CTO Career Path: Before & After

Being a CTO is a dream job for some people. They want to manage big teams, innovate cool things, or run a unicorn startup.

Those all sound like fun. But what happens after you become a CTO?

Before discussing that, let’s talk about how to become a CTO, including my own CTO career path. Understanding what makes a good CTO is critical because it directly relates to what you do after you become one.

How I Became a CTO, My CTO Career Path

I did a very (non)scientific poll on LinkedIn about how people become a CTO, and about half gave the answer I expected: They started their own company.

That is also the best way to get the experience and skills to be a good CTO.

One of my favorite quotes is, “You can’t learn to swim by reading a book.”

I love it because there are so many things in life you cannot learn unless you do them.

The best way to learn to be a CTO is by starting your own tech company.

I was a CTO at 22 when I started my first company, VinSolutions. I had no idea what I was doing, but like everyone else, I learned it trial by fire as the company grew. After 20 years, I learned how to do and how not to do many things.

Starting your own company is critical to becoming a CTO because it forces you to be in charge of the roadmap. You are forced to have higher-level thinking around priorities. That is a far cry from the average developer who works on JIRA tickets and doesn’t understand why.

The best CTOs at tech companies are Visionary CTOs. No matter what industry they work in, they are working every day to innovate and change it.

How You Can Become a CTO

If you can start your own company, even if it is a bootstrapped small company, I highly recommend it. If not, your best bet is to climb the corporate ladder but focus on the product side.

Never forget this:

I became a great CTO because I talked to customers weekly and understood their problems. Most developers never talk to any customers and think they know more than the customers (they don’t).

I spent all my time researching the industry, our competitors, and what other solutions existed on the market.

Based on everything I heard and saw, I could figure out unique and innovative ways to solve our customers' problems. I knew what the industry and competitors were doing and could copy or improve their ideas.

Ultimately, I owned the roadmap. Owning the roadmap forces you to think strategically and make business decisions.

When a CTO owns the roadmap, they envision building a team and architecting a solution to bring it to life. That is when stuff gets done fast and correctly.

I firmly believe in Visionary CTOs, hence the name of this blog.

Be the person in your company who is the expert on the customer’s problems, the industry, and the product. That is the person who eventually rises up to be CTO. 

Industry and product expertise is a rare and valuable skill almost irreplaceable in a company. In contrast, a company can hire virtually anyone to write code.

Understanding how to identify and solve business problems with technology is the fundamental skill of a CTO.

What Comes After Being a CTO?

You built some cool stuff, scaled a company, succeeded, sold it, rang the bell on Wall Street, or accomplished your dream.

What now?

You can take your expertise in identifying and solving business problems with technology to do many things.

We will review all of these in-depth:

• Become a Founder

• Become a CEO

• Technical Sales

• Become a Consultant or Fractional CTO

• Board Member or Advisor

• Venture Capital

Become a Founder

If you were hired as a CTO somewhere before and weren’t a founder, it is probably time for you to be a founder.

If you are a first-time founder, I recommend finding a co-founder with whom to start the company. Find someone with industry connections and a great business idea that you can bring to life.

Starting your own company can also start as a side project until it grows and needs your full-time attention. Most startups don’t even need a full-time CTO.

When I started my first company, I worked full-time at my other job for about 18 months before I quit and went all in on my company. I worked around the clock nights and weekends, trying to get it off the ground.

Another option is to keep your full-time job and hire a developer to write all the code. You can just oversee the project and help out. You can hire offshore developers at an affordable cost to help.

Be the CEO: From Product Vision to Company Vision

After I sold my first company, I decided to start my own SaaS company. I decided not to have any business partners. At 29, I was stepping out on a limb to be CEO of my tech company.

At first, I will admit it was a big leap. There was a lot about sales, marketing, operations, and running a business that I was not experienced with.

I knew how to talk to customers. I knew how to build a SaaS product.

To some degree, I didn’t know what I didn’t know. But that isn’t much different than being a CTO for the first time. Now, I was in trial by fire as a CEO instead of a CTO.

Looking back I kind of wish I had a co-founder to help with that company. Instead, I hired an amazing Chief Operating Officer who was critical to every step of the way in the company. I also hired other amazing talent to run sales, marketing, customer success, and even a CTO.

I had one thing that nobody else had, and you can’t easily hire for.

The company and product vision.

The biggest difference in going from CTO to CEO is also going from the product vision to the entire company vision. The product vision part of it was easy for me. I could do that in my sleep.

Figuring out the company vision required solving some very hard problems.

• What kind of company are we?

• Who are we going to sell the product to?

• How are we going to sell it to them?

• How do I get all the company leaders to buy into my vision?

Learning how to go from building the product to how to actually take the product to market was a big leap.

Being a CEO typically requires being a thought leader. It requires spending a lot of time talking to customers, analysts, partners, and people. Even if it doesn’t seem like it, it is largely a sales job.

The most important thing is having a strong vision for the company and product. You can hire people to do sales, marketing, operations, etc. You can’t hire someone with the vision.

The best CEOs of tech companies have both a tech background and are good at sales.

The Highest Paying Job in the World: Sales

Maybe you don’t want to be or aren’t ready to be the CEO of a company. That is OK. But maybe you are ready to be a full-time salesperson.

You probably already know this. The highest paid people in the world are generally salespeople.

While you were making $300,000 a year as a CTO, the top salespeople at your company were probably making 2-3x that.

Most CTOs have to be at least decent salespeople. They have to be able to go to an executive meeting and convince the rest of the team why they should bet everything on the product roadmap the CTO has put together.

The weekly sales job of a CTO includes:

• Selling the dev team on why we are doing things a certain way

• Selling the CEO on their budget and hiring needs

• Selling other departments on the output of the dev team’s work

• Literally selling customers and analysts on the company’s products

• Thought leadership activities

• Strategic partnerships

Sales is a big part of the job. It could also be your next job.

From CTO to Sales Engineer

Most salespeople are not very technical. Being able to marry your deep technical skills with sales is extremely valuable. There is a huge demand for sales engineers who have the technical aptitude to help sell enterprise products.

If you are considering something new, being in technical sales in one form or another is a great option.

The CTO of one of my former startups became an expert in Microsoft Azure while working at our company.

Guess what he went to do?

Turns out that being on the sales team for Azure is highly lucrative. It pays more than being a CTO working for someone else.

Since then, he has started his own company selling custom outdoor kitchen cabinets online. That side hustle grosses over $1,000,000 a year, and you can listen to my podcast episode with him.

Become a Consultant or Fractional CTO

A CTO and consultants have a rare ability that virtually nobody else has. A skill that companies will pay $200, $300, $400 or more an hour to solve.

Your expertise in tech products allows you to go anywhere, like Rambo, and solve any problem.

You have seen enough problems with software, teams, cloud deployments, and everything else to instantly recognize them and know how to solve them. That is a scarce and valuable skill set.

You could work for yourself or a large consulting company as a consultant. Some people love being consultants because of the constant challenges and variety of work.

The new term for this that is popular these days is fractional CTO.

I have talked to many fractional CTOs who charge $5,000 - $10,000 monthly to work 1-2 hours daily. That is all smaller companies need from a CTO caliber person. They have multiple clients and really enjoy the variety and challenges. There are even CTO-as-a-service companies.

Be an Advisor or Board Member

Like being a consultant or fractional CTO, you could be a board member or company advisor.

Many companies could use your industry expertise and experience building technology products. This is especially true if you have deep industry product knowledge and expertise that could be very beneficial as an advisor.

I have worked in this capacity before as an advisor. They paid me a few thousand dollars a month to have a couple of phone calls monthly and attend a quarterly board meeting.

The insights and experience I had with them were invaluable. Your experience might also be.

The Venture Capital World

Bankers and finance professionals don’t know anything about technology except for how to use Excel.

Many private equity and venture capital funds hire previous CTOs and startup founders to work in their funds to help with due diligence, be board members for their companies, etc.

I always thought it would be to work in this world, but I have never done it outside of doing some of my investments.

The CTO Career Path

In summary, I think there are key things to know about becoming a CTO on the career path.

The most important is focusing on the product and understanding business needs. Being a good coder does not make someone a CTO. A CTO should be an expert at understanding challenges and opportunities and how to solve them with technology.

I highly recommend starting your own tech company. The experience you can gain from it is unlikely any other.

Once you have been a CTO, there are a lot of things you can do afterward. I took the path of being a founder and CEO. Today, I run an offshore software development company and spend much of my time on technical sales activities. I enjoy every second of it.

Regardless, you will always be a CTO at heart once you become a CTO.

Being good at identifying and solving problems is a lifelong, valuable skill.