Roomsie: a marketplace rebuild launched in 8 months

Taking over a stalled project

In late 2017, Roomsie's CEO, Jacob Chaney, asked us to help with a project that had spent years in development across several teams without producing a working product. He already ran a local business helping interns find housing in Washington, D.C., and wanted to extend it through a marketplace for interns and students.

The design and development team, hired through an expensive talent agency, was struggling with slow progress, buggy features and an unsustainable burn rate. Jacob needed ownership of the development process and features that were built, tested and delivered on time.

The first ten days

We inspected the codebase, observed the process and spoke with every team member, individually and together. Some members lacked the technical experience needed. Management was too complex and led by people without project-management experience. Developers overlapped on features, with no clear ownership or accountability for missed deadlines.

We wrote a report for Jacob and brought in an established D.C.-based technical consultant for a second opinion. Within a week, the team went from 5 contractors to 2.

The rewrite

The codebase had many bugs and very little of the application worked. We recommended a complete rewrite despite the budget already spent.

Over the following months, we delivered more working features than the previous teams had produced in two years. We used Rails for the backend and React for the frontend, kept daily stand-ups, and worked through product trade-offs with Jacob. His housing-industry knowledge informed the product decisions; we explained their technical implications.

After several months, we soft-launched a first version for real users.

The first bookings

Before launch, we added Mixpanel and Hotjar, listed an initial batch of properties and ran small marketing campaigns. The first booking request arrived within days and converted. Within weeks, Roomsie was generating revenue.

We spoke with early users about friction in the product. Usage patterns and conversion data informed every new feature and UX change.

Marketplace features

Hosts and renters had separate workflows, dashboards and permissions, with an admin layer for the Roomsie team. Property search handled geography, date-range availability, price and amenities while keeping responses fast.

Medium-term housing meant larger payments and more complex flows than short stays. We built payment processing with escrow logic, automated payouts and dispute handling. In-app messaging kept real-time host and renter conversations organized and accessible.

Launch

Roomsie launched as a working, revenue-generating product 8 months after the rewrite began. A team of two with clear feature ownership delivered what the larger team had struggled to finish.