Evolution of a Founder CEO: 4 Ways Your Role Will Transform as You Scale

In 2019 alone, we’ve brought on five new executives here at BetterCloud: Chief Product Officer, Chief Marketing Officer, Chief Customer Officer, Chief Technology Officer, and Chief Revenue Officer. 

Now with a full executive team in place, I’ve gone through yet another transformation as CEO. Since starting BetterCloud almost 8 years ago, we’ve grown to over 300 people, and this is the fourth incarnation of the CEO role that I’ve been in. Each time the role changes, it requires new skills, responsibilities, priorities—and it feels like I’ve had to reinvent myself each time.

I’ve noticed that every time I’m in a group of other founders/CEOs, this is a consistent topic of conversation: how to manage within these stages, and how to evolve to keep pace with the business. I’ve far from nailed it, but I’m sharing what I’ve learned and experienced in the hope it helps others as they scale. 

The Player Coach (1-40 people)

From the beginning to 30-40 people, my role was the Player Coach. I was on the field with my team, doing the same work they were doing day in and day out, but I had the added role of pointing everyone in the right direction. It was a flat organization; there were no managers between me and the vast majority of the team. 

Depending on the week, day, or even hour, I was the office manager, a sales rep, a customer support agent, product manager, IT manager etc. I interviewed every candidate who applied for a job at BetterCloud. 

There was hardly any intentional strategic planning happening; the farthest I could really think was a month out. Everyone knew everything that was going on and what we needed to get done. It was easy for me to see and feel my contribution every day (whether it was solving a customer’s problem, setting up new employees with their laptop/phone, or successfully ordering snacks that took into account everyone’s dietary restrictions). 

The Frontline Manager (40-100 people)

From the Player Coach stage, I graduated to what felt like a Frontline Manager, which lasted until we reached ~100 people. At this point we realized we were an actual company. People had been in roles for more than a year or two, and now they wanted more structured feedback, more frequent guidance, and performance reviews (as they should!). So I started doing one-on-ones more regularly, giving people feedback on their career growth opportunities at BetterCloud. 

A layer of Player Coaches in different departments also started to emerge, so I wasn’t as involved in the day-to-day of those groups (especially Engineering). Instead, I started to spend more time in the areas that are my natural strengths: sales, marketing, and operations. I was able to start thinking and planning about a quarter out. 

This is also when we started doing more regular company communication. We needed a consistent cadence of emails and company meetings to keep people updated on the business, because we were reaching a size where not everyone could get updates from me firsthand.

I could still feel like I was making an impact every day, but it wasn’t as direct. For example, I was doing things like implementing a new process across the sales team to track leads through the funnel in Salesforce, or prioritizing the product roadmap for the next quarter. 

The Context Switcher (100-300 people)

From 100 to 300 people, I found my role had to change yet again. It became a mix of a Frontline Manager and executive based on which department I was interacting with. 

For some departments, we had experienced executives who outright owned their areas. For others, we had high-performing individual contributors who had come up within the company, were now managing teams, and reported directly to me. 

This phase was probably the most difficult time for me. It was the most context switching I’ve had to do. Meeting topics would range from a customer feature request, to a full department restructure, to office expansion plans and floor layouts, to an employee relations issue with an entry-level hire, to our annual operating plan. All the mental context shifting from meeting to meeting, plus needing to be 100% present to give feedback and contribute, left me feeling tired at the end of many days.

The Value Multiplier (300+ people)

Now, with about 320 employees, I’m in yet another stage of the CEO evolution. I spend a lot of time recruiting. The challenge for where we are is that I’m looking for people who can help us scale but will also fit our culture and have the right mindset for this stage of business. 

That said, after more than eight months of recruiting, I’ve been able to bring on an incredible, full executive team, and with that my role has changed drastically. I’m now thinking about where we’re going to be 12-18 months from now. I spend almost all of my time with my direct reports, who are all C-level execs. My job is to make sure the group works well together as a high-performing team, has what they need to be successful, and is operating against our vision, the North Star that we’re all navigating toward together. 

Among the broader company, my primary job is to be a communicator, constantly reiterating our values, our culture, our wins and our vision. This is critical in a rapidly growing company where new people bring pieces of their own culture and might be unaware of our vision and strategy.

This is how I know things have changed: Up until this stage, I knew every little feature being released into the product, every prospect in the pipeline for the quarter, every open role. I don’t know all of those things anymore, at least not at that level of detail.

I’m spending more of my time talking to people outside the company, like investors, customers, and partners. It’s getting very difficult, if not impossible, to see the impact I make on a daily basis. But if I spend my time correctly, I can make a much bigger impact. For example, I can prepare for a keynote that hundreds of customers will hear at our annual customer conference, I can work on a partnership that will double our business over a two-year period, or I can recruit world-class executives who have scaled businesses like BetterCloud before. 

The future

I know that this experience may not match up perfectly with other founder CEOs’ experiences. I’ve seen some people who are on their third or fourth company start their businesses where I am today with a full executive team in place. I’ve seen others scale with the exact team they started with. 

This evolution also isn’t exclusive to CEOs. Executives and managers who oversee large, growing teams and/or have a diverse set of responsibilities in an org go through this same kind of evolution. With all of that being said, I know my role is going to continue to evolve, and I look forward to the next set of learnings and challenges.