The Abstract

What do you need to know if you're considering taking on the people function? What's the difference between a chief people officer and a CHRO? And are GCs well-positioned to take on both of these roles simultaneously? Rachel Olchowka, Former Chief People Officer and General Counsel at Fetch and current Chief Administrative Officer at Prizm Insurance, had no hesitations when she volunteered to operate a complex, metrics-driven people function in addition to her responsibilities leading in-house legal at a fast-paced organization. Not only did she learn how to do both roles—she learned how to do them well. Listen as Rachel shares how she was able to find balance between two very different executive positions, know whether expanding into a people role is right for you, establish a game-changing comprehensive parental leave plan, craft culture within a company and executive team, and more. Read detailed summary:  https://www.spotdraft.com/podcast/episode-5 [https://www.spotdraft.com/podcast/episode-50]1 Topics: Introduction: 0:00 Taking on the chief people officer role while serving as general counsel at Fetch: 2:25 The difference between CPOs and CHROs: 5:25 Encountering pushback from the executive team on HR policies: 9:01 Crafting culture within an executive team: 12:35 Establishing a comprehensive parental leave plan: 14:53 Approaching the hiring process as a CPO: 19:38 Comparing in-office policies against remote work: 24:40 Dealing with emotionally charged issues in the CPO/CHRO role: 30:57 Recommendations to GCs who want to take on multiple executive roles: 36:34 Considering the right candidate for dual GC and CPO roles: 42:39 Book recommendations: 46:37 What you wish you'd known as a young lawyer: 50:19 Connect with us: Rachel Olchowka - https://www.linkedin.com/in/rachel-olchowka/ 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 [https://www.spotdraft.com/] to learn more.

In this episode of The Abstract, host Tyler Finn speaks with Shanti Ariker, Chief Legal Officer at JFrog, about her unconventional journey from taking a six-year career break to leading legal teams at Salesforce, Twilio, Zendesk, and beyond. Shanti shares lessons on reinvention, resilience, and empathetic leadership — from returning to work as a contracts manager to navigating billion-dollar acquisitions and leading through global crises. Whether you're building your in-house career or leading a team, this conversation offers practical insights on growth, adaptability, and finding purpose in every chapter. Read detailed transcript: https://www.spotdraft.com/podcast/episode-115         Topics Introduction and career overview – 00:00 Stepping away from full-time work and returning after six years – 02:41 Re-entering the legal workforce in Canada and taking a step back – 05:47 Breaking into Salesforce through networking and early contributions – 12:50 Building the Salesforce Canada legal team and launching pro bono work – 15:30 Becoming General Counsel at salesforce.org and leading through learning – 19:20 Innovative legal models and lessons from the salesforce.org structure – 22:17 Transitioning back to for-profit legal roles and rebuilding GC credentials – 24:56 GC role at Zendesk: From steady start to activist investors and take-private – 33:44 Managing governance, communication, and morale during high-stakes transitions – 37:35 Joining JFrog and leading through the Israel crisis – 43:03 Evolving leadership style through personal and professional challenges – 47:07 Rapid-fire Questions – 51:45     Connect with us: Shanti Ariker - https://www.linkedin.com/in/shanti-ariker/ 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.

Want more contracting insight to see how your team compares? SpotDraft recently launched their 2025 Contracting Efficiency Report! Download the report: https://hubs.la/Q03DNYkH0   In this episode of The Abstract, Monica Zent, serial entrepreneur, legal tech investor, and legal innovation pioneer, shares her journey of founding ZentLaw and helping shape modern legal operations before the term even existed. She unpacks the founder's mindset, how to lead through ambiguity, and why taking bold bets early pays off. Monica also shares guidance on embracing AI, identifying scalable legal tech ideas, and forging unconventional paths in a traditionally risk-averse industry.   Read detailed transcript: https://www.spotdraft.com/podcast/episode-114    Topics Introduction – 00:00 Embracing entrepreneurship from a young age – 02:23 Founding ZentLaw and challenging traditional models – 03:25 The founder paradox: balancing vision and risk – 05:49 Early struggles and inflection point for ZentLaw – 08:36 Overcoming pushback and evolving with client feedback – 10:09 Integrating innovation into legal workflows – 11:52 Handling setbacks and staying agile as a founder – 15:10 Choosing an unconventional legal path – 18:01 Advice for law schools and future legal professionals – 22:11 Becoming a legal tech investor and mentor – 25:55 Signals of a Scalable Legal Tech Startup – 27:14 Legal tech trends: compliance, privacy, and predictive AI – 29:03 AI's role in reshaping legal teams and workflows – 31:18 Rapid-fire question – 36:18   Connect with us: Monica Zent • https://www.linkedin.com/in/monicazent/ • https://www.monicazent.com/   Venture Legal Newsletter • https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7302735858552446976   Companies • https://www.lawinnovationagency.com/ • https://zentlawgroup.com/   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.   #legaltech #foundermindset #theabstractpodcast

In this episode of The Abstract, Tyler Finn sits down with Emmanuel Smith, former NFL linebacker, Super Bowl champion, substitute teacher, and now legal tech professional. Emmanuel shares his remarkable journey from the football field to the classroom to corporate America, opening up about resilience, reinvention, mental health, and the power of community. From being cut in the NFL to rediscovering purpose while substitute teaching, Emmanuel's story is a powerful reminder that setbacks can become setups for something greater.    Read detailed transcript: https://www.spotdraft.com/podcast/episode-113   Topics Introduction: 00:00 What inspired him to play football and gives an overview of his career:02:00 The mental preparation, challenges in college, and lessons from his coach that shaped his journey:04:36 His most proud accomplishments from his NFL career: 7:57 Transition out of the NFL & mental health: 09:01 Rediscovering joy in football through teaching & mentorship – 17:38 Transition to corporate America & legal tech: 24:46 Joining Qualitas & sales approach: 29:31 What excites him about legal tech:36:58 Rapid-fire questions: 39:20   Connect with us: Emmanuel Smith - https://www.linkedin.com/in/emmanuel-smith-a79650101/ 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.

Want more contracting insight to see how your team compares? SpotDraft recently launched their 2025 Contracting Efficiency Report! Download the report: https://hubs.la/Q03DNYkH0   In this episode of The Abstract, host Tyler Finn sits down with Viraj Joshi, VP: Legal & Regulatory at Zerodha , India's largest bootstrapped brokerage firm. Viraj shares his unconventional career journey—from big law to public policy, and finally to building cross-functional impact at Zerodha. He reflects on lessons from working across law, finance, and government, the role of community in shaping careers, and Zerodha's growth philosophy. The conversation also dives into his work with Rainmatter, Zerodha's long-term investment arm focused on fintech, health, and climate startups, and the cultural values that have fueled Zerodha's success.    Read a detailed transcript: https://www.spotdraft.com/podcast/episode-112    Topics Introducing Viraj Joshi – 00:00 Viraj's Early Career in Big Law - 01:47 Shift from Law to Policy & Finance - 03:44 Applying legal training beyond traditional legal careers - 09:41 Building Community: Lawyers Not Lawyering - 11:05 Changing Job Market Dynamics - 14:40 Joining Zerodha & Its Growth - 16:51Viraj's Current Role & Regulatory Work - 19:19 Rainmatter Investments: Mission, Long-Term Philosophy, and Focus on Fintech, Health, and Climate - 26:08 Opportunities Beyond Big Cities - 29:44 Adapting to Investing Through Small Checks and Building Conviction Over Time - 31:45 Leadership & Culture at Zerodha - 33:10 Legal Tech & Contracting Challenges - 38:57 Rapid Fire Questions - 45:05   Connect with us: Viraj Joshi - https://www.linkedin.com/in/viraj-joshi/?originalSubdomain=in 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.

Want more contracting insight to see how your team compares? SpotDraft recently launched their 2025 Contracting Efficiency Report! Download the report: https://hubs.la/Q03DNYkH0 In this episode of The Abstract, Tyler Finn sits down with Rohit Kumar, former SVP and General Counsel at Ola and a seasoned in-house leader. Rohit reflects on his journey from corporate law firms to building scalable, tech-driven legal teams in high-growth companies. He shares insights on embracing legal technology early, managing global litigation, navigating regulatory challenges, and shaping team culture. From career pivots inspired by Charlie Munger to implementing CLM solutions ahead of the pandemic, Rohit's story is a masterclass in reinvention, resilience, and leadership in the evolving legal landscape. Read detailed transcript: https://www.spotdraft.com/podcast/episode-111     Topics Introduction 00:00 Rohit's early career journey: choosing law and working across India and international firms 02:04 Moving from law firm life to in-house: time, control, and motivation 04:40 Adapting to in-house culture, stakeholder management, and leadership mindset 06:47 Early adoption of legal tech and compliance solutions at UPL 10:09 Pandemic-driven adoption of CLM and collaboration tools 15:21 Transitioning from traditional enterprises to founder-led tech companies and scaling Ola's legal team 19:50 Leadership evolution: building teams, specialized roles, and creating a strong culture 22:58 High-stakes legal challenges: managing litigation and settlement strategy in Ola's UK class action case 30:28 Regulatory complexities: two-wheeler taxis and navigating government pushback in India 37:20 Contracting efficiency: blockers to CLM adoption, improving processes, and scaling efficiency 42:37 Rapid-fire Questions 48:13    Connect with us: Rohit Kumar - https://www.linkedin.com/in/rohit-kumar-5153715/?originalSubdomain=in 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.

In this episode of The Abstract, Tyler Finn is joined by Tina Hwang, Head of Legal at ClassDojo, whose career spans Google, WhatsApp, Ancestry, and Twitter. She built a career by staying curious, stepping outside her remit, and proactively solving legal and product challenges. She talks about starting out as a commercial attorney, finding her way into privacy and regulatory strategy, and how she learned to lead initiatives without being asked. Tina also shares actionable advice for junior and senior lawyers on navigating career growth, finding the right environments, and redefining legal's value in cross-functional teams. Read detailed summary: https://www.spotdraft.com/podcast/episode-110    Topics Introduction – 00:00 Finding fit in the legal profession: from courts to Google—01:05 Discovering the business side of legal at Google—04:56 From Google to WhatsApp: chasing the excitement of building —07:20 Scaling the legal team at WhatsApp: lessons in hiring and growth – 10:44 Leadership evolution: from problem solver to team developer – 13:46 Mindful management: a four-part framework for legal leaders – 18:54 Evaluating new opportunities: people, trust, and executive chemistry – 22:00 Building the legal function from scratch at ClassDojo – 25:42 People, process, tech: where to start when scaling legal—28:26 Metrics that matter: proving legal's impact to the business – 33:10 Hiring for adaptability and stage-fit in legal teams – 42:21 Rapid-fire Questions – 49:32   Connect with us: Tina Hwang - https://www.linkedin.com/in/tina-hwang-a9556a19/ 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.

What's on the bookshelf of today's top legal leaders? In this special bonus episode, host Tyler Finn asks general counsels, founders, and legal innovators one simple question: What book would you recommend to our listeners? From legal thrillers to leadership classics, personal growth memoirs to spiritual texts — the answers are as wide-ranging as the roles these leaders play. Hear how books like Give and Take, The Culture Code, Ikigai, The Hard Thing About Hard Things, and 100 Saturdays have helped shape how these professionals think, lead, and live. Whether you're looking for your next business read or something more soul-stirring, this episode is your perfect reading list. Read detailed summary: https://www.spotdraft.com/podcast/episode-109    Topics Introduction: 00:00 Rob Chesnut, Former GC and CEO at Airbnb, on writing a book that started as a dinner-table idea: 00:33 Dana Rao, Former GC & CTO, Adobe, on falling for fiction through Here One Moment by Liane Moriarty: 05:52 Shashank Bijapur, Co-Founder & CEO, SpotDraft, on how Zero to One and The Hard Thing About Hard Things guided his transition from lawyer to founder: Akshay Verma, COO at SpotDraft, on the leadership lessons from Getting Naked: 07:07 Tim Hirsch, GC of Mars Science & Diagnostics, on the untold Holocaust history in 100 Saturdays: 08:48 Manu Kanwar, Founder and CEO, LexSolutions, on trauma, ADHD, and human flourishing: 11:17 Alex Herrity, Director of Global Legal Solutions, Adidas, on contract design and building a second brain: 14:52 Keita de Souza, GC at Ryse, on Likable Badass and redefining influence: 17:00 David Cowen, President at The Cowen Group, on how books shape leadership and connection: 19:33 Joon Park, Chief Legal Officer at Extend Enterprises, Inc., on the spiritual depth of the Tao Te Ching and his wife's Pulitzer-winning biography: 21:14 Tyler Finn, Head of Community & Growth at SpotDraft, on books that shaped his values, legal curiosity, and political awareness: 23:01     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.

What happens when a former law firm CMO and Uber's head of legal ops pulls back the curtain on the business of law? In this episode, Tyler Finn sits down with Ken Callander, Managing Principal at Value Strategies, to explore the evolution of law firm pricing, the rise of AI, and how in-house teams can save millions by shifting to value-based fee arrangements. From the politics of partnerships to actionable strategies for better outside counsel management, Ken brings unmatched candor and clarity on how legal teams must adapt in a rapidly evolving landscape.    Read detailed summary: https://www.spotdraft.com/podcast/episode-108    Topics Introduction—0:00 How Law Firm Business Models Drive Political Risk-Taking and Brand Fallout – 01:49 Inside the Law Firm Model: Power Partners, Payout Structures, and Why Change is So Hard—09:02 Challenges with hourly billing and how law firm economics are misaligned with client value—16:32 Why Ken left the law firm world for legal ops at Uber—26:34 Moving to value-based pricing and how it impacted Uber's legal spend—30:10 Why predictability in pricing is often more important than savings—34:21 How AI is disrupting law firm pricing, staffing, and the associate career path—37:33 How In-House Teams Can Improve Law Firm Relationships, Reduce Spend, and Drive Change—49:14 Rapid-fire questions—56:25 Connect with us: Ken Callander - https://www.linkedin.com/in/kencallander/ 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.

In this episode of The Abstract, host Tyler Finn sits down with Andrew Epstein, General Counsel of Demandbase, for a candid conversation on building a legal career rooted in curiosity, intentionality, and creative risk-taking. From starting his career in the GC's office of the Washington Nationals to handling high-stakes spinouts at LiveRamp, Andrew shares how he made bold choices, built trust across functions, and scaled legal teams strategically. He dives deep into building legal ops, leveraging AI thoughtfully, and what it really takes to thrive as a first-time GC. A must-listen for in-house leaders, aspiring GCs, and legal professionals navigating a rapidly evolving legal landscape. Read detailed summary: https://www.spotdraft.com/podcast/episode-107 Topics Introduction – 00:00 Andrew's intentional path to law school and first job at a GC's office – 02:28 Working for the Washington Nationals and using that experience to stand out – 04:38 Choosing O'Melveny for its cross-office structure and California links – 08:10 From Capital Markets to Privacy: Why Andrew Left Big Law for In-House at LiveRamp – 09:49 Managing complex transactions: M&A, spinout from Axiom, NYSE listing – 17:18 Privacy, Adtech, and Proving Your Value in a Changing Legal Team – 22:04 Getting hired as GC at Demandbase through cross-functional trust – 27:33 Scaling the legal team intentionally for IPO readiness – 29:41 Growing as a first-time GC through peer mentorship – 32:43 Building a lean, flexible team that integrates AI and legal ops – 35:35 Encouraging AI experimentation over shiny tools – 40:08 Rapid-fire Question – 46:04 Connect with us: Andrew Epstein - https://www.linkedin.com/in/andrew-epstein-3b22a471/ 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 [https://www.spotdraft.com/] to learn more.

What does it take to scale a legal team in high-growth environments? In this special bonus episode of The Abstract, we feature insights from five legal leaders who have each helped their organisations scale — and survived the chaos that comes with it. From building global teams at Carta to laying the legal foundation at early-stage startups, our guests reflect on the personal and professional lessons learned along the way. You'll hear how legal ops, AI adoption, prioritisation frameworks, and even IKEA furniture assembly play a role in building agile, resilient legal teams. Whether you're the first lawyer in the door or leading a 50-person department, this episode is packed with takeaways for legal professionals navigating scale. Read detailed summary: https://www.spotdraft.com/podcast/episode-106    Topics Introduction - 0:00 April Lindauer, GC at Carta, on scaling legal from 200 to 2000 employees post-Series C – 0:35 Adam Becker, Head of Legal Ops at Cockroach Labs, on building connective legal infrastructure and enabling smarter AI adoption – 2:42 David Cowen, Founder of The Cowen Group, on legal ops maturity and leading in the age of AI agents – 4:54 Tommie Tavares-Ferreira, Chief Strategy Officer, Lawtrades, on aligning legal priorities with business impact and enabling cross-functional trust – 8:52 Jordan Hatcher, Co-Founder & CLO/COO, The Grid, on scaling legal internationally and staying grounded through hypergrowth – 14:11 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.

What if the legal system punishes the victim instead of the attacker? That question drives Andy Lunsford, founder and CEO of BreachRx, to rethink how companies prepare for and respond to data breaches. In this episode, Andy joins host Tyler Finn to share his journey from litigation consultant to legal tech entrepreneur—and why he believes incident response should be treated like any other core business process. Separating privileges from factual records to rethinking executive liability, Andy offers practical insights for legal counsels navigating a regulatory maze, rising risk, and increasing accountability. Read detailed summary: https://www.spotdraft.com/podcast/episode-105    Topics Introduction – 00:00 Andy's path into privacy law: From philosophy to shaping early FTC breach cases—02:07 The shift from rare black swan breaches to everyday business risk—6:19 How GDPR's 72-hour rule changed incident response expectations – 08:54 Founding Beacon Group: bridging litigation, incident response, and expert testimony—13:53 The law punishes victims: why breach response is legally broken—16:53 Defending the defenders: Mental toll and leadership under breach pressure—21:00 Personal Risk in Cybersecurity: Why CISOs and Legal Leaders Need Protection Too – 22:48 How GCs Can Prepare for Breaches: Building Systems, Not Just Plans—27:28 Rising executive accountability: how GCs can protect their teams and companies—32:23 From legal consultant to tech CEO: building BreachRx as a category-defining platform—34:49 The challenge of early-market education and building industry standards—40:52 Rapid-fire Questions—42:35   Connect with us: Andy Lunsford - https://www.linkedin.com/in/andersonlunsford/ 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.

In this episode of The Abstract, host Tyler Finn is joined by Joon Park, Chief Legal Officer at Extend Enterprises, Inc., for a candid conversation about building a legal career defined by integrity, adaptability, and curiosity.    From navigating the collapse of Refco early in his career to leading legal at high-growth fintech companies, Joon shares how high-pressure moments shaped his risk mindset and leadership style. He unpacks why startups need legal guidance from day one, how to embed compliance without slowing down, and why modern legal counsel must be both partner and protector. Along the way, Joon reflects on finding purpose, embracing uncertainty, and staying curious through every chapter.    Read detailed summary: https://www.spotdraft.com/podcast/episode-104    Topics Introduction - 00:00 Early career influences: philosophy, parenting, and curiosity - 01:54 Holistic thinking and law as systems navigation – 05:00 Transitioning from Big Law to in-house for financial security – 07:01 Refco collapse: a crash course in legal ethics and resilience – 10:35 Risk mindset: documenting decisions and staying aligned – 14:05 Generalist vs. specialist: finding fit during the Citigroup bailout – 17:02 Moving to startups: autonomy, prioritisation, and risk ownership – 21:59 Legal as an enabler, not a blocker, in startup environments – 24:35 Building scalable compliance without killing speed – 26:17 Legal's role in shaping company culture and accountability – 28:21 Following curiosity to stay motivated and engaged – 30:19 Rapid-fire Questions – 32:21    Connect with us: Joon Park - https://www.linkedin.com/in/joon-park-147a9a92/ 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.

In this special episode of The Abstract, host Tyler Finn speaks with Tommie Tavares-Ferreira, newly appointed Chief Strategy Officer at Lawtrades and longtime legal ops leader, community builder, and podcast host.   Tommie walks us through her unconventional path from the music industry to Peloton, Rakuten, Cedar, and now the executive team at Lawtrades. She shares lessons on scaling companies, embracing curiosity, balancing parenting with leadership, and how legal ops leaders can (and should) step into strategy roles. It's a personal, powerful conversation about evolving careers, future tech, and the next phase of legal work. Read detailed summary: https://www.spotdraft.com/podcast/episode-103 Topics: Introduction: 0:00 Tommie's early career in music, HBO, and the spirit of DIY creativity: 2:26 Legal ops as a career by necessity, not design: 5:03 Legal ops as a creative discipline and never-ending work: 6:53 Helping businesses scale through legal ops alignment and prioritization: 8:39 Love of technology, fears of automation, and the case for balance: 13:46 Bringing legal teams into the AI journey and overcoming resistance: 19:24 Why Tommie joined Lawtrades and what she hopes to build: 24:55 Legal ops as strategy and expanding the role into go-to-market leadership: 33:15 The glass ceiling in legal ops and the need for executive pathing: 36:52 Rapid-fire questions: 41:17 Connect with us: Tommie Tavares-Ferreira - https://www.linkedin.com/in/tommie/ 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.

In this special live-recorded episode of The Abstract from CLOC in Las Vegas, host Tyler Finn sits down with David Cowen, founder of The Cowen Group and creator of the SOLID Summit Series. David shares his journey from staffing to shaping the legal ops ecosystem, the moment he foresaw the rise of e-discovery, and why community is the most powerful response to chaos. He discusses the evolution of legal operations, the future of AI and agentic teams, and why trusting your talent matters more than ever. From frameworks on scaling legal to using ChatGPT as an executive coach, this episode offers a playbook for building a career and community in a rapidly changing industry. Read detailed summary: https://www.spotdraft.com/podcast/episode-102   Topics: Intro: 00:00 David's career journey: From staffing to community building: 2:22 The moment he discovered e-discovery's potential: 5:10 How TED Talks inspired the SOLID Summit format: 6:49 Chaos as the ideal condition for community building: 8:43 Overbuilding in legal tech: problem or opportunity?: 10:52 Spotting innovation through curiosity, not prediction: 13:02 Legal Ops turns 10: What's next for the profession?: 17:33 Climbing the legal career "jungle gym," not a ladder: 21:03 How to manage anxiety and disruption in an AI-driven future: 25:53 On coaching, preparation, and using ChatGPT as a partner: 28:25 Legal Ops' evolving role in helping businesses scale: 32:49 The future of legal tech: use cases and AI agents: 37:12 The GC as catalyst: Top-down transformation is here: 39:46 Creators, Builders, Consumers: Who shapes the industry?: 42:54 What excites David most about the next 10 years: 45:35 Rapid-fire Questions: 47:25 Connect with us: David Cowen – https://www.linkedin.com/in/davidcowen/ 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.

What does it mean to lead legal operations when there's no clear blueprint? In this episode of The Abstract, host Tyler Finn sits down with Adam Becker, Director of Legal Operations at Cockroach Labs and board member at CLOC, for a candid conversation about evolving careers, scaling legal departments, and the growing scope of legal ops. From breaking the "lawyer mold" to embracing AI-native strategies, Adam shares personal lessons on confidence, curiosity, leadership, and why legal ops is entering a new season of strategic impact. The discussion also explores how CLOC's community and resources help elevate the field, and why every legal ops professional should see themselves as a partner to the GC — not just a process owner. Read detailed summary:  https://www.spotdraft.com/podcast/episode-101   Topics Introduction and career arc overview: 0:00 Early clues that pointed to process thinking: 1:14 Breaking out of the lawyer mold and recognizing transferable skills: 2:09 Confidence, curiosity, and pivoting into legal ops: 5:51 Driving impact at MetLife and Endeavor: 8:33   Why legal ops requires conviction, not just thick skin: 11:09   The people-process-tech triangle — and why "people" matters more: 14:13   Culture and collaboration at Cockroach Labs: 16:36 Balancing scale with flexibility in a fast-growing company: 18:53 How legal ops has evolved through CLOC's growth: 21:14 Is legal ops at a crossroads? And what's CLOC's role in the future?:  26:22 Rapid Fire: 32:59 Connect with us: Adam Becker - https://www.linkedin.com/in/adam-becker-896a7a3/ 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.

In the 100th episode of The Abstract, the mic flips as SpotDraft's Chief of Staff, Nakta Alaghebandan, interviews our podcast's usual host and creator, Tyler Finn.   From his start in public policy to shaping one of the most influential legal communities at SpotDraft, Tyler shares the pivotal career moments, risky leaps, and trust-building lessons that defined his path. He reflects on navigating early career detours, becoming a privacy leader despite skepticism, and building trust from scratch with executive stakeholders and customers.   The conversation dives deep into community-building philosophy, the value of calculated risk, and how Tyler sees "increasing your surface area" as the most underutilized career growth strategy. You'll also hear how the podcast came to life, what he's learned after 100 episodes, and his advice for creating lasting impact — with humility, humour, and heart.   Read detailed summary:  https://www.spotdraft.com/podcast/episode-100   Topics Introduction: 0:00 Tyler's early pivot from public policy to legal tech: 3:15 Choosing privacy despite warnings against it: 5:40 Building trust after entering a low-trust role: 8:33 Becoming the go-to for high-anxiety customer: 12:04 Why cross-functional thinking matters in legal leadership: 15:52 Sitting in the grey: layoffs, uncertainty, and consulting: 19:03 Taking calculated risks and trusting your gut: 22:51 From outsider to community leader at TechGC: 25:20 What real community building looks like: 29:28   How to design a community where people actually open up: 30:55 Building trust and reputation intentionally: 31:25 How SpotDraft went from a consulting client to employer: 36:26 Community as a future-facing marketing strategy: 40:18 How Tyler now evaluates executive teams and companies: 43:22 Why the CEO and executive team matter more than you think: 46:33 What great executive teams do to support internal community: 47:42 Why Tyler launched The Abstract and his goals for it: 50:12 Personal lessons from 100 episodes: 56:04 "Increasing your surface area" and embracing uncertainty: 1:01:56 Favourite part of the day: 1:05:12 Professional pet peeve: 1:06:11 Book recommendations: 1:07:09 Advice to younger self: 1:11:21    Connect with us: Tyler Finn - https://www.linkedin.com/in/tylerhfinn Nakta Alaghebandan - https://www.linkedin.com/in/nakta/ 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.

Download the AI Impact Report now:  https://www.spotdraft.com/ai-impact-report-2025 What does it take to thrive in law without losing yourself in the process?    In this episode of The Abstract, host Tyler Finn is joined by Keita de Souza, General Counsel of Ryse and a former big law attorney turned wellness advocate, for a conversation that redefines what it means to be successful in legal practice. From pushing herself to burnout in her early law firm years to navigating the emotional toll of winding down a startup, Keita opens up about how personal health crises sparked a shift toward sustainability, intentionality, and self-compassion. Keita discusses her unique path from big law to in-house roles, the lessons learned from yoga and physical setbacks, and how she's learned to prioritize both career and care. She also shares what it was like to lead legal through the closure of a company — and why she decided to take the leap again with a new startup.   This episode is a candid and empowering look at resilience, leadership, and how to keep your center while leading others. Topics Introduction: 0:00 Early years in Big Law and unsustainable pace: 3:07   Physical breakdowns and health wake-up calls: 5:2   Small habits that transformed wellness: 11:42   Transitioning from law firm to in-house counsel: 13:30   Differences Between Law Firm and In-House Legal Work: 14:54   Developing Wind-Down Strategies and Daily Resets: 18:50   Aggressive Self-Care Days: A Personal Practice: 18:55   Leading Through a Company Wind-Down: 23:05 Staying Grounded in Crisis: Leading with Calm and Integrity: 26:57 How yoga helped her survive high-stress moments: 29:11   Starting over as General Counsel at Ryse: 30:22 Balancing ambition with intentional self-care: 32:12    Redefining legal excellence beyond perfectionism: 34:15    Building confidence and shedding self-doubt: 39:03    Daily Rituals for Reset and Recovery: 42:35 Professional Pet Peeves: 44:23   Book Recommendations: 46:37   Advice to Younger Self: 49:32 Connect with us: Keita de Souza - https://www.linkedin.com/in/keitadesouza/ 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.

May is Mental Health Awareness Month, so we've pulled together some of the most vital stories from some of the star legal and business experts we've featured on The Abstract about managing stress, achieving a healthy work/life balance, dealing with tragedies at home, leaving toxic working environments and more. Keep listening and feel inspired to make a positive change in your life and career. Read detailed summary:  https://www.spotdraft.com/podcast/episode-98 Topics Introduction: 0:00 Ryan Nier, General Counsel at Nova Credit on imposter syndrome and feeling like an outsider in the legal community: 0:43 Joe Sullivan, ex-Chief Security Officer at Uber, Facebook, and Cloudflare on managing the stress of a federal indictment: 6:49 Lawtrades Co-Founders Raad Ahmed and Ashish Walia on how to support your business partner during difficult times: 11:36 Dan Haley, General Counsel and Corporate Secretary at Guild, on balancing work and life after a cancer diagnosis: 14:07 Zoe McMahon, Head of Legal Ops at HP, on mindfulness and bringing parts of your private self into the workplace: 16:47 Laura Frederick, CEO of How to Contract on the importance of seeing a therapist: 18:59 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 [https://www.spotdraft.com/] to learn more.

What's it like to be the first European legal hire for a fast-growing tech company? How do you build out a European legal team? And where is the European tech sector headed? Join Volker Weisshaar, General Counsel EMEA at Sonos, as he talks about establishing and scaling European legal teams for US tech giants NetApp and Sonos, and what it takes to help these companies thrive in the regulation-heavy and culturally diverse landscape of the EU. Listen as Volker discusses his approaches to hiring at NetApp and Sonos, taking on an operator function and getting your hands dirty as you build a new office, evolving your leadership style in a growing business, key differences between European and US regulations, and much more. Read detailed summary:  https://www.spotdraft.com/podcast/episode-97 Topics Topics Introduction 0:00 Living and working in Amsterdam: 2:24 Europe's tech and startup scene: 2:27 What motivated Volker to become a tech lawyer: 3:44 Being the first European legal hire at Sonos and NetApp: 11:10 Approaches to building out a legal team: 14:54 Being a lawyer and an operator: 16:52 Joining Sonos: 19:01 Evolving as a leader: 23:12 Managing your relationship with a global CLO: 26:10" Differences between US and EU regulations: 28:48 Europe's start-up scene and regulation: 34:41 Biggest challenges at Sonos: 40:24 Leveraging AI: 44:41 Proudest accomplishments at Sonos: 47:29 Rapid-fire questions: 49:07 Connect with us: Volker Weisshaar - https://www.linkedin.com/in/volkerweisshaar/ 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 [https://www.spotdraft.com/] to learn more.