Ep 87: Building a Culture of Integrity with Rob Chestnut, former Airbnb Chief Ethics Officer

How do you make the move from building a legal career in the US to one in Europe, scale one of Europe's hottest unicorns, and transition to launching your own start-up?Join Jordan Hatcher, co-founder, CLO, and COO of The Grid, a blockchain-based tech start-up, as he shares his experience as a Texas-born lawyer living and working across Europe in senior counsel  roles at Optimizely, ARM, and Hewlett Packard before joining Staffbase as GC and ultimately co-founding his own cutting-edge Web3 company.Listen as Jordan discusses his early work writing and advocating for open data licenses, offers advice to US companies looking to build or scale in Europe, explains the value of a well-timed career break, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-96TopicsIntroduction: 0:00Living in Amsterdam: 3:08Working in IP, Web3, civil liberties law: 5:54Collaborating with engineers at HP and ARM: 8:14Open source data and standards making: 10:37A throughline from open source to Web3 Leading legal at Staffbase: 14:57Signs that you’re overworking: 19:22Dual perspectives on business culture in the US and Europe: 23:40Building a business in Europe: 26:50Biggest accomplishments at Staffbase: 29:58When to leave a GC role: 31:38Taking a career break: 35:38Diving into Web3 with The Grid: 36:30Reflecting on entrepreneurship: 39:40Starting a non-profit: 46:16Raising a child with a disability: 48:56Rapid-fire questions: 53:39Connect with us:Jordan Hatcher - http://linkedin.com/in/jordanhatcher/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

Where is the legal innovation space headed? Is this an area where European businesses are actually investing more deeply than their American counterparts? And how can you transition your team to focus more on innovation and a little less on the law?Join Alex Herrity, Director of Global Legal Solutions at Adidas, as he offers expert takes on the future of legal tech and legal ops, including adopting new technology like AI, leaning into change management, scaling innovations globally, and more.Listen as Alex discusses his transition from lawyer to “legal tech guy,” the growing acceptance of ops roles in inhouse legal departments, legal innovation’s big moment, hosting the Law://WhatsNext podcast, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-95Topics Introduction: 0:00 A big moment for legal innovation: 2:33 Characterizing legal innovation: 5:28 From lawyer to legal ops director: 7:50 Adopting technology vs. change management: 9:12 Avoiding mistakes in legal tech: 15:41 Leading with AI: 18:52 Deciding to be a lawyer: 21:09 Becoming a “legal tech guy”: 26:18 Directing global legal ops for Adidas: 27:40 Managing teams in multiple countries: 30:54 The future of legal ops at Adidas: 34:21 Advice to future legal ops professionals: 36:50 Hosting the Law://WhatsNext podcast: 42:24 Rapid-fire questions: 46:02Connect with us:Alex Herrity - https://www.linkedin.com/in/legalopshezzle/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How important is the culture of an organization to its success? How can legal leaders cultivate high-performing cultures for their teams and their companies? And why is this something that a lot of legal teams struggle with?Join Manu Kanwar, Founder and CEO of LexSolutions, as he shares how he improves his clients’ legal teams and why he focuses on strategy, culture, and relationships as the cornerstones of legal innovation.Listen as Manu discusses strategies for changing work cultures, fixing toxic situations, and maintaining a healthy self-image, why he left Yahoo! after ten years to start his own legal consulting firm, the problem with “doing more with less,” and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-94Topics Introduction 0:00Founding LexSolutions after ten years at Yahoo!: 2:07Approaches to legal innovation: 5:07Shifting cultures: 7:11The rewards and challenges of consulting: 9:44What’s wrong with “do more with less?”: 12:14Why corporate culture is so hard to get right: 19:25Who is responsible for changing culture? 26:22Reinforcing psychological safety: 31:06Fixing toxic cultures: 32:38Advice to lawyers in toxic situations: 34:16Why lawyers struggle with self-image: 41:48Considering authenticity: 45:58How to connect with Manu: 52:44Rapid-fire questions: 53:07Connect with us:Manu Kanwar - https://www.linkedin.com/in/mkanwar/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you navigate a crisis? Data breaches, bank collapses, CEO transitions, and global recessions are just a few of the hazards that can challenge general counsels and other executives and threaten the future of their businesses.  In this episode, we’re sharing stories of resilience and tough lessons learned from some of the legal and business leaders who have joined us on The Abstract. Keep listening for advice that could prove handy in an emergency.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-93  TopicsIntroduction: 0:00Vanessa Wu, GC at Rippling, on surviving the collapse of Silicon Valley Bank: 0:42Joe Sullivan, CEO of Joe Sullivan Security, on the personal fallout from a data breach at Uber: 7:45Heath Tarbert, Chief Legal Officer and Head of Corporate Affairs at Circle, on gaining career momentum from the great recession: 12:40Kristin Sverchek, former President of Lyft, dealing with executive roles and hiring during a crisis: 15:07Dan Haley, General Counsel and Corporate Secretary at Guild, on managing CEO transitions in a time of crisis: 18:25Sean West, Co-Founder at Hence Technologies, on how general counsels can get better at navigating political risks: 21:55Chelsea Grayson, Managing Partner of Corporate Restructuring at Pivot , on sitting on a corporate board during a crisis: 24:21 Connect with us: Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

Can your pets inspire you and shape the direction of your career? How can practicing abroad open doors? And what personal and professional lessons can you draw from training for and completing an Ironman triathlon?Join Tim Hirsch, General Counsel at Mars Science and Diagnostics, as he talks about making transitions: from practicing law in the EU to practicing in the US; working in-house at huge companies like Mastercard to becoming Head of Legal at Collibra, a ten-person start-up; taking the leap to co-found his own business, DoggyChef; and leveraging that experience in pet care into his current role as GC at one of the biggest names in the industry.Listen as Tim discusses the different expectations on lawyers in the US versus Europe, how to have influence in a huge in-house legal team,  what it takes to turn an idea into a company, operating a start-up while working full-time, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-92Topics   Introduction 0:00 Starting a legal career in Europe: 4:27 Bringing a different perspective to in-house legal: 8:59 Becoming Head of Legal at Collibra: 11:25 Learning business skills on the job: 14:24 Developing the confidence to start a business: 20:02 Co-founding DoggyChef: 21:29 Moving into a GC role at Mars Petcare: 30:08 Switching between large and small organizations: 34:58 Training for an Ironman triathlon: 39:34 Rapid-fire questions: 49:36Connect with us: Tim Hirsch - https://www.linkedin.com/in/timothyhirsch/ Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.   Visit https://www.spotdraft.com to learn more.

Why is technology the right leverage point for improving how a legal team works together? What did it take to start and sustainably grow SpotDraft? And how do you transition from a more traditional legal career to one leading a legal tech business?Join Shashank Bijapur, SpotDraft’s Co-Founder & CEO and Akshay Verma, SpotDraft’s COO as they sit down with Tyler Finn at the SpotDraft Summit 2025 and break down their journeys from lawyers to tech executives and legal innovators.Listen as Shashank and Akshay discuss the origins of Spotdraft, offer their expert predictions on the future of legal work and AI, explain why legal operations professionals should aim for COO roles, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-91TopicsIntroduction: 0:00What inspired Shashank to start SpotDraft: 2:38Leading strong customer success teams: 4:40Approaches to fundraising: 6:38Looking back on Legal Ops at Facebook: 9:14Where is the legal ops profession headed?: 11:45Hiring a legal ops professional for COO roles: 13:06Seeing yourself as a lawyer in the business world: 15:48Building balance on an executive team: 18:19Advice to lawyers looking to pivot: 21:27How AI will evolve the way in-house teams work?: 25:06Will lawyers accept AI risks?: 27:52The future of law firms and AI: 32:50Rapid-fire questions: 38:52Connect with us:Shashank Bijapur - https://www.linkedin.com/in/shashankbijapur/Akshay Verma - https://www.linkedin.com/in/akshay-verma-esq/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management needs. Visit https://www.spotdraft.com to learn more.

How do you make the transition from IP lawyer to general counsel in a typical path? Help Adobe navigate a transition to the cloud, and then the AI era? And make time for your family through all the ups and downs?Join Dana Rao, former general counsel at Adobe and IP and Licensing expert at Microsoft, as he discusses how he capitalized on his electrical engineering background to skyrocket himself from a patent attorney to the forefront of some of the most consequential technology decisions of the last two decades—including topics like copyright, AI, litigation, and more.Listen as Dana explains how he became invaluable to Janet Reno’s justice department, how to make ethical business decisions, influencing legislation to combat patent trolls, and more more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-91TopicsIntroduction: 0:00Relaxing and writing after retirement: 2:23Transitioning from electrical engineer to DC lawyer: 10:51Doing the right thing for your company and the world: 21:48Leaving politics to become tech counsel: 27:21Combating patent trolls: 36:03From Microsoft to Adobe general counsel: 41:42Rapid-fire questions: 51:48Connect with us:Dana Rao - https://www.linkedin.com/in/dana-rao/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you build a legal marketplace with more than 75,000 community members? Find the right investors to join you on the journey? And help the business navigate the inevitable pivots that will come along with its growth?Join Hannah Konitshek, COO and Founder of Legal.io, Business Operations and Strategy, as she dives deep into the business of legal tech, and how a relationship built during a hackathon transformed into the premiere marketplace for in-house legal talent.Listen as Hannah explains how attending law school in San Francisco guided her legal career, founding and growing a start-up with a legal background, how to balance your convictions with investors, and learning that the biggest risk is not taking a big enough swing.Read detailed summary:  https://www.spotdraft.com/podcast/episode-89TopicsIntroduction: 0:00Going into legal tech directly from law school: 2:10Do law schools prepare students for careers outside big law?: 6:25Getting started with Legal.io: 9:20Defining yourself as a “second-term founder”: 11:31Hannah on conviction and experimentation: 14:50Approaching fundraising: 19:06Advice to business leaders on pivots: 23:21How Legal.io works with AI: 28:45Upcoming trends in the legal hiring market: 30:47The future of Legal.io: 36:04Rapid-fire questions: 37:29Connect with us:Hannah Konitshek - https://www.linkedin.com/in/hannah-konitshek/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you make the transition from federal prosecutor to security leader? Help secure some of the world's largest technology companies? And build yourself back up after being convicted by a federal jury for your company's handling of a data breach?Join Joe Sullivan, CEO of Joe Sullivan Security and the non-profit Ukraine Friends, as he reflects on the trial and sentencing he endured for a data breach at Uber to interpret the manifold challenges the chief security officers face each day.Listen as Joe shares his journey from the first full-time cyber federal prosecutor in the country to legal and security leader at eBay, Paypal, Facebook, Uber, and Cloudflare, why lawyers need to work closely with security teams, the relationship between security and privacy, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-88TopicsIntroduction: 0:00Becoming the CEO of Ukraine Friends: 2:43Getting a start in cyber: 13:55Transitioning from tech-savvy prosecutor to trust and safety at eBay and Paypal: 17:18Taking on security at Facebook: 22:20The challenges that face chief security officers: 24:03How legal teams and security can work better together: 26:23The difference between a chief security officer and a CISO: 30:03Navigating the fallout of the data breach at Uber: 32:02Working at Cloudflare during the Uber trial: 37:21Building a private security practice: 38:28Joe’s biggest learnings from the trial: 44:01Rapid-fire questions: 46:08Connect with us:Joe Sullivan - https://www.linkedin.com/in/joesu11ivan/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

What role does integrity need to play in your company's culture? How can legal teams and corporate leaders foster it? And where do you get started if you want to write a book on it?Join Rob Chesnut, author of Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution, as he discusses his path from prosecutor at the Department of Justice to tech industry legal leader at eBay, Chegg, and Airbnb, and how integrity and ethics became the cornerstone of both his career and his personal philosophy.Listen as Rob discusses scaling global legal teams for some of the biggest disruptors in the world, embedding integrity into your company’s corporate culture, transitioning from general counsel to author and thought leader, and much more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-87TopicsIntroduction: 0:00Transitioning from prosecutor to tech counsel: 2:12Joining eBay in the early years: 4:13Building eBay’s trust and safety functions: 5:01Making the leap to general counsel: 7:21Reflecting on mentorship: 9:13Knowing when to move on to new opportunities: 13:13Leading legal at Airbnb: 15:50Signature interview questions: 20:56Developing the “Chief Ethics Officer” role: 23:04Writing Intentional Integrity: 32:10How a company can start their integrity program: 34:31The changing integrity landscape: 41:13How to contact Rob: 42:50Rapid-fire questions: 44:07Connect with us:Rob Chesnut - https://www.linkedin.com/in/robchesnut/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.