Hiring a CTO

What to Ask Before You Start
Mar 4, 2020
James Hornick
Woman in flowered top sitting at desk with computer monitor in foreground

Share This Blog

Hiring at the executive level is hard. If you don't have a plan of action before hitting the streets for the perfect candidate, you've already set yourself up to fail. Here are a few elements to align internally before you start to engage with talent.

Chief Technology Officer: What to ask before you start your search

For many companies, especially in the tech world, identifying the right person to oversee your Technology team might be the most crucial hire you make. Before kicking off the search, encourage your leadership team to think about the following:

1. Why are you looking for a Tech Leader?

  • Are you adding someone new?
    • Think about what's prompting the "need." Do you have tactical or executable business challenges? Is it purely a need for more people management? A mix of both?
    • Are you replacing an incumbent?
      • If you're replacing someone, why? For companies undergoing tremendous growth, it's very common to outgrow the initial person overseeing your Technology/Engineering function. The person that built your initial app may not be the person to scale you to 50+ engineers.
  • Does the incumbent know you're making a change? How do you plan to let them know?

2. Which role are you actually hiring for? 

Do you actually need a CTO? A CTO differs from a VP of Engineering, which differs from a Director of Technology. First, list the skills you absolutely must have in this role--and make sure everyone is on the same page. Titles will vary a ton based on company size and industry. The skills and experience of someone coming out of a Fortune 500 company are completely different than someone coming from an early-stage, 50-person software company. So focus less on the title, and more on the skills and responsibilities that matter. Prioritize across three main areas: Strategic Vision, People Management and Technical Experience.

Here's how you can envision each tech leadership role:

  • CTO - the hire to make when you have a highly functioning team of 30+ (with multiple technical managers or directors in place). If you have a team of fewer than 10 people or expect this person to be able to "get in the code," you may be better off rethinking the title.
    • Often presents to board-level audiences.
    • Communicates effectively with technical and non-technical people. 
    • Came up through the technical ranks, but most likely is 5+ years past any day-to-day, hands-on technical skills.
    • Strong people manager
    • Strategic leader    
  • VP Engineering/Technology - if you need this person to code on a day-to-day basis, you'll most likely have to prioritize that over the people management and strategic vision aspects of the role.
    • While this person won't be coding daily, they should be comfortable discussing technical architecture and reviewing code.
    • Great at leading and communicating with a technical team.
    • Strong communicator, but may struggle in front of a non-technical or board-level audience.
    • Oftentimes an equal mix of strategic leader, people manager, and technical expertise
  • Director of Engineering/Technology - This role varies the most across companies.  At small companies (think less than 15 people on the Tech team), this person will oversee the whole department. They may be a strong generalist, or specifically focused on development OR the infrastructure side of IT.  At larger organizations, this role will be more focused on leading one specific team.
    • Typically a 50/50 mix of technical skills and people management. If this person comes out of a larger shop, they will be a comfortable people manager. If out of a smaller shop, maybe 100% hands on.

3. How do you prioritize skills?

How would you prioritize people management, hands-on technical skills and strategic Vision?  Do you need someone that can roll up their sleeves and code?  If you think you'll find an expert in all three, you are most likely in for a rude awakening.

  • Do a thorough assessment of the current technology organization--what works and what doesn't work? If you don't have the ability to assess in-house, utilize a tech advisor or consulting firm to provide an assessment. You need to figure out whether your technical environment is stable.
    • If no,- how will this new hire fix it? There's a pretty good chance the task will involve fixing the plane while you're in the air. So you need someone who has done it before.
    • If yes - how will this new hire keep it that way and continue to innovate?
    • Are you sure that the current technology stack/solution is the right fit for your business? If not, how is this person going to change the direction of those solutions, and who will they include in that discussion?
    • How technical do you expect this person to be? If you want this person to be 100% heads-down coding, be prepared to forgo other areas, such as experience managing large teams, effective communication skills with board members and non-technical leaders, and experience scaling enterprise software. If you want someone who can implement processes, set the technical strategy, and do occasional code reviews, that is a very different person. Either way - how do you plan on vetting this?
    • How is the work getting done now? Do you rely on offshore teams, external vendors, or is all the development in-house? Should that process change in any fundamental way?

4. What else should you be thinking about?

  • Consider the org chart. Who will this person report to? If the CEO/founder is very aggressive, you may want to add a layer in between that person and your tech leader. Who will they oversee - engineers, support, devops, product?
  • Will the person be building out their team? Or will they be inheriting an existing structure? Hiring tech talent is hard - you’ll want a well-networked leader that can retain existing employees and attract new talent.
  • What are you doing to attract candidates across the whole technology organization? How will this new person fit in and enhance that process? You want to hire someone who aligns with the good things you do to attract talent.
  • Think about who will be involved in the selection process. Does the panel have a clear, transparent view of what to look for and how to assess candidates? Is a board of directors, external advisors, or private equity involved? How are you going to vet candidates? This is a particular concern when the rest of the executive team is not technical and you do not have a technical advisor.  If the person is going to be hands-on, you can probably use some sort of technical assessment, but if not, those are a waste of time.
  • Are you now, or in the near future, going to navigate any M&A activities? Any rounds of funding? How will you convey these things to a prospective candidate?

This is a lot—we get it. We’ve also seen a lot of companies miss on crucial hires, because they didn’t take the time upfront to think about these things. If you don’t have an expert managing the process for you (i.e someone who has facilitated the hire of numerous key executives), there’s an even higher likelihood of making the wrong hire. The key is implementing a thoughtful process before you even begin your search, followed by a thorough process to identify candidates and vet them well. (Shameless plug for Hirewell: We’ve been doing this for 15 years. Our process is unique and blends the best of utilizing an internal resource and an external search firm.)

James Hornick

More Blogs Written by James

Sign-up for the latest talent insights because you need to know what you don't know.