Published by Rich Kershaw on November 22nd, 2020

Growing a CTO

It's common for small companies to have a CTO who, in reality, is a senior developer with the nominal title "CTO", and whose role is actually lead architect and coder. They might be a co-founder or employee #1. Either way, it's common to have a CTO who's rising into the job title from a pure engineering background. This might sound a lot like you!

A tech startup without a proof-of-concept doesn't need a heavyweight C-suite. A startup's hiring priorities should lean towards getting an MVP completed. Giving promising developers and engineers the "CTO" title (and maybe options), is a popular way for cash-poor, equity rich startups to give incentives before their funding's in.

The down-side is that once your idea is out in the world, questions about your roadmap come up. That's especially true of impatient shareholders, excited by growth and new markets! Roadmaps beget product and market strategy, and the pressure is now on the "CTO" to be an actual CTO, with all that entails. And thus, a good software developer is worrying about doing a bad job of managing their team and their responsibilities to their investors.

If you're in this position, or you're supporting someone who is, it's a big responsibility! I've been in this position myself, and I've spoken to many other career CTOs who started out this way.

The unexpected weight of strategy

First, a bit of detail: I've written about this in the abstract so far, but we can be quite specific about the thing that's changed. Early on, developer #1 has to worry about a "good enough" product. It should show that the idea has value, and maybe get a few customers on board. It's definitely not easy, but it is a reasonably straight line - blank canvas to version 1.0. Your customer base is probably small , so hopefully not too much to deal with. You're not making tricky decisions about scaling yet, and team management means daily stand-ups with the guy working on the front-end UI.

Transitioning to your stakeholders' idea of a "proper" CTO can be overwhelming. You'll be expected to have thought carefully about your roadmap, key milestones and strategic sales targets. You'll need to think about how your product scales as the user base grows - and how that affects everything. Hosting costs, development processes, QA and load testing, financial projections, recruitment plans are now your problem, and a lot more on top. In a word, your job is now strategic.

A few things about this might be familiar to anyone who's been there:

  • Second-guessing your decisions on things which affect long-term strategy

  • An instinct to bury your head in work you're familiar with - often coding - at the expense of strategy and confident management

  • Reluctance to delegate things you can do yourself (but probably shouldn't) for fear that it won't get done the way you want

  • At the far end, burnout and stress/anxiety issues if you're unsupported for too long

It's so common that investment due diligence examines the strength of technology and product leadership as a matter of course. It's incredibly normal to find some combination of lack of experience, leadership and confidence, and without a plan it's a big red flag. It's why a lot of investors will push for replacing management soon after fundraising, with founders moving into individual contributor roles instead.

That can be a gutting move for founders. They've put their heart and soul into the project, and it feels like a vote of no confidence in them. And it comes from the same people who just gave them the total opposite, in the form of a big chunk of cash and faith! But it's pragmatic: leadership can make or break a company. A startup's leadership is often the majority of the value it holds. Investors are naturally inclined to protect their investment.

So, as a founding CTO of a burgeoning startup, how can you prepare yourself? How do you take a path that leads to professional and personal growth, avoiding burnout? After all, investors will be investing in you. At Seed or Series A, an investment in the company is investment in its founders. Angels and VCs want to keep the visionaries at the reins if they can!

Support and growth

If you've founded an engineering company, you're already in the habit of thinking of the world of technology as mutable - that is, open to change. Becoming a CTO involves expanding that way of thinking and your problem-solving skills. You'll hopefully be trying to take a view of commercials, finance and operations. That's an intimidating challenge, and it can feel like a gated area you don't have the key for. It's natural for to feel like you're in the deep end.

In a word, the single most important thing to find is support. No-one expects you to magically know everything. Investors (especially accelerator funds and VC houses) understand that becoming a C-level executive is a journey, guaranteed. I'm firmly of the belief that this should be a normal part of the investment process, and something investors themselves should take lead on. After all, they have a volume of founders, experience and networks to make it happen. And, actually, this increasingly is part of their process. Especially in the accelerator and incubator space, a lot of time is spent on personal development for founders.

But there are things you can do if your investors don't offer this type of support, too. Here are a few.

  • Be kind to yourself and remember that you got here because you're good at what you do and you've got this. Remember to check-in regularly with your stress levels. You might find yoga or daily meditation apps like Headspace or Calm are helpful for clearing your mind of the mountain of things on your to-do list. If you need something more active talk to your GP or check out the Talkspace or BetterHelp websites for online counselling. Sometimes it's enough to talk through how you're feeling, but don't be afraid to take steps to manage your stress. It's not a sign of weakness, it's a sign of self-awareness and managing your health!
  • Join CTO communities like CTO Craft, who have a paid plan but also a free Slack community. Find networks of founders and entrepreneurs like you who can be sounding boards for your concerns as you grow your skills.

  • Up-skill yourself via executive training such as CTO Academy, or the many others you can find elsewhere. Startups often treat professional development as a low priority (and a costly one) when they're starting up! Keeping your team at their best, yourself included, is no less important than investing in good software or equipment.

  • Find a mentor or coach who can help guide you through this growth process. There are lots of ways to do this: CTO Craft offer mentoring and coaching. Level39 (for which I'm a mentor) and GrowthMentor can help you find one, and Level39 offers great networking and support alongside that. There are many other similar organisations out there too, if you're not in the UK or the US. If you're not yet funded, joining a startup accelerator or incubator can give you leadership mentoring alongside funding and skills.

The key things to keep in mind is that you're not alone, however isolating the startup process might feel. You'll do yourself and your company a favour by planning your professional transformation as early as you can!

If you'd like to hear more about preparing for funding, due-diligence and growth into a mature leadership team, get in touch with me - we'll talk! I'm passionate about helping startups through these tricky stages in their growth. With guidance on product, process, tech strategy, leadership and fundraising, I can help you navigate your roadmap and put you in touch with a network of specialists who can help you prepare for what lies ahead.

I'm currently available for short and long-term projects, including interim and non-executive CTO positions.

Get in touch!