5 Tips for Hiring a Rockstar Chief Technology Officer

Written by EO Executives on Aug 23, 2017

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In this blog, Technology Practice Lead Ben Walton focuses on how in a competitive market, C-Level leaders of rapidly growing, digitally first companies can better attract and retain top Chief Technology Officers into their businesses...

As an Associate Director and Head of Technology practice at EO Executives, I am privileged to meet with some of the most talented, innovative and forward-thinking Chief Technology Officers (CTO’s) in the country on a regular basis. 

Speaking with such inspirational leaders and partnering with so many awesome businesses gives me a unique opportunity to stay up to date with what is happening in the market, and ensures I stay engaged with my client’s key priorities.

Having such a strong network in the technology space means I get invited in by C-Level leaders of rapidly growing, digitally first companies for various reasons. Some are struggling to align their Technology and Sales functions, many are concerned about spiraling costs and are worried about turning fast ROI for investors, and others are frustrated about their inability to attract and retain the very best talent in a market that is increasingly competitive.

The latter of these issues is what I will focus on in this blog, with a particular focus on CTO hires as this is a core niche of mine and an area I have extensive experience in.

Over the years, I have seen many challenges that organisations have gone through to entice and retain top talent into their business. For some, the process is easier than others but in the end every business needs to implement a hiring strategy that works for them (especially in the war for talent).

So, how do you hire a Rockstar Chief Technology Officer (CTO)?

I have outlined my 5 tops tips below:

1. Plan & design

One of the first mistakes business owners or decision makers go through is trying to run a full-scale recruitment process on their own. After all, how hard can it be?!
However, without a well-thought-out strategy hiring will inevitably become difficult to manage, especially when coupled with the day to day duties of running a business. Unless you strike it lucky, what you may initially see as a cost saving exercise will soon become a drain on your time and resources, taking your attention away from your core goals.

Your strategy should be that you are hiring someone based on their competency to do the role but most importantly you should believe they can achieve beyond key business initiatives, align to your business goals and be a strong cultural match.

Your search partner will give you a clear indication of what ‘top talent’ looks like and what you should be bench marking against for the role. My advice would be to look for someone who has experienced a similar growth trajectory and built something similar to what you are trying to achieve. As an example, for CTO’s you may want to look for individuals who have formalised development methodology, built best in class teams, brought successful products to market or simply those who have a strong technical understanding of a similar tech stack to yourself.

Another key point in the hiring process (that often gets missed) is the importance of sticking to time frames. Have a set date of when you need someone to start, agree this with shareholders/ stakeholders and partner with a firm who can work with you to execute your recruitment strategy. Be realistic on this though – you need to factor in not only the time to identify the talent in the first place but also the time to interview, negotiate and then the inevitable notice period (which can be up to 6 months these days).

2. Partner & Go to Market

Once you have a clear strategy in place you need to think about how you’re going to source and entice the talent you need. Therefore, collaborating with a search firm who aligns with your goals and understands your business will be crucial. If you are VC/PE backed your investors can sometimes look inside their own portfolio and leverage from within.

If you are unsure on what search firm to use, select from three/four firms you are aware of, do some background research on their reputation/ success rate and what experience they have of working with fast growing companies in your sector. Ask them to talk you through recent searches they have delivered within your sector and relate to your business model.

When deciding on which search firm to collaborate with, you should look at the company’s value proposition and ask them to demonstrate how their proposition can do these three things. 1: De-risk the hiring process, 2: Increase ROI and 3: Represent your brand.
Hopefully they will align with your expectations. Ultimately, your partnering firm needs to understand the journey your business is going to embark on and why you want to make the hire. Ask them to provide a thorough break down of the current market, trends, remuneration trends and their own understanding of your business.

The final step of this stage is to confirm your partner and agree the deadlines for delivery!

3. Interview & Implement Rigour

It is crucial to agree and communicate the interview process with your search partner upfront. They will manage candidate expectations and ensure they are nurtured through the journey. If a candidate does not feel they have received an excellent candidate experience, then they will be less likely to accept the role (if offered) and may even choose not to work with your business again. Remember, CTO’s are hugely sought after and you are competing at every stage.

Conversely, if candidates are successfully nurtured through a process they are more likely to feel valued, bought in to your vision and will want be part of the journey with you.

Perhaps contentious, but despite the above I would also advise making candidates jump through a few hoops – this is healthy and will rule in/out the candidates that are fully bought into you and your business. There is a fine line on this though so seek professional advice from your search partner.

Break the interview process up into three stages. This shouldn’t drag on though as momentum is crucial:

Stage 1: Cultural/informal meeting.

The first stage should be centred around your relationship with the candidate. You will quickly know if the candidate is a good cultural fit for your organisation.

Keep the discussion top line. Give enough away that will make them intrigued about the role but also keep your cards close. At this stage, you should be assessing whether you can work with them day to day and if your clients/team will respect them!

Ask them to give you high level examples of teams they have built, products taken to market and challenges they have faced.

To ensure the candidate is a good cultural fit, EO Executives use our advanced and award winning technology to match candidates to a business on both technical competencies and behaviours (see here for more details).

Stage 2: Formal on-site interview with key stakeholders and involvement of senior members of your team (if appropriate). Tech out in more detail if necessary.

Asking candidates to meet your team is a beneficial way of getting additional buy-in from your colleagues and making your employees feel valued and part of the process. Ultimately, you don’t want to be bringing in a CTO whom your Head of Development/Product doesn’t believe he can learn from or doesn’t respect or you risk a divide and potential clashes further down the line.

Since this is a technical hire you should also involve some technical screening at this stage. For a CTO hire you’re unlikely to be solely looking for how well this person can code but, before talking to any CTO candidates, it’s vital to map out the list of skills that you are seeking in the role.

Your people are the bedrock to your success and involving them in this journey can be valuable.

Stage 3: Final Stage

By this time, you are likely to have a preferred candidate and are nearing an offer. You probably have a few lingering concerns or areas for consideration that you want to delve into in more detail but overall, you are comfortable.

Bringing the potential CTO back in one more time not only gives you the chance to address the considerations from your side but also theirs. Remember – Interviews are a two-way process.

Give them a chance to formulate any questions they may have and to allow them to see the operation in its normal running. Their questions will be very insightful and tell you about how bought in they are to what you are trying to achieve.

Switch up from buyer to seller, make them know you want them to be part of the journey and show them why you are so passionate about the company. Paint a picture of how they will fit in and get them excited about your plans.

You are also well advised to obtain references at this stage. Obviously, you can’t get them from their current employer but ask for previous employers/clients/colleagues. Your search partner should carry this out on your behalf but many of my clients also like to have a conversation themselves at this juncture.

4. The close:

One of the biggest mistakes companies make when closing the deal is failing to provide clarity and detail to A: the candidate or B: their search partner.

Would you sell a house without providing the market or potential buyers with detailed information? Highly unlikely, right? The same rules apply here. You are making a critical business investment that could either make or break your growth!

Additionally, you should never underestimate the quality and potential ROI of a best in class candidate. Trying to get a ‘bargain’ and cut costs on your hire/offer will only impact your business in the future. My advice would be to put your best offer forward from the get go because the impact of low balling a candidate can be detrimental.

Remember, the search firm you choose to partner with should provide you with all necessary information, guidance and advise at any part of the hiring process. Leave the closing of the candidate to them; they should have your best interests at heart and if they are good it should be a done deal.

5. Aftercare:
For many businesses, the hiring process stops once the candidate has been placed and is in role. Sounds normal but the issue is whether the candidate will continue to meet expectations or be the right cultural fit for the organisation.

At EO Executives, we understand the importance of ensuring a thorough process both before and after the placement has been made. Ensuring the candidate receives the most effective on-boarding and is settled into their new role is key for guaranteeing long-term success. This is why our team offer a 90 day on-boarding process and work with both the candidate and client to fast track success. Learn more here: http://www.executivesonline.co.uk/en/executive-recruitment/

My top tip would be to avoid cutting corners. Ensure you make the time and effort to thoroughly on-board your new Chief Technology Officer. In the end, you’ll end up with a strong Technology function and overall a better business.

What are your experiences of hiring for a CTO role? I'd be keen to hear your thoughts, so comment below or drop me an email at: ben.walton@eoexecutives.com.

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