Founding Account Executive at Cinnamon
- Location
- London, United Kingdom
- Compensation
- Not Disclosed + Equity
Cinnamon is rebuilding the $300B+ real estate transaction market with AI agents to replace 30-year-old infrastructure, and as a Founding Account Executive in Aldgate, you will join this high-intensity, VC-backed team to own a market segment and build the sales playbook from scratch. This is a rare opportunity to get in at the ground floor with significant equity and report directly to the CEO as you scale an AI workforce already seeing traction across the UK and US.
What's the next step?
Cinnamon are hiring from Jack's network. Talk to Jack for free and get a direct introduction to the team, if a good fit.
Role overview
As a Founding Account Executive, you will be one of the first three commercial hires responsible for building the company’s sales engine from the ground up. You will own the full sales cycle—from cold outreach to closing £10k-£20k deals—while directly shaping the repeatable playbook that will scale Cinnamon’s AI workforce across the global property market.
About Cinnamon
👋 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 three 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.
Nobody has built the definitive AI agent layer for real estate yet. That’s what we’re doing.
cinnamon.io is a platform of AI employees that handle the property transaction end to end.
Our first AI hire is already live with agencies across the UK.
What you will do
- Execute a high-volume, full-cycle sales motion including 100+ daily touchpoints across cold calls, emails, and LinkedIn to target multi-branch estate agency directors and franchise heads.
- Manage the entire deal journey from initial discovery and MEDDIC-based qualification to running founder-level demos and closing contracts without handoffs.
- Document and refine successful sales tactics into a repeatable motion, using tools like Clay and Claude to automate prospecting and scale Cinnamon’s outreach efficiency.
Who this is a fit for
- Possesses 3+ years of full-cycle B2B SaaS sales experience with a proven track record of consistently crushing £1.2M+ annual quotas in high-velocity SMB markets.
- Demonstrates mastery of structured sales methodologies like MEDDIC and is comfortable managing high-volume deal cycles involving numerous £10K-£20K contracts.
- Is an AI-native operator who thrives in a fast-paced, in-person startup culture and is excellent at performing demos that lead with business problems rather than just product features.
Why this role is remarkable
- Join as a founding commercial member with meaningful equity and the unique opportunity to build a global sales playbook for a category-defining AI agent platform.
- Work in a high-intensity, in-person environment in Aldgate, backed by top-tier VCs and Entrepreneurs First, with a product already live and generating revenue.
- Benefit from direct access to the founder in a flat hierarchy where promotion is determined purely by performance and hitting milestones rather than tenure.
How Jack & Jill work together
What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI agent for hiring, working for the company. She recruits from Jack’s network.
If your profile’s a match and Cinnamon wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.