How to Hire a CTO in a limited tech landscape
Dominic Miraglia
Covey’s how-to-hire series offers unique insights from people ops professionals on the front lines of tackling the challenges of talent sourcing today.
SERIES INTRO:
Tech layoffs jumped 417% from November 2021 to November 2022, according to Challenger, Gray & Christmas, Inc. With so many cuts, there’s an overwhelming number of candidates for startups with open roles.
A full candidate pool might seem like a blessing. But the reality is a large pool of candidates doesn’t mean they’re all qualified. You might be vetting thousands of applicants a week to fill a single role. That’s a lot of work—especially if you’re the only person at your startup handling hiring.
Today, we hear from Chief Commercial Officer at Savoya, Dominic Miraglia. He’ll be sharing his insights from 15+ years in leadership cultivating highly technical teams, including hiring for a CTO at Savoya.
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A CTO is one of the most critical roles in an organization; they will lead innovation and, ultimately, your ability to grow as a company. So, finding the right candidate during the hiring process is as crucial as it is challenging. At Savoya, we had the unique challenge of hiring in a demographic area (Dallas-Fort-Worth, Texas) with a limited tech landscape and few candidates for a role like CTO. It’s not like San Francisco, where there’s a CTO on every corner. We knew we needed an incredibly accurate sourcing process to sift through talent and find the right candidate for this role.
1. Map where the future CTO needs to take your team
Your CTO will drive the strategy and implementation of product development, so it is imperative that you know where you want the person in the role to take your organization before you begin hiring. Start by mapping the future of your product, taking into account your company's current size and state.
Consider Savoya. Before COVID-19, it was a service business, and our CTO functioned more like a VP of technology than a true CTO. And that's all we needed at the time.
But coming out of the pandemic, we were pivoting from a service business to a SaaS product and needed a CTO to drive that change. It was crucial in our search for a new CTO to have internal alignment around where we were going as a company and what kind of person we needed to succeed in this role.
Our leadership team was looking for a CTO who:
- Could maintain the current product while also building something new. We had a legacy code base that was foundational to our current product. So, we needed someone familiar with those languages who could build on top of what already existed. Basically, this person couldn't be just anyone with an engineering background.
- Wasn’t just a part of building something new but had led teams building something new. We needed someone with five or more years of experience leading innovative teams as a CTO.
- Knew the technology as well as their team. We couldn’t afford to hire a large team to fill in the gaps for a more junior candidate, so this person needed to be capable in their own right. It’s not that we wanted our CTO to code full-time—we just needed somebody who could step in and code if necessary and wasn’t completely removed from the development process.
- Was curious, open-minded, and could bridge the gap between product and marketing. We needed someone who understood the nuances of product and marketing and wanted to build a connection between the two. Silos between these two parts of the business, especially when the product is evolving, would have led to constant misalignment and chaos.
2. Don’t be overly prescriptive with your job descriptions
In hiring for the CTO role, we've realized that there is a lot of nuance that cannot - and should not - be defined in a job description.
Overly prescriptive job descriptions will result in interviews that are simply an echo chamber of the requirements you include. Candidates will just prepare canned responses based on what they think you want to hear rather than how they really operate.
If the “must-haves” list is too extensive, some qualified candidates are more likely to self-select out of the hiring process as well. A broader talent pool often surfaces the best candidates because you get a more accurate baseline of talent and leave room for hidden talent to rise to the top.
3. Look beyond the obvious candidates
Recent tech layoffs have flooded the market with candidates, but that doesn't mean finding the right talent is easier. It makes it more difficult to look beyond the obvious, wade through the superficially qualified talent, and uncover what each candidate brings to a team.
Some candidates may have been laid off due to an organization's financial instability or mismanagement through no fault of their own, while others were laid off due to poor performance. And that's not to say someone low-performing at one organization will be a low-performer at the next.
Rather than passing over candidates based on the assumption they are or are not qualified, ask probing questions to uncover why they may have been less successful in prior roles. I’ve found there are usually two reasons:
- Misaligned candidates are typically brought on to a company that they don’t share the same vision with. They may be incredibly skilled, but their experience doesn’t match the needs of where their past employer wanted to go.
- Mistrained candidates are not given the developmental structure to succeed in a role. The former employer may not have invested in necessary onboarding resources or may have lacked an understanding of what upskilling employees needed as their role evolved.
An easy way to tell if someone falls into one of these categories or is unmotivated is if they blame their failures on the organization. Someone who won’t take some accountability for both their successes and shortcomings is a sign of someone who doesn't have a personal drive to grow or challenge themselves. A person's ability to take ownership will fundamentally change how they work and their impact on your work culture as a whole.
4. Trust Your Instincts
The hardest part of finding the right CTO candidate is making sure they are a good cultural fit. The interpersonal attributes of a person are just as important as technical skills.
While there isn't an exact formula to gauge cultural fit, informal conversations with each candidate helps. These conversations will help you understand how candidates interact beyond the more prescriptive question-and-answer part of the interview process. The best advice I can give here is to follow your intuition.
We had several technically strong candidates for CTO make it to the end of the interview process, but our hiring team felt uneasy about it. When we sat back and assessed why that was, it came down to the fact the candidate was fundamentally opposed to our way of working as a team. And so we made the hard decision to eliminate them.
One of the biggest red flags for us was someone who had a big ego. We wanted a technical partner who could talk business and tech without being condescending to people with different levels of understanding.
Other candidates came in with their minds already made up about how an organization should run without taking the time to evaluate how things were currently working. A hallmark of a strong candidate for us was someone that came with an open mind and was eager to collaborate.
Your organization may have different values. Whatever they are, stick to them. The right candidate for one organization might be entirely wrong for the next. A CTO needs to have the same approach to product development and team dynamics as the rest of your organization to have the greatest impact.
5. Play the long game
The top talents are often passive candidates, so you have to be the one to start that relationship. And, just as quality products take time, so does cultivating a relationship with the right candidate.
One of hiring managers' biggest mistakes is trying to sell the role in a single message. Splitting up your list of selling points over a multi-message campaign makes it more digestible. It also increases your chance of catching a candidate with the right message at the right time. A job offer that doesn’t resonate with a candidate one day, presented in a new way on a different day, may actually interest them. The more varied messages you send over time, the more touch points you have to connect in a meaningful way with a prospective candidate.
These messages should feel genuine and personalized to each candidate for the greatest impact. Selling a role is like selling a product - it's based on trust built over time, meeting someone in a moment when they are ready for something new.
I get it if you think a long-term campaign sounds impossible to achieve with everything else on your plate. At Savoya, we have a small team that doesn't include a full-time recruiting team, so automating our candidate pipeline was critical to our success.
Using Covey for augmented sourcing and communication allows us to stay small but look bigger. We can automate a lot of the busy work to increase the volume of messages while still standing out through easy personalization. In Covey, you can quickly edit templates with message tags to include details specific to each candidate. You're not sending out just another generic campaign that likely won't even be opened. With Covey, we saw an 80% email response rate, which was previously unheard of for us.
6. Never stop sourcing
I've seen a lot of companies pull too far back on hiring during economic changes to their detriment. Hiring should never stop, even if there is economic uncertainty or layoffs within a company. You never know when things will change; if you wait until you need talent, you're already behind the curve.
For example, layoffs (either internally or externally) can cause uncertainty for the next employee, causing them to quit unexpectedly even if their job is secure. So even if you think you have a full house, you never know when you might end up with an empty desk.
It’s imperative to insulate yourself from being put in a position where you’re so desperate to hire you make a hiring decision that isn’t a good fit. The easiest way to do this is by continually cultivating a bench of qualified candidates in the event a role opens up unexpectedly.
Use Covey instead of outsourcing recruiting
Covey is an augmented sourcing and recruiting tool that has revolutionized how we recruit at Savoya.
We used to rely on expensive tech recruiters to bring us two or three of the first mediocre candidates they found that fit a generic profile. Recruiters also took so long that we were desperate by the time we had a candidate to interview. At that point, we would feel forced to make hiring decisions against our better judgment out of necessity.
With custom-built augmented sourcing, Covey has saved our budget and made our recruiting more efficient and effective. Covey gives me confidence that I don’t have to make a poor hiring decision out of fear of finding another candidate. I can easily just send another wave of the best candidates through Covey and look at someone different.
A recruiter will also never be able to sell our business like we can. Covey helps you sell your business to prospective candidates without getting bogged down in busy work. We build our own messaging, but Covey automates it—multiplying our efforts and our passion. Even when we get a “no,” we end up with referrals. With Covey, we can’t lose.
Don’t wait to pivot from outdated recruiting models and get left behind.