Brandon McGathy – Jeeves

For Brandon McGathy, the allure of in-house law was always about building—teams, frameworks, and trust. As general counsel for Jeeves, he has done all three. When he joined the global financial platform in 2021 as one of its early employees, Jeeves was an ambitious fintech startup with a small legal department, global subsidiaries, and a rapidly expanding international footprint. Today, it operates globally with more than 150 employees, and Jeeves’ legal, regulatory and compliance functions have become a cornerstone of that success.

Brandon McGathy | Jeeves | General Counsel

Jeeves is redefining how global businesses manage money. Its all-in-one platform allows companies to open multi-currency accounts, issue corporate cards, send cross-border payments, and manage expenses seamlessly. Backed by leading investors including Y Combinator, CRV, and Andreessen Horowitz, the company’s technology adapts to businesses of any size and stage, streamlining complex financial operations that traditionally required multiple vendors and currencies.

As the company matured, McGathy’s challenge was clear: design a legal structure as nimble as the platform itself.

“When I came on board, we needed to put a corporate governance structure together, handle debt financing, and guide the Series B and C rounds—all while creating a legal function built for a global company.”

What began as a small legal function is evolving into a high-impact team that integrates directly into Jeeves’ leadership decisions. That proximity to the business is exactly what McGathy imagined.

“Historically, legal was a responsive unit,” he says. “Now, we’re becoming a bigger part of those decisions from the beginning.”

Navigating expansion in Latin America

Jeeves’ rapid expansion has taken it deep into Latin America—specifically Brazil, Colombia, and Mexico—markets rich with opportunity but complex in their regulatory expectations. Jeeves’ legal and compliance roadmap has become essential in ensuring the company’s long-term capabilities.

“In Latin America, the goal is to secure fintech and banking licenses in each country,” he explains. “Right now, we rely on licensed partners, which works, but our priority is to become as independent as possible.”

Those licensing efforts, he adds, can take years, especially in markets where fintech regulation is still maturing.

To manage this, McGathy has been methodical in building a local presence. Jeeves’ first regional hire was in Brazil, followed by plans to add team members in Mexico and, perhaps someday, elsewhere. Each addition reflects not just growth, but trust.

“The process of hiring in Latin America is different,” he says. “Resumes don’t always tell you what you need to know. You must understand how their experience fits what we do, ask scenario-based questions, and determine how they’ll react in a startup environment.”

He looks for people who can thrive amid change. Some people can ride that wave; others get freaked out. At a startup, the pace of change can be intense, and you need people who adapt quickly, he explains.

That adaptability is critical as Jeeves positions itself for greater autonomy in regulated markets. With Latin American fintech oversight tightening, having localized legal expertise allows the company to move faster, anticipate shifts, and maintain compliance while scaling.

Launching innovation, legally & strategically

While licensing and compliance efforts run in the background, McGathy’s team also plays a central role in Jeeves’ product innovation—most notably its cross-border stablecoin launch. The initiative aims to streamline money movement for customers and improve cross-border transaction speed across Jeeves’ geographies.

“Two years ago, a project like this would have taken the whole company,” McGathy says. “Now we have the right people and processes to get it done quickly and efficiently.”

He strives for the legal function to operate like an internal accelerator, enabling innovation rather than slowing it down.

“We focus on solving problems, not just identifying them,” he explains.

The stablecoin launch reflects Jeeves’ broader ambition to lead in international payments while maintaining regulatory confidence. It also shows how the legal department’s evolution has paralleled the company’s own—moving from reactive support to proactive strategy.

In parallel, McGathy’s team is creating new special-purpose entities to support international financing partnerships. These structures allow Jeeves to generate revenue in creative, compliant ways across different jurisdictions.

“Every country has its own rules,” he says. “By tailoring our entities, we can operate efficiently and legally while continuing to innovate.”

This dual focus—facilitating innovation while ensuring regulatory soundness—embodies what McGathy calls a “business-forward legal mindset.” It’s a philosophy that helps Jeeves maintain its agility while preparing for greater maturity and scrutiny.

“This year we became a more mature unicorn,” he says. “We already have great products; now we’re refining how we deliver them faster and tailor them for larger clients.”

As Jeeves looks ahead, its focus is on building the next layer of scaffolding for even greater growth in 2026. This year has been about momentum—strengthening its foundation, refining its structures, and aligning cross-functional teams worldwide. A key example is the rollout of a more unified customer strategy: working to ensure every new customer is on subscription, no matter what they purchase from Jeeves. It’s a move that reflects a deep commitment to predictability, accountability, and scale. In parallel, Jeeves is deepening investments in key strategic partnerships to build a tightly integrated channel ecosystem that will secure future revenue streams and reinforce platform resilience. “Together, these initiatives mark a major step forward in maturing Jeeves’ operations and setting the stage for its next phase of global expansion,” says McGathy.

Leadership, learning & the joy of building

McGathy’s path to the general counsel’s chair was anything but linear. Raised in Michigan and later Florida, he first encountered the law on his way to becoming an Eagle Scout through local mentors—Boy Scout troop leaders who practiced law in his small hometown.

“I appreciated that good, thoughtful lawyers could impact things that help people,” he says.

That early inspiration carried him through a business degree at the University of Central Florida and a J.D. at Boston University, where he focused on finance and corporate law.

After graduation, he joined Ropes & Gray in Boston, launching his career in private equity and M&A. He thrived in the firm’s demanding environment and eventually helped build its West Coast private-equity practice.

“One of my favorite parts of private practice was mentoring junior associates,” he recalls. “It was one of the hardest practice areas, but seeing others develop was rewarding.”

That instinct to teach and develop people has shaped how he leads at Jeeves. “I’m hands-on and try to be helpful without micromanaging,” he says. “We’re a small but mighty team, and you need to empower people to flourish.”

When evaluating candidates, his priorities have shifted since his law-firm days.

“Back then, we paid attention to schools, credentials, and big-name employers,” he says. “Now it’s about personality and problem-solving. How do they think? Can they adapt? Do they fit our pace?”

He designs onboarding plans that immerse new hires quickly in projects and people.

“With remote work, there’s no office tour,” he explains. “In Brazil, we scheduled calls for our new attorney in his first week. I wanted him to talk to the right people, get context, and feel part of the team immediately.”

That approach mirrors his own journey from law-firm hierarchy to startup chaos—a transition he embraced during the pandemic. Before Jeeves, he worked in-house through Axiom, supporting eBay’s divestiture of its European classifieds business.

“It gave me a view into how big legal departments operate and how bureaucracy affects business decisions,” he says. The experience confirmed his desire to join a smaller, faster-moving company where legal could sit at the center of strategy.

He found that at Jeeves, where his mix of legal acumen and business instinct has become indispensable.

“I really enjoy being part of the solution, not just answering questions,” he says. “Most of our issues are international, dealing with new laws I wasn’t taught in school. That keeps me fresh and makes me a better attorney.”

A lawyer’s startup mindset

Now approaching his fourth year at Jeeves, McGathy remains energized by the constant evolution of both his team and the company. He has guided Jeeves through multiple core changes, built its legal infrastructure across continents, and embedded his department into the company’s strategic core. Yet he still describes his work as a learning journey.

“You learn a lot at a startup—and fast,” he says. “I’m still finding new ways to grow.”

Outside the office, he stays connected to the broader legal and business community through a general counsel peer group and advisory work with startups. Those interactions scratch an itch for networking and mentorship that harkens back to his Ropes & Gray days.

“I miss that energy sometimes,” he admits. “Helping others navigate growth is something I’d like to do more of.”

Professionally, his long-term goal is to see Jeeves through to a successful liquidity event—perhaps an IPO—and then apply that end-to-end experience to other startups down the road.

“Seeing a company from beginning to end, through all its stages, would be incredibly fulfilling,” he says. “It’s what I’ve always wanted to do as a lawyer.”

For now, though, his focus remains on execution: expanding in Latin America and beyond, securing regulatory licenses, launching stablecoins and other new products, and guiding Jeeves through its next phases. Through it all, McGathy continues to blend the precision of a lawyer with the mindset of a builder.

“I love that every week is different,” he says. “One day I’m deep in compliance, the next I’m helping build a product. That variety keeps me learning—and that’s what keeps it fun.”