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Olly Headey

Co-founder of FreeAgent. 37signals alumni. Freelance CTO. Indie maker.

Olly Headey is a tech entrepreneur and photographer based in Edinburgh, Scotland. He co-founded FreeAgent, a cloud accounting software company, in 2007.12 As the CTO, he helped grow FreeAgent to 120,000 customers and 260 staff, leading it through an IPO and successful acquisition.2

After leaving FreeAgent, Headey served as Director of Engineering at 37signals in 2022/23.2 Currently, he focuses on helping tech companies build productive engineering teams, maintains side projects like Pagecord and Feedgrab, and pursues photography.23

Headey's career highlights include:

  • Co-founder and CTO of FreeAgent (2007-2022)12
  • Director of Engineering at 37signals (2022-2023)2
  • Consultant helping tech companies build engineering teams (present)2
  • Photographer specializing in street and travel photography3

He maintains a personal website at headey.net and can be found on LinkedIn with the username oheadey.4 Headey also writes a blog covering topics such as technology, business, music, and life in general.2

Highlights

Nov 21 · twitter

I'm on the Gemini Pro (not Ultra) plan. No access to Gemini 3 on the CLI but I'm on the waitlist. Anyone know if Pro users are being onboarded? Kinda pointless subscribing 🤷‍♂️ #ai #google #gemini

Sep 13 · twitter

I'm looking for recommendations of high quality blogs or news websites of ANY category (for @feedgrab). Tech, Music, Theatre, Food and Drink, Climate, whatever. Basically your favourite "will always read" content. Hit me up in the comments or the DMs... 🙏

Related Questions

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Olly Headey
Olly Headey, photo 1
Olly Headey, photo 2
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Location

Edinburgh, Scotland, United Kingdom