Growing Pains: Disfunction to Cross Function

I like to think of startups in terms of dog years; 1 year in a startup is the equivalent of 7 in your average company. Things tend to happen quickly and sometimes, uncomfortably. This discomfort keeps things exciting and fresh. Although, when you’re trying to move at high velocity, you may forget to stop and look around.

Over the past year we have substantially scaled the Product and Engineering organization at Breather. Last September we were approximately 20 employees,

five months later we doubled the team.

We added PM’s, developers, designers and data scientists.

This was great, we built a bigger team and that meant more speed…or so we thought. In actuality, we slowed down; and it took some reflection to figure out why. We were not effectively organizing our teams. Product/Design, Marketing, Engineering/Insights, Operations were all separate and silo’d. This led to miscommunication, group think, lack of risk-taking and a host of other problems.

Nothing we couldn’t fix though.


Prior to adding these new employees, the teams were small, coordination was relatively easy. Information didn’t fall through the cracks, designs were easy to openly discuss. We needed a fix.

We discovered several different issues

  • Lack of Diversity of ideas
  • Lack of Speed
  • Lack of Ownership

Ben, our CTO and I felt at some point that we would go cross functional, but we were pushed by one of our PM’s, Bill; to pull the trigger. We got a few stakeholders throughout the org in a room and discussed a bunch of ideas around structure. We also watched the Spotify Series on cross functional organizations. After that,

we ripped the Band-Aid off.

Side note, anyone who is scaling a Product/Engineering team should watch the Spotify videos.

We looked at our Product through the User Journey

and came up with five teams with the following goals:

  • -1 Awareness: Helping people discover and become interested in Breather. This was primarily a marketing team with visits as the main metric.
  • 0-1 Activation: Converting a visitor to a 1st booking.
  • 1-2 Re-Activation/Experience: Getting the user to their 1st reservation and converting them to a 2nd booking.
  • N High-Value: Generating more revenue from our business customers.
  • K Factor Virality: Person-to-person sharing of Breather.

Each team was a mini startup that could plan, execute and measure whatever they built.

Teams consisted of a PM, designer, data Scientist, front end, backend and mobile engineer, marketing and city representative. We didn’t have enough PM’s for all the teams so I took the role of PM’ing the Virality Team, and Julien, our CEO took the Awareness team. Monthly goals were set for each team and we were off to the races.   

Here we are 10 weeks later; in hindsight, we made the right move. Taking a look at many of the initiatives that have rolled out, we have shipped some of the best work to date.


  • V3 of our app with numerous feature enhancements such as discovery, favourites, packages and a new navigation.
  • The Library, a new type of shared workspace in NYC.
  • Completely redesigned Invite system that’s far easier to use.
  • Our standalone Breather for Business Portal for our corporate users.

Not only that, our teams feel empowered.

Engineering is now fully involved in the product development process, and were using our data scientists to validate all of the work.

These are just the highlights, we managed to ship many other projects as well. This experience has been stressful but incredibly rewarding.

I am proud of our team.

We’ve just hit the tip of the iceberg, there’s plenty of work left to do.

We are about to embark on V2 of our cross functional initiative. These teams will continue to evolve to meet the ever changing needs of our business. I’m excited for what the future has in store.

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