You’re a startup/scaleup founder looking to support your exec-team with some heavy-hitting CTO brains; or you’re a founding CTO looking for guidance from more experienced, “grey-hair”, CTOs. You figure a ‘Fractional CTO’ (fCTO) is the solution; great – now how do you find one?
When: your Network … is a “NotWork”
If you’re in this situation then usually you already hit up ‘your network’, possibly several times, over the past few years, with limited results. So all those “first: try your network!” blog posts are missing the point.
When: the Unknown unknowns hurt
How do you test a person on their answers to questions when your original problem is that you don’t know which questions you should be asking? Interviewing these people would be … impossible? Cue: vague assessments like “Seems nice to me”, “Definitely knows something (I’m not sure what/how much/whether it’s relevant to me)”.
Classic response: hire a Recruiter!
You’ve already got (at least one) recruitment agency on-tap; you ask, and they’re keen – very keen! – to find you an fCTO. Great! Get going! …NO. Ask your recruiter:
“How many fractional CTO’s have you placed this year?”
“How many in the preceding 5 years?”
“How many days/month were they working?”
“How were they paid?”
Listen to the silence and shuffling of feet. The answers will tell you what you need to know: Recruiters generally have little or zero experience in this area at the moment (that will change over time, but not yet).
Warning: many are salivating to hire you a fCTO, and will dodge the tricky questions, because:
- ‘C-level’ positions net them higher fees
- Grateful C-levels are likely to send them extra business for hiring their reports
- Recruitment industry is in a huge downturn recently, and they are desperate to invent new products: “fractional” roles is a great product (for them). You get to be their first!
Better response: hire a fCTO!
Think about what you want an fCTO for: it’s not a pure-tech engineer who hates talking non-tech; it’s not a pure salesperson who’s going to sign a contract then have other people do the work; etc … rather: it’s someone who’s great at:
deep and broad understanding,
communicating across, up, and down
seeing to the heart of engineering and product problems
knowing how to see people problems that hide as tech problems
knowing how to see tech problems that hide as people problems
convincing and soothing teams, egos, fears, building consensus
long experience of making this all work smoothly
… someone with those skills is extremely easy to recognize when you see them!
Look for the signs: a great CTO will:
Here are some common side-effects / symptomatic items for someone who can do the things you’re hoping they’ll do if you hire them:
you learn something new about your own business within the first 1-2 meetings
they challenge you, make you work, but constructively not painfully
they have 3 or more stories/previous experiences to illustrate every point
when you describe your challenges they seem to have heard much of it before
they already know more about your unusual tech than you expected anyone to know
they live and breath “build vs buy” and are obsessed with choosing well
they read management accounts/finance spreadsheets with fluency and ease
they have a lot of friends in Product and Engineering roles, across the industry
their bias is to “how LITTLE time can I get away with spending here, and yet still solve your problems?”
… despite often being paid by the hour/day/month
… I’m not specifically recommending any of the above, just cherry-picking from the many CTO friends I have – these are some off-the-top-of-my-head recurring traits of those that do fractional work.
So. We feel confident that “I don’t know what/where/how I’m looking for, but I’ll know it when I see it”. But how do you fill the funnel, how do you get some candidates to start talking to?
What do fCTOs want – why be a Fractional CTO?
(c.f. my previous posts about different types of fCTO and CTOs at different stage of company.)
(c.f. my previous post about the minimum experience (“have been a successful full CTO several times before”))
…if you’re happy with those, then the motivations of fCTOs tend to align with:
- “Time is my most precious, non-scalable, non-replaceable, finite resource” — and they want to change the balance of how much time they spend ‘at work’ vs ‘non-work’.
- “I can work anywhere; so I won’t work places I dislike” — they’re picky. They can afford to be.
- “Ambiguity is fun” — you don’t do something as unusual/undefined/open-to-interpretation as fCTO unless you have a very happy relationship with ambiguous situations and problem-spaces.
- “I don’t want to be a high-paid contract Engineer” — because that’s the OTHER option for many of them; so if they’ve chosen the fCTO route then they’re broadcasting that they prefer: people problems, org problems, product/sales problems, and the intersection of all of those with tech, engineering problems, etc.
Where the Fractionals wander
Generally: fCTOs have the luxury of more free time than classic CTOs, and especially: more brain-time / intellectual energy (because it’s not being drained out of them 60 hours/week). That means they are often found indulging their intellectual interests. Places I’ve bumped into fCTOs who I already know are highly experienced/veteran CTOs include:
- LLM/GenerativeAI meetups — lots of us are taking the opportunity we have (some spare time) to aggressively upskill on LLMs/AI while we can, before we get called to work on AI projects in the near future
- Investor-hosted events — lots of the high-skill fCTOs started their careers as startup-CTOs before exiting, making $$$ for their investors – and remain as alumni, popping-up at portfolio-company events for those same investors. But not the big events, never the ‘fireside chats’ – no, the small ones: the private dinners etc.
- Mentoring their former reports — people who choose to be fCTOs are often heavily biased towards ‘giving back’ and helping other people in the industry – and in supporting the engineers, the managers, the product owners, etc that they already worked closely with. They maintain rich networks (see above: because they have the time to do so!). So precocious but skilled/high-potential staff in your org might well be getting informal help on the side from an fCTO friend of theirs (e.g. I have quarterly/bi-annual catchups with former colleagues, free dinner in return for sharing 2nd opinions, advice – and sometimes intro-ing them to companies that are hiring and would love to have them).
- Writing deep-tech articles / publishing tech PoC’s — CTOs are often (not always) deeply technical, but as a CTO rarely get to express / utilise that tech interest, they’re too busy dealing with org/arch/business problems. fCTOs often go back to their roots: I’ve seen them at Hackerspaces (3d printing and welding, building robots); I’ve seen them launching new micro-electronic products (scratching an itch: an intelligent trash/bin); … but always: a bias to action, to shipping, to ‘having something to show’.
Are they busy?
A properly experienced fCTO is probably busy – at any given moment they have a lot of options – and a long line of recruiters trying to tempt them back into permanent/full-time roles for a single company.
BUT: most of them do this work because they love it, not because they’re building (say) a Management Consultancy firm. That means: they don’t really invest in Sales or Marketing – they don’t need to! Until the day they do need it, and then they suddenly find themselves with no work at all. Recruiters (as noted above) have no idea how to handle this work, so the fCTO’s own contacts often prove useless at finding new roles.
So at any given moment there’s – ironically – both “a lot of great fCTOs too busy to talk to you” and “a lot of great fCTOs immediately available with no other commitments”.
Sticking the landing: payment
I’ve seen a lot of CEOs lean towards recruiters for finding a fCTO mainly from a fear that they don’t know how to set the remuneration for this tricksy role. That’s entirely the wrong response: you don’t know because it’s open to be adpated TO YOUR COMPANY — and the recruiter can only make that less effective.
The fCTO does this with every company they meet/work for, so they will have decent experience and can guide you on it. As noted above: they’re not in it to sell you a pitch, and ‘time’ is their most precious resource, so … their incentives are to “find a mutually happy deal”, not to “get the most I can” (and if they don’t give that ‘everyone wins’ vibe … you should consider running away, they may not be what they seem).
Next post will probably be: how to attract them? What gets me excited about inbound requests for me to do a Fractional role?