Kerrie Forbes has spent her career in some of the most complex legal airspace in the industry. Sixteen years at Southwest, leading litigation, employment law, and regulatory strategy through major transformations at America's most beloved airline.
Southwest was also her family’s airline of choice, so when it came time for Kerrie to tell her mother she was leaving the company for JSX, she was a little hesitant. Turns out, her mother had already been sending regulators letters on behalf of the small carrier. Kerrie was stunned.
“My mother is a loyal Southwest fan. I mean, she flies Southwest all the time,” Kerrie said. “She's a Southwest credit card holder. She flies all of my nieces and nephews to go visit her on Southwest. But she really thought JSX had the better argument here and I agreed.”
Now, as CLO at JSX, the fast-growing semi-private carrier that passengers can't stop talking about and regulators won’t stop trying to shut down. Her personal motto: find the right business solution, build the right relationships, and never confuse legal conservatism with legal excellence.
What JSX Is (And Why the Big Carriers Hate It)
JSX stands for Joyful Simple Experience. The company legally operates under Part 135 and Part 380 of The Department of Transportation’s public charter regulations. Benefits for flyers include a maximum of 30 passengers per flight, departures from Fixed-Based Operators (FBOs) and smaller airports, and a private TSA-approved security program that gets you from car to aircraft in under 20 minutes. Other perks? No middle seats, free drinks, and no bag fees. Reddit reviewers describe it as flying private without the price tag.
The big carriers have called the model a regulatory loophole. Kerrie is very clear on that point: it isn't.
"These are regulations that have been in existence for decades,” Kerrie said. Our business just celebrated our ninth anniversary, and we have safely and securely flown millions of passengers on hundreds of thousands of flights.”
The company's origin story is uniquely relevant to Kerrie. JSX's CEO, Alex Wilcox, was a summer intern under Herb Kelleher, the lawyer who founded Southwest and spent years fighting incumbent carriers in the process. Wilcox also co-founded JetBlue. He knew exactly which regulations would allow JSX to operate differently, built the product around them, and created something customers genuinely love. Now companies like Southwest are pushing back.
Note from CZ: I was GC on Alexa, and when I first heard what it was, I was certain it was impossible. Not every lawyer runs toward the gray area. The ones who do, and who do the work to get comfortable with it, tend to end up in the most interesting rooms.
Reading the Regulations: Why Kerrie Decided to Take the Job
Not every lawyer is built to work at an industry disruptor. Most in-house attorneys see regulatory complexity as risk to be managed rather than territory to be mapped. Kerrie decided to take a different approach when the JSX offer arrived: she read everything she could about the space. Every public filing, every regulatory briefing, and every legal argument in the public domain. She wanted to form her own view on the merits of the company before she gave them an answer.
"I felt like, you know what? I think this company's got the right argument here, " Kerrie said.
That independent conviction matters more than it might seem. Leading legal at a company that larger competitors are actively trying to shut down isn't a role for a passive personality. You have to believe in the argument you’re defending to go up against the giants and win.
Before joining an industry disruptor, ask yourself:
Have you read the actual regulatory framework, and not just the headlines?
Can you make the legal argument for the product yourself, without just repeating marketing copy?
Do you believe in the product enough to be a zealous advocate in court?
What does your gut tell you?
And, Kerrie said, if your Southwest-loyal mother has already filed public comments on the other side's behalf, you’re probably on the right track.
Note from CZ: The lawyers I most admire at companies disruptors like Airbnb and Uber all had this quality: a willingness to sit with complexity long enough to form their own opinion. That's the type of thinkers companies like JSX need.
The Orange County Playbook: Changing the Narrative
JSX had been battling the Orange County airport in court for years before Kerrie joined the company. It was the kind of standoff where both sides have dug in, there’s adversarial history, and the path forward is unclear.
“I came into it very far along in the process where this had been ongoing for a long time,” Kerrie said. “We were able to get it resolved over the course of the last year, and we just recently had a ribbon cutting!”
What changed? Kerrie decided to shake up who was in the room when they met with Orange County officials. She started by promoting Ken Edmondson internally to lead airport affairs. Around the same time, the airport got a new director. And the entire tone of the relationship shifted almost immediately.
"Changing up the people who were involved really changed the narrative,” she said. “We went in trying to be good partners, trying to understand what their concerns were, and trying to explain that we really were a good partner for them."
The case was eventually dismissed, and JSX and Orange County are now happy operating partners.
For in-house lawyers, the lesson is the importance of relationship-building, whether it be with cross-functional partners, regulators, airport officials, or other decision makers in your space. You never know when you’ll need a little bit of goodwill. And if all else fails, change up the voices in the room.
The Mindset Shift from Firm to In-House
Sometimes, in-house legal looks a lot like outside counsel with a company badge. The job is to research the law, deliver the guidance, and advocate for your position. Kerrie has spent her career building a different type of in-house legal team, and she's intentional about instilling that difference in new hires.
Kerrie describes it like this: at a firm, the goal is to know the law inside and out and fight for your client's position. In-house, however, the goal is to find the best business outcome, which sometimes means getting creative. That may include settling a case you know you could win, and almost always means maintaining a relationship you'll need long after the matter closes.
"If you're at a firm, you probably want to have the litigation because that's how you make the money,” Kerrie said. “In-house, our goal is to not get into litigation."
The shift from firm to in-house requires reframing how you look at regulation, how you approach opposing counsel, and how you advise the business. The best next move for an in-house lawyer is the one that actually moves the business forward.
Shifting your mindset from firm to in-house:
Instead of: what does the law say?
Think: what does the business need?
Instead of: we fight and win
Think: we maintain the relationship first
Instead of: be conservative to avoid risk
Think: creative solutions within the law
Instead of: racking up billable hours
Think: litigation avoidance is the best strategy
Kerrie is clear about one caveat here: when the facts warrant a fight, you fight. The skill is knowing when it’s time to go to battle versus preserve the relationship.
How AI Is Changing the Next Generation of In-House Talent
Kerrie’s daughter, Lily, recently finished her 1L year at University of Virginia. Their dinner table conversation these days is often about how AI is changing how new lawyers are trained and in-house teams operate.
“I’m using GC AI, and our intern, who doesn’t have a law license yet, uses an AI program from her school that's been helpful to learn,” said Kerrie. “Legal AI is absolutely the future. Everybody's gonna have to get on board with it, whether you like it or not."
Kerrie offers some additional advice for in-house lawyers who want to prove their value to their organization as more work is replaced by AI: say yes to the retreat, maintain the relationships, give yourself grace for the different seasons. You never know which room will change everything.
And in the meantime, start sharpening your legal AI skills and join Kerrie on GC AI! Request your custom demo or try it out for free today.
