In Episode 4 of GC Sidebar, Jasmine Singh, General Counsel at Ironclad, joins host Trista Engel for a candid and energizing conversation about navigating today’s evolving legal landscape. From redefining what success looks like in a legal career to leading through complexity and change, Jasmine shares how values, clarity, and curiosity have shaped her path, and how AI is transforming both the work and the role of the GC.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Jasmine Singh, General Counsel at Ironclad
Trista Engel:
Hi! I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Jasmine Singh, General Counsel at Ironclad, a leading AI-powered digital contracting platform for legal teams.
Jasmine began her legal career in Big Law as a litigator in San Francisco before moving in-house at 24 Hour Fitness, Pinterest, and Patreon. She stepped into her first General Counsel role at Binti in 2022 and joined Ironclad as GC in 2024.
Along the way, she has also found time to be a spin instructor and founder of The Dinsert Movement, a decentralized philanthropy initiative supporting local nonprofits.
Jasmine, I’m so excited to have you here. Thanks for joining.
Jasmine Singh:
Thanks so much for having me. I’m also really excited to be here.
Trista Engel:
Awesome. Let’s dive in. What’s the biggest challenge facing GCs and in-house legal teams today?
Jasmine Singh:
I think we’re living in an incredibly unique moment. We’re in the middle of a huge technological revolution with AI, and we’re also at a unique phase in terms of the greater geopolitical and socioeconomic environment. It’s also a very unique moment for the legal profession. All of these things are happening at once, and navigating them simultaneously is complicated.
GCs have to consider how their teams use AI, how AI is governed across the enterprise, how companies are developing AI products, and the broader implications of global shifts on the employee base. Legal isn’t just about risk mitigation, it’s also about value maximization. We play a dual role.
And we’re being asked to do more, with tighter resources and shorter timelines. It’s an exciting but not easy position.
Trista Engel:
Absolutely. And I can’t help but think that you’re in an even more unique position in the Venn diagram of AI and legal, given that your company provides AI to legal teams.
Jasmine Singh:
Absolutely. We think and talk about this all the time. Internally, we have conversations about how to ethically absorb, adopt, and use legal AI. We also talk to customers about how they can do the same and navigate best practices.
Legal is in a fascinating position, we’re both the gatekeepers for AI and super users of it. We partner with security to decide how AI comes into the organization and how it’s governed, all while using it ourselves. Not many teams sit at that intersection, and it gives us a unique vantage point.
Trista Engel:
It really does. You have a head start on encouraging adoption and leveraging AI. That’s very cool.
Jasmine Singh:
Yeah, it’s really fun.
Trista Engel:
What’s the most valuable lesson you’ve learned as a GC?
Jasmine Singh:
There have been so many, but one of the most important is understanding the objective behind the work or the issue. What’s the goal? What’s the business trying to do?
You need to know the company’s direction intimately , not just in a high-level way. You have to be specific so that you can offer alternatives and see around corners. And then you need a North Star, a sense of what’s right for the company overall.
Sometimes what you’re being asked might not align with what’s best for the business. As GC, you always have to think: what’s best for the company? That keeps your compass straight.
Having that clarity has helped me stay grounded, feel fulfilled in my work, and maintain a consistent approach to risk. It’s not about doing the politically easiest thing , it’s about doing what’s right.
Trista Engel:
I love that , the way you talk about staying grounded in what’s best for the business, and bringing your legal brain to bear on it. That orientation makes all the difference.
Jasmine Singh:
Absolutely.
Trista Engel:
What’s one career moment that changed your trajectory?
Jasmine Singh:
Quitting my job and becoming a spin instructor.
I had been a litigator at big firms for almost eight years. I was so narrowly focused on just getting to the next year, doing the work, and climbing the ladder. I never stopped to ask what I actually wanted to do. I was operating out of obligation, student loans, expectations, the grind.
Eventually, I realized I wasn’t happy. I didn’t like being a lawyer at the time. I thought I was bad at it. So I quit. My fiancé was in Las Vegas, and I moved there with no plan.
I sat around for two weeks, convinced I had ruined my career. But I started making lists: what do I love? Who do I want to be?
Fitness had always been a passion, so I got certified and started teaching spin classes at 6 a.m., three days a week. And it was amazing. I felt fulfilled. People were grateful. It reminded me how important values alignment is in work.
Eventually, I realized I did want to be a lawyer , just in a different environment. That’s what led me to go in-house, starting with a fitness company, which felt like the perfect bridge.
Trista Engel:
That is fantastic. It really does take a lot of courage to step off the path, especially when you’re driven and high-achieving. I love that it helped you find your alignment and speed up, not slow down.
Jasmine Singh:
Yeah. And it wasn’t easy. I was definitely self-conscious at first, I worried people would think I failed. But now I tell this story to show that sometimes success means stepping away, not pushing harder.
If something’s not working, don’t force it. Go where you fit.
Trista Engel:
That’s amazing. Good for you.
If you weren’t an attorney, what would you be?
Jasmine Singh:
Definitely a toss-up between a fitness instructor or something in the dance world. I was a competitive Bhangra dancer and a hip hop dancer for a long time.
In one alternate universe, I’m a backup dancer for Rihanna or Justin Timberlake. In another, I’m a talk show host or professional panelist. I love talking to people, hearing their stories, and creating space for others to learn. So something in that space would be my path.
Trista Engel:
That’s amazing. Given the amount of travel and conferences you’ve done this year, you’re well on your way to professional panelist status.
Jasmine Singh:
Let’s see what qualifies. Maybe we’ll send this to the Today Show and find out.
Trista Engel:
And the bonus question , who’s your favorite fictional lawyer?
Jasmine Singh:
I loved Suits, especially early in my big law days. Every now and then I’d be watching it thinking, “I want to be a lawyer,” and then I’d remember, “Oh wait , I am one.”
My favorite character was Jessica Pearson. She was a boss , always five steps ahead, strong, fearless. I just really admired her character.
Trista Engel:
Totally agree. That was really fun, Jasmine. Thank you so much for joining me and for sharing your journey and your stories.
Jasmine Singh:
Thanks so much for having me. This was really fun.
Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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