Everyones talks about how hard it is to get to $10M ARR in SaaS. Fewer talk about what it takes to go from $10M to $25M. Here are my 5 tips for founders getting ready to scale their team: When Retention.com hit $10M, there were only 6 of us. We were all individual contributors, wearing multiple hats, doing whatever it took to make things work. It was intense, but simple in its own way. Fast forward three years: we’re 40 people strong. Scaling from 6 to 40 was far harder than scaling revenue. The challenges completely changed. At $10M, it’s about hustle. At $25M, it’s about building a company that can operate at scale without you doing everything yourself. Here are my 5 tips for founders getting ready to scale their team: 1) Let go of control. Trust others to own outcomes. And recognize that what made you great at $10M may actually hold you back at $25M. 2)As your team grows, your culture stretches — sometimes uncomfortably. The challenge is keeping your early scrappiness alive while adding the structure that growth demands. Hire people who can handle ambiguity and bring process. 3) Scaling communication is just as important as scaling sales. It never hurts to over-communicate: vision, priorities, expectations, and context. 4) You can do 10 good things or 3 great ones — choose the 3. Say no to the shiny but low-impact projects. Double down on what’s already working and go deeper, not wider. 5) Operational excellence isn’t bureaucracy — it’s what gives your team the freedom to execute faster and smarter. Look at implementing EOS (Entrepreneurial Operating System) or a similar framework. It’s been a lot of learning, unlearning, and rebuilding along the way. But what I’m most proud of? 62% of our team have been here for 3 years (part of our very first hiring cohort).
Diana Ross That's really impressive. The shift from “doing everything” to “building what runs everything” is one of the hardest transitions for any founder. Getting people, systems, and revenue to scale together is the real challenge, and the moment a business becomes built to last.
Great perspective - scaling people is always harder than scaling revenue. Love the point about operational excellence not being bureaucracy - it’s structure that enables speed.
That's right!!! June 2022!! Let's go...
"Scaling from 6 to 40 was far harder than scaling revenue." -- this is the REAL boss battle.
Was $10m-25m more challenging than $0-10m?
Six to forty people somehow feels harder than zero to six, which makes no sense until you're living it. Nobody warns you that "letting go of control" means watching someone do your job differently and biting your tongue about it.
Noted! 0-10M with 6 people? that is AWESOME! and this right here is very steady growth, 0 to 25 in 6 years, NICE! on the 0-10 as we speak. wish us luck!!!
Solid insights! Awesome that you highlighted the importance of scaling people. As companies grow, culture widens, performance standards become more apparent, and identifying HOW you develop your people becomes part of the action plan. Thanks for sharing!
The Retention.com team is killing it, Diana Ross!
CEO @ Fractional Ops | We build in-house AI Sales Systems for B2B Services CEOs so they don’t have to hire agencies.
3dExactly. The shift from 10 to 25M is less about pushing growth and more about building the machine that sustains it.