frames one-way-door decisions for the executive team and the board, making sure everyone locks arms before crossing a threshold that has no return ticket. - AI governance at a public fintech: How NerdWallet balances a culture of rapid experimentation and vibe coding with scaled governance, and why Ekumene believes legal needs to advise at the same velocity the business creates. - Deploying agentic AI in legal: How Ekumene's team cataloged every routine workflow, prioritized low-risk use cases like vendor agreements and NDAs, and is now building an AI-powered "ask me anything" Slack agent to eliminate 30+ daily triage questions per person. - The case for legal operations: Ekumene's top tip for GCs diving into AI: if you don't have a legal operations function, get one. He calls it a non-negotiable for any in-house team that wants to scale. (00:00) Introduction (01:04) Why Ekumene built the Trust and Safety org (04:54) NerdWallet's business model and how trust shows up (08:10) Setting risk priorities at a public fintech company (11:24) Pragmatic risk-taking: saying yes, but making it durable (14:45) One-way doors and "eyes wide open" decisions (16:08) AI governance and scaling creativity with discipline (21:07) Product counsel in the room: the Air Canada chatbot breakdown (27:02) Customer-first lawyering (even when it makes you cringe) (30:08) Legal as an operating system, not a bottleneck (35:08) Picking AI use cases and top tips for GCs implementing AI (39:29) The Slack triage win: building an AI-powered ask-me-anything agent (41:51) Lightning round: the mentor who taught common sense problem-solving (45:15) Takeaway: decision discipline and the future of in-house legal Follow us on all social platforms to get each new episode when it drops. ⁠@Cecilia Ziniti⁠ [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn ⁠@CeciliaZin⁠ [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X ⁠@GC AI⁠ [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X ⁠gc.ai [https://www.getgc.ai/]⁠ website

"Yes If" Thinking: Sharon Johnson of MODE Global on AI, Logistics and Legal Leadership

Sharon Johnson took a winding path to the GC seat. Before law school, she worked in marketing, sales, project management, and contract management at Verizon, and she credits that experience with shaping how she leads legal today. As Chief Legal Officer, Corporate Secretary, and Chief Compliance Officer at MODE Global, she runs a team of six lawyers across a $3 billion logistics business, with 100% AI adoption and KPIs to prove it. Her team was a finalist for Best Use of AI at the 2026 Legalweek Leaders in Tech Awards, alongside Meta, Uber, and DHL. In this episode, Sharon walks through her "Yes If" framework for keeping the business moving forward instead of defaulting to no, how she cold-called the GC of Verizon (who happened to be Bill Barr) while still in law school, and the full-circle story of returning as general counsel to the company that once turned her down for a contract manager role. She and Cecilia also get into what AI adoption looks like on a lean legal team, why judgment matters more than speed, and the career advice she wishes she'd heard earlier: having a lot of ideas can be as dangerous as having none. Follow Sharon: @Sharon Johnson [https://www.linkedin.com/in/sharon-m-johnson1/] on LinkedIn Show notes: AI adoption that works: Sharon tracks KPIs, saves the equivalent of two headcounts per week using AI, and has achieved 100% adoption across her legal team. Working in the business before law school: Sharon's time in contract management, sales, and project management at Verizon gave her a commercial fluency that law school alone cannot teach. Her advice for aspiring GCs: go work in the business first. Cold calling as a career strategy: Sharon cold-called the General Counsel of Verizon while in law school, got career-defining advice, and later became GC of the company that once turned her down for a contract management role. Judgment in the age of AI: Why Sharon believes judgment becomes more valuable as AI handles more of the work, and what she looks for when hiring now. Tariffs, logistics, and regulatory monitoring: How Sharon uses AI to track federal register notices, executive orders, and trade policy signals so her team can advise the business before issues require action. Building a lean legal team: What it takes to run a $3 billion business with six lawyers, and why Sharon says there is no place to hide when you are lean. (00:00) Introduction (01:19) Sharon's business-first background before law school (02:35) Contract management at Verizon and what AI changes about that role (05:48) Why working in the business before practicing law is a career advantage (08:11) The "Yes If" framework for decision-making (09:13) "Yes If" in action: structuring a deal in Mexico (11:34) Running a six-lawyer team across a $3B business (14:27) Strategic work AI unlocks: compliance, risk assessments, regulatory monitoring (17:00) 100% AI adoption and how the business has noticed (18:41) How AI changes who you hire (20:44) Why judgment becomes more valuable with AI, not less (22:37) Cold calling as a career hack (25:03) The CompuCom full-circle story (27:03) Getting comfortable being uncomfortable (31:36) Collaboration and the Women's General Counsel Network (34:08) Lightning round: myths, mentors, and books (35:31) The Bezos lesson on having too many ideas (37:04) Closing reflection: a closed door is not a permanent door Follow us on all social platforms to get each new episode when it drops. ⁠@Cecilia Ziniti⁠ [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn ⁠@CeciliaZin⁠ [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X ⁠@GC AI⁠ [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X ⁠gc.ai [https://www.getgc.ai/]⁠ website

The GC-to-Board Playbook, with Executive Coach Anne Marie Segal

Anne Marie Segal spent 15 years as an attorney - at White and Case, a hedge and private equity fund, and her own firm - before becoming an executive coach to general counsel and senior executives across six continents. She knows what it takes to make the leap, and what holds most lawyers back from making it. In this episode, Cecilia and Anne Marie get into the psychology behind lawyer identity, why so many high achievers stay stuck, and what it looks like to grow beyond the legal function, whether that means taking on a board seat, building toward a CEO role, or starting something entirely new. Follow Anne: @Anne Marie Segal [https://www.linkedin.com/in/annemariesegal/] on LinkedIn segalcoaching.com You'll hear: * Why the GC role is expanding faster than ever and what the best ones are doing about it * The mindset shift lawyers have to make before they can get on a board (hint: you are not the GC on the board) * How to know if you have a fatal flaw blocking your next move  and what to do about it * What AI is changing for junior lawyers, senior lawyers, and everyone in between * The one question every lawyer should be asking themselves right now: what wouldn't you want to delegate? 00:00 Introduction 01:03 Anne Marie's "When Harry Met Sally" moment leaving law for coaching 04:06 The fear behind staying: money, identity, and worst-case scenarios 07:38 Anne Marie's career path: White and Case, hedge funds, and letting go 12:50 Shedding the lawyer identity without losing what makes you good 17:03 Why lawyers are uniquely valuable and what that actually means 18:45 The expanding GC role: 70% of Fortune 1000 GCs now own two or more functions 25:07 GCs and board seats: the mindset shift most lawyers miss 30:36 Fatal flaws and how to find yours before they find you 36:11 AI and the legal profession: what boards are asking and what students are getting wrong 40:53 Advice for junior lawyers: what wouldn't you want to delegate? 44:54 One thing every week: how to actually make the move 47:21 Lightning round: the book that shaped Anne Marie and what she wishes she'd known before law school Follow us on all social platforms to get each new episode when it drops. ⁠@Cecilia Ziniti⁠ [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn ⁠@CeciliaZin⁠ [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X ⁠@GC AI⁠ [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X ⁠gc.ai [https://www.getgc.ai/]⁠ website

The Kanye Clause, Taylor Swift IP, and AI: Mary Ambacher of EverQuote and Lauren Anderson of Wayfair

What does it look like to build a legal team from first principles in 2025, with AI at the center from day one? Cecilia sits down with Mary Ambacher, Deputy General Counsel and Assistant Corporate Secretary at EverQuote, and Lauren Anderson, Senior Counsel at Wayfair, to talk through exactly that.  Mary just started a new GC role after eight years at Wayfair and walked in to find the calculus for headcount had already changed. Lauren stayed behind to run a leaner team covering hundreds of contracts a cycle. They cover how to triage contracts by risk, why termination for convenience is worth fighting for in every deal, what "B+ work" means in a world where AI is closing the gap on junior associates, and the genuine open question nobody has a clean answer to. If AI does the reps, how do the next generation of Mary and Laurens develop the business judgment? Plus: the Kanye clause (yes, it's a real thing), Taylor Swift's IP filings as a masterclass in legal strategy, and what a viewership-tied marketing deal teaches you about creative lawyering. Follow Mary and Lauren: @Mary Ambacher on Linkedin.  Mary Ambacher is Deputy General Counsel at EverQuote, a publicly traded insurance marketplace. Before EverQuote, she spent eight years at Wayfair, most recently as Deputy General Counsel overseeing the commercial legal function. @Lauren Anderson on LinkedIn Lauren Anderson is Senior Counsel at Wayfair, where she leads contract review for one of the largest e-commerce companies in the US. She covers commercial agreements, influencer and affiliate deals, privacy, and emerging technology issues. Topics covered in this episode: - Building a legal team from scratch with AI as a first-principles assumption - How Wayfair's legal team handled 300 contracts in a 10-week window with a team of three - The two-bucket contract triage system Mary and Lauren built together - Why the B+ answer is often the right answer, and when it isn't - The junior lawyer pipeline problem nobody has solved yet - Non-renewal clauses, termination for convenience, and breakup fees - Taylor Swift's AI likeness filings and their implications for commercial IP - What the Kanye clause is, where it came from, and why Lauren is negotiating one right now - What the legal department looks like in five years - When to call outside counsel and when to keep it in-house 00:00 Intro 01:00 Mary's first day at EverQuote after 8 years at Wayfair 02:46 What does success look like when you're building from scratch with AI? 04:01 Clean-sheeting a legal department: starting fresh vs. inheriting a big team 06:36 Lauren on taking on a larger scope at Wayfair with a leaner team 09:14 The volume reality: 300 contracts in 10 weeks, 50 agreements per attorney per cycle 11:26 How to measure legal team performance with AI: OKRs, metrics, and contract triage 15:17 Will AI replace lawyers? The B+ answer and the junior attorney pipeline problem 19:07 Big wins: SLAs, liquidated damages, and creative lawyering 21:05 Why every contract needs a non-renewal clause (especially in an AI tool world) 22:58 Termination for convenience and the breakup fee 27:54 How junior lawyers build business judgment and confidence 30:45 Risk tolerance: the optimal number of plates to break 34:12 Taylor Swift's IP filings and what they mean for every artist 36:04 Taylor Swift's 2015 letter to Apple 37:28 What is the Kanye clause? 42:24 Lightning round: what does the legal department look like in 5 years? 45:02 What do you still use outside counsel for? 46:09 Books, leaders, and advice to your younger self Follow us on all social platforms to get each new episode when it drops. ⁠@Cecilia Ziniti⁠ [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn ⁠@CeciliaZin⁠ [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X ⁠@GC AI⁠ [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X ⁠gc.ai [https://www.getgc.ai/]⁠ website

Risk, Calibration, and 5,000 Bad Haircut Lawsuits with David Schellhase, 3x GC and Okta Board Member

David Schellhase has been general counsel at three public companies - Salesforce, Groupon, and Slack - and he's learned that great in-house lawyering is less about knowing every law and more about knowing your company's risk appetite cold. In this episode of CZ and Friends, David joins Cecilia to share what three decades in Silicon Valley taught him about risk, prioritization, and when to push back on your CEO. David and Cecilia cover: * Why the best in-house lawyers "always be calibrating," reading their company's risk profile the way a trader reads the market, and adjusting advice accordingly. * How technology has made lawyers more available than ever, and why that's a problem worth solving. * What it was like to be GC at Slack through explosive global growth, and how Stewart Butterfield's obsession with craft shaped David's own approach to legal work. * Why David told his CEO, who called from Dublin at midnight, having read the actual GDPR text, that he hadn't read it yet and wouldn't for six months, and why that was the right call. * How Groupon ended up with 5,000 lawsuits in Brazil over bad haircuts, and what that taught him about scaling globally without a legal map. * Why happy hours are technically criminal in New York (it involves liquor pricing law and a rat-encrusted menu). * His thesis that innovation is crime, and why the best in-house lawyers have to believe in their product enough to push the law forward. * What "strong opinions, loosely held" and "disagree and commit" look like in practice as a GC. * Why he thinks in-house lawyers should seek out productive narcissists, and what makes that combination so powerful in a founder. David now sits on the board at Okta, co-teaches Ethical Issues in Global Technology Product Design at Stanford, and is Entrepreneur in Residence at Ballistic Ventures. Follow David:  @David Schellhase [https://www.linkedin.com/in/david-schellhase-209391/] on LinkedIn Chapters: 00:00 Preview 00:12 Welcome and intro: David Schellhase, Okta board member and EIR at Ballistic Ventures 00:25 What David is working on today 02:53 How technology has increased stress in the legal profession 06:52 Always be calibrating: understanding your company's risk appetite 11:12 The difference between in-house and BigLaw prioritization 14:30 Slack, Stewart Butterfield, and the midnight GDPR call 20:45 Innovation is crime: Uber, Airbnb, and the Overton window 25:57 Groupon: happy hours are criminal in New York 30:05 Groupon: 5,000 bad haircut lawsuits in Brazil 34:19 Strong opinions, loosely held, and disagree and commit 43:24 AI: underhyped, and why labeling AI content matters 50:11 Why in-house lawyers should work for productive narcissists 52:43 Lightning round: myths, books, and advice for your younger self Follow us on all social platforms to get each new episode when it drops. ⁠@Cecilia Ziniti⁠ [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn ⁠@CeciliaZin⁠ [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X ⁠@GC AI⁠ [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X ⁠gc.ai [https://www.getgc.ai/]⁠ website