Why is technology the right leverage point for improving how a legal team works together? What did it take to start and sustainably grow SpotDraft? And how do you transition from a more traditional legal career to one leading a legal tech business?

Join Shashank Bijapur, SpotDraft’s Co-Founder & CEO and Akshay Verma, SpotDraft’s COO as they sit down with Tyler Finn at the SpotDraft Summit 2025 and break down their journeys from lawyers to tech executives and legal innovators.

Listen as Shashank and Akshay discuss the origins of Spotdraft, offer their expert predictions on the future of legal work and AI, explain why legal operations professionals should aim for COO roles, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-91

Topics
Introduction: 0:00
What inspired Shashank to start SpotDraft: 2:38
Leading strong customer success teams: 4:40
Approaches to fundraising: 6:38
Looking back on Legal Ops at Facebook: 9:14
Where is the legal ops profession headed?: 11:45
Hiring a legal ops professional for COO roles: 13:06
Seeing yourself as a lawyer in the business world: 15:48
Building balance on an executive team: 18:19
Advice to lawyers looking to pivot: 21:27
How AI will evolve the way in-house teams work?: 25:06
Will lawyers accept AI risks?: 27:52
The future of law firms and AI: 32:50
Rapid-fire questions: 38:52

Connect with us:
Shashank Bijapur - https://www.linkedin.com/in/shashankbijapur/
Akshay Verma - https://www.linkedin.com/in/akshay-verma-esq/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft

SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management needs.

Visit https://www.spotdraft.com [https://www.spotdraft.com/] to learn more.

Ep 91: Why Legal Work Will Never Be the Same with SpotDraft’s Shashank Bijapur and Akshay Verma

How do you make the transition from IP lawyer to general counsel in a typical path? Help Adobe navigate a transition to the cloud, and then the AI era? And make time for your family through all the ups and downs?

Join Dana Rao, former general counsel at Adobe and IP and Licensing expert at Microsoft, as he discusses how he capitalized on his electrical engineering background to skyrocket himself from a patent attorney to the forefront of some of the most consequential technology decisions of the last two decades—including topics like copyright, AI, litigation, and more.

Listen as Dana explains how he became invaluable to Janet Reno’s justice department, how to make ethical business decisions, influencing legislation to combat patent trolls, and more more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-91

Topics
Introduction: 0:00
Relaxing and writing after retirement: 2:23
Transitioning from electrical engineer to DC lawyer: 10:51
Doing the right thing for your company and the world: 21:48
Leaving politics to become tech counsel: 27:21
Combating patent trolls: 36:03
From Microsoft to Adobe general counsel: 41:42
Rapid-fire questions: 51:48

Connect with us:
Dana Rao - https://www.linkedin.com/in/dana-rao/
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 90: From Engineer to Top Lawyer at Adobe and Microsoft with Dana Rao

How do you build a legal marketplace with more than 75,000 community members? Find the right investors to join you on the journey? And help the business navigate the inevitable pivots that will come along with its growth?

Join Hannah Konitshek, COO and Founder of Legal.io, Business Operations and Strategy, as she dives deep into the business of legal tech, and how a relationship built during a hackathon transformed into the premiere marketplace for in-house legal talent.

Listen as Hannah explains how attending law school in San Francisco guided her legal career, founding and growing a start-up with a legal background, how to balance your convictions with investors, and learning that the biggest risk is not taking a big enough swing.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-89

Topics
Introduction: 0:00
Going into legal tech directly from law school: 2:10
Do law schools prepare students for careers outside big law?: 6:25
Getting started with Legal.io: 9:20
Defining yourself as a “second-term founder”: 11:31
Hannah on conviction and experimentation: 14:50
Approaching fundraising: 19:06
Advice to business leaders on pivots: 23:21
How Legal.io works with AI: 28:45
Upcoming trends in the legal hiring market: 30:47
The future of Legal.io: 36:04
Rapid-fire questions: 37:29

Connect with us:
Hannah Konitshek - https://www.linkedin.com/in/hannah-konitshek/
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 89: From Hackathon to Legal Game-Changer with Hannah Konitshek, Founder, Legal.io

How do you make the transition from federal prosecutor to security leader? Help secure some of the world's largest technology companies? And build yourself back up after being convicted by a federal jury for your company's handling of a data breach?

Join Joe Sullivan, CEO of Joe Sullivan Security and the non-profit Ukraine Friends, as he reflects on the trial and sentencing he endured for a data breach at Uber to interpret the manifold challenges the chief security officers face each day.

Listen as Joe shares his journey from the first full-time cyber federal prosecutor in the country to legal and security leader at eBay, Paypal, Facebook, Uber, and Cloudflare, why lawyers need to work closely with security teams, the relationship between security and privacy, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-88

Topics
Introduction: 0:00
Becoming the CEO of Ukraine Friends: 2:43
Getting a start in cyber: 13:55
Transitioning from tech-savvy prosecutor to trust and safety at eBay and Paypal: 17:18
Taking on security at Facebook: 22:20
The challenges that face chief security officers: 24:03
How legal teams and security can work better together: 26:23
The difference between a chief security officer and a CISO: 30:03
Navigating the fallout of the data breach at Uber: 32:02
Working at Cloudflare during the Uber trial: 37:21
Building a private security practice: 38:28
Joe’s biggest learnings from the trial: 44:01
Rapid-fire questions: 46:08

Connect with us:
Joe Sullivan - https://www.linkedin.com/in/joesu11ivan/
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 88: From Prosecutor to Security Leader – Joe Sullivan (ex-CSO: Uber, Facebook, Cloudflare)

What role does integrity need to play in your company's culture? How can legal teams and corporate leaders foster it? And where do you get started if you want to write a book on it?

Join Rob Chesnut, author of Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution, as he discusses his path from prosecutor at the Department of Justice to tech industry legal leader at eBay, Chegg, and Airbnb, and how integrity and ethics became the cornerstone of both his career and his personal philosophy.

Listen as Rob discusses scaling global legal teams for some of the biggest disruptors in the world, embedding integrity into your company’s corporate culture, transitioning from general counsel to author and thought leader, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-87

Topics
Introduction: 0:00
Transitioning from prosecutor to tech counsel: 2:12
Joining eBay in the early years: 4:13
Building eBay’s trust and safety functions: 5:01
Making the leap to general counsel: 7:21
Reflecting on mentorship: 9:13
Knowing when to move on to new opportunities: 13:13
Leading legal at Airbnb: 15:50
Signature interview questions: 20:56
Developing the “Chief Ethics Officer” role: 23:04
Writing Intentional Integrity: 32:10
How a company can start their integrity program: 34:31
The changing integrity landscape: 41:13
How to contact Rob: 42:50
Rapid-fire questions: 44:07

Connect with us:
Rob Chesnut - https://www.linkedin.com/in/robchesnut/
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 87: Building a Culture of Integrity with Rob Chestnut, former Airbnb Chief Ethics Officer

Why build a big tent community of in-house lawyers without restrictions on who can join? How do you manage the transition from in-house lawyer to founder? And can you keep space for your religious faith during the process?

Join Shai Mehani, co-founder and CEO of In-House Connect, as he shares why he left his career as a corporate counsel behind to lead a thriving community of more than fifty thousand in-house lawyers that offers connection, education, professional advancement and more.

Listen as Shai discusses his journey from matrimonial law to corporate counsel, transforming a regular meetup for lawyers into an extraordinary organization, finding unexpected benefits in fractional work, the best way to quit a job, and the importance of prioritizing personal faith and family over your career.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-86

Topics
Introduction: 0:00
Why Shai went to law school: 2:46
Starting his legal career in matrimonial law: 5:34
The beginnings of In-House Connect: 12:49
Expanding beyond NYC and online: 19:45
Taking an inclusive big tent approach: 23:47
Taking on fractional work: 30:15
Going all-in on In-House Connect: 36:52
The best way to quit job: 42:47
Finding guidance in your faith: 46:00
What’s next for In-House Connect: 50:09
How to contact Shai and get involved: 55:29
Rapid-fire questions: 56:17

Connect with us:
Shai Mehani - https://www.linkedin.com/in/shaimehani/
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 86: Why In-House Lawyers Need Each Other with Shai Mehani, CEO In-House Connect

What if you never really wanted or expected to become a lawyer? How do you navigate imposter syndrome? And where do you find meaning in your work?

Join Ryan Nier, General Counsel, Chief Compliance Officer, and Head of People at Nova Credit, as he shares his career path from being a self-taught computer programmer who founded his own start-up to a decade as a litigation associate at a global law firm, eventually landing as a general counsel at companies with a positive impact on the world.

Listen as Ryan discusses his struggles with imposter syndrome, feeling like the only person in the room with a unique background, hiring great people for roles you’ve never done before, and his side project of creating a documentary podcast about the time he and his brother dug up some (literal) buried gold.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-85

Topics
Introduction 0:00
Starting as a software engineer: 2:17
Enrolling in law school: 5:34
Managing imposter syndrome: 9:58
Hiring diverse talent: 16:44
Why representation matters: 23:42
Transitioning to in-house legal: 27:08
Making the leap to general counsel: 32:22
Expanding beyond legal into the people function: 39:52
Creating and hosting a podcast about your family: 45:18
Rapid-fire questions: 53:30

Connect with us:
Ryan Nier - https://www.linkedin.com/in/ryannier/
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 85: From Coding to the C-Suite with Ryan Nier, GC Nova Credit

Is it possible to carve out a meaningful career in law by following your passions? What's harder: building a non-profit or a business? What do lawyers have to learn from animators?

Join Adam Stofsky, CEO of Briefly and founder of the New Media Advocacy Project, as he shares how he used high-production documentary video to advocate for human rights across the globe and started a company to help lawyers better communicate with their clients.

Listen as Adam discusses the challenges of non-litigation career paths, founding nonprofit and for-profit companies, the trauma of human rights work, working with creative professionals like animators and voice actors, the importance of bearing witness to human rights abuses, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-84

Topics:
Introduction: 0:00
Why Adam wanted to become a lawyer: 2:29
Starting your career at Debevoise & Plimpton: 5:48
Transitioning into human rights work: 7:20
Founding the non-profit New Media Advocacy Project: 10:48
Dealing with the challenges of human rights advocacy: 17:52
Adam’s biggest accomplishments at NMAP: 23:18
Living on a farm in Upstate New York: 26:20
Founding Briefly: 33:38
Helping lawyers communicate better: 43:46
Lessons from creative professionals: 47:26
Expanding Briefly’s customer base: 50:27
Rapid-fire questions: 56:33
Book recommendations: 59:20

Connect with us:
Adam Stofsky - https://www.linkedin.com/in/adamstofsky/
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 84: Why Lawyers Struggle with Communication with Briefly CEO Adam Stofsky

What does 2025 hold for legal tech and the legal ops profession? Will legal ops ever become a standard part of every in-house legal team?

Join us in this very special episode as Tyler invites Kevin Cohn, Chief Customer Officer at Brightflag, and Matt Wheatley, VP of Client Strategy at Priori, for a very special, no-holds-barred discussion about  legal operations in an ever-changing industry.

Listen as Matt and Kevin share their thoughts on legal ops conferences, gender and wage disparities, whether legal ops is more of a legal role or an operational role, 2025’s uncomfortably tight labor market, AI disrupting the legal ops field, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-83

Topics:
Introduction: 0:00
Working with customer advisory boards: 3:11
Are there too many legal ops conferences?: 12:34
Connecting GCs and legal ops professionals: 20:10
Analyzing survey data: 34:52
Do you need a JD?: 40:28
Thoughts on hiring: 46:57
AI in the legal landscape: 53:04
Market consolidation: 57:19
Rapid-fire questions 1:04:44

Connect with us:
Kevin Cohn - https://www.linkedin.com/in/kevinacohn/
Matt Wheatley - https://www.linkedin.com/in/matthew-wheatley-288146a2/
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 83: The 2025 Legal Ops Playbook with Brightflag’s Kevin Cohn & Priori’s Matt Wheatley

How do you build a fintech juggernaut and redefine how employees think about ownership in businesses, navigate regulatory roadblocks along the way, and build a global team to make it happen?

Join April Lindauer, General Counsel at Carta, as she discusses her start-up’s tremendous journey from 200 employees to more than 2000, as the software platform that allows users to manage equity, build businesses, and invest in the companies of tomorrow as they expand into an ever-growing list of international markets.

Listen as April offers tips for working with regulators, navigating several financing rounds, building out legal operations, working with great outside partners, and hiring the perfect team, and much more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-82

Topics:
Introduction: 0:00
Joining Carta and overseeing tremendous growth: 1:58
Cultivating a career in financial services: 4:10
Carta’s growth from 200 employees to 2000: 6:26
Transitioning from deputy general counsel to general counsel: 8:23
Hiring for a global legal team: 12:30
Navigating the GC role during the COVID-19 pandemic: 14:34
Working with the executive team to make tough decisions: 16:57
Working with financial regulators: 18:22
Leading legal through multiple financing rounds: 22:21
Leveraging Carta’s wealth of data: 24:21
Rapid-fire questions: 27:48
Book recommendations: 29:00
What you wish you’d known as a young lawyer: 30:36

Connect with us:
April Lindauer - https://www.linkedin.com/in/april-lindauer-2174104/
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 82: How Carta Built a Legal Team from Scratch & Scaled 10X with April Lindauer, GC

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

SpotDraft's Show

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

SpotDraft

Shows