Your CTO Should Be Spending Your Money (And 9 Other Things You're Not Getting)

I'll be honest with you.

When I first encountered this kind of business training, I walked out of the room. I'm not kidding. I looked at the setup—the energy, the promises—and thought, "I will not be part of a little hype session."

But I stayed. And I wrote hundreds of pages of notes. Because sometimes the things that make us most uncomfortable are exactly what we need to hear.

So let me make you uncomfortable.

The Question Nobody Wants to Answer

Quick poll: Do you have a CTO in your company?

Great.

Do you know what they actually do?

Because here's the truth most founders won't admit: we treat the CTO role like some kind of magical technical priest. We don't really know what they do. We just ask them to do stuff, and then things either happen or they don't. When things don't happen, we have what I call a "pussy conversation"—we renegotiate, we adjust, and suddenly things work again.

Sound familiar?

The colloquial agreement is that a CTO is just the person who knows the most about tech. That's it. That's the job description we've collectively settled on.

And it's killing our companies.

The Scale vs. Growth Trap

Let me show you something. Imagine your revenue chart. We're all building SaaS companies because we want that hockey stick, right? We don't want linear growth. We don't want slow, steady climbs. We want scale.

But here's where it gets weird.

When it comes to our technology—the thing our entire business is built on—we have this bizarre, almost dysfunctional relationship. We understand there's a cost. We have a love-hate thing going on because we don't really know what's happening inside the black box. We know what we want the product to do. We know how we want customers to feel.

But what's actually happening in there? That's the CTO's problem.

So we struggle. We struggle with requirements, velocity, quality. And our solution? We try to grow our technology by spending as little as possible.

Anybody can grow. You just spend more money, make a little more money, spend more money, make a little more money. That's not scaling.

Scaling means you put business models and teams in place so you're making significantly more money than you're spending.

And when it comes to technology, we hit this wall. We stop investing right when we should be accelerating. We want to make more money over here while just "dealing with this crap" over there.

Let me be blunt: Your CTO needs to spend your money.

If you don't have a CTO and you're building a tech company, you have a problem. Not a future problem. A right-now problem.

The Ten Things Your CTO Actually Owes You

I made this pyramid. It has ten blocks. Did you know that ten blocks make a pyramid exactly like this? Fascinating, right?

But seriously—this structure changed how I think about the CTO role, and it's changing how CTOs around the world operate.

The Foundation (The Things That Matter Most)

Dollars 💰

I hate it when people tell me the CTO is a technical role. I genuinely hate that.

Technical people can build code, design architecture, and scale infrastructure. The CTO is your partner in the leadership team focused on what drives revenue. If they're not working in the currency of business outcomes, they're not doing the job.

Budget

To build a team. Not just to hire developers. To build the team that will build the technology that will drive your revenue.

Business Objectives

Not OKRs. Not KPIs. Business objectives. B1, B2, B3 in my model. How are we actually going to make this money? This is where the wrestling match happens—and it should. You should be struggling inside the C-suite to figure out what actions will drive revenue.

Action

Given our revenue targets, our budgets, our team composition, and our business objectives—what are we actually building? What technical actions are we taking?

Technology

The actual product roadmap, ticket management, deployments. Most CTOs live here. But without the foundation below it, this is just expensive chaos.

The Support Structure (The Things Nobody Talks About)

This is where it gets interesting. These four pillars provide insight into what the hell is actually going on:

Speed: Someone in your company needs to be obsessed with delivery velocity. How are we getting code shipped? If your CTO says, "I don't do that stuff anymore," find another CTO.

Stretch: How does the organization need to expand to deliver on our promises? This is where uncomfortable conversations happen. "I know your budget was X, but we need 2X to actually do this." Your CTO is going to spend your money—but they should be telling you exactly what you're buying.

Shield: What threats are we facing? What does our decision today mean for our business in three years? If we build our MVP in Elixir, it might ship in two days. But in three years, we won't be able to hire anyone. That's a conversation you want to have now.

Sales: How is technology supporting customer success, onboarding, sales, product marketing? When we talk about revenue, the CTO should be in those conversations. How is our technology speeding up onboarding, which could triple our revenue?

The Exercise That Changes Everything

Here's what I did at the end of my talk, and you can do this right now:

Write down three numbers:

1. Pick any number between 0 and 10 (this is your "lie" number)
2. What does success look like for your company? If PayPal is a 10+, where do you want to be? Write that number.
3. Where is your tech organization actually at right now? Be honest.

Most founders discover something uncomfortable: there's a massive gap between where they want to be and where their tech organization actually is.

You might want to be at a 6. You might even think you're at a 6.

But your tech organization? It's at a 3. Or a 2. Or—and this is more common than you think—it's at a 1.

The CTO Levels Framework

This is why we built the CTO Levels framework.

It's simple: based on your budget and team size, we can tell you what level you should be operating at. Spending $100K on one person? That's one level. Spending $4M on ten people? That's a different level entirely.

Then we assess: Are you actually operating at that level?

Because here's what we discovered: CTOs aren't failing because they lack technical skill. They're stuck because nobody showed them what operating at their level actually requires.

You're expecting your CTO to operate at level 5, but they're stuck at level 2. And you don't even know it because you're non-technical and you think your CTO is telling you the truth about billable hours.

The Hard Truth

In order to scale your business, your technology organization needs specific competencies at specific stages. But you're non-technical. You don't know what "good" looks like. You think you know what to do, or you trust what your CTO is telling you.

The Levels model gives you an unequivocal glimpse into how healthy your tech organization is based on where you need to be.

Not where you wish you were. Not where you think you are. Where you need to be to hit your revenue targets.

The Thing About Always Needing a CTO

My friend Sri—the CTO at PayPal—and I have this ongoing debate. People tell me all the time: "I don't need a CTO right now. I'm only at $25K MRR. I can't afford a CTO."

Here's my counter: You always need a CTO. Always.

You always need someone, at some level, thinking about this for you. Otherwise, you're signing up for disaster. Because those 10 developers you've been managing yourself? They become untenable. Impossible to manage.

At any stage of a startup, you need someone partnering with you, thinking about what scaling your organization actually looks like.

Not just your systems. Not just your teams. You.

The Real Job

The chief technology officer isn't just the person who builds your product.

They're the person partnered with you to answer: How do we grow this company's revenues? What do we need to budget? What does the team look like that's going to take us there?

That's what I love to see in a CTO. Someone building the team that's going to build the technology.

If your CTO isn't asking these questions—if they're not challenging you on budget, on business objectives, on the threats three years from now—then you don't have a CTO.

You have an expensive technical lead.

And that's a problem you can't afford.

Want to know where your tech organization really stands? We built a quick assessment that takes less than 5 minutes and gives you your target level versus where you're actually stuck. Because the gap between those two numbers? That's your scaling problem, defined.