4 Tips for Hiring the Best Chief Technology Officer

Here are the questions you need to ask.

Written by Natalie Ryan
Published on Apr. 29, 2022
4 Tips for Hiring the Best Chief Technology Officer
Brand Studio Logo

It’s common knowledge that world-class engineering teams are the driving force behind top-tier technology companies. Therefore, hiring the right chief technology officer to lead your engineering organization and technical strategy is one of the most critical steps to your company’s success. As a partner at SPMB who has led dozens of CTO searches for growth-oriented businesses, here are my top tips to evaluate the most effective Chief Technology Officer for your business: 

4 Tips for Hiring Your CTO

  1. Don’t confuse your CTO and your VP of engineering.
  2. Assess your candidate’s ability to hire, develop, and retain tech teams.
  3. Look for visionary skills over technical proficiency.
  4. Match the candidate’s skill sets to your business stage and model.


1. Don’t Confuse Your CTO and Your VP of Engineering

A typical vice president of engineering focuses on “making the trains run on time.” In other words, their primary objective and responsibility is to increase the technology team’s productivity and performance. This leader will likely be hands-on doing and/or reviewing the technical groundwork to ensure the development, design, user experience and quality standards are achieved and streamlined. 

In comparison, a chief technology officer should be seen as the face of the technology organization and as the connective tissue between technology and the business. This type of leader drives the technology strategy to advance the business, versus taking a hands-on approach to the product development and quality work, which is typically led by a VP of engineering.

There are also situations where a CTO is both managing product and engineering together. Titles do not always carry the same meaning and role responsibilities differ from company to company, so to analyze whether a candidate fits in the true CTO category, I always ask:

  • Walk me through your biggest achievements/big wins throughout your role at X company? 

This question allows the candidate to describe how their team’s technology efforts and innovations have advanced the business through revenue growth and other key metrics. Additionally, a strong leader should describe their success in growing and developing the talent within the organization, which leads to my second hiring tip... 

Another Perspective on the VPE or CTO Question on Built In’s Expert Contributors NetworkIs the Time Right to Hire a VP of Engineering or a Chief Technical Officer?


2. Assess Your Candidate’s Ability to Hire, Develop, and Retain Tech Teams

It’s a competitive market for technical talent so it’s critical to hire a CTO that can attract, develop, and retain a strong team. Your new CTO should have employees from their last gig that want to follow them. They should also be skilled in hiring the very best talent out there, and know how to develop the company’s “leaders of tomorrow.” To vet this capability, I like to ask: 

  • Tell me about what your team looked like when you joined versus now?
  • How did you attract new talent to the team and what was your involvement in the recruiting process?  
  • Did employees follow you from your last company? 
  • Give me an example of a few employees that moved on to do bigger, better things after being on your team? 

CTOs don’t have to be the best recruiters but they should be capable of instilling a strong engineering culture while inspiring and motivating their prospective and current employees.


3. Look For Visionary Skills Over Technical Proficiency 

Yes, your CTO needs to win the respect of their team and the market by having a certain level of technical depth and an understanding of the different operations and methodologies to develop products like Agile, DevOps, or Scrum. While this is true, remember not to over-index technical skills above the candidate’s ability to lead and drive business results through technology innovation. 

Your CTO should be able to partner closely with the CEO to set a long-term strategy and roadmap for the business through a technology lens. Some CTOs play more of an internal-facing role by being the voice of the technology side of the business in key leadership decisions. Another type of CTO role is more focused on external marketing-facing responsibilities: speaking at conferences, building relationships with key customers, and being the technology evangelist for the company. 

For either type of CTO role, these leaders don’t need to be coding on the weekends (although some of them still do!), but they are required to have knowledge of the software development process and, moreover, how to use technology to create successful business outcomes.  


4. Match The Candidate’s Skill Sets To Your Business Stage and Model

CTO candidates’ skill sets vary by business stage and type. Bring in a CTO who has the experience to understand your growing pains and pace of doing business. 

If you’re in a growth-stage business, you want to determine if the candidate can roll up their sleeves and get their hands dirty in a fast-paced startup environment — but also has experience within a later-stage company in order to share best-practices at scale and potential pitfalls your company may face in the future. 

Some sample talk tracks may include: 

  • Walk me through your decision-making process. How do you get things done? Walk me through the revenue, team size, and product offering scale over your time at X business…
  • Do you have experience taking a company from a single product offering to a platform/multiple product line offering?

If your company is in a transformation period, questions you might ask are: 

  • Have you transitioned an organization from a waterfall to agile methods?
  • Can you share some war-stories around managing technical debt while balancing quality and speed?   

Based on your unique business model, you could ask the candidates:

  • Walk me through the scale and complexity of your user-base and customer-base.
  • Talk to me about the platform and customer data volume. 
  • Walk me through your unique customer needs and the post-sales requirements of your subscription business. 

Probing in these areas will allow you to delve into the business complexities and dynamics that are tied to their past successes. Having this knowledge will better enable you to make a judgment call regarding which qualities are critical to the role, and which ones are just nice-to-haves. 

Hopefully, these tips will allow you to pinpoint and assess the right CTO for your company as it can be a costly mistake to make the wrong hire. On the other hand, bringing in the right CTO for your business can lead to a thriving engineering organization and culture, and an optimized product development process — one that celebrates innovative engineering efforts that customers and users love. This, in turn, will drive more revenue and success for your business.

Read More About Recruiting on BuiltIn.comThe Importance of Proactive Recruiting in 2022

Hiring Now
Cloud • Fintech • HR Tech • Information Technology • Software • Business Intelligence