Clover Connect
Head of Technology
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Head of Technology — Clover Connect
Where tech leaders are one.
Company Description
Clover Connect is a private community for senior technology leaders — CIOs, CTOs, CISOs and their direct reports. Membership is by invitation and application, not open sign-up, because the value of the network depends entirely on who's in it.
We're small, founder-owned, profitable and growing, based on Lower Marsh Road, a minute from Waterloo. The Clover app is the product — profiles, connections, event booking, research, vendor intelligence. It's not a marketing site with a login; it's how the business scales beyond the number of rooms we can fill.
Role Description
This is our first Head of Technology role, and it means owning the Clover platform end to end.
You won't be building it yourself — development is delivered by a third-party software partner. Your job is running that relationship properly: sprint oversight, scope and change control, and the judgement to know when you're being told what you want to hear rather than what's true. You'll work closely with our Product Lead to shape where the platform goes next, and you'll be accountable when something ships late or breaks.
Beyond the platform, you'll set our direction on AI — models, patterns, build versus buy, and where the real value sits versus the noise — and keep an eye over our internal IT estate (Microsoft 365, Intune, HubSpot). Budget to outsource the operational side; you're setting the standard, not resetting passwords.
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This is a leadership role, not a hands-on build role. We're a small team with an ambitious roadmap, and whoever does this well grows with it — the role is written into our option scheme as a CTO seat. That's a real path, not a recruiting line.
Benefits
- £70k–£75k base salary
- EMI share options, paying out on a sale or listing rather than vesting year by year — we'll talk openly about timeline and grant value at offer stage
- Two days a week on Lower Marsh, three from wherever suits you (some weeks will ask more than 40 hours — we'd rather say that up front)
- Direct access to senior IT and technology leaders — the people most engineers spend a career trying to get in front of
A word on the salary: London pays £95–110k for a role with this scope, and we know it. We're a small founder-owned business, and every pound of salary is real money out of the company rather than someone else's balance sheet. In practice you're trading roughly £20–25k a year for share options, a title step-up, and a fast route to CTO in a company small enough that you'll genuinely shape it. If we get the outcome we're working towards, the options are worth considerably more than the salary you gave up. If we don't, they're worth nothing.
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Qualifications
- Several years building software, with at least some experience leading or line-managing engineers
- Real experience managing external development partners or agencies — or a clear view on how you'd do it
- You've built with LLMs yourself. Not a course, not a demo — something that shipped and had users
- Enough technical depth to challenge an architecture decision you disagree with, and win
- A serious eye for detail
- Comfortable in the ambiguity of a small company where the answer often isn't written down yet
Someone stepping up into their first head-of role is exactly who we have in mind.
How to apply
Send a CV and a few lines on the most interesting thing you've built with AI to admin@cloverconnect.io. First conversation is a 30-minute video call with Craig, one of our co-founders — no prep needed.
Clover Connect is an equal opportunities employer. We make decisions on merit alone.
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