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Pearl Takes Home the First Green Jacket

A conversation with Pearl Chan

By Zak Biggs

From the ShamWow to billion-dollar cannabis deals — Pearl Chan’s legal career has been anything but boring. Zak Biggs spoke with her about flexibility, loving work, and being named 鶹Ƶ of the Year.

ZB: You’ve worked in energy, tech, cannabis and even psychedelics. What’s that kind of range taught you?

PC: I started out as sole counsel for a company that sold infomercial products — remember ShamWow? Eventually, I somehow found myself in the role of public company GC, negotiating and closing what was, at the time, the biggest cannabis merger in U.S. history.

It’s been a wild ride! But those experiences taught me that no matter the industry, what makes you valuable as counsel is when you find out what the business wants to accomplish, and using a combination of your legal and business expertise, helping them find a way. Being in the trenches with your team, solving problems together, building something real, that’s what’s always drawn me to in-house. ZB: What drew you to try fractional?

PC: I was a newly single mom looking for a new role structure that fit my life. One night, I googled “fractional in-house counsel.” I reached out to several providers, but when I spoke to Pauline and the 鶹Ƶ team, I knew – this is it.

ZB: What do you like about this model?

PC: It lets me focus on the parts of law I love: solving business problems, working closely with clients, being part of the team. I also get to be more intentional about the work that I do and the clients I work with. I don’t have to deal with business development, invoicing, or internal politics. Just the good stuff. Before joining, I had a wish list. I wanted remote work. Flexible hours. Sophisticated clients who appreciated me. Work I loved. A comfortable living. I didn’t think it was possible, but I’ve been able to tick off all five.

ZB: You were just named 鶹Ƶ of the Year — how does that feel?

PC: It’s been surreal. Honestly, I already felt like I had won. This career shift changed my life. The award is just the cherry on top.

ZB: If you could change one thing about the legal profession…

PC: I’d make it more human. People expect in-house lawyers to be all-knowing, but I think the best ones are collaborators – they say, “I don’t have all the answers, but let’s figure it out together.”

Connect with Pearl Chan on LinkedIn and check out the full list of Future of Law Award winners here .

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