Roomsie

Roomsie is an online marketplace that connects hosts with interns, students, and recent graduates looking for medium-term housing in Washington, D.C. A complex product built from the ground up.

First contact

In late 2017, I was approached by Jacob Chaney, Roomsie’s CEO. He spoke to me about the project and the multitude of challenges he was dealing with. Roomsie was a project long-time in the making and over the past couple of years various development teams failed to deliver a working product.

It pained me to hear this since Jacob is a brilliant entrepreneur who runs a thriving local business that helps interns find housing in Washington D.C. This makes him an ideal founder of a company that’s looking to solve the same problem on a bigger scale.

At the time we met, the project burn rate was high, since the current design & development team was sourced from an expensive talent agency. The team was having major issues, especially with the front-end part of the application; the progress was slow and the delivered features were buggy and unpolished. Jacob was looking for someone to take ownership of the development process and to make sure features were properly built, tested, and delivered on time.

Indentifying the problems

I spent the first ten days inspecting the codebase and observing the development process. I spoke with all team members together but also individually, trying to understand their point of view and identify the underlying source of the problems.

I found several issues including but not limited to:

  • Lack of technical expertise of some team members
  • A complex dev management process led by people who don’t know how to manage projects, on a project that doesn’t require a complex process in the first place
  • Multiple developers working on same features and stepping on each others toes
  • Lack of feature ownership, no one was held responsible for failing to deliver

I wrote a lengthy report, spoke to Jacob about my findings, and even hired an established D.C. based consultant to offer a second opinion on the state of the project.

Within a week, we downsized the design & development team from 5 contractors down to 2.

Starting fresh

Since not much of the application was built and the delivered features were ridden with bugs, we opted for a complete rewrite. It turned out to be a good decision because in the following couple of months, we delivered more working features than the previous teams delivered during the past couple of years.

Project Timeline

We held daily stand up meetings to make sure everyone was informed and knew what was happening at all times. Jacob gave me valuable insights into the nitty-gritty details of his industry, while I guided him through the development process and made sure he was aware of pros and cons of each development related decision.

After a couple more months of work, we were ready to stealth-launch the first version of Roomsie and start testing with early users.

Property Page

Validating the product market fit

Before going live, I implemented a custom Mixpanel and Hotjar analytics setup to better understand how people use the product. We listed a couple dozen properties and did some small scale marketing to attract the first batch of early users.

Within days, we received our first booking request and it went through. Within weeks, we already had $XXX,XXX in revenue.

We spent a lot of time talking with our early users in an effort to understand them and gather valuable feedback. We also embraced a data-driven approach to developing new features and improving the existing ones.

The path forward

With the first version of the product completed, the focus has shifted from development to growing the user base. Before leaving the project I connected Jacob with another developer from my local network who is still maintaining the product and adding new features when necessary.

Building Roomsie with Jacob was pure joy. It was one of those awesome moments where the needs of the client perfectly overlapped with my own expertise, allowing me to inject heaps of value into the project.

Ivor helped me identify and correct key issues in the development process that were tormenting me for years. The end result was a highly performant product that quickly started making revenue, placing me miles in front of my competitors.

Jacob Chaney
Jacob Chaney,
CEO at Roomsie

Get in touch 👋

I'm happy to talk business or simply give you some free advice. If both sides see value in working together, we’ll move forward. If not, that's okay too. Worst case we both had a nice chat and received some free feedback.