How to 
find a CTO
 in 2023

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. Theirexperience 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.

⚠️ 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 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 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.

ℹ️ The best of both worlds.
It might be a relevant choice if your project is estimated more than $30 000. And if you want to master your costs. You would have an experienced CTO who would have an incentive to share their experience with you. You would also have a team of cheap and highly motivated juniors.

ℹ️ Hard to find good interns.
Good interns are head hunted. AI might change that. In some countries interns have no minimum wages. It will be relevant to propose them at least $700/month (North America or North Europe) in order to attract good ones. Furthermore the value they will add to your company will largely deserve at least this amount. You will also want to find ways to keep them motivated. Provided your CTO will be patient enough to take the time to coach them properly.

ℹ️ At some point in your journey, you will focus on sales.
It might be not smart to have a full-time CTO during few months. You can discuss with your CTO if he would accept some freelancing and work as fCTO to reduce some costs. And then come back.

⚠️ Don’t hire an intern/developer, then find an Fractional CTO.
Very few will accept to lead developers they didn't hand picked. Most of them have seen that casting mistakes are very costly. The human factor plays a major role in a startup's failure or success. And chances are that you would have failed to recruit a relevant profile. The Fractional CTO will more easily hire developers who will match better to your project and their leading style. Make sure to discuss with them about the company's culture you are looking to build/avoid.

⚠️ You don’t want a project manager who will only delegate tasks.
You want someone able to build your project's foundation in a pragmatic way. And then being able to embark and empower your team.

⚠️ Few CTOs will be comfortable with this way of working.
Especially accepting to reduce costs by hiring juniors or interns. Some might simply refuse your proposal. Be transparent upfront.

⚠️ Make sure your CTO has not more than 3 projects in parallel.
Unless they are a 10x developer, they won’t be able to keep up the pace while remaining efficient. Be ready to take the initiative to propose a retainer. Aim is to incentivize them not looking for more projects. And making sure they will prefer your project over others. Ask them to be transparent on that. It is too risky for your startup.

⚠️ Inexperienced Fractional CTOs tend to burnout quickly.
A Startup is not a sprint, nor a marathon. It's a relay race. Make sure your Fractional CTO is aware of that.

🚩 Red flag if your CTO asks the juniors to create your project's foundation and then just plays the overseer role. They should spend their initial time preparing the project for the others.

🚩 Red flag if your CTO is not aware of the Product/Market fit concept.

🚩 Red flag if your CTO is not forcing you to advance in an iterative way.

🚩 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.

🚩 Red flag if your CTO using a framework/technology without knowing why. Especially a recent one. They should demonstrate you that their choice is junior-friendly. Controversial topic: Javascript and Java are not the most junior-friendly technology. Far from it.

ℹ️ If your project is estimated less than $20 000 by a North American or West European agency. A highly motivated junior might do the job. You might not have the need for an experimented CTO. You can still ask for advice punctually to an experimented Fractional CTO if you want to be reassured.

ℹ️ Some juniors if they were lucky were trained using the cutting edge technologies.

ℹ️ Junior developers provided you manage to build a high quality environment (and avoid toxic management) tend to have a better retention rate. They should be seen as an investment.

⚠️ Having a developer full-time for a small project might lead them to over-engineer things. Some don't like boring technologies. Juniors will tend to use buzzword technologies without trying to understand if these technologies would be relevant or too risky for your project's sustainability. Buzzword technologies require some experience to take full advantage of them. Otherwise you might end up with an unmaintainable product. Some projects die too early because of this.

⚠️ You might prefer to not give them the CTO title (and neither the Lead title). Since if all is going the right way you will then have to hire a real CTO. You don’t want to kill their motivation and have them leaving your boat before the experimented CTO really took on the lead on the project.

⚠️ Hiring a junior might be risky for your business. You don't want to be in a position where you found your Product/Market Fit and got traction. But you are unable to scale. Leading your competitors (who have a good foundation) to be able to steal your market shares surfing on your own marketing expenses.

⚠️ If your junior developer is negotiating a very low working hours schedule. Chances are that they are already building their own project and they just needs some extra money to expand their own runway.

🚩 Red flag if your junior developer is over-confident on their abilities. This would clearly mean that they didn't fail YET. Meaning they lack of experience. Every CTO failed at least one time in their career. Therefore they know there are a lot of uncertainties.

🚩 Red flag if your junior developer is negotiating their salary. Chances are that they are already connected to head hunters and they will leave your ship at the 1st opportunity.

ℹ️ Once a developer has tasted the freelancing world. Chances are that they would never accept a full-time job anymore. Keep in mind the differences between a freelancer Vs an employee on your management strategy.

⚠️ Expect that if this freelancer is not motivated enough to continue on your adventure. They might leave for another more profitable (or less risky) project. You would then struggle to find another developer accepting the full responsibility of your project. Even if your project has passed the “Ramen Profitable” threshold and you would be able to pay them more. You might lose some precious opportunities. Some projects die too early because of that.

⚠️ Expect that they might be reluctant to continue on the project and maintain it after the Version 1. A project with bad foundation is hard to maintain and not enjoyable. It will cost you a lot. Therefore you will feel the need to put more pressure on your freelancer. It can then become simpler for a junior freelancer to accept a new project. Expect to negotiate a raise.

🚩 Red flag if your junior CTO wants to use an exotic technology. You want a technology widely used to simplify the recruitment process. Developers are already scarce. It would be risky to use a technology very few developers are using.

🚩 Red flag if your junior CTO wants to use a technology they have no track record with. Some just want to add keywords on their resume. A more experienced developer could adapt quickly. But it would be costly/risky to pay someone to learn a new technology. Consequently having the foundations not built by someone experienced enough. Some projects die because of this.

ℹ️ Some freelancers consider themselves as senior after a few years in the industry. A senior freelancer should have at least 8 years in the industry. They should have track record of regularly using state of the art technologies and methodologies. Of course giving an arbitrary year amount is irrelevant. This depends also on their experience and mindset. A freelancer used to work with big companies with rigid organization might not be interesting for you as the pace in startup is not the same. You might prefer someone who already joined some startup to benefit from its experience.

ℹ️ It might be a good choice if you struggle to find an experienced CTO as co-founder. And if your project is estimated more than $30 000 by an agency. It can be especially relevant if you just want a quick Proof of Concept (PoC)The minimal amount of work necessary to make sure your project is feasible. This shall not be underestimated especially if you have to connect to third parties API. allowing you to assert if your project is feasible with the nowadays technologies. You would know ASAP with few capital if the project is technically viable or not. But then you might reconsider who will take care of your Minimum Viable Product (MVP)The minimal amount of work necessary to sell your product so as to demonstrate a Product/Market Fit. Not enough polished, with some bugs but sellable to an early customer. If you are proud of your MVP it means it is too polished. Some renamed it as Minimum Sellable Product. (or Version1).

⚠️ It might be inefficient to have an experienced freelancer doing the small or repetitive tasks of you project. Which in some cases could represent nearly 50% of your expenses. You might want to negotiate with them so that they would delegate these tasks to a less experimented freelancer (or an intern) in order to avoid wasting money. And in order to keep an optimal velocity while reducing the Bus FactorThe minimum number of team members who could suddenly disappear before leading a project to die. Worst number being 1.. If they are reluctant to delegate, consider this as a red flag.

⚠️ Make sure your freelancer is comfortable leading other freelancer. At least that they would be ready to help you being autonomous once your are ready to scale. Or you might end up alone trying to recruit new developers. And very few will be tempted to join you and take the responsibility on your project.

⚠️ An experienced freelancer will be reluctant to lose their freedom by joining a company full time. Keep this in mind the day you try to convince them to join your company on the long term. You will have to adapt your management style and to prepare a compensation.

🚩 Red flag if your CTO just wants to be involved in the early development (less than 3months). The early months of the project are usually the simplest part. A charlatan can easily conceal a lack of skill during this period.