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

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.

Ep 105: Punishing the Victim: What’s Broken in Cybersecurity Law

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.

Ep 104: Jack of All Trades, Master of Risk: How Joon Park Navigates Modern Legal Work

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.

Ep 103: Building What Doesn’t Exist Yet: Inside the Legal Career of Tommie Tavares-Ferreira

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.

Ep 102: What Comes After Legal Ops? A Conversation with David Cowen

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.

Ep 101: How Legal Ops Became the Center of Strategy with Adam Becker, Cockroach Labs

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.

Ep 100: Community as Strategy: Your Guide to Growth with Tyler Finn

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.

Ep 99: Resilience, Wellness, and the Law: Keita de Souza on Building a Sustainable Legal Career

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"

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