Ep 115: From Career Break to CLO: How Shanti Ariker Rebuilt Her Legal Career

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 – 00:00Stepping away from full-time work and returning after six years – 02:41Re-entering the legal workforce in Canada and taking a step back – 05:47Breaking into Salesforce through networking and early contributions – 12:50Building the Salesforce Canada legal team and launching pro bono work – 15:30Becoming General Counsel at salesforce.org and leading through learning – 19:20Innovative legal models and lessons from the salesforce.org structure – 22:17Transitioning back to for-profit legal roles and rebuilding GC credentials – 24:56GC role at Zendesk: From steady start to activist investors and take-private – 33:44Managing governance, communication, and morale during high-stakes transitions – 37:35Joining JFrog and leading through the Israel crisis – 43:03Evolving leadership style through personal and professional challenges – 47:07Rapid-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 – 00:00Embracing entrepreneurship from a young age – 02:23Founding ZentLaw and challenging traditional models – 03:25The founder paradox: balancing vision and risk – 05:49Early struggles and inflection point for ZentLaw – 08:36Overcoming pushback and evolving with client feedback – 10:09Integrating innovation into legal workflows – 11:52Handling setbacks and staying agile as a founder – 15:10Choosing an unconventional legal path – 18:01Advice for law schools and future legal professionals – 22:11Becoming a legal tech investor and mentor – 25:55Signals of a Scalable Legal Tech Startup – 27:14Legal tech trends: compliance, privacy, and predictive AI – 29:03AI’s role in reshaping legal teams and workflows – 31:18Rapid-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: 00:00What inspired him to play football and gives an overview of his career:02:00The mental preparation, challenges in college, and lessons from his coach that shaped his journey:04:36 His most proud accomplishments from his NFL career: 7:57Transition out of the NFL & mental health: 09:01Rediscovering joy in football through teaching & mentorship – 17:38Transition to corporate America & legal tech: 24:46Joining Qualitas & sales approach: 29:31What 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 – 00:00Viraj’s Early Career in Big Law - 01:47Shift from Law to Policy & Finance - 03:44Applying legal training beyond traditional legal careers - 09:41Building Community: Lawyers Not Lawyering - 11:05Changing Job Market Dynamics - 14:40Joining Zerodha & Its Growth - 16:51Viraj’s Current Role & Regulatory Work - 19:19Rainmatter Investments: Mission, Long-Term Philosophy, and Focus on Fintech, Health, and Climate - 26:08Opportunities Beyond Big Cities - 29:44Adapting to Investing Through Small Checks and Building Conviction Over Time - 31:45Leadership & Culture at Zerodha - 33:10Legal Tech & Contracting Challenges - 38:57Rapid 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/Q03DNYkH0In 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 00:00Rohit’s early career journey: choosing law and working across India and international firms 02:04Moving from law firm life to in-house: time, control, and motivation 04:40Adapting to in-house culture, stakeholder management, and leadership mindset 06:47Early adoption of legal tech and compliance solutions at UPL 10:09Pandemic-driven adoption of CLM and collaboration tools 15:21Transitioning from traditional enterprises to founder-led tech companies and scaling Ola’s legal team 19:50Leadership evolution: building teams, specialized roles, and creating a strong culture 22:58High-stakes legal challenges: managing litigation and settlement strategy in Ola’s UK class action case 30:28Regulatory complexities: two-wheeler taxis and navigating government pushback in India 37:20Contracting efficiency: blockers to CLM adoption, improving processes, and scaling efficiency 42:37Rapid-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 – 00:00Finding fit in the legal profession: from courts to Google—01:05Discovering the business side of legal at Google—04:56From Google to WhatsApp: chasing the excitement of building —07:20Scaling the legal team at WhatsApp: lessons in hiring and growth – 10:44Leadership evolution: from problem solver to team developer – 13:46Mindful management: a four-part framework for legal leaders – 18:54Evaluating new opportunities: people, trust, and executive chemistry – 22:00Building the legal function from scratch at ClassDojo – 25:42People, process, tech: where to start when scaling legal—28:26Metrics that matter: proving legal’s impact to the business – 33:10Hiring for adaptability and stage-fit in legal teams – 42:21Rapid-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: 00:00Rob Chesnut, Former GC and CEO at Airbnb, on writing a book that started as a dinner-table idea: 00:33Dana Rao, Former GC & CTO, Adobe, on falling for fiction through Here One Moment by Liane Moriarty: 05:52Shashank 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: 07:07Tim Hirsch, GC of Mars Science & Diagnostics, on the untold Holocaust history in 100 Saturdays: 08:48Manu Kanwar, Founder and CEO, LexSolutions, on trauma, ADHD, and human flourishing: 11:17Alex Herrity, Director of Global Legal Solutions, Adidas, on contract design and building a second brain: 14:52Keita de Souza, GC at Ryse, on Likable Badass and redefining influence: 17:00David Cowen, President at The Cowen Group, on how books shape leadership and connection: 19:33Joon Park, Chief Legal Officer at Extend Enterprises, Inc., on the spiritual depth of the Tao Te Ching and his wife's Pulitzer-winning biography: 21:14Tyler 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/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 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—0:00How Law Firm Business Models Drive Political Risk-Taking and Brand Fallout – 01:49Inside the Law Firm Model: Power Partners, Payout Structures, and Why Change is So Hard—09:02Challenges with hourly billing and how law firm economics are misaligned with client value—16:32Why Ken left the law firm world for legal ops at Uber—26:34Moving to value-based pricing and how it impacted Uber’s legal spend—30:10Why predictability in pricing is often more important than savings—34:21How AI is disrupting law firm pricing, staffing, and the associate career path—37:33How In-House Teams Can Improve Law Firm Relationships, Reduce Spend, and Drive Change—49:14Rapid-fire questions—56:25Connect with us:Ken Callander - https://www.linkedin.com/in/kencallander/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.

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-107TopicsIntroduction – 00:00Andrew’s intentional path to law school and first job at a GC’s office – 02:28Working for the Washington Nationals and using that experience to stand out – 04:38Choosing O’Melveny for its cross-office structure and California links – 08:10From Capital Markets to Privacy: Why Andrew Left Big Law for In-House at LiveRamp – 09:49Managing complex transactions: M&A, spinout from Axiom, NYSE listing – 17:18Privacy, Adtech, and Proving Your Value in a Changing Legal Team – 22:04Getting hired as GC at Demandbase through cross-functional trust – 27:33Scaling the legal team intentionally for IPO readiness – 29:41Growing as a first-time GC through peer mentorship – 32:43Building a lean, flexible team that integrates AI and legal ops – 35:35Encouraging AI experimentation over shiny tools – 40:08Rapid-fire Question – 46:04Connect with us:Andrew Epstein - https://www.linkedin.com/in/andrew-epstein-3b22a471/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 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   TopicsIntroduction - 0:00April Lindauer, GC at Carta, on scaling legal from 200 to 2000 employees post-Series C – 0:35Adam Becker, Head of Legal Ops at Cockroach Labs, on building connective legal infrastructure and enabling smarter AI adoption – 2:42David Cowen, Founder of The Cowen Group, on legal ops maturity and leading in the age of AI agents – 4:54Tommie Tavares-Ferreira, Chief Strategy Officer, Lawtrades, on aligning legal priorities with business impact and enabling cross-functional trust – 8:52Jordan Hatcher, Co-Founder & CLO/COO, The Grid, on scaling legal internationally and staying grounded through hypergrowth – 14:11Connect with us: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.