AI, compliance leadership and the future of fintech: Inside Rooted in Compliance session 2

As AI and automation continue to change the way compliance teams operate, what does this mean for the people working in the industry, and how are businesses preparing for what's next?

On October 15, Lawrence Harvey welcomed fintech compliance professionals back to its New York office for the second session of Rooted in Compliance, a community initiative led by Kendall Maylor.

Following the first session earlier this year, which focused on the changing compliance landscape, Session 2 took the conversation a step further with the theme Turning Change Into Action in the Next Era of Fintech.

The evening was moderated by Eli Green, Head of Financial Crime Strategy & Controls Architecture at Gate US, who guided discussions around AI and automation, regulatory change, digital assets and the future of compliance leadership.

With professionals bringing their own experiences and perspectives to the table, the conversation raised some interesting questions about how the industry is evolving and what that means for the people working within it.

We caught up with Kendall and Eli after the event to hear what stood out to them and what they'd like to see the community explore next.

Looking back on Session 2 with Kendall Maylor

As the driving force behind Rooted in Compliance, Kendall works closely with compliance professionals across the fintech industry. We asked her about the discussions that stood out and what they could mean for the future of compliance.

What were the main topics and challenges discussed throughout the evening?

"A big theme was how compliance leaders are navigating an increasingly complex regulatory environment while trying to keep pace with innovation. We explored the practical implications of AI and automation, the uncertainty surrounding stablecoin regulation a bit, and how compliance functions need to evolve as fintech businesses mature. What tied everything together was the challenge of balancing innovation, regulatory expectations, and accountability, particularly when the rules and technology are evolving so quickly."

Was there anything discussed that particularly surprised you?

"One of the most interesting areas for me was some conversation around the future of compliance talent. We often talk about AI replacing repetitive tasks, but less about what that means for developing the next generation of compliance leaders. If technology takes over the foundational work that many senior professionals built their careers on, how do we ensure future leaders develop the same judgment and experience? I think that's a really interesting challenge for the industry, particularly from my perspective working in recruitment."

What was your biggest takeaway from Session 2?

"Besides AI and automation, my biggest take away is that the role of the compliance leader is changing. It's no longer enough to simply understand the regulations. Leaders need to understand technology, influence business decisions, build the right teams, and navigate uncertainty, often simultaneously. I think that's also what makes bringing these individuals together so valuable. Different businesses may be at different stages of maturity, but many are navigating similar challenges, and there's a lot to be gained from sharing those experiences."

A moderator's perspective: Eli Green

Joining the community as moderator for Session 2, Eli brought his experience across financial crime, compliance and digital assets to the discussion.

We also wanted to hear about his experience of the evening, what stood out to him and why he believes bringing professionals together is particularly important as the industry continues to change.

What was your experience of moderating Rooted in Compliance?

"It was honestly a great experience. Everyone was incredibly engaging, kind, and open to sharing their perspectives. In many ways, they made my job as moderator easy because the conversation flowed naturally, everyone was attentive, and people were genuinely interested in what others had to say. That made for a really enjoyable evening and the kind of discussion that reminds you why getting people together in person is so valuable."

Having heard everyone's experiences, what stood out to you most from the discussion?

"The idea that really stuck with me was that, in the long run, the differentiator might just be the vibes. As AI makes increasingly similar capabilities available across different products and organizations, the technology itself may become less of a differentiator than we expect. How people feel working with you, the trust you build, the culture you create, and the way you show up for others can be much harder to replicate. I thought that was a really interesting and memorable point because, despite all the technological change happening around us, the human element may be what ultimately sets people and organizations apart."

What was your biggest takeaway from the evening?

"I think one thing that became clear is that, regardless of whether someone is optimistic, pessimistic, or somewhere in between when it comes to AI, almost everyone is thinking about what it means for their future. The technology is moving quickly, and it’s natural to wonder where we fit into a world that’s changing this much. For me, the takeaway is that we need to be intentional about finding ways to remain valuable, continue learning, and develop skills that complement what AI can do. That doesn’t mean competing with the technology at everything it does. It means understanding where we can bring something different to the table and how we can continue to contribute meaningfully. The landscape is changing, but I think evenings like this are a good reminder that we don’t have to figure it all out in isolation."

Why do you think it's important to have spaces like Rooted where compliance professionals can openly discuss the challenges they're facing?

"As AI continues to reshape the way we work, I think it’s important that we don’t lose sight of the human side of our profession. Technology can give us new capabilities, but there’s still enormous value in bringing people together to share experiences, challenge each other’s thinking, and learn from the things that don’t always make it into presentations or industry reports. These conversations help us grow professionally, build stronger relationships, and ultimately become better at what we do. In an industry where the stakes are high and the landscape is constantly changing, having a community where people can speak openly and learn from one another is incredibly important."

What's next for Rooted in Compliance?

With two sessions now completed, Kendall is already thinking about where the community can take the conversation next. One area she'd particularly like to explore is the future of compliance leadership, including how AI, automation and changing regulatory expectations are influencing the skills businesses need.

As Kendall explains: "Ultimately, I want Rooted in Compliance to continue evolving around the challenges that leaders are actually facing, rather than just the headlines we're seeing in the market."

That's exactly what Rooted in Compliance aims to provide: a space for professionals to share their experiences, ask questions and learn from others working through similar challenges.

A big thank you to Eli for moderating Session 2, and to everyone who joined us and contributed to the discussion. We're looking forward to continuing these conversations with the community.