Scaling Pains

The Crisis Nobody Prepared You For

At last the company found the hockey stick growth curve. VCs have invested and there is lots of money flowing in. The board wants velocity. You hired fast. The team doubled, then tripled.

But something’s broken. Shipping is slower than when you had half the engineers. Bugs are up. People are frustrated. The CEO keeps asking “why is everything taking so long?”

This is the scaling crisis. Almost every CTO hits it somewhere between 15 and 50 engineers. The playbook that got you here - the informal communication, the shared context, the “we all know what needs to happen” culture - stops working.

The triad of pain hits simultaneously: engineering velocity drops, code quality suffers, and team culture starts to crack. You’re drowning, and adding more people seems to make it worse.

Contrary to all other industries, growing means: More effectivity and impact but less efficiency. This creates tremendous pressure on the CTO from business with demands going up and velocity going down.

Warning Signs You’re In The Scaling Crisis

You know you’re in trouble when:

• Shipping slows down even though you have more people
• Dependencies become blockers - teams waiting on other teams
• Meetings multiply - meetings feel random - everyone needs to align on everything
• Quality drops - more bugs, more incidents, more firefighting
• People are frustrated - your best engineers start looking elsewhere - explorers leave the ship and are replaced by villagers
• You’re the bottleneck - nothing moves without your input

If three or more of these sound familiar, you’re in the crisis. The good news: this is solvable. The bad news: it requires changing how you work, not just adding process.

Growing means, all edge cases become mainstream. If you have 5 customers, your app has many edge cases. If you have 500.000 customers, there are no more edge cases, every eventuality needs to be considered.

The Scaling Playbook

Stage 1: 1 → 10 Engineers

This is where most CTOs first feel pain. The informal culture breaks at ten people.

What changes:

• You need engineering managers (not just tech leads)
• Communication moves from all-hands to structured
• Written documentation becomes essential
• Teams need clear ownership boundaries

Key question: When to hire your first engineering manager? When you have more than 7 direct reports, or when coordination is eating more than 20% of your time.

Stage 2: 10 → 30 Engineers

Now you’re building an organization, not just a team.

What changes:

• You need a layer between you and the teams
• Architecture decisions affect multiple groups
• Hiring and onboarding need real processes
• Culture can no longer be implicit

Key question: How do you maintain velocity while adding structure? By making the structure serve the work, not the other way around.

Stage 3: 30+ Engineers

You’re running a department not only a team. Your job fundamentally changes.

What changes:

• You’re managing managers, not engineers
• Strategy matters more than tactics
• Cross-functional coordination becomes your main job
• You need VP-level leaders

Key question: Are you scaling yourself, or becoming the bottleneck?

Levels

Important is the deepness of the hierarchy below you. Do you directly tell people what to do? Do you need to manage through team leads? Through two levels of managers, heads and team leads? The bigger your organization grows, the more difficult does it get to influence behavior and results of individual contributors because they are farer and farer removed from you.

The jumps are from directing people to managing through people. The second jump is from managing leads to managing senior managers.

Common Mistakes When Scaling

Adding process without removing friction. Every new process should eliminate more overhead than it creates. Most CTOs add meetings and checkpoints that slow things down.

Hiring too fast without absorption capacity. New engineers need ramp time. If you’re hiring faster than you can onboard, you’re making things worse.

Keeping the flat structure too long. Engineers love flat orgs. But past 15-20 people, someone needs to make decisions, resolve conflicts, and unblock work.

Ignoring culture until it’s broken. Culture is how people behave when you’re not watching. If you don’t intentionally build it, you get whatever emerges - and it’s usually not what you want.

Solving organizational problems with technology. Microservices won’t fix communication problems. Better tooling won’t fix unclear ownership. Sometimes the problem is human, not technical.

That’s okay. Neither had any other CTO the first time they did it.

The CTOs who navigate scaling successfully have one thing in common: they learn from people who’ve done it before. They find mentors, coaches, or peers who’ve seen the patterns and can help them avoid the expensive mistakes.

Scaling is a skill. It can be learned. But learning it the hard way - through trial and error while your company depends on you - is costly.

I’ve helped 80+ CTOs scale their engineering teams from 10 to 30, 30 to 100, and beyond. I’ve seen what works at each stage and what doesn’t.

If you’re drowning in scaling challenges, let’s talk.

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