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Tips for Hiring the Chief Technology Officer
Oct 13, 2022

Tips for Hiring the Chief Technology Officer

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It’s well understood that world-class engineering teams are the driving force behind any top tech company. Therefore, hiring the right chief technology officer to lead your technology team is one of the most critical steps to any tech company’s success. At Weekday we have led dozens of CTO searches for growth-oriented startups, and here are our top tips to evaluate the most effective Chief Technology Officer for your startup:

1. Don’t Confuse the CTO with the VP of Engineering

The primary objective and responsibility of vice president of engineering is to increase the technology team’s productivity and performance. He will likely be doing hands-on 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 link between technology and business. A CTO 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, you should always ask: Walk me through your biggest achievements/big wins throughout your role at X company?

This question allows the candidate to describe how his 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.

2. Assess the 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. The new CTO should have employees from their last job that want to follow him. They should also be skilled in hiring the very best talent out there, and know how to develop leaders for the company. A CTO should be able to instill a strong engineering culture while inspiring and motivating their prospective and current employees. For this, you may would like to ask these questions to the candidate:

a. Tell me about what your team looked like when you joined versus now?

b. How did you attract new talent to the team and what was your involvement in the recruiting process?  

c. Did employees follow you from your last company?

d. Give me an example of a few employees that moved on to do bigger, better things after being on your team?

3. Look For Visionary Skills Over Technical Proficiency

Yes, the 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.

The 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

A 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. For this you may include below questions for the candidate:

a. 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 time at X company.

b. Do you have experience taking a company from a single product offering to a platform/multiple product line offering?

Probing in these areas will allow you to delve into the business complexities and dynamics that are tied to the candidates' 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.

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