Why Growing Your Remote Team Might Be the Thing That Breaks It

If you’re still in every decision after hiring, it’s not your team. It’s your systems.

Ryan’s AI startup was on fire. Early traction. Paying customers. He finally started hiring, doubling his core team in a couple of months: a PM, two engineers, a designer. He thought everything would get easier with more hands to do the work. Instead?

• Slack blew up with questions

• Deadlines slipped

• He was in every meeting

• He had no idea what people were doing all day

“I’m acting like a therapist half the time,” he told me.

“The other half I’m just trying to keep the lights on.”

Sound familiar? You’re not alone. And you’re not failing. But your systems probably are.

What Breaks When Remote Teams Grow

When you’re 3–5 people, everything runs on instinct.

• Priorities live in your head

• People just ask you what to do

• You decide fast and move fast

But when you grow to 7, 10, 15?

The “just ask me” system breaks.

• Everything stalls

• New hires feel lost

• You’re in the loop on everything

And the ironic part? You hired to remove the work. Instead, you added complexity. And without real systems, that complexity falls back on you.

Your Team Isn’t the Problem—Your Systems Are

Ryan’s PM was brilliant. But without shared priorities, async workflows, or a roadmap…

Every decision still ran through him. He wasn’t scaling – he was substituting himself for a system.

How to Know if This Is You

If you’re:

• Still in every decision

• Spending your time managing emotions, not execution

• Not sure what people are working on

• Waking up dreading your calendar

You don’t need more people.  You need better systems.

I break it all down here, including a checklist to help you diagnose your ops today:

Read the full blog post + checklist →

P.S. If this hit close to home, reach out to me. I help early-stage founders build remote operations that scale – without breaking you in the process.