cinnamon.io
Founding Head of Sales
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£100-140K OTE (base + commission) + equity
Hoxton, London. In-office 5 days a week. Travel to prospects and customer branches across the UK.
You might be a founding AE who wrote the playbook and then built the team that ran it. A top performer who's ready to own the whole motion, not just their slice of it. Someone who has carried a number for years, still loves the chase, and wants to be the one who cracks it here.
This is a front-line role before it's a leadership one. Day one, you're the one on the phone and in the inbox. Prospecting, booking meetings, running demos, closing deals.
You smash the number yourself before you ask anyone else to, then build the playbook and the team that let others do the same.
👋 What we're building
Property is one of the most important parts of people's lives. It's where you raise your kids. It's most people's biggest financial decision. And the experience of buying, selling, or renting one is still shockingly bad.
We live in a world where you can send money across borders in 3 seconds, hail a car with a tap, and have your entire medical record on your phone. But when it comes to property? You're waiting for a call back from a branch that closes at 5:30. Your offer is being managed in a spreadsheet. Your tenancy renewal is stuck because someone forgot to send an email.
The infrastructure that powers how people find homes, move between them, and manage their biggest asset has barely changed in 30 years. CRMs built in the 2000s. Processes designed for paper. Compliance workflows held together by memory and sticky notes.
Nobody has built the definitive AI agent layer for real estate yet. That's what we're doing. cinnamon.io is an AI workforce for the entire property transaction.
🏗️ About us
- Backed by Entrepreneurs First and top-tier VCs
- Live with agencies across the UK with early US traction
- Based in London. In-office 5 days a week
🛠️ What you'll do
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First, you carry the bag yourself.
Be the one on the phone and in the inbox. Prospect, book the meetings, run the demos, negotiate, close.
Hit the number personally before you ask anyone else to. You're the top performer, not the manager of one.
Work live deals alongside the founder. He's still in sales. You're carrying it together.
Own the CRM as the source of truth. Every deal, every stage, every forecast, accurate and current.
Then, you build the playbook.
Turn what's working for you and the founder into a documented, repeatable process.
Codify the pitch, the discovery framework, the objection handling, the pricing logic.
Design it so a rep hired in month six can run it without you in the room.
Then, you build the team.
Once the motion works, bring on the first reps. SDRs, AEs. Build the team as we scale.
Coach, manage, and hold the bar. Set quota, run pipeline reviews, ramp new hires fast.
Build the culture of a sales floor. High standards, high energy, no excuses.
Throughout, you're the voice of the market.
Bring structured, specific feedback back from every deal. Not "they didn't buy" but "here's exactly where we lose them and why."
Tell us which segments convert, which objections keep recurring, and where we're leaving money on the table.
Translate between branch-manager-speak and engineering-speak, in both directions.
Already be or become an industry thought leader.
🎯 You'll be a great fit if
- 📈 You're a closer, first and foremost. You've carried a real target at a B2B or SaaS company and personally smashed it, again and again. You're a top performer, not just someone who manages them.
- 📞 You still love the doing. Cold calls, the inbox grind, chasing the meeting, running the demo. None of it is below you. You'd rather be closing a deal than sitting in a management review.
- 🧱 You've built, not just inherited. You've stood up a sales motion, a process, or a team from a messy early starting point. Not just run a machine someone else built.
- 🧠 You think in systems. You turn what's working into a documented, repeatable process, and you're rigorous about pipeline hygiene and forecasting.
- 🧑🏫 You can hire and coach when the time comes. You know what great looks like in a rep, you can spot it in an interview, and you can ramp someone to quota once the motion's proven.
- 🤖 AI-native. You use AI tools to move faster. Research, outreach, CRM automation, deal prep.
- ⚡ Hungry, and ready to own something. You want to build the function, not inherit it. You're energised by owning revenue at a company that's still writing its GTM from scratch.
- ⭐ Bonus points
- Early-stage or founding sales experience at a B2B SaaS or AI startup
- Sold into real estate, PropTech, or SMB / mid-market operators
- Built a sales team from the first rep up
- Comfortable on UK rail. You'll be on trains to prospects and branches across the country regularly
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🚫 This role isn't for you if
- You want to manage a team from day one instead of carrying the number yourself
- You think prospecting, cold calls, and the inbox grind are below your pay grade
- You want to inherit a fully built machine and keep it running
- You optimise for predictable hours or work-life balance
- Five days a week sounds exhausting rather than energising
🔥 How we work
We work hard. We're rebuilding a $1T+ industry and we don't think that happens on a 9-to-5.
We're also having fun. The team is sharp, ambitious, and genuinely enjoys the work.
🎁 What we offer
- Meaningful founding equity
- Private health insurance
- Deliveroo dinners in the office
- Monthly home clean
- Brand new MacBook
But the real offer is ownership. You own revenue at cinnamon.io. You build the playbook. You hire the team. You decide what exceptional looks like.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
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