June 22, 2021

Hiring a CTO


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.

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.)

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