Building the Foundation for Acquisition

I joined Semana when it was two founders, an idea, and not even a pitch deck. A year later, I handed off to the CTO I’d hired — and the foundation we built carried the company to acquisition four years after founding.

The Setup

Semana was building hybrid office management software — COVID had forced companies to figure out how to coordinate who’s in the office and when. The founders (ex-Google CEO, scientific background COO) had identified the opportunity early but had limited technical experience.

We had three people and needed to get a product into paying customers’ hands fast.

The Integration Choices

The product sat at the intersection of two systems: people’s calendars and office floor plans. Both had hard integration choices.

On the calendar side, some companies use Google, some Microsoft, some something else. We picked Google Calendar only — narrowing the market but shipping months earlier.

On the spatial side — letting people choose where to sit — we needed office floor plans in the app. The question was whether to model them ourselves or integrate with a third party. I bootstrapped it by drawing the SVG floor plans myself and making them interactive in the app. It wasn’t scalable, but it got us to paying customers.

The pivots over the first 12 weeks weren’t about adding or cutting features. They were about how to model the domain — how calendars, floor plans, and team presence fit together.

Speed vs. Maintainability

I chose technologies I could move fast in, not ones that would scale to millions of users. Skipped infrastructure that would matter later (proper CI/CD, monitoring, redundancy) in favor of things that mattered now (rapid deployment, easy debugging, direct database access for customer support).

But I knew someone else would inherit this codebase, so every shortcut was a conscious bet. The compromise: prove the product fast enough to survive, but don’t make it impossible to build on later.

That bet got tested early. We had a critical demo with a potential anchor customer. Two days before, the floor plan feature was functional but visually underwhelming — it wouldn’t land. I rebuilt the entire visualization in SVG with interactive components: clickable seats, hover states, visual feedback. Finished at 2am the night before.

They became our second paying customer.

The Outcome

We got to 20 paying customers. I hired a CTO who would lead the company through the next phase, and ran a structured 6-week handoff: architecture docs, customer relationship intros, decision log.

Deskbird acquired Semana in 2025, four years after founding. The codebase and product design I built are still visible in the product today.

What I Learned

This was my third time as an early-stage founding engineer, after Kliqed and Growth Intelligence. Looking back, the job was TPM work without the title, as it often is.

I scoped the roadmap with the founders. I was the technical liaison for B2B customers. I set launch criteria and go/no-go reviews. I defined the CTO role, ran the hiring process, and executed the handoff.

At AWS, I’d later do all of this again, at a different scale and with different constraints, but the same core skill: closing the gap between what a team wants to build and what actually ships.