Data, AI, and Knowing When to Let Go - with Tommy Cotter

Definitely, Maybe Agile

Definitely, Maybe Agile
Data, AI, and Knowing When to Let Go - with Tommy Cotter
Jun 18, 2026 Season 3 Episode 204
Peter Maddison and Dave Sharrock

Tommy Cotter is Director of Data Products at Benzinga, a financial media company building the data infrastructure that sits behind trading platforms and investment apps used by millions of people daily. He's been navigating the shift to AI-assisted workflows in a space where speed and accuracy aren't just nice to have - getting it wrong has real consequences.

In this episode, Peter and Dave talk with Tommy about what it actually looks like to build data products responsibly in a fast-moving AI environment. They get into where humans still need to be in the loop, how compliance has become a competitive signal, and why being nimble matters more than picking the perfect architecture from day one.

Three things to take away from this conversation:

  1. Self-agency is real now. If you have a strong conviction about a product or problem, the barrier to building something has never been lower. That's a genuine shift from even five years ago.
  2. Security and compliance are no longer just internal concerns. In a world where AI startups spin up overnight, having invested in SOC2 or GDPR signals to customers that you're a legitimate, trustworthy operation. It's a market differentiator.
  3. Humans still belong in the system. Not everywhere, but in the right places. For low-risk, deterministic processes, let AI run. For anything client-facing or accuracy-critical, keep a human in the loop. Knowing the difference is the skill.

If this conversation sparked something for you, send us your thoughts at feedback@definitelymaybeagile.com. And if you haven't already, hit subscribe so you don't miss the next one.

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