Issue 03: Who to Hire First at $1M-$5M ARR

Hey friend,

At $1M ARR, you’ve already proven people want what you built. But now you’re stretched thin - still shipping features, running demos, answering support, even writing posts yourself.

That grind got you here, but it won’t take you to $5M. The next stage is about bringing in the right people, at the right time, so growth doesn’t stall.

Here’s how I’d think about it 👇

When you hit $1M+, the first thing that usually breaks is product velocity. Features take longer, bugs pile up, and every decision still runs through you. That’s where your first key hire comes in:

This is usually the first pressure point. Features slow down, bugs pile up, and progress depends too much on you.

At this stage, you don’t need a 20-year CTO, but you do need someone with 3-6 years of solid product or engineering experience, ideally from another startup. They’ve seen enough to ship quickly, cut scope when needed, and keep momentum without getting lost in process.

They’ll own the roadmap with you, so you can focus on growth instead of fixing bugs at 2am.

Early users forgive clunky design. The next wave won’t.

Here, look for a 2-5 year product designer - someone who’s already shipped live products, not just portfolios. They should know UX flows cold and have enough range to cover both web/app design and brand polish.

The job isn’t just making things pretty. It’s making the product usable, simple, and delightful. They’ll save you from duct-tape UI and help your product feel like it belongs in the hands of paying customers.

Think of this person as your right hand. Not a specialist, not a VP, but a scrappy generalist with 3-5 years across marketing/ops/analyst roles.

Their superpower is adaptability: one day they’re setting up an email drip, the next they’re chasing invoices, the next they’re writing a Notion doc so your ops aren’t chaos.

What you want here is curiosity over pedigree. They should be the kind of person who says “I’ll figure it out”, and then actually does.

Churn is the silent killer here. If customers aren’t sticking, new sales won’t matter.

This hire doesn’t need decades of account management. What works best is someone with 2-4 years in customer-facing roles (support, onboarding, CS) who loves solving problems and building relationships.

They’ll talk to customers daily, spot patterns, and bring feedback straight to product. Their goal isn’t just answering tickets — it’s making sure customers win with your product.

If you’re B2B, every sales call still runs through you. That’s fine early, but it won’t scale.

The right AE here has 3–6 years of quota-carrying sales experience — ideally selling to your type of customer (SMB, mid-market, etc.). You don’t want someone too senior who expects everything handed to them, but you also don’t want someone so green they need hand-holding.

They’ll take warm leads, build repeatable processes, and free you to focus on big strategic deals.

You don’t need a full-time CFO yet, but a fractional finance/ops advisor (even 5–10 hours a month) can save you from messy books and help you think clearly about cash. At $1M–$5M ARR, clean numbers = better decisions.

Don’t hire just because “that’s what startups do.”

Only hire when what you’ve already tested is working, and you need more hands to scale it. Bring people in one by one, so you can see the impact of each hire without burning unnecessary cash.

Scaling from $1M to $5M is really about buying back your time and focus. That’s how you keep momentum without losing your edge.