Dive Deeper
Transcript
Episode Overview
Moving from a law firm to in-house means trading "what does the law say" for "what does the business need," according to Kerrie Forbes, Chief Legal Officer at JSX.
Founded by former Southwest and JetBlue executive Alex Wilcox, JSX built its semi-private model on decades-old FAA and DOT public charter rules, growing from a scrappy startup into a carrier now marking nine years of safe, regulated flight.
That mindset shift covers business-first framing, litigation avoidance, and retraining firm-trained lawyers to think commercially, and it is how she runs legal at the disruptor that bigger carriers have tried to shut down.
About Kerrie Forbes
Kerrie Forbes is Chief Legal Officer, Corporate Secretary, and Head of Government Affairs at JSX. She spent 16 years at Southwest Airlines before joining JSX, and began her legal career at Jones Day.
Key Takeaways
Business-first thinking, not legal-only guidance, drives the in-house mindset shift. Forbes trades "what does the law say" for "what does the business need," and treats litigation avoidance as the winning strategy.
JSX's regulatory model is decades-old, not a loophole. Operating under Part 135 and Part 380 rules, the carrier has "safely and securely flown millions of passengers on hundreds of thousands of flights" over nine years, Forbes says.
A three-person legal team runs on GC AI, not headcount. Forbes, one other attorney, and a summer intern cover litigation, regulatory, employment, and government affairs work, and she credits GC AI as the biggest driver of the team's productivity.
Fight only when a fair resolution is off the table. Forbes would rather negotiate an outcome both sides can live with than run a winnable case to the Supreme Court, but she'll fight for "that fundamental sense of fairness in what's right" when the other side won't budge.
Changing who sits at the table ended a years-long standoff. When JSX promoted a new VP of Airport Affairs and Orange County brought in a new airport director, a combative legal fight turned into a partnership and the case was dismissed.
What Is JSX, and Why Are Bigger Carriers Trying to Shut It Down?
JSX (short for Joyful Simple Experience) is a semi-private carrier that operates under Part 135, the FAA's operating rules, and Part 380, the Department of Transportation's public charter regulation.
Those rules cap its flights at 30 passengers and let JSX fly from FBOs and smaller airports. They also allow a TSA-approved security program, a Twelve-Five Standard Security Program (TFSSP) rather than the major carriers' Aircraft Operator Standard Security Program (AOSSP), that gets passengers from car to cabin in minutes.
Larger carriers have attacked the model as a loophole. Forbes rejects that framing outright.
Forbes said:
"These are regulations that have been in existence for decades. ... We just celebrated our ninth anniversary. We have safely and securely flown millions of passengers on hundreds of thousands of flights."
The passenger experience explains the customer devotion Cecilia found in Reddit reviews describing JSX as flying private without the price tag: no middle seats, free drinks and snacks, free Wi-Fi, no bag fees, and 50-seat Embraer 135s and 145s converted to 30 seats of business-class legroom.
The origin story runs straight through Kerrie's old employer. JSX CEO Alex Wilcox was a summer intern at Southwest who worked directly with Herb Kelleher, the lawyer who co-founded Southwest and spent years fighting incumbent carriers to do it.
Wilcox went on to help found JetBlue, then built JSX around regulations that had been on the books for decades. Now the disruptor's playbook is being run against the descendants of the original disruptor.
Should You Take the Legal Job at a Disruptor? Do the Regulatory Homework First
Before saying yes to JSX, Kerrie formed her own view of the merits. She read the regulations, the briefing that had been submitted, and the legal arguments available in the public domain, then decided the company had the better argument.
That is the test she models for any lawyer weighing a role at a company under regulatory attack. Your conviction has to be yours, built from the source documents, because you will be the one defending it.
She said:
"I did a lot of research, a lot of reading on the regulations. I read the briefing that had been submitted, everything that was out there in the public domain that I could find. And I felt like, you know what? I think this company's got the right argument here."
Leading legal at a company that larger competitors want shut down is no role for a passive personality. Before joining a disruptor, ask yourself:
Have you read the regulatory framework itself, and not the headlines about it?
Can you make the legal argument for the product yourself, without repeating marketing copy?
Do you believe in the product enough to be its zealous advocate?
What does your gut tell you?
And, as Kerrie's story suggests, if your Southwest-loyal mother has already filed public comments on the other side's behalf, you are probably on the right track.
"She's a loyal Southwest fan. She flies Southwest all the time. She's a Southwest credit card holder. She flies all my nieces and nephews to go visit her on Southwest. But she really thought JSX had the better argument here, and I agreed."
How Do You End a Years-Long Airport Standoff? Change Who Is in the Room
JSX had been battling the Orange County airport for years before Kerrie arrived, a standoff over whether the carrier could keep operating there at all. The matter turned when new people took over on both sides.
Kerrie's team promoted Ken Edmondson to VP of Airport Affairs, and the airport hired a new director around the same time. The two sides moved from combat to partnership, the case was dismissed, and they held a ribbon cutting.
Forbes said:
"When we changed up the people who were involved, we really changed the narrative. We went in trying to be good partners with the airport and with the county, trying to understand what their concerns were, what their needs are, and trying to explain to them that we really are a good partner for you and we add value."
For in-house counsel, the relationships themselves are worth protecting. Airports, regulators, FBO landlords, and county officials are counterparties the company will deal with for years, so goodwill built now becomes leverage later.
When a matter has hardened around clashing personalities, changing who sits at the table can do more than another round of briefing.
What Changes When You Move From a Law Firm to In-House?
At a firm, the training is to know the law cold, give conservative guidance, and win the fight. In-house, the goal is the best business outcome, which can mean settling a case you would win, getting creative inside the lines of a regulation, and protecting a relationship long after the matter closes.
Kerrie has spent her career building teams around that difference, and she is intentional about instilling it in lawyers making the jump.
She said:
"If you're at a firm, you probably want to have the litigation because that's how you make the money. Our goal is to not have the litigation. My goal is to keep us out of litigation."
How she coaches lawyers making the jump:
Start from what the business needs, then find the answer the law allows.
Protect the working relationship, even when you could win the fight.
Look for creative solutions inside the regulation.
Treat litigation avoidance as the winning strategy.
She is equally direct about what being a business partner requires day to day, especially on a lean team where your office sits in the middle of the people you serve and everyone wants an answer now: triage, prioritize, learn to say no, and learn to buy time.
"It's really important to be a good business partner, to understand the business, to develop those relationships with the business people, to understand the business needs, and to be a part of the team in making those decisions."
When Should In-House Counsel Fight Instead of Settle?
Kerrie's rule is to pursue the resolution that makes sense on the specific facts, for both sides, and to fight when it becomes clear that resolution is off the table or the other side will not let go.
What is right for the company is not always the strongest available legal argument. A winnable case can still be the wrong case to run when a negotiated outcome preserves a relationship the business needs.
Forbes said:
"It might be a situation where I could take something all the way to the Supreme Court and win. But I can reach a resolution by negotiating an outcome ... where we can all live with it and be happy with it. ... And if we can't, then I'm going to fight for that fundamental sense of fairness in what's right."
Kerrie describes a strong fundamental sense of fairness as the trait that took her to law school, and playing fair as her first value, one she does not see in some of the companies trying to bring JSX down. When the facts warrant the fight, she fights.
How Does JSX's Legal Team Use GC AI?
JSX runs a strikingly lean legal department: Kerrie, one other attorney with deep aviation experience, and a summer intern. Together they cover litigation, regulatory work, employment matters, airport and FBO agreements, and government affairs.
JSX adopted GC AI about six months before this recording, and Kerrie says it has helped the team's productivity more than anything else they use.
She said:
"We just invested in GC AI probably close to six months ago, and it's been a great choice for us."
Asked separately for a productivity tip, she pointed to the same platform:
"I think GC AI is probably what's helped us the most with productivity and trying to be more efficient and effective with our time."
On a team this small, covering this much regulatory and litigation ground, a platform built for in-house legal work carries more of the load than a general chatbot could. See how other small in-house teams use legal AI to scale without adding headcount.
How Should In-House Lawyers Build AI Fluency?
Start now, learn in the open, and let the next generation pull you forward. Kerrie's daughter Lily finished her 1L year at the University of Virginia, JSX's summer intern arrived with an AI program from her school, and the dinner-table conversation at the Forbes house is how AI is reshaping legal training and in-house work.
Her read on where the profession is heading is blunt:
"It's absolutely the future. I think everybody's gonna have to get on board with it, whether you like it or not."
She predicts the change reaches beyond legal workflows to the economics of the department, including reduced outside counsel spend, without replacing lawyers. The lawyers it rewards are the ones who, like her intern and her 1L daughter, got comfortable early. Lawyers looking to build that fluency now can start with GC AI's free legal AI classes.
Is It Too Late to Change Careers After 16 Years at One Company?
No, and Kerrie is the proof. Sixteen years into Southwest, she assumed she would retire there.
A legal retreat, the same one where she met Cecilia, and a friendship with Rebecca Fike, now at Reed Smith, rebuilt her confidence and sense of purpose. When the JSX opportunity arrived, she fought the self-doubt she notes is more common among women, and took the leap.
Forbes said:
"You never know if you don't try. Last year was one of the hardest years of my career. I worked really, really, really hard, but I enjoyed every minute of it, and I feel like I'm getting more comfortable in my role this year. But I absolutely love my job."
Her advice for lawyers at any stage is to say yes to the retreat, the lunch, and the network you once skipped for the sake of the to-do list. Keep relationships alive across job changes, because in-house work runs on a network of trusted outside counsel. And give yourself grace for the different seasons of a career, because you never know which room will change everything.
Kerrie's small team relies on GC AI to cover litigation, regulatory work, and government affairs at once. Ready to try the platform her team uses with your own?
Recommended Reading
Fewer Bottlenecks, More Efficiency: Chuck Kable on What It Takes to Lead Legal in Private Equity: another in-house leader on running a lean legal department and cutting inefficiency.
How Great GCs Think About Growth, Risk, and Crisis Management: the general counsel mindset for balancing risk, business needs, and team efficiency.
AI for Startup Legal Operations: How Lean Legal Teams Scale: how small in-house teams use legal AI to handle more work without adding headcount.
