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Secrets of Success: Hywel Carver, co-founder and CEO, Skiller Whale

Upskilling tech teams in meaningful, productive sessions that actually work.

The idea for Skiller Whale came from the pain that Hywel and his co-founder, Dave, experienced first hand as software engineers, and tech leaders in fast-growth environments.

Both were getting frustrated to find that a huge amount of their time was spent finding and filling the gaps in knowledge that our teams weren’t aware that they had. After trying all the usual suspects – video libraries, content subscriptions – they saw no real skill improvement. 

Realising that upskilling tech teams was consistently one of the biggest headaches CTOs and Heads of Engineering face, they knew that if they could solve this problem it would be transformative for the industry.

Enter Skiller Whale …

What products or services do you provide?

Skiller Whale provides Deep Coaching for companies with ambitious tech strategies. This means personalised, live, expert-led, micro-coaching sessions in small groups, focused on specific tech skills required by the team.

What type of businesses do you work with?

Start-ups, scale-ups, large tech companies. Really, anyone who is tech-first and ambitious in what they want to achieve.

We currently work with a number of scale-up Fintechs and Unicorns, such as Omnipresent, Wagestream, Gousto, Drizly and PensionBee.

What is your USP?

Traditionally, if you want affordable learning, you have to get access to generic content for self-study (low engagement, low impact). On the other hand, if you want high-impact learning, you have to dedicate a week or more of intensive time for expensive ‘bespoke training’.

With Skiller Whale, we created a third way: teams get the impact of live, intensive coaching, at a pace and price that’s affordable and sustainable. With the subscription model, it’s low stakes to try for a month and cancel or pause if it’s not working for you.

In developing our approach, we tried many things that failed. But some things worked, and we kept exploring and refining those. Eventually, we realised that 4 criteria had emerged as foundational to tech coaching effectiveness.

Diagnostic – it must be relevant to each individual’s knowledge – what they don’t know, and what they need to know.
Expert-led – it must be challenging, with feedback – this means it needs to be led live by a domain expert.
Experiential – it must be hands on learning, not just theoretical or passive
Problem-based – it must have scenarios with real-world application, not just ‘hello world’ or foobar.

These rather obligingly spell out ‘DEEP’, which with its aquatic connotations felt like the perfect term for our company!

We got some help with this structure from our third co-founder, Hayley, who previously ran a company developing skill matrices for organisations like HSBC and Microsoft. By the time we’d defined Deep Coaching, we collectively realised that the criteria echoed our experiences at the university we all attended (and where two of us met) – Cambridge.

In the Oxbridge model, learning is led in small groups by domain experts. However, at university everyone is assumed to have the same pathway. This certainly isn’t the case once you’re working, so the diagnostic element is key to our approach being relevant for mid-career folks.

No individual element of what we do (DEEP) is new, but the combination is unique.

Our view is that if we can get the learning experience right, then we’ll solve the rest of the scaling as we grow. We have a 94% completion rate (compare that with 12.5% median MOOC completion), and 99% of learners give our coaching 4 or 5 stars, so we think we’re doing something right.

What are your company values? Have you ever had them challenged and if so how have you dealt with it?

We’ve made our company values internal documentation public.


The descriptions in our public page address some of the challenges we’ve addressed. Specifically:

Openness is our most important value, and we’ve defined it as enabling openness through gratitude. Many organisations expect openness, but don’t create the conditions to make it possible. It must be easy to give bad news. It must be acknowledged that it’s hard to give negative feedback, not just hard to receive it. Psychological safety is a must have.

Rationality has been challenged as a word that has been used as a weapon against women. We considered changing the word, but couldn’t find another that fitted our meaning better, so we continue to use it but with the explicit acknowledgement that it has been weaponised, but our meaning of it is that everyone can follow the steps of each decision and understand (not necessarily agree with) how we arrived somewhere. It’s also worth noting that we do not believe that rationality is the antithesis of emotion. Sometimes the most rational thing to do is to prioritise the emotional impact of a decision.

How do you ensure that you recruit a team that reflects your company values?

We’re very clear about our values internally and externally; and we want them to be reflected by everyone in the company, that is why we take hiring seriously.

The recruitment process provides a really great opportunity to not only discuss our values but embody them right the way through the candidate experience. We are open and transparent about our salary banding with all advertised roles, our approach to flexible working and our commitments to improving diversity within the tech industry.

We make a point to deliver feedback to any candidate who applies and we ensure that values based questions are woven within the process, rather than simply the traditional competency approach.

Any finance or cash-flow tips for new businesses starting out?

Prioritise revenue over capital. Early revenue is the strongest signal you can get that your idea might be successful. It’s a sign that you’re doing something valuable, bottom-up. Investment is a sign that your market exists top-down, and that you can describe it compellingly to investors – that’s a weaker signal for long-term success.

Sell early – sell earlier than you think you possibly can. From the start, our vision for Skiller Whale was a remote-first, technology-driven coaching environment – slick, integrated into our user’s workday without friction. But the first version our customers paid for, had none of that – it was me travelling across London to the offices of our customers, sliding pieces of paper across the table in a stuffy meeting room, looking over their shoulders and answering questions. I’d probably spent less than 10 working days on the business at that point. Not only did we get revenue sooner, but we were able to experiment and iterate much sooner. I think that approach is why we were able to invent a new learning model, and it’s why our users love us so much – everything about our service came directly from watching users experience it.

If you could ask one thing of the government to change for businesses what would it be?

Modernise and simplify – allow for more integrations (like Making Tax Digital – that’s a great start). I tried to read the rules on taxable and non-taxable benefits recently, and they don’t reflect a modern world where people are increasingly working from home, part-time, and changing jobs every couple of years.

Each new form we’re required to submit, each new field on a tax return, each new scheme to apply for, is an extra burden for an innovative, growing company. The more admin and bureaucracy there is around the running of a company, the less time we have to work on the company itself – and ensuring we’re compliant becomes a real burden, expensive in terms of money and time.

What is your attitude towards your competitors?

Right now, we don’t have direct competitors. However, there is a lot of content out there and a lot of providers of traditional e-learning for tech skills. We think it’s great that there’s so much available, and that so much of it is free! But our view is that it’s like a gym membership – go whenever you want, do whatever you want (and probably don’t). Our brand of coaching is like a personal trainer focused on getting a team ready to win a league. It’s just a completely different thing with different goals. Personal trainers don’t think gyms should be abolished, but they probably also don’t think they are enough.

Any thoughts on the future of your company and your dreams?

We’re always keeping up with the changing tech landscape and responding to the needs of our customers. On our roadmap, we are expanding our offering beyond language-specific coaching to broader topics such as writing clean code; data modelling, as well as soft skills such as pair programming and time management.

Beyond that, we will be expanding to other skill domains beyond tech. Watch this space.

Read more:
Secrets of Success: Hywel Carver, co-founder and CEO, Skiller Whale

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