From $10M to $20M ARR: Building the Machine

What got you to $10M ARR won’t get you to $20M ARR in <12 months.

This is part of a 4 part Series about how to get from $1M → $3M ARR, $3M → $10M ARR, $10M → $20M ARR, and $20M → $50M ARR.

Welcome to the scale stage, where process beats hustle. This is when you slowly but surely need to transform from speedboat captain to orchestra conductor - without losing momentum.

"When you have to generate over $10M ARR in one year, it takes coordination. You need a crew."

At this point, you can't touch every deal or keep all the context in your head anymore.

You need systems.

For founders, letting go is hard. All the sudden, your job isn't closing deals anymore - it's building the machine that closes deals. That means hiring great people, giving clear playbooks, and getting out of their way.

When done right, revenue becomes predictable. X pipeline with Y conversion yields Z closed business.

On the sales side, start by bringing on sales ops. Find someone who wakes up thinking about process, data, and efficiency.

You're about to hire 20+ people who need to be productive fast. Without systems, each takes three months to ramp. With good ops, you cut that to one month.

Two months saved times 20 hires equals 40 months of productivity. That's hitting your number versus missing badly.

Most founders think process means bureaucracy.

But good process is invisible - it means accurate CRM data, onboarding that gets reps selling in week two, lead routing that catches everything. Document the basics: how we demo, price, handle objections. Recipe cards, not 100 page manuals.

A big challenge this stage is maintaining agility while adding structure.

You're not done innovating but you also can't run on chaos either.

What often works: keep your core machine humming while carving out small teams to experiment. Maybe testing enterprise deals while staying mid-market. Maybe exploring new verticals.

Importantly, protect experiments from your efficient machine that will try to kill anything different.

On top, you need great data. Below $10M, you could eyeball numbers. Now you need dashboards, forecasting, pipeline analytics—your early warning system.

Lastly, your hiring mix also changes at this stage.

You now need more "maturity people" - folks who've seen scale and want to execute proven playbooks (vs thriving in new and chaos).

But avoid the trap: VCs push you to hire VPs who scaled from $10M to $100M. They bring enterprise playbooks for the company you might become in five years, not today. This mostly ends badly.

Instead, promote from within and hire experienced ICs from outside. That crushing SDR? Make them a team lead. That engineer who helps with sales calls? Your first sales engineer.

Pair internal promotions with experienced ICs who can teach management mechanics.

That’s how you build a winning sales org for this stage.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Russ Thau, a seasoned sales leader who helped scale Intercom, Box, and Envoy from single digit $M through IPO.

Youtube | Apple Podcast | Spotify

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