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.

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

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

Ep 114: Building Outside the Box: Monica Zent on Legal Ops, AI, and Bold Bets

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.

Ep 113: Tackling Change: Emmanuel Smith’s Journey Beyond Football

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.

Ep 112: Risk, Reward, and Reinvention: Viraj Joshi on Law, Policy, and Startups

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.

Ep 111:  Lessons from Ola’s Former GC: Leadership, Risk, and Reinvention

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.

Ep 110: From Product Counsel to Privacy Leader: Tina Hwang’s Journey

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.

Ep 109: Books That Stay With You: Legal Leaders Share Their Shelf

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.

Ep 108: Reimagining Law Firm Pricing: Ken Callander on Value, AI & In-House Strategy

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.

Ep 107: From Big Law to GC Before 35: Andrew Epstein’s Journey on Navigating Modern Legal Careers

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.

Ep 106: Scaling Legal at Speed – Lessons from Carta, Cockroach Labs, and More

Savvy and strong legal leadership is only becoming more critical in a complex world.

On The Abstract, we'll be interviewing leading legal executives about how they’ve nurtured their careers, grown in their roles, and become true operators within their businesses. At some points, we’ll deal with the pressure of leadership.

We care deeply about helping in-house counsel grow alongside each other. Join us for insightful and interesting conversations with legal leaders.

The Abstract

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Tyler Finn - Head of Community and Growth at SpotDraft and Host of the podcast "The Abstract"

SpotDraft

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