Name: Vicky Wills

Current position: CTO at Zego

Bio: Vicky joined the London-based InsureTech in 2019, bringing with her a wealth of knowledge and experience of both hands-on engineering and engineering management gained at tech startups including Depop, and Opendesk.

Her speciality is building and scaling technology teams in both early-stage and high-growth companies, with a particular focus in team structuring and processes.

Hi Vicky, thanks for joining us today! Tell us about your life before leadership – what kind of roles and projects did you work on?

Before leadership, I worked in hands-on software engineering roles, mostly backend engineering. I started out in an investment bank, and soon made the move to startups where I’ve worked across TV, fashion, and manufacturing to name a few industries!

How did your first leadership position come about, and was it intentional on your part?

I first started leading teams at Depop. I was their Lead Backend Engineer and also took on the responsibility of managing a cross-functional team, which was great fun. I wouldn’t say it was intentional, in that I wouldn’t have been able to tell you what the plan was at the time. However, people leadership and tech strategy are such interesting areas for me that it felt like a natural progression. I was very lucky to have some great mentors at the time who encouraged me into the role and helped me work on the skills I needed. 

How did you manage the transition? What came easily / what was difficult?

I managed the transition with a lot of help – there’s no way I could have done it on my own! The technical side of the role was a continuation of the work I had been doing, so it felt relatively easy. The people side was a mixed bag – I’ve always enjoyed getting to know people and working out how best to set them up in their roles. Doing it in the context of ever-evolving business requirements was a learning curve that took some getting used to. 

What was your biggest failure in that first leadership role?

I’ll be honest, there’s plenty to choose from! I’m going to go with handling the inevitable (and constant) change that comes with being in a growing startup. I wasted a lot of time and energy worrying (and resisting) when I could have been embracing the positive aspects of an evolving team and company. Interestingly, I’ve learned the lessons from that period after the fact, in subsequent roles. Recently, I’ve been particularly aware of how powerful it is to frame change constructively and positively for your team. This is something that I didn’t appreciate earlier on in my career.

What made you keep doing it?

I love org building – putting together the skills, environment, and systems needed to realise a technical vision.

Technical leadership roles – and especially the CTO role – give you the opportunities to set a technical strategy and work on the organisation to build it. I won’t pretend I don’t miss being a hands-on engineer, but I find my role so interesting and exciting that it more than makes up for the lack of coding.

Tell us a fun fact that nobody knows about you

Something that nobody knows is a stretch! I absolutely love music and have spent a lot of time playing various instruments through the years. At university, I was in a ska band called Skasky and Hutch 🙂

What are the three key skills you think every leader needs?

The most important one for me is empathy. The CTO role is a constant balancing of business needs with human dynamics, so leaders need to be skilled in listening and understanding different perspectives to inform decisions and communication.

Communication as a skill is a cliche, so I’ll be more specific for the second skill, and say being able to address varying sizes of groups to land a message. I found it quite a learning curve to go from 1:1 conversations, or one small team meeting, to the entire department or even the whole company. Learning how to tailor a message according to the number of people, or the type of audience is a very valuable skill in leadership.

Lastly, for me, prioritisation is so important. So the ability to synthesise all the information you have into a coherent set of priorities for the team, is vital for a leader. Highlighting what isn’t prioritised is just as important as what is. I really admire leaders who are transparent in their approach, and manage to make it absolutely clear to their teams what results they do and don’t care about and why.

What have you learned about acquiring and retaining talent?

The industry is crazy for acquiring talent at the moment – actually, if everyone reading this could just stop hiring for a bit, that would be great, thanks!

Yes, salaries are high and you need to be competitive to land top talent. However, you can’t overlook other factors: interesting work, great culture, opportunities for learning and progression etc. I find that it’s well worth investing time in the interview process for candidates to meet the team, learn about how we work and what problems we’re solving. Good candidates have their pick of amazing roles, so it’s best to accept that and be excited and open about the role you’re offering….warts and all – remember engineers like solving problems and honesty goes a long way! 

How do you motivate your team and manage their stress levels?

There isn’t a blanket rule here; everyone is motivated in different ways in my experience. The key for me is to ensure you really understand what types of work and problems someone is excited to tackle, and find the best match in the organisation. There are times when the best fit is in another team outside engineering completely, but that’s a win for me if you find someone’s passion! 

How do you manage your own stress levels and productivity?

Personally, I really struggle if I find myself constantly context switching. For instance, my brain just can’t cope with instantly going from a very technical problem into a company-wide issue – and I’m not sure I’ve met anyone who can really do this. I try to give myself time during the day to process and switch gears without having to jump straight from one problem to another – I’m a big fan of the phrase ‘thinking is work’. If a context switch is unavoidable, I take comprehensive notes through meetings or working sessions to get my head into the topic later on when I have a bit more space.

How do you stay in sync with other parts of the business?

I have a number of formal processes, such as attending commercial meetings or reading regular updates from other teams. As well as this, I find it really helpful to personally get to know leaders in other parts of the business and try to get under the skin of their work and the problems they’re solving.

Where do you see yourself in five years’ time?

Honestly, I have no idea. I love what I do, so I’d like to think that I’ll be doing something along the same lines – working on building interesting tech and teams.

What product do you wish you’d invented?

I love products that are enablers, powering a whole set of other products or providing the tools to enable people to apply their skills. So I’m going to go with Git for this question. It appears all over our industry and is a critical system in the development of countless technical products that are built. I particularly like that it’s open-source – people have built amazing products on top of it as service offerings – and follows a distributed model. The engineer in me loves it when technical products have a real impact, and Git is certainly up there for me!

Thank you, Vicky!


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