Former Combat Pilot Turned GTM Leader: The One System Every Startup Needs Before $5M

Most startups think they need systems when they hit $5M ARR. Or maybe $10M. Or when they raise a Series B.

Roee Hartuv, Head of GTM at Willingness to Pay and former combat helicopter pilot, says you're measuring the wrong thing.

The moment you need systems isn't tied to revenue. It's tied to who you're hiring.

When Superstars Stop Being Enough

In the beginning, startups run on superstars. People who can do everything. They don't need processes. They don't need checklists. They figure it out.

But at some point, you need to scale. And that means hiring what Roee calls "normal people."

Not mediocre people. Normal people. People who are good at their job but need structure to execute consistently.

That's when the wheels fall off without systems.

No onboarding process. No documented sales methodology. No clear handoffs between departments. Every new hire becomes a guessing game.

Roee learned this the hard way as a helicopter pilot. In the cockpit, you don't wing it. You follow the checklist. Every time. Because when you're flying a $20 million machine in combat, improvisation gets people killed.

That same discipline transferred directly to building revenue teams.

The Problem Leaders Miss

Roee has led sales, customer success, and marketing simultaneously at multiple startups. That's rare. Most leaders run one function and never see the full customer journey.

Running all three at once revealed something most organizations miss: the breakpoints happen between departments.

Sales hands off to customer success. Marketing generates leads that sales doesn't follow up on. Customer success renews accounts but never expands them.

Each department makes sense on an org chart. But from the buyer's perspective, it's a mess. They interact with all three, and the seams are showing.

Systems thinking fixes that. Not by adding more process. By designing the whole journey from the buyer's point of view.

Customer Success Is a Revenue Lever Not a Cost Center

One of the biggest mistakes Roee sees: companies treat customer success like customer service.

They're not the same.

Customer service responds to tickets. Customer success drives expansion, retention, and growth.

The problem? Customer success as a discipline is only 10 years old. Sales has been around forever. Everyone knows what a BDR does. Everyone knows what an AE does.

But customer success? Every company builds it differently. Some treat it as renewal insurance. Some treat it as account management. Some still think it's support with a new title.

Roee's recommendation: tier your customers. Not everyone gets the same level of service.

Segment by what they're paying and what their potential is. High-value, high-potential customers get proactive engagement. Low-value, low-potential customers get self-service.

Sounds obvious. Most companies don't do it.

What Tech Can Learn from 100 Year Old Companies

Marcus shared a story from his time at Cintas, a $10 billion company that's been around for over a century.

They had what SaaS companies now call "customer success teams." Cintas called them Service Sales Reps. And they had clear KPIs: revenue growth, retention, expansion.

Not NPS. Not customer satisfaction scores. Revenue.

Their managers had KPIs that rolled up from their team. They ran sales contests. They trained on growth. They treated post-sale as a sales function, not a support function.

Roee's point: the principles aren't new. Mature industries figured this out decades ago. SaaS is still catching up.

The Signal You Need Systems

You don't need systems when you hit $5M. You need them when you can't onboard a new hire without them sitting next to your best rep for three months.

You need them when your top performer says "I just have great relationships" and can't explain what they actually do.

You need them when the handoff between sales and customer success feels like a game of telephone.

That's the signal. Don't wait for an ARR milestone. Wait for the moment when heroics stop scaling.