Better techies • Better tech

How to hire a startup CTO

Will Britton

— April 4, 2021

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This post looks at the approach startup founders might take in identifying a suitable early stage CTO

Most new founders ask the question "when should I start looking for a CTO" fairly early on in their journey.

Some, as I've discussedopen_in_new, try to jump straight in to commissioning development work, either by hiring permanent development staff, or by outsourcing.

It's not unusual to see job postings for work in early stage startups like "Developer / CTO wanted" or "Lead Developer / CTO wanted". More often than not, these job postings come with an explanation that the successful applicant will be expected to write software (to specification, presumably) full time to start with, and may then be eligible to "graduate" to CTO once they've proved their mettle. Sometimes these roles are explicitly referred to as "CTO in waiting". One way of interpreting this is that startup CTOs are essentially senior software developers.

But is that really true?

A CTO is not a software developer!

Okay, let's get the easy one out of the way first, shall we?

Clearly, a CTO in an established company isn't a software developer. Nobody imagines that the CTO of HSBC or Sky or Tesco is hacking away cranking out code all day (or indeed any of the day!)

Even established tech companies wouldn't expect their CTOs to be doing much, if any, actual hands-on engineering work.
If this sounds wrong to you, take a moment to think about other roles in those companies. You wouldn't imagine that the CMO (Chief Marketing Officer) of, say, Facebook — or even a smaller company like Monzo — is writing copy and managing AdWords campaigns and posting to Instagram, would you?

Of course, saying someone doesn't normally do a thing isn't to say they shouldn't and certainly not to say they couldn't.
In particular, in the early days of a startup it's very usual to find the leadership team mucking in and doing all the jobs that need to be done.
Here, CMOs do write copy, CEOs do make sales calls, COOs do run the payroll themselves and — sure — CTOs often do smash out some software.

But just as a CMO might not actually be that great at writing copy, or managing social, so might a CTO's strongest suit not be software development. Perhaps they are more of a product person, or a process person, or a futurist, or a visionary.
Perhaps they are really a people person and happen to be an amazing motivator of software developers, rather than one themselves.
To assume that the route to CTO can only be traveled via software development is really to misunderstand the breadth of the field of software product development, and at the same time to do a disservice to all the other integral, skilled professionals who are a part of building tech companies.

A CTO can't be inside a "tech bubble"

Despite the fact that a CTO isn't just a software developer with a fancy title, they should still be 100% on top of what's going on. This is no more critical than at the very earliest stages, when funds are severely limited, and one misstep can mean lost opportunity cost and a potentially ruinous outcome for a fragile new business. At the earliest stages, an effective CTO needs to be completely attuned to the business itself — all the comings and goings and subtle shifts in direction that tend to occur on a daily basis — as well as specifically their domain, which is creation of software product.

In this respect, it's a serious error to hire a CTO who advocates carving out a siloed "tech bubble" away from the rest of the company; and likewise to hire a CTO who is not granted the trust and autonomy befitting the highest level of leadership in an organisation. In other words, the "C" in CTO has to be legitimate, not just a gimmick to lure in software developers with delusions of grandeur!

The tech bubble, and the "them and us" attitudes it so often leads to, will certainly be the subject of another blog, but it is worth noting that it seems to be particularly prevalent amongst software developers.

Here are some of the subtle and not-so-subtle signs of a tech bubble forming:

Software developers use language like "Devs" to refer to the in-group (them) and "The Business" to refer to the out-group (everyone else)
Software developers (in particular) complaining that "nobody [outside the bubble] understands what it's really like for Us Devs"
Events, whether work or social, being regularly organised which are explicitly labelled "Dev-only" or "Just the Devs"
People from outside the tech bubble saying things like "I'm not a tech person", or "I don't understand tech". One of my personal favourites is someone walking behind a screen of code and announcing, smugly, "It all looks like gibberish to me — I'll never understand it!"
People from outside the tech bubble making generalisations — like software developers are generally introverted, or bad with people, or have a special need or desire for flexible working in a way that others don't, or simply that they are special and different from everyone else

It's worth noting these last two points arise from "non-technical" people and only serve to reaffirm any divide, rather than work to break it down.

If your startup really is a "tech" business, then by definition, technology (usually software) is at the very core of what it does: what it builds, and the product it sells. With that in mind, doesn't it seem just crazy to risk siloing that core part of your business away inside a bubble? And doesn't it seem equally crazy to choose a CTO to run it who is nothing more than a (sometimes very inexperienced) software developer with a fancy title, rather than someone with deep and proven commercial and people management experience?

A CTO should be 100% aligned

It's fair to say that any ideal employee, regardless of their position should be 100% aligned with the business, but the world is seldom an ideal place, and we can usually tolerate a degree of compromise on alignment. For anyone with that magic "C" on the front of their job title, however, there's really no margin for misalignment. What kind of things need to be aligned?

Vision & purpose — of the business as an entity
Values & culture — leading by example is not optional here
Commercial strategy — how the business makes money cannot afford to be a mystery!
Goals — even after we've agreed where we're going, the plan for how we get there must be shared and agreed by all leaders and executed consistently

These are really fundamental components of a business, and misalignment of any of them by a senior leader will eventually (if not immediately) be problematic. It's all too common to hear stories of technical leaders not agreeing with the rest of founding teams, and the destructive influence that can very quickly have on a leadership team. Whilst one often hears similar stories involving other departments, in my experience misalignments in those other departments are much more seldomly tolerated, and much more quickly resolved (often through the departure of the problematic leader).

I think the reasons for this common trope are two-fold:

The aforementioned "tech bubble" — tech professionals are often seen as being able to freely operate under different rules and expectations from their peers. It might be inconceivable that a CMO wouldn't understand or care about the commercial strategy of a business, for example; but it seems to be fairly common to justify the same shortcomings in a CTO by reasoning that "tech" and "business" are just inherently different things.
The apparent scarcity of tech professionals in general and tech leaders in particular does tend to lead us down very dangerous paths, one of which is to tolerate from tech professionals behaviour which we would never condone in others. As a side-note, maybe one for another article, another really dangerous reaction to scarcity of tech professionals is the almost immediate and pathological tendency to build a "key person(*open_in_new) dependency" (more recently "key person risk") **around that person and make them mission-critical [6open_in_new]. Let's think about this one for just a second — it's really hard to find someone with a particular skillset, so when we find one we're going to allow that skillset to remain in them and actually build critical dependencies on top of it!? Can anyone say "red flag"!?

I suppose what I'm really getting to here is that, in a tech company in particular, you should probably apply the same assessment criteria to a CTO as you would to any co-founder, regardless of whether or not your CTO actually is a co-founder, or has a significant equity stake in the business. If your CTO is actually a co-founder, then for heaven's sake don't give them special dispensation just because they appear to be in high demand. If the deal doesn't feel right, better to just walk away. You are more likely to survive without a technical co-founder for a while than if you hire the wrong one. For non-founding CTOs I'd say the same logic applies. It's amazing the amount of damage the wrong senior hire can make in a relatively short space of time.

A good test of alignment for any leader, not just a CTO, is whether they "bang the drum" for the company. Sometimes used in a negative sense (similarly to "drinking the Kool Aid"), here I mean more positively, that the leader actively and openly is seen to support the company generally, and specifically in the four areas I list above. I've worked with leaders who keep up the pretence of being onboard with a company's vision but who under their breath (or get a few drinks in them...) will freely let rip and show you just how much misalignment they really harbour. Those leaders don't tend to last too long, but they can have a deeply unpleasant effect in the short term, which is magnified the more senior they get, because at the top there are progressively fewer people who can get clear visibility on that behaviour or feel comfortable calling it out.

Practical hints for finding a CTO

I hope this article isn't too much of a tease. I know many founders really want a Yellow Pages(†) for CTOs and sadly I can't recommend any. Instead, here's an easily digestible set of Do's and Don'ts which I hope will be helpful in the search:

DON'T just hire a software developer as your CTO unless you genuinely think they are a leader
DO consider a broader range of tech professionals: product managers, project managers, UX designers, agile coaches, engineering managers, quality engineers, etc. etc. — you might be surprised! (Obviously you can hire someone who's already a practising CTO... 🤪)
DON'T give prospective CTOs a pass on qualities you'd normally expect in a leader
DO apply the same assessment criteria to hiring a CTO as you would for a co-founder
DON'T get too hung up on specific technologies. Technologies can and do change, just as surely as startups pivot. Remember you are trying to hire a technolog-ist, not a technolog-y.
DO look for people who appear to be pragmatic, flexible, technology- and process-agnostic and — in my opinion at least — humble.
DON'T hire someone who doesn't really get your vision. This won't happen right away — it might take several rounds of conversations — but if you aren't on the same page by the time you hire them, there's a risk you'll never be.
DO value people who will be able to challenge you. Although you ultimately need alignment on vision, you equally don't want someone who accepts everything you say unquestioningly.
DON'T expect to find someone who will solve all your problems, even all your technology problems. Just because you "don't understand" the tech and prefer to keep out of it, doesn't mean your CTO doesn't need help and support just like any other leader.
DO consider looking at things like strengths profiles before hiring a CTO, or at the very least asking them questions like "what don't you like doing?" rather than simply "what are you able to do?"
DON'T ever, ever hire someone who makes you feel stupid, or inadequate, or scared, or confused. Some technologists have a habit of using technical jargon or esoteric ideas just to try and impress. It's not "normal for techies", it's just rude: end of story. A decent CTO will be able to have a conversation with you that you feel makes proper sense and is delivered with the respect and humanity you'd expect from a professional in any other field.

Footnotes

Commonly seen written as "key man dependency". But wake up people, it's 2021!

† The Yellow Pages is what we had before the internet. Look it upopen_in_new 👀