My startup tripled in size in 2020: Here’s what I learned

Many founders openly talk about the challenges and triumphs that come with expanding product offerings and adding customers. But adding colleagues — especially in a remote environment — comes with its own set of growing pains and valuable lessons. 

I experienced that first-hand last year when my team tripled in size. It wasn’t easy, but I learned great lessons that made me a better entrepreneur. So let me share what I discovered while scaling our team at a rate that none of us had anticipated.

First up: Context

When my team closed our $15 million Series A funding round last August, I wouldn’t have guessed that just six months later we would follow up with our $38 million Series B round.

However, as a provider of enterprise-grade cloud components that enables software teams to add in-app chat and activity feeds to their products, maybe it shouldn’t have come as a surprise. Our rapid growth came as chat emerged as the dominant medium for day-to-day communications in our new virtual reality. 

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So to sum up our growth: in 2020, we saw a 517% increase in revenue from our chat API product, while more than doubling our user base to support more than a billion end users.

Our team size tripled from 31 to 93 employees, and the headcount continues to increase almost daily. Today, we employ 116 people across our offices in Boulder, Colo., Amsterdam, and remotely worldwide. 

A lot of people and a lot of challenges, here’s what I learned from it.

Take one step back, two steps forward  

One of the most pressing issues we faced as a team while expanding was a customer onboarding bottleneck. We prioritize supporting our customers with quick response times and thorough solutions, and this became increasingly difficult to maintain while simultaneously ramping up hiring. 

As Stream’s customer base grew, I found it presented a catch-22: there was a need to focus energy on onboarding new customers and ensuring customer satisfaction, but we needed the personnel resources to do so.

Then to keep up with customer demand, our new team members had to hit the ground sprinting. While that might be an easy default when things are hectic, it wasn’t setting employees up for success.

That’s why my team and I took a step back to assess our processes, and ultimately, we temporarily shifted our focus to ensure we were properly hiring and training new employees. Of course, doing so required resources from existing team members, and as a result, some core competencies and initiatives had to be paused. 

For many founders and leaders, this might feel like a hard pill to swallow during a high-growth period, but I think it can definitely be worth it. It’s a short-term decline in speed that will allow you to pick up ten-fold in the long run. 

Support existing employees  

As the team grows, existing employees will naturally develop in their roles. Particularly, employees who were previously one-person departments may start managing teams for the first time.

This was especially true for us because we often intentionally hire people who might be one level below the title, and we encourage them to grow at Stream. Snowflake CEO Frank Slootman writes about this concept in his book Tape Sucks, if you want to dive deeper into it.

While there is ample value in this hiring approach, I soon realized I needed to make sure new managers had the proper resources and felt supported in their accelerated growth.

Over time, I became better at coaching managers to clearly communicate goals and check in regularly with their direct reports. I think it’s also smart to look for the tools that can help you at this point. For me, Lattice was the right to help us streamline this process and create organized accountability. 

I also discovered that as a founder of an early-stage startup, you’re directly leading people who do the work and execute. As the team expands, that leadership role evolves and becomes more indirect.

So in order for your startup to successfully scale, it’s imperative that you and early employees trust incoming leadership hires to run their respective departments. This process can be hard because founders especially are used to having a hand in everything, but it’s necessary to relinquish some control and let others make decisions.

Evolve the culture

Lastly, the culture will evolve whether you want it to or not, and it’s essential to take an active role in shaping it. 

In the early days of a startup with a small team, you naturally develop close relationships with your co-workers as you’re working long hours in close proximity. As that team doubles, triples, and even quadruples, the dynamic will inevitably shift. This is where it’s key to step in with intention. 

Initially, my co-founder Tommaso Barbugli and I leaned on HR for help, focusing on the obvious things like benefits, perks, and fun team-building events. However, as the dust settled, we realized we needed to think bigger in terms of the culture we wanted to cultivate. 

We agreed that it’s important to us to make Stream a place where people can learn the skills they might need to pursue their own projects or startups in the future, as I believe employees feel most content when they are progressing and acquiring new abilities.

To accomplish this, we’re starting to develop open resources such as dedicated Slack channels for learning about startups and certain coding languages, weekly technical training opportunities for employees outside the engineering department, and more. 

The lesson here is that during this liminal (and hectic) period, there’s actually ample opportunity to thoughtfully mold your company culture. A happy, healthy team is the best investment you can make as a founder to sustain your business for the long term. 

Scale with intention

Ultimately, the resounding lesson in scaling our organization can be best summarized as pause, assess, and move forward with intention.

I know it can be tempting to continue at full speed when the momentum of growth really sets in, but a purposeful slowdown to address necessary issues can go a long way in achieving organizational goals.

Moving quickly is a non-negotiable in the startup world, but that doesn’t mean you can’t also move purposefully.