There’s a tech talent war in New York City right now. The established firms like Facebook and Google are only getting bigger, and there are more tech startups than ever making NYC their home. As a result, hiring great tech talent is more challenging than ever.
Yet, as a startup founder, it’s critical to find a great CTO. For overseeing quality of work from the tech team, running effective agile retrospectives, and meeting the goals of the business team, hiring the right CTO can have significant improvements to your company.
There is no one right time to find a CTO. Some startups can go a long time without a CTO, while others need one early on. Regardless of the stage of your startup, if you are looking to hire a CTO, follow these seven steps to find your ideal candidate.
The seven steps to hiring your startup CTO
Use the links below to jump to specific sections of the post.
- Consider bringing on a technical advisor before you hire a CTO
- Define the CTO role requirements and craft a job description
- Create 1:1 mapping
- Prioritize motivation, integrity, and culture fit
- Sell the position
- Find the best candidates
- Make an offer they can’t refuse
1. Consider bringing on a technical advisor before you hire a CTO
What’s the difference between a technical advisor and a CTO? A technical advisor keeps their day job. The technical advisor works for you 2–4 hours per month and serves as someone who’s not in the weeds with you, day to day. They might do weekly or monthly code reviews, act as a sounding board for your CTO, and serve as a checks-and-balances system with your CTO. If you find a technical advisor first, this person can be a huge help with finding the right CTO. They can vet CTO candidates, do interviews, and review job descriptions.
Finding a technical advisor will likely be easier than finding a CTO, because you aren’t asking someone to quit their job to come work for you. Rather, you are asking them to keep their job and take on an advisory role that takes a few hours per week.
In some cases, you can get away with having a technical advisor and not hiring a CTO. One company I advise has two co-founders who are entrepreneurs. They hired a great offshore software engineering team to code their MVP. They are happy with the offshore team’s results but can’t read code themselves. They thought they needed a CTO, but we found a technical advisor instead. The technical advisor reviews the offshore tech team’s code weekly and gives a high-level code assessment to the founders. So far, all is going well, and the technical advisor is giving the cofounder confidence that their offshore team is writing high-quality code.
If this works for you, great. Step 1 is all you need. If you do want to hire a CTO, read on to steps 2–7.
Learn how a Stride Interim CTO can help you hire a full-time CTO.
2. Define the CTO role requirements and craft a job description
Determine what your ideal candidate “looks like.” What soft skills do they possess? What tech talent do they bring to the table? Consider these:
- Ideally, you want to find someone who will see this job as a rung up on the ladder in their career, such as a senior software developer or technical team lead who is hungry to take on the CTO role.
- You might want someone who’s walked your path before. If you are a 40-person company trying to grow to 100, having someone who’s seen what that looks like can be valuable.
- Find someone who approaches things from a “seek to understand” perspective, not someone who thinks they have all the answers.
- Look for someone who can pick up multiple technologies (perhaps including back end, front end, and mobile). Avoid people who say they’ll only program code in one language.
- Look for someone who wants to wear multiple hats. I know many amazing senior-level web developers who specifically do not want the CTO role, because they want to be coding most of the time.
To define what success looks like, ask yourself these questions:
- What does success look like for the person in this role in 3 months, 6 months, and 12 months?
- What SMART (specific, measurable, achievable, realistic, timely) goals are there for this role?
- What are your company values, and how do these tie into success in the role?
- What approach to problem solving are you looking for?
Make sure you identify elimination factors. For example:
- Is lack of experience with a specific tech stack a deal-breaker, or is it something they can learn?
- Does your company sponsor H1B visas, if needed?
- Is working remotely an option?
Tie it all together by using all this information to craft your job description.
3. Create 1:1 mapping
The best CTO for your startup is going to be one who has the right mix of technical skills and soft skills, and the one who has a strong cultural fit. We’re not solely looking for how well this person can code. So, before talking to any CTO candidates, it’s vital to map out the list of skills you are seeking in the role. Create a map that looks like the one below, with each skill mapping to one interview step. That is, at what point in the interview process will you specifically “test” whether the candidate has the skill? It’s also helpful to prioritize the skills. For example:
|Ruby on Rails||High||Pairing session|
|Works well with others||High||Pairing session|
|Can work in NYC||High||Phone screen|
|Learns new things quickly||Medium||?|
|Can implement continuous deployment independently||High||?|
|Compensation and benefit needs are aligned with what we are offering||High||Phone screen or offer|
|Performance review experience||Medium||?|
|Culture fit||High||Phone screen|
You will likely find that some things aren’t currently specifically “tested” in any interview activity. These are indicated with “?” in the chart above. This tells you that you must create an interview activity to evaluate this skill.
4. Prioritize motivation, integrity, and culture fit
Interview for motivation and integrity first, experience and knowledge second.
And never underestimate the importance of a cultural fit, for a CTO. This is someone you’ll be working with intimately and trusting with the very core of your “big idea,” so making sure they fit with your company culture is as important as making sure they have the right technical skills.
Dee Hock, ex-president of Visa, says,
Without integrity, motivation is dangerous; without motivation, capacity is impotent; without capacity, understanding is limited; without understanding, knowledge is meaningless; without knowledge, experience is blind. Experience is easy to provide and quickly put to good use by people with all the other qualities.
5. Sell the position
Starting with the job description and lasting through the offer, keep in mind that the best CTOs will have multiple offers. It’s your job to sell the role to them throughout the interview process. You know that your startup is the most exciting, innovative, amazing company to work for. But keep in mind that the candidates probably don’t know that yet. You need to sell your startup. Don’t just list the qualities you need in a CTO; list what they will gain from working with you: exciting challenges, the opportunity to be a part of x, y, and z. Will the CTO get equity? Will they have autonomy?Whatever unique qualities your startup has, sell them well. Be sure to explain the position with gender-neutral language to attract a balanced and diverse applicant pool.
6. Find the best candidates
Many of the best candidates are the passive ones who aren’t looking for a new role, or who are discreetly looking. When it comes to finding candidates, never underestimate the power of your network, regardless of how big or small it is. Look around you. Who do you know who could possibly fill this role? Who do you know who might know potential candidates? Ask yourself, “Who do I know who knows the most CTOs?” Reach out to that person and ask for their help.
Talk to peers at other firms who have recently hired a CTO. Ask two questions:
- What advice do you have for me?
- Can you introduce me to any great CTO candidates who weren’t a fit for you but might be a great fit for my company?
Look at your online networks to find people who are talking about the topics relevant to your startup and the position. People who are passionate about what they do often love to talk about it. The following are great places to look for candidates:
- Social media standards: Twitter, LinkedIn, and Facebook. They're not just for talking, they're for listening. Look for candidates in niche tech communities. For example, if you want someone passionate about Node.js, see who’s tweeting #nodejs and related hashtags.
- Stack Overflow
- General Assembly
- Meetup.com: Posting an announcement to a meetup group can be a great way to find candidates. Try asking the organizer of the meetup to post the announcement for you. They likely have a strong network of possible candidates, and their announcement will have more weight than if you make one on your own.
- Local and national tech events
(This list could go on for 15 pages. You get the idea.)
7. Make an offer they can’t refuse
Ask yourself, “Why is the ideal CTO candidate going to choose my startup over another company?” There is no one-size-fits-all compensation package. You must first decide what you are able and willing to offer. You may not be able to offer the kind of package they can get from a more established company, but you can offer them equity. Giving someone equity in your company could help to them feel personally invested and deliver better results. Be prepared to answer any questions they may have on available benefits and bonuses. Be sure to do research on typical compensation and equity-based packages.
Always make the offer in person, if at all possible. This is an important role, and you’ve put a lot of thought into the process from day one, so make sure you finish the process strong, with a personal, well-thought-out offer that you can feel confident about.
Don’t expect to find a great full-time CTO if all founders aren’t committed to the startup full-time. Too often, I see founders who still have another day job but are looking for a full-time CTO. Why would a CTO quit their job to work on your startup full-time if they see that you’re not willing to do the same? Don’t ask CTO candidates to commit more than you are currently committed.
There are CTOs of all flavors—some who have scaled businesses before, some who are technical wizards, some who are visionaries, some who have walked your path before, and some who haven’t. Take the time to follow these seven steps, and you’ll increase your chances of finding the perfect CTO for your startup.
Want to learn more strategies to help your company increase velocity and productivity? For Agile teams, proper use of retrospectives is key to a consistently improving team. Our free guide covers everything you need to know to facilitate your retrospectives like a pro.
Editor’s Note: This post was originally published in September 2014 and has been revised and updated for freshness, accuracy, and comprehensiveness.