Founding Operator

cinnamon.io; Slough; On-site; GBP 45,000 - 70,000; Full time

Benefits offered by this job

Meaningful founding equity

Private health insurance

Wellhub Gym/Wellness plan

Dinners in the office

Brand new MacBook

Job summary

cinnamon.io is hiring a Founding Operator in London (Aldgate) to bridge customers, product, and engineering. You’ll spend most time speaking with customers, mapping workflows, and driving adoption across UK branches.

The role blends consulting, product, and SaaS implementation, with a focus on turning insights into scalable processes. The position is office-based five days a week with occasional travel to customer sites across the UK.

Qualifications

• You’ve spent time in front of customers in consulting, CS, implementation, onboarding, account management, product management, or similar.

Responsibilities

• Sit inside branch offices and map daily workflows.
• Build training and implementation playbooks (docs, videos, certifications).
• Own adoption: daily active usage per branch as north star.
• Collect structured feedback from customers to shape product roadmap.
• Translate between branch manager language and engineering language.
• Turn repeated problems into better processes, training, or product improvements.

Skills

Customer facing

PM thinking

Structural thinking

AI-native

Job description

About the job

£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, or product improvements.

You’ll also build the function.

• Take messy early implementations and turn them into repeatable playbooks.
• Define what great onboarding, training, and customer adoption look like at cinnamon.
• Build the systems and processes that allow us to onboard more customers without the experience getting worse.
• Use AI and automation to make the customer function faster and more scalable.
• Help shape what the customer success and implementation team looks like as we grow.

You’ll be a great fit if

• ? You have a teacher’s instinct. Maybe you were one. Maybe you just think like one. You can read the room when someone isn’t getting it. You break things into steps. You don’t sigh. You adapt until it lands.
• ? You've spent time in front of customers consulting, CS, implementation, onboarding, account management, product management, or another customer-heavy role. You know what good adoption looks like and how to get there.
• ? You think like a PM. You notice when something is confusing before the customer tells you. You come back from site visits with specific, structured feedback. You care about why things aren’t working, not just that they aren’t.
• ? You're structurally minded. You can take a messy first implementation and turn it into a repeatable playbook by customer #3.
• ? You're comfortable getting into the detail. You want to understand how the product works, how customers use it, and where things are breaking. You don’t just forward every issue to engineering.
• ? You're AI-native. You use AI tools to move faster. Training docs, onboarding videos, follow-up summaries, internal workflows. You don’t wait for someone to build you a template.
• You're genuinely customer and product obsessed. You care whether branch staff actually use cinnamon every day. Customer pain isn’t just something to manage, it’s something to understand and fix.
• You're ambitious and ready to own something. You want to build the function, not inherit it. You’re energised by being the person responsible for making cinnamon’s customers successful.

Bonus points

• Background in teaching, training, or education before moving into tech
• Customer success, implementation, onboarding, or product experience
• Experience working in a field-heavy industry where customers use software in the real world, not just behind a desk
• Comfortable understanding technical products and working closely with engineers
• You’ve built onboarding, training, or adoption processes from scratch before
• Comfortable on UK rail. You’ll be on trains to branches across the country.

This role isn’t for you if

• You actually want to be an engineer (we’re hiring engineers separately, this isn’t the path)
• You want to only speak to customers from behind a screen
• You think customer-facing work is beneath your skill set
• You’d rather pass customer problems to someone else than work out what’s actually going wrong.
• You optimise for predictable hours or work-life balance.

How we work

We work hard. Five days a week in person. 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. If this sounds exhausting rather than energising, this isn’t the role for you.

What we offer

• £45K-£70K base depending on experience
• Meaningful founding equity
• Private health insurance
• Wellhub Gym/Wellness plan
• Dinners in the office
• Brand new MacBook

But the real offer is ownership. You define what the operator role . You build the playbook. You decide what world class looks like.