CPO · PROPTECH SAAS · FOUNDING TEAM
Early stage startup. First roadmap. Foundations built for what came next.
[ THE SITUATION ]
Retail real estate is having a moment. Vacancy at a near all time low of 4.8% in Q1 2025. I tell you this to paint the picture. Spaces filling fast, deals moving quickly, specialty leasing managers, the people managing short term leases in retail real estate, anything from a day to perhaps even a year, busier than ever. More locations, more licences, more invoices, more complexity. A lot goes into those brand pop ups or activations. Or those short term displays in Selfridges. Eye opener.
Specialty leasing now accounts for 10 to 15% of revenue at the best performing destinations. At a major regional mall that is a significant revenue line. And most of the people managing it are doing it on software that was never built for them. Spreadsheets. Workarounds. WhatsApp. Tools designed for something else entirely.
That is the gap Squarefeet was built to close. Founded by people who understood the problem from the inside, with the kind of domain depth most SaaS companies spend years trying to acquire. I joined as CPO to help them scale what they had.
What I walked into was a classic early stage setup. A lean founding team moving fast, a product with real potential making impact, and no product infrastructure yet. No roadmap, no backlog, no delivery rhythm. Just a lot of ground to cover and genuine appetite to cover it.
[ WHAT I BUILT ]
When I landed, while onboarding and trying to get my head around this new category, I did a full product audit. Every flow, every friction point, every place the product asked too much of its users. It is amazing what mapping the information architecture can give you. Not to make a list. To understand the whole picture.
Then I built the operating system from scratch.
The first ever product roadmap and prioritisation framework via welcoming Jira to the team gave the founding team and engineering a shared view of what we were building and why. Introducing Scrum and a structured backlog in Jira turned ambition into a delivery rhythm, made velocity visible, and gave us a way to absorb shifting priorities without everything becoming urgent at once. This enabled us to ship significant changes on a weekly basis. It is the fastest pace place I have had the pleasure of working in.
I led customer discovery and usability testing, grounding every decision in what real users actually needed rather than what we assumed. Ran biweekly product reviews with board stakeholders. Simplified the platform by removing low value functionality and focusing effort where it mattered.
Two areas where we moved fast: calendar booking and invoice management. Heartbeats of a specialty leasing manager's day.
But the real insight did not come from the roadmap. It came from discovery.
We thought the problem was invoice creation. It was not. The problem was uncertainty. Users were jumping between spreadsheets, emails and accounting systems just to answer one question: where is the money?
That reframed everything. The work stopped being about building a better invoice dashboard and became about building visibility and confidence into the core workflow. Knowing what space is available and when. Knowing what has been invoiced, paid and what needs chasing. One place. One source of truth.
Multiple UX options prototyped, tested with real users, iterated and shipped. Weekly. I worked closely with the CEO on product strategy, roadmap priorities and commercial thinking. Product decisions and go to market sitting in the same conversation. That is how it should work.
[ WHAT CAME OUT OF IT ]
Several new shopping mall locations onboarded. Booking and invoice management redesigned around how people actually work. A delivery cadence that did not exist before I arrived. A go to market strategy I helped shape. A platform with less noise and more value.
[ WHAT IT TAUGHT ME ]
Building product infrastructure from zero while simultaneously shipping, doing discovery and managing stakeholders is a different kind of job to inheriting a functioning team. You have to be comfortable holding strategy and execution in the same hand.
The biggest lesson was not about process. It was about clarity. When a team understands the customer problem deeply enough, decisions get faster, roadmaps get simpler and momentum follows. Most product problems are clarity problems in disguise.
That combination of founder energy, genuine customer access and the freedom to build properly is rare. I will always chase it.
