Late last month, we invited the CEOs from Octopus Ventures-backed companies to our Holborn HQ for a lesson in hiring. Specifically, how non-technical CEOs should approach the challenge of hiring the right CTO, equipping them with the team they need and, crucially, keeping abreast of whether (or not) they’re doing their job. 

We welcomed a couple of luminaries in to lead the session. Mike Hancock, CTO at OakNorth Bank, and Timothy Kimball, CTO at Confused.com. Both are domain experts, with years of experience building and managing technical teams. Before starting his role at OakNorth, Mike was the CTO at Fluidly, an Octopus Ventures-backed business acquired by OakNorth in 2021. Timothy, meanwhile, worked as Head of Engineering at Many Pets, another business from the Octopus Ventures portfolio. 

Together, they boast a wealth of knowledge in the tricky business of ensuring a development team keeps pace with a scaling start-up. Over salmon sandwiches (nicer than they sound – we had pretzel buns, too), they shared their wisdom.  

The challenge 

Pioneering business acumen and technical genius are by no means mutually exclusive categories – but neither is there any expectation that the two things are necessarily embodied in some mystical, venture-capital-ideated Platonic Ideal of The Founder.  

The truth is, barring a few notable exceptions (Jeff Bezos and Satya Nadella, for example, both have engineering on their CVs), most CEOs have little hands-on experience at the engineering coalface. And even if they do – paths rapidly diverge. The qualities and skills that reward good CEOs are not the same as those that might make an industry-leading CTO.  

The Octopus Ventures People + Talent team exists to support the founders and CEOs of the companies we back, and the question of how a CEO with (relatively) little technical know-how can properly supervise the work of their CTO and development team is one we hear time and again. Last year I joined forces with my colleague, B2B SaaS investor Constanza Diaz, to offer some insights into the metrics a company’s leadership team can use to track their development team’s performance. At our event, Timothy and Mike went further, laying out some key principles CEOs can use to answer the burning questions related to engineering talent acquisition.  

Mike explained the ideal arrangement in simple terms. As a company scales, from Pre-Seed, through Seed stage and on to its Series A, the demands it makes on its engineering team shift. This change can be tracked, simply, as the transition from ‘hunters’ to ‘farmers.’ 

Hunters…

At the outset, a world-changing idea needs to be made. At this stage, the team is small. A single tech lead or CTO is likely all that’s called for. This person needs to epitomise the hunter. They need to be prepared to venture out, explore new ideas and test their impact. They need to be adaptable, prepared to think on their feet and respond to challenges and obstacles as they come up – even while holding on to a clear idea of the bigger picture. 

At the very early stages, they may even need to build new features, to help the CEO find new angles to the solution that add value to customers. CEOs hiring for this role need to consider these qualities and ensure the individual they bring onboard is a competent, outgoing generalist, prepared to get their hands dirty and unlikely to get bogged down in the details. These, after all, come later.  

With this keen hunter onboard, and your solution on its way to market, it’s time to employ more. The hunter should be able to help with this. They’ll need to build the team, to find more people like them with the ability to switch contexts quickly and solve problems as they come up – wherever they are in the architecture of the solution.  

When they’re hiring this first hunter, CEOs need to ensure they have the talent-spotting and people skills necessary to make these subsequent hires. This is the team that will be refining the solution to the point of optimisation that it finds product-market fit. 

…and farmers 

That’s the point at which things change. Perhaps the business has been through a successful Seed round and clients are being onboarded. The CEO may be starting to eye-up a later stage round. It’s now time to hire farmers.  

A crucial part of managing a rapidly scaling organisation lies in recognising that as its needs change, so do the demands it places on talent. Where the very early stages reward context-agnostic generalists, prepared to roll up their sleeves and dive in wherever they’re needed, a solution with product-market fit requires individuals who are happy to take ownership of specific areas, iterating and scaling to make the solution as predictable and stable as it can possibly be.  

It’s less a question of exploration, more a question of maintenance and optimisation, patiently building incremental improvements over time. From a talent perspective, it means either convincing hunters to become farmers – or recognising that it’s time for them to move along. 

Clear communication – and other jobs for CEOs 

This may sound ruthless, but in fact, as CTOs of enterprise-scale organisations both Timothy and Mike challenged this interpretation. Individuals are cut out for different things. CEOs and CTOs boast complementary, but different, skillsets. Some hunters are happy to become farmers; many aren’t.  

Clear communication is crucial with early hires, alongside the recognition that while some will be prepared to adapt, or even thrive as the company changes form, others will want to seek out new opportunities. Start-ups aren’t for everyone: the unique risks attract a certain type of person, for whom the challenge of building something from scratch can be as important as compensation. 

Maintaining open and honest dialogue ensures that the earliest hires remain clear-eyed about the changing needs of the organisation and their role within it. Both Mike and Timothy suggested that at the very early stages, the ideal CTO might be younger, driven to build a world-beating solution and hungry to scale up their career. Approaching a Series A, a safe and proven pair of hands, able to maintain the solution to the highest standard, with the experience on their CV to reassure investors, is often a better candidate. 

Beyond this, Timothy and Mike emphasised the importance of supporting the CTO in building a robust talent function. CEOs and CTOs need to work together to ensure that the talent is recruited at the right time. As both our guests acknowledged, CTOs can be evasive. CEOs need to challenge them, hold them accountable to agreed-upon metrics and ensure they’re getting the most out of their team. 

For their part, CEOs need to spend time thinking about which metrics to track. Our guide, linked above, offers some good places to start. Measuring how many lines of code engineers write might seem like a good idea, but its more meaningful to get them connected to the commercial impact of what they’re doing, and how the customer experiences it. They need to understand the impact on the end user. It also falls to CEOs to liaise closely with CTOs on what’s achievable: promising the world to clients or investors when it simply can’t be delivered doesn’t look good. It’s the CEOs responsibility to ask and listen to the CTO for a clear understanding of deliverables over a timespan. 

Ultimately, it’s a two-way street. In a company with future-shaping ambitions everyone needs to play their part. The CEO needs to trust the CTO, giving clarity on what they need and when, while the CTO needs to be clear about what’s possible – and deliver. An overly granular obsession with the wrong metrics doesn’t help anybody; equally, a CTO needs to understand what their team can achieve, hold them to it, and communicate it clearly to a CEO.  

Mike and Timothy’s input comes from the technical side of things; for the CEOs we back, their expertise was invaluable. As our breakfast session wrapped up, there was a clear feeling of excitement and energy, with CEOs reporting genuine clarity on what is, unavoidably, a difficult set of challenges.

All the companies we support get dedicated support from the Octopus Ventures People + Talent team. Like Mike and Timothy, we’ve built our expertise over years of operational experience and, chances are, whatever the problem – we’ve seen it before. Learn more about the value we add, and if you like what we read and have a world changing idea that could use our support, pitch us. 

Later this month, we’ll be running another session, dedicated to helping our CEOs unravel their knottiest recruitment challenges. Check back in for our write up.