In mid-July I took the plunge into the world of fractional work. Over 3 months in, I wanted to share with you my learnings so far, where I’m at today and what I’m going to be focusing on next.
Show me the 💵
Full transparency: I’ve still yet to be paid a single pound, dollar or crypto-token as a Fractional CTO. I’ve issued my first invoice for a day’s work, and there are several conversations with prospective clients that are going well, but the bald fact is that after 3 months I’m still waiting to be paid.
I have a year’s runway, so I’m not panicking, but I’d be lying if I said that I was expecting it to take this long.
Talking with other fractional CTOs and freelancers more generally has been helpful and reassuring in this regard; 3 months seems to be considered a pretty standard minimum, and for fractional engagements 6-9 months seems to be the average.
As someone coming from full-time employment for most of my life, with a pay cheque landing every month a staple, the shift into financial precariousness and uncertainty has been… uncomfortable. In the meantime, aside from an open-source bug fix and some deliberate upskilling around Ai and Ai tooling, I haven’t written any code during this time. My focus has been selling, and learning how to sell. Nothing else matters to begin with.
Feeling niche-y
My initial focus has been on super early-stage startups with non-technical founders. I chose this for a few reasons:
Their need for technical expertise is obvious.
Finding and hiring a full-time CTO is expensive and maybe unnecessary (most companies are tech-enabled, not tech-first), so fractional makes sense.
I really like entrepreneurs and the passion of early-stage founders, and so working with these kinds of people appealed to me.
I’m glad I did this, as I’ve met a tonne of amazing folks, and starting off with a narrow focus also helped me make a few other decisions that were otherwise potentially paralysing given the number of options available. I still think there’s a lot of value here, and I’m not giving it up entirely, but I’ve since revised my Ideal Customer Profile (ICP) as I’ll discuss below.
The (lead) Generation Game
I decided early on to try and focus on in-person networking in order to generate leads. My reasoning was as follows:
A huge part of hiring as a founder, especially in the early days, is trust.
Meeting people in person will build more trust than a website ad or cold LinkedIn message.
I can be pretty extroverted and enjoy in-person events (in moderation).
I’m currently based in London, and so I can get to events (relatively) easily.
There’s a healthy amount of founder networking events in London as well as some cool accelerators I connected with (shout out to Rare Founders and Zinc in particular!).
How I feel about this decision now:
Pros
I generated some warm leads. This was the main aim, and in this regard it was successful. Although none have yet converted, I’ve gotten enough feedback to tell that there is at least some interest and value in what I’m pitching.
I got to practice my pitch a lot. Even when chatting with people who would never conceivably hire me, I still had to describe what I do and why I do it. It meant I got to rehearse and revise my pitch, standing in front of other human beings with various degrees of interest, and see what lands and what doesn’t.
I’ve met a bunch of founders and got more insight into the kinds of things they’re building and the kinds of challenges they’re facing, and made genuine connections regardless of whether or not they’ll ever need my services. Who knows how these will pan out in the future?
They were fun! It’s invigorating to meet new folks and be around smart people who are passionate about what they’re doing.
Cons
I’ve still not landed any paid clients as of yet. Until I do, the jury has to remain out on this as an approach.
Going to in-person events is tiring and expensive. Not just in terms of the cost of the ticket, if there is one, but the opportunity cost of other things I could have been doing with that time and energy.
Hard to scale (there’s only one of me!), and difficult to keep a rhythm. Once you’ve got a solid bank of warm leads, it’s tempting to take the foot off the gas, but once those dry up or go cold, suddenly you realise you need to get back on the horse.
Overall I have no regrets, but the difficulty in sustaining this as a primary method for lead generation is another factor in stepping back and reviewing my approach.
The Perfect Client
I read a lot about how important it was to define your ICP (Ideal Customer Profile) when I started out on this journey, and I thought I had done a pretty good job of defining it. To recap:
Early-stage startup (pre-seed, seed)
Non-technical founders
Tech-supported rather than tech-first businesses (I’m not going to be able to help you build a new AI-specific GPU).
Given the conversations I’ve had over the last few months and the feedback I’ve received, I think I can clearly offer value to customers who fit this profile. There was one big piece I missed though, which is whether these were the ideal customers for me.
Companies in this segment often have low or limited funds, a desire to stay lean and spend as little as possible, and often haven’t actually encountered many of the problems I’m aiming to help them avoid. I can talk about optionality and the importance of engineering thinking all I want, but until they’ve been burned by some of these problems they’re just not going to feel that pressing. There’s nothing to say that this is the wrong approach, either.
Ultimately what I’ve been promoting is a hypothesis, a theory. It’s still one that I back, which is why I won’t rule out working with these clients, but I have yet to test it in practice many times. I’m taking a risk by working with them and, to some extent, they’re taking one with me too. I back myself, but given the risks on both sides it limits how much I feel comfortable charging (setting aside the question of their ability to pay).
So if these folks aren’t my ICP, who is?
Finding the sweet spot
One of the unexpected outcomes over the last few months is that I’ve stumbled upon another niche right beneath my nose, one that I believe makes a lot more sense to focus on.
Through serendipity, I’ve ended up chatting with many more later-stage companies than I anticipated, including those with active CTOs and co-founders. I would have ruled these out as potential clients, but a common thread emerged which has changed my mind: the challenge of engineering leadership.
There’s a whole different post I could write about this topic, but in brief:
Companies of a certain size (Seed - Series A/B) need to start scaling, and pain points appear.
Hiring the first few engineers is a different challenge to hiring the next 5, 10, or 20. A different level of hiring process is required.
Initial engineers either need more mentoring and development than the founding engineer or CTO can provide, or they need to step into leading and managing as teams start to grow.
As a result, the clamour for senior engineers who can provide this increases, but hiring seniors, tech leads and EMs is expensive and time-consuming, with long lead times.
It’s expected that founder CTOs at a certain stage will transition into COO roles in order to best leverage their knowledge of the business.
Thus a VP or Head of Engineering to come in and support is appealing, but frequently leads to clashes and ultimately firings as they seek to do it ‘their’ way rather than the company’s way (the problem with hiring ‘established’ candidates in startups generally).
This level of company also makes a lot more sense for me personally:
I’ve been a VP of Engineering at a company with this exact profile, and successfully navigated it
I’ve had many years of experience as a tech lead and engineering manager, and have helped folks develop into these roles, so it’s something I’m supremely confident I can do with a track record to prove it.
The value proposition is pretty clear: develop your own talent from within before looking outside, and even if you do need a permanent hire I can support your engineers immediately while you wait for the 6+ months it will take that senior hire to land.
This stage of the company is likely to be revenue generating, willing and able to invest in their people and has probably begun to encounter some of the issues I’m specialised in solving. Getting paid is less of a headache.
There’s so much I can offer within this space, from workshops on how to ship faster without sacrificing quality to helping refine the hiring process, but I’m starting with something simple: coaching. I’m focusing on those looking to develop their leadership and managerial skills within the technical context of software engineering, whether they’re stepping up into one of these roles for the first time or simply looking to broaden their skillset as raw coding ability gets increasingly commodified by Ai.
If this is you, or it’s someone you know, you can reach me here on Substack (just hit reply in your inbox, I read every response) or hit me up on LinkedIn. I’m working on the page for my site and will update this with the link once it’s done.
This post was longer than I had planned! Hopefully, you found it useful and have a better insight into what the early stages of fractional CTO-ing looks like, and maybe some of the decisions you’d make if you ever decided to try anything similar. I still have plenty to learn, but I definitely feel like I’m making progress and getting closer to AMF (Alex Market Fit). I’ll keep you updated with how it goes!
Thank you for your openness about the process!