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Trust your gut: The leadership advice I'd give my younger self
Table of contents
About this episode
Early in his career, Darragh Curran looked for permission. He'd seek validation from people further along, when what he really wanted was cover to do what he already believed was right. Now CTO and Head of Engineering at Fin, Darragh sees that habit as expensive, because a leader caught up in second-guessing stops acting on their own conviction.
"My advice to my younger self would be to just act on your conviction and not drag your heels on things you care about."
He's had plenty of time to learn that lesson. Darragh joined Fin, the AI customer service company formerly known as Intercom, as one of six early employees and spent more than 14 years helping it grow to around 1,400 people. Along the way, he helped distill the implicit values behind its engineering culture and learned to be opinionated about how teams work. He also explains why he hires for traits over experience, and why a bit of naivety helps startups survive.
He also walks Matt Peters through Fin's pivot to AI. The company reshaped its product strategy around AI first, then changed how its own engineers worked. Darragh told the team the change was fundamental and framed it as an opening for bigger impact, where the deepest specialists stand to gain the most.
Darragh closes on what happens to engineering craft when writing code, long the slow and expensive part of building software, becomes the easy part. The value moves to knowing what to build and owning the whole problem, and taste matters even more. The engineers who were always the best, he says, are the ones having the most fun right now.
"There's craft in solving customer problems, and there's elegance and craft in how we shape the systems."
What you'll learn in this episode
- Why seeking permission can stall a leader's growth
- How to act on conviction instead of second-guessing
- What scaling from six people to 1,400 teaches about engineering culture
- How to distill a team's implicit engineering values
- Why to hire for traits over skills and experience
- How to frame an AI shift as an opportunity for your team rather than a threat
- Why writing code has become the easy part of building software
- Where engineering craft and taste live when AI writes the code
About Darragh Curran
Darragh Curran is the CTO and Head of Engineering at Fin, the AI customer service company formerly known as Intercom. He joined as one of six early employees and spent more than 14 years helping the company grow to around 1,400 people, roughly 500 of them across product and engineering, with revenue moving from zero to hundreds of millions.
Along the way, he helped shape the company's engineering culture, its early stance on working in person, and its pivot to building around AI. He is a longtime champion of the product engineer, someone who owns customer problems end to end.
Resources mentioned
About the host
Matt Peters is the CEO and Co-Founder of Fixify, where he's redefining the IT help desk for the AI era. Before founding Fixify, he was Chief Product Officer at Expel and held senior leadership roles at FireEye and Mandiant, where he helped pioneer some of the earliest managed detection and response services.
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