In this episode of GC Sidebar, Heather Stevenson, General Counsel at Red Cell Partners, a venture capital firm and incubator building technology-led companies in healthcare, cybersecurity, and national security, joins host Trista Engel for a sharp conversation about doing more with less, choosing tools that actually move the needle, and why trust with leadership is the linchpin of effective in-house counsel.
From Big Law at Sullivan & Cromwell to launching Thirst Juice Co. in Boston, then returning in-house at Boston Globe Media before stepping into her first GC role at Red Cell Partners in 2022, Heather shares how an entrepreneurial detour sharpened her business instincts and impact as a GC. She reflects on making legal advice actionable through trust, avoiding shiny-object distractions in the AI tooling wave, and the mindset she builds outside work, after 15 marathons and training for her second ultra, to stay resilient and focused.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Heather Stevenson, General Counsel at Red Cell Partners.
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 Heather Stevenson, General Counsel at Red Cell Partners, a venture capital firm and incubator for technology-led companies in healthcare, cybersecurity, and national security.
Heather began her legal career at Sullivan & Cromwell, then took an entrepreneurial detour to launch Thirst Juice Co., a plant-based juice and smoothie business in Boston. She later returned to law in-house at Boston Globe Media, and in 2022 stepped into her first general counsel role at Red Cell Partners.
From complex litigation, to green juice, to media, to startups, Heather’s career path is anything but ordinary. Heather, I’m excited you’re here. Thanks for joining me.
Heather Stevenson:
Thanks so much for having me.
Trista Engel:
Let’s jump in. What is the biggest challenge facing GCs and in-house legal teams today?
Heather Stevenson:
I think doing more with less has always been one of the biggest challenges facing legal teams. What’s new is that we now have so many tools and options available that it can become overwhelming, and sometimes distracting from actually making an impact.
In the past it was just a question of who you leverage for what. Now it’s also which tools, which AI, and how do you make sure the tools you choose aren’t just shiny objects, but actually help you get more done.
Trista Engel:
That’s a great take. It’s not just that “do more with less” is harder because the work and company complexity has increased, it’s also that the abundance of solutions can make choosing the next step its own challenge.
Heather Stevenson:
Exactly.
Trista Engel:
What’s the most valuable lesson you’ve learned as a GC?
Heather Stevenson:
That building trust with your internal team, and especially with leadership, is your number one priority. If you don’t have their trust, even excellent legal advice will go ignored. I’ve seen it happen, lawyers giving great advice that wasn’t followed because the business didn’t fully trust them.
In contrast, if you’ve built that trust, your advice gets listened to. And it also gives you credibility in tougher situations, like when you have to tell someone they can’t do something they want to do, or can’t do it the way they hoped.
Trista Engel:
That’s such a great point. The soft skills matter just as much as the substantive ones.
What’s one career moment that changed your trajectory?
Heather Stevenson:
In 2014, I had a big career moment when I decided to leave Big Law in New York, move home to Boston, and start a juice bar.
At the time, I thought I was switching from lawyer to entrepreneur, but it turned out to be a really rewarding detour. It put me on the path to becoming an in-house lawyer, and ultimately, a GC. One with real business experience to draw on.
That perspective has made me far more impactful than if I’d only had Big Law training as a litigator. That experience was valuable, but very different than what I learned running a business.
Trista Engel:
That resonates with me. My career path has also been a little non-traditional, and I agree, stepping off the expected path can make a big difference in both your legal skills and perspective.
What’s something people watching might not know about you?
Heather Stevenson:
I’m a distance runner, maybe not the fastest, but definitely competitive. I’ve run 15 marathons and I’m currently training for my second ultra.
It started as something I did for health and mental health, and more recently it’s become about setting big goals completely outside of work. Things like qualifying for Boston, or running Rim-to-Rim-to-Rim in the Grand Canyon.
These goals don’t make me a better lawyer, but they give me something to aim high for, and a real sense of accomplishment when I achieve them. And even if I don’t, at least I tried.
Trista Engel:
That’s amazing. Congrats on all of those accomplishments, and good luck with the training. I’m sure it’s fun, hard, time-consuming, all the things.
Heather Stevenson:
All the things. Thank you.
Trista Engel:
Alright, bonus question. Who is your favorite fictional lawyer?
Heather Stevenson:
I know there are a lot of popular answers I could give to sound impressive, but honestly, I love Elle Woods. She’s my favorite because she represents two things I admire.
First, not being what she appears. She comes across as ditzy, maybe not very smart, but she’s incredibly impactful. And second, she leans hard into who she is and is still effective. I think we could all use more examples of lawyers like that.
Employee Portal
Apply