A podcast from Checkbox

Open DoorCandid conversations on the future of in-house legal leadership.

Hosted by Somya Kaushik, Chief Legal Officer at Checkbox, the conversations legal leaders usually only have behind closed doors, with the GCs, CLOs, and legal ops leaders shaping what comes next.

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Hosted by Somya Kaushik

Listen to Open Door episode 2

Jasmine Singh inherited a very specific picture of what a successful lawyer looks like. She built her career by letting most of that picture go, moving from BigLaw litigator through pivot after pivot to the GC seat at Ironclad.

Episode overview

Jasmine Singh, General Counsel of Ironclad, joins Somya Kaushik to talk about quitting BigLaw, unlearning perfectionism and what in-house lawyers can put down in the AI era.

Main topic

The identity lawyers inherit before they ever practice, and why a profession steeped in perfection can't stand to let a single ball drop.

Guest perspective

Jasmine left BigLaw litigation to teach spin classes, then came back in-house as a builder. Her lesson is that you can be two things at once.

Key takeaway

Ego is dust in the eyes. Legal leaders see more clearly when they step back, ask what is really driving a decision and admit their own mistakes.

What comes next

Close the door on never letting a ball drop. Open the one where legal is a strategic partner that helps the business move faster.

Meet your host and guest

Somya Kaushik

Host

Somya Kaushik

Chief Legal Officer, Checkbox

A former New York trial attorney turned legal tech founder turned CLO, Somya has spent her career on both sides of the table, practicing law and building the technology that changes how it's practiced. That dual lens is what Open Door is about: legal leaders who don't just manage change, but build through it.

Jasmine Singh

Guest

Jasmine Singh

General Counsel, Ironclad

Jasmine leads legal and compliance at Ironclad and advises the company on legal product innovation. Before Ironclad, she held in-house roles at Binti, Patreon, Pinterest and 24 Hour Fitness after starting her career as a litigator in San Francisco. She serves on the boards of Public Advocates and California Change Lawyers and founded Dincert, a decentralized philanthropy initiative.

"Choosing different doesn't mean you are a failure. It just means you have the liberty of choice that maybe people who came before didn't have."
Jasmine Singh, General Counsel at Ironclad, on Open Door

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Open Door is brought to you by Checkbox, the AI front door for legal teams.