An already seasoned CTO able to help you both by executing well and sharing their experience. This will ultimately be your objective. But you might have already noticed their scarcity and their high salary/equities expectation.
Principal Characteristics
Short Term Costs
High but Mastered They should be seen as an investment not a cost. Otherwise you might be doing something wrong.
Proof of Concept
High Their experience and their availability will allow you to experiment the right way. Some knows how to keep iterating from their prototype. So no need to throw everything away once the Proof of Concept (PoC) is validated.
Long Term Costs
Medium but Mastered You should take shortcuts thanks to their experience. They would unlock some opportunities. Opportunities created shall repay the initial cost 10x and Technical Debt shall be low. Good foundation will ease the recruitment process.
Risk
Medium Keep in mind the Bus Factor. Make sure your CTO is aware that for the next 2 years they will have to take care of the whole development including all boring tasks. If they leave, you will struggle to find a replacement.
Future Proof
Good Your project shall scale allowing more developers to join pretty easily. Provided you don’t have an elitist CTO expecting an imaginary dream-team to join him. Make sure they do the necessary efforts to simplify enough the code base.
Ability To Pivot
Good They shall embrace feedback and changes by delivering small iterations regularly. Their business experience shall help you to make the right decisions. At the right time.
Reassuring for investors
High Investors usually bet on your team’s ability to execute as much as on your elevator pitch. They know a good CTO will allow building a great team.
Ease to find
Low The more you can pay (or the more equity you can give), the more likely you will convince one to join you. Expect a fifty-fifty split for early CTO without salary.
You can try :
- YCombinator (startupschool.org/cofounder_matching)
Key Advantages
ℹ️ Having a CTO who already was a founder is a real plus
Provided it was a real startup and not just a side project. Especially if you are a first time founder. Their experience will boost your understanding of the whole eco-system.
ℹ️ By giving them significant equities, you will have them incentivized
They will then be less prone to deliver something mediocre. And then disappear with the money at the first difficulty. Foresee ~50% equities split for a good one if you just bring an “idea”. Don’t abuse on your vesting schedule strategy. Or you take the risk that they will leave to another startup too soon. And you will have to start all over again. Reading some YCombinator articles about how to split equities might help you. Keep in mind that experienced CTO will notice if your are trying to con them.
ℹ️ You could try to negotiate equities in order to give the minimum.
But be sure that if it’s not fair, your CTO will leave your project. As they will most likely receive better opportunities. No second chance. You can look at the “Slicing Pie” book for more information. Be prepared to accept the truth : an idea without any ability to execute worth nothing. Don’t abuse on your vesting schedule strategy. Make it simple and fair.
ℹ️ Good soft-skills are mandatory whenever a CTO builds their team.
Their ability to not build a toxic team and to empower their team-member rather than trying to control them will make the difference on the mid/long term. On some company it can be a 10x positive or negative factor. It will ease your ability to attract and especially retain talented people at a lower cost.
ℹ️ Someone who is a tech leader could help.
Having a CTO who is active on tech social media can help you reach a niche if you plan to do some B2B2C. If they give tech conferences or write articles, it will also help you to reach a niche (if your customer are devs). Some very good CTO simply don’t take the time to bother on social tech stuff. Don’t take it as an important criteria when selecting your CTO.
Warnings
Make sure to discuss about all of the subjects below during your interview.
⚠️ By definition a CTO is experienced enough.
However, some people had the notorious CTO title in their former company. But they were merely a Lead Dev. It might not be the kind of profile able to scale your company the way you intend to. Depending on your project’s complexity, make sure they have managed to scale their team to at least 8 developers.
⚠️ On the contrary, some CTO were focused only on the strategy and the business side.
They might not be the best coder anymore. Make sure they are still able to build something. And not just a prototype that will collapse after 6 months.
⚠️ Furthermore be vigilant on CTOs who are used to manage more than 15 developers.
They most likely didn’t code for a while. Unfortunately all the technologies became way more complex since 2015. Hence the emergence of highly specialized developers (SRE Vs Backend Vs Frontend Vs Integrator). It might be hard for them to keep up with the current pace.
⚠️ Don’t look only at CTOs involved in “successful” companies.
Luck is a major factor in a startup’s success. Some people were appointed CTO simply because they were at the right place at the right time. A lot would not be able to explain you how to repeat their previous success. Building a successful Startup was way easier 10 years ago. Technologies were simpler, users were expecting less and there was less competition. Furthermore most startups failed because their marketing didn’t manage to find a Product/Market fit.
Focus on CTOs with a track record of being able to deliver quality products. Not only their past company success.
⚠️ Beware of CTO coming from the corporate world or even the FANG world.
If it is their first experience in the startup world. Make sure they understand it will be completely different. And assess how they would comply with the emotional roller-coaster of your startup. Also you want your startup to be built on robust (most likely “old) technologies. But still be able to use bleeding edge ones. Corporate world is not the best place to learn them.
⚠️ Make sure your CTO knows enough about
Your CTO must knows enough about DevOps, BackEnd, Architecture, Security, Quality Assurance and now AI. Be advised some Mobile developers, FrontEnd developers, Machine Learning developers or Data Scientists sell themselves as CTO. But you will want someone with a broad view of your project’s technical landscape (aka. the Stack). Better having a generalist lightly specialized in a component you might need, than a specialist unable to understand the whole landscape of your project. Consequently unable to prepare your product to scale well, in a robust, maintainable and pragmatic way. If they are not able to create the project from A to Z without any help (except for design), they might be not the right CTO for you.
⚠️ If you found a CTO who is used to manage more than 10 developers.
You might ask them first if they are ready to spend at least 2 years without a team to manage. Some just want to be manager and to delegate the work. They might leave your project early because coding all day is not their passion anymore. Or push you to accept aggressive investors so as to get a team ASAP. Whereas hiring a team too early might not be in your best interests.
⚠️ If you found a CTO involved in multiple companies.
You might ask them first if they are ready to focus on your startups. What if one of their other babies sky rocket ? Would they leave you ?
Red flags
🚩 Red flag if your CTO is expecting to manage a team and no more code within the next 2 years.
🚩 Red flag if your CTO is too confident on their ability to deliver on a tight schedule. An experienced CTO would know there are always unforeseeable blockers.
🚩 Red flag if your CTO is not pushing you back on some feature. A less experienced CTO would not dare saying no.
🚩 Red flag if your CTO is not forcing you to advance in an iterative (Lean Startup) way.
🚩 Red flag if your CTO is not aware of the Product/Market fit concept.
🚩 Red flag if your CTO is not aware of the Feature CreepProjects tend to have way more features than necessary. Each feature creates technical debts and maintenance costs. Try to implement only features your product really needs. Reading the book ‘The Mom Test’ might help you to avoid it.
concept.
🚩 Red flag if your CTO doesn’t acknowledge that the human factor plays a major role in a startup’s failure or success.
🚩 Red flag if your CTO is not taking the time to regularly read articles, books or attend to tech conferences.