Meet Hywel Carver, CEO at Tech Deep Coaching Company: Skiller Whale

Skiller Whale does Deep Coaching for scale ups with ambitious tech strategies.

The idea came from pain that my co-founder, Dave, and I experienced first hand as software engineers, and tech leaders in fast-growth environments.

We were both frustrated to find that a huge amount of our time was spent finding and filling the gaps in knowledge that our teams weren’t aware that they had. We desperately wanted to throw money at the problem, but after trying all the usual suspects (video libraries, content subscriptions), we saw no real skill improvement.

As a Founder, a consulting CTO and CTO coach, I found that upskilling tech teams was consistently one of the biggest headaches tech leads face. In fact, most tech leaders find this problem so insurmountable that they opt to hire (a long and often painful process itself!) when they have new and changing skill requirements.

From this, I knew that if we could solve this problem it would be transformative for the industry.

We defined 4 criteria that we believe should be true for upskilling to be effective:

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

Finally, we looked at what was feasible in terms of both time and money, and created a subscription model so that each developer gets 2 focused hours of learning per month for £200.
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What do you think makes this company unique?

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’. No start-ups are going to risk pausing their dev team for that long, let alone the upfront outlay of funds.

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.

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

I think our success comes down to what we care about. We’re not a SaaS just trying to scale servers; instead, we’re trying to achieve real tangible outcomes from learning. That means dealing with aspects of our own business that don’t scale easily, like live coaches, and spending huge amounts of time writing a really interesting, challenging scenario so that every 1-hour session has an ‘aha!’ moment.

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.


How has the company evolved over the last couple of years?

At the end of 2019, we were two people who believed we were onto something.

Today, we have £2.8M in funding, a core team of 18 brilliant people, a large network of freelance trainers and fast-growth scale up customers such as Wagestream. Omnipresent, PensionBee and Gousto. I was selected as a speaker at Lead Dev London in June to talk about our approach to tech learning, and I’m scheduled as a keynote speaker for CTO Craft Con in November. So.. quite an evolution!

What can we hope to see from Skiller Whale in the future?

We’re always keeping up with the constantly 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 modeling, 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!