Founding Operator

cinnamon.io; City Of London; On-site; GBP 45,000 - 70,000; Full time

Benefits offered by this job

Founding equity

Job summary

Founding Operator at cinnamon.io in Aldgate, London, is an in-office role five days a week with £45K-£70K base plus meaningful founding equity. You will help bring cinnamon to real-world property teams across the UK.

Most days are customer-facing, mapping branch workflows, building adoption playbooks, and translating feedback between customers and engineering to shape the product roadmap and ensure adoption sticks.

Qualifications

• Brilliant with customers and able to understand their workflows.
• Structurally minded and able to map complex processes to simple outcomes.
• Able to think from first principles and translate feedback into product improvements.

Responsibilities

• Sit inside branch offices and map daily workflows to fit cinnamon.io.
• Build the training and implementation playbook from scratch, with docs, videos and modules.
• Own adoption metrics and daily active usage per branch to drive success.
• Translate between branch-manager-speak and engineering-speak to keep teams aligned.
• Turn recurring customer problems into better processes and training materials.

Skills

Customer-facing

Structured thinking

First principles thinking

Job description

About the job

The basics

£45K-£70K base + meaningful founding equity

Aldgate, London. In-office 5 days a week. Occasional travel to customer branches across the UK.

We're hiring our Founding Operator. The person who understands customer, psychology and helps takes our product into the real world and makes sure it actually sticks.

You’ll sit between our customers, product, and engineering teams. Most of your time will be spent speaking with customers, understanding how teams actually work, analytics, adoption and making sure cinnamon becomes part of their day-to-day.

You might come from consulting, product management, customer success, implementation, account management, product, training, or a field-heavy SaaS environment.

What matters is that you're brilliant with customers, structurally minded, think from first principles, charismatic and naturally notice where products and processes could work better.

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.

About us

• Backed by Entrepreneurs First and top-tier VCs (our first investor was early investor into Canva)
• Live with agencies across the UK with early US traction
• Based in Aldgate, London.

What you’ll do

Most days, you're customer-facing.

• Sit inside branch offices. Watch negotiators and property managers work. Map their daily workflows. Configure cinnamon.io around how they actually operate.
• Build the training and implementation playbook from scratch. Docs, videos, certification paths, refresher modules, and repeatable onboarding processes.
• Own adoption. Daily active usage per branch is your north star.
• Spot where adoption is slipping before the customer has to tell us and work out what needs to change.
• Build strong relationships with customers so they trust you enough to tell you what is and isn't working.

Every day, you're the bridge.

• Bring structured, specific product feedback back from every customer visit. Not 'they're confused', but exactly where they drop off, what they expected to happen, and why.
• Translate between branch-manager-speak and engineering-speak, in both directions.
• Own the feedback loop that makes the product better. What you see in the field should directly shape the roadmap.
• Work closely with product and engineering to prioritise the customer problems that matter most.
• Protect engineering from unnecessary customer interruptions by understanding the product deeply enough to answer questions and solve issues yourself where possible.
• Turn repeated customer problems into better processes, training, documentation,