What keeps today’s general counsel up at night, and what gets them out of bed in the morning?
In GC Sidebar, Paragon Legal’s Trista Engel sat down with senior legal leaders from Grammarly, GE Vernova, Intercom, Circle, Ironclad, and more to find out.
Across every conversation, one theme stood out: The modern GC isn’t just managing complexity — they’re redefining how legal delivers business impact.
Here’s what’s shaping the next generation of in-house leadership — straight from the GCs living it.
Artificial intelligence is reshaping the legal landscape, and not always comfortably.
“AI is the one biggest change in the last five to ten years that’s impossible to ignore.” — Jennifer Miller, Grammarly
While augmentation tools boost efficiency, Miller noted,
“It’s hard because some of these tools are not people-replacement ready. That leads to a really uncomfortable tension where you have to do more with less.”
JFrog’s Shanti Ariker echoed that tension, asking:
“Will we become more efficient, or will we be at risk because of bias, copyright issues, and more?”
Others see opportunity instead of risk:
“Technology doesn’t replace; it enhances,” said Rich Foehr, GE Vernova,
while Intercom’s Ji-Hyun Park called the moment “so fun,” though it requires “getting your hands dirty.”
Takeaway: AI isn’t just a new tool; it’s redefining how legal teams deliver value.
Shrinking budgets and rising expectations have become the new normal.
“The ‘do more with less’ has now been put on steroids.” — Mark Kahn, GC, Oakland Ballers
Heather Stevenson, Red Cell Partners, warned that the flood of new tools can “overwhelm and distract from actually making an impact.”
For many GCs, the solution is focus.
“Simplify,” advised Foehr. “If you can simplify communication, you become more reliable as a trusted partner.”
Ron Bell, Collective Health, added, “You don’t have to win every battle, just the ones that matter.”
Takeaway: Discernment is the new productivity.
Today’s GCs see themselves as part of the business engine, not just advisors.
“I view myself as a business executive with a legal lens.” — Jennifer Miller, Grammarly
“GCs are the dot connectors, they know what all the functions are trying to achieve.” — Sarah Wilson, Circle
Leadership now means translating legal judgment into business impact.
“If you don’t have [the business’s] trust, even excellent legal advice will go ignored.” — Stevenson
“You have to frame your initiative in a way that’s impactful to the listener.” — Andrew Epstein, Demandbase
Takeaway: The best GCs aren’t just protecting the business, they’re driving it forward.
Behind every successful GC is a strong team — and a clear sense of purpose.
“Who’s here because of you?” — Jaci Lee, Flynn Group
A reminder that mentorship and culture are lasting legacies.
“I have to be values-aligned with whatever work I’m doing.” — Jasmine Singh, Ironclad
“Be the company’s steady hand. No one wants a GC running around with their hair on fire.” — Sarah Wilson, Circle
“You don’t need to be reactive, you need to be patient and solution-oriented.” — Bita Goldman, UNiDAYS
And for Eunice Buhler of G2, leadership is about loyalty and longevity:
“My greatest pride and joy is my legal team. We’ve rebuilt contracts from scratch, solved problems together, and had no turnover.”
Takeaway: Resilience and empathy are the quiet superpowers of modern legal leadership.
Change isn’t just something GCs manage; it’s something they embody.
Heather Stevenson (Big Law to juice entrepreneur), Mark Kahn (WhatsApp to baseball), and Delida Costin (GC to founder) all shared how stepping off the expected path transformed their careers.
“Sometimes you have to get off the track to survive on the new one.” — Delida Costin
Takeaway: Reinvention isn’t failure, but adaptation.
Across every story runs a single truth: today’s GC is a strategist, translator, and humanist.
“Being a GC now isn’t about issue-spotting,” said Ron Bell. “It’s about navigating ambiguity.”
The future doesn’t belong to the loudest or the most technical; it belongs to the calmest, clearest, and most connected leaders who can see both the business and the human story at once.
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