Tom is VP of Engineering at Hofy, leading a team of thirty. Hofy equips people everywhere with the tools they need to do their best work in one click. Tom’s focus is to build a world-class technology platform, team and business, aligning with Hofy’s vision, tackling technical challenges, coaching and growing the team, and setting a clear technical strategy.

With 15 years of engineering and product development experience at hypergrowth startups, scaleups and Fortune 100 enterprises, Tom has previously worked in senior engineering roles at Bother, Bulb and JP Morgan.

At our CTO Craft Conference, he’ll present a lightning talk on, ‘Lessons Learned! How to manage culture during tough times, dealing with failure and proactively building resilience for future challenges.’ In true lightning talk style, he joins us for a quick-fire question round to discuss what he’ll be sharing at the conference, how he’s created a culture of innovation and his experience at Hofy and Bulb.

Tom Hipwell

Hi Tom, welcome to the CTO Craft Spotlight Q & A. You’re a day 1 speaker at the CTO Craft Con and VP of Engineering at Hofy. Can you give us a teaser about what you might share with our audience at the conference?

Learning is often a case of trial and error, error, error. I’ve been unlucky enough (lucky enough?) to have been at a couple of startups, like Bulb and Bother, where even though we were executing well, the business itself failed.

History and the raft of leadership-related literature tend to be written by the winners. But there are advantages that you get when you’ve lived through interesting times – you get a negative feedback loop, as well as the positive feedback loop that you get when things are going well. This gives you additional information about what works and doesn’t work, and this is what I’ll be focussing on in my talk.

As a leader, what approaches do you use to create a culture of experimentation and innovation within your team?

I think one thing that can influence a culture of experimentation and innovation is having constraints. If you have to make do with a bit less, you’re forced to think differently than how you normally would.

One of the key constraints is time. I think this is why regular hackathons are a good technique. Sandboxed time to experiment with ideas that can come from anywhere. That time constraint and the short half-life of what you create forces you to work very differently from how you normally solve problems.

I think having that experience of working in a different mode on a regular schedule also helps to create a culture of urgency. Moving quickly is a muscle, and hackathons are a chance to exercise that muscle. Being used to moving quickly in teams that have rapidly formed around a new idea can help you in the hard times, too. 

A second technique is showing where it’s safe to experiment and where it’s not. So, with technical choices, for example, we’ve followed the classic technique of using a Technical Radar to show how we’re thinking about new technologies, but we also plot adopted technologies onto a “Pyramid of Consistency” to show which choices are up for debate, and which aren’t.

I think there are some nice second-order effects from this type of thing as well. For example, if you open up this type of decision-making and allow more folks to participate in the big calls, that drives up engagement. This, in turn, increases productivity but also means the group will stay together when things get tough. 

How do you prioritise and balance competing business objectives and stakeholder needs?

We have a clear product strategy at Hofy. We know where we’re going, and that product strategy has a single vision for the product, platform and company at its core. That makes these types of decisions easier, as you can see what does and doesn’t align with the strategy, and you can use that to drive the bigger prioritisation calls.

Doing that well, as most leadership books will tell you, gets you through the vast majority of calls. Of course, there’s a lot of nuance around the day-to-day reality of this balance; what if there’s a great ROI on a project which doesn’t align with the strategy?

Or what about work which everyone agrees feels valuable but where the payoff feels more ambiguous? This is where it gets stickier. I’m not sure there’s one simple answer in that case, and I’m still learning my way through it.

I think, though, as a leader, your strategy should be twofold. One, step towards the problem and really understanding the detail; what’s driving the recommendation to do the work? Two, take a step back and look at the mix of work you are prioritising. Is the mix right to get you delivering on your overall goals? 

In your opinion, why should someone come to CTO Craft Con?

When I look at the folks who are attending, I’m just really looking forward to the chance to listen to and learn from a really strong peer group, both in the scheduled sessions and also in the mixers. I know from following along in the community that there’s a lot of wise heads in the group, so I’m looking forward to catching up with a few folks in person and getting some questions answered.

What talk are you most interested in hearing?

It’s got to be Michael Lopp, hasn’t it? Can’t wait for that one!

Finally, can you recommend a book or a podcast that every technology leader should read or listen to either in the space of strategy, development or leadership in general?

I have so many book recommendations, and when I read this type of thing, that’s normally what I’m looking for, so bear with me while I share a few.

I really enjoyed The Art of Doing Science and Engineering by Richard Hamming, just for the way he breaks down how to do great work and really commit to a life of lifelong learning.

Thinking in Systems by Donella Meadows. Peak by Anders Ericsson is, for me, an underappreciated masterpiece on how to form expertise through deliberate practice.

All the obvious ones are good as well. So, if you’ve seen Five Dysfunctions of a Team or Good Strategy/Bad Strategy on a hundred of these types of things already and haven’t read them yet, I’d recommend those.


We’re thrilled to announce that some of the most exciting tech leaders will be joining us at the CTO Craft Con on 7-8 November 2023 at the Tobacco Dock in London.

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