Case study: Skiller Whale's new category
How Skiller Whale is creating a new category for online technology training.
“It was so dreamy,” says Hayley McCarthy, co-founder of Skiller Whale. “I'd explain what we did to a CTO and they'd just be like, I had no idea this existed! Where do I sign?”
Hayley is reflecting the sense of Product-Market Fit she found in her early sales conversations with Skiller Whale, compared to some of her previous EdTech adventures. She puts this down largely to the benefit of her two cofounders having experienced the problem themselves.
“Hywel and Dave were both technology leaders who had managed teams and have experienced the problem that we are trying to solve,” she says. “It makes commercial discovery so much easier because my co-founders are proxies for our customers.”
Hayley (CMO) and Hywel Carver (CEO) had come up with their solution to the challenge of upskilling technology teams in 2018. Hayley was about to have her first child so Hywel began exploring on his own. He was joined by Dave Millican (CTO) in 2019 with Hayley coming onboard fulltime in 2020.
Despite often finding an immediate ‘click’ once they spoke to their ideal customers, there was a catch: they were taking a new approach and they needed to find ways to reach notoriously hard to reach technology leaders.
“CTOs are incredibly good at avoiding being contacted,” says Hayley. “It is really hard to get attention. But once we have it, we find that what we do resonates incredibly well.”
Rather than traditional self-paced online courses, Skiller Whale offers ‘micro-workshops’, where software engineers are coached in small groups to understand new technologies or approaches by experienced practitioners.
Hayley and Hywel have taken the time to talk to me today about how they found product-market fit by postponing building anything until they had tested their ideas and then deliberately creating a new category. And how, by engaging with their community, they grew to reach profitability - even against the headwinds of the great tech layoff.
Identifying the problem and an approach
“When I was running teams, I wanted something that I could just basically point at my team and say, make these people better at [the coding framework] Rails, this person better at JavaScript, and this person better at React.js.” says Hywel.
Hywel had started coding when he was nine. At 13 he started making websites, including one about The Simpsons for the school intranet. He and Hayley met at Cambridge University where he studied Engineering, specialising in machine learning and information engineering and she took English Literature.
After starting a PhD and having adventures with various startups, Hywel co-founded the university guidance platform BridgeU with Lucy Stonehill, where he was Chief Technology Officer. But after four and a half years he knew that he had an itch to do something else.
“I have curated a lifestyle, hobbies and a job, all of which enables me to always be learning new stuff. I've even done a whole load of TV quizzes!” he explains. “I started seeing the separation between the learning of information and the learning of skills.”
He explains, “I felt that all of the options I had available were about learning knowledge. This is useful for some things, but there is a gulf between that and being able to use it and apply it as a skill. For example, if you’re learning to drive, knowing what the steering wheel and pedals are for isn’t enough. You need to experience steering and using the pedals and to have someone tell you where you’re going wrong.”
As he reflected on this with Hayley, his fellow Cambridge graduate co-founder, he was reminded of his time as a student. “At Cambridge you go to your lectures, but you also have these small group sessions as a science student called ‘supervisions’, where you would go away to try and work on stuff after lectures,” he explains.
“A Masters student would help bridge that gap between the theory and the practice. Not just knowing something, but understanding how to use it to actually solve a problem. For me, that was where all of the learning of my degree happened.”
This became the starting point for a new approach to the challenge he had experienced as a CTO. “We realised that there was this big need for hard skills where people were actually able to do the thing,” he explains. “Not just having enough information to have a bash by yourself, but being able to do it and get feedback from someone who knows what they're talking about.”
They wanted this focus on skills to be reflected in the name of their new venture. But everything they thought of seemed too worthy. “I couldn’t say something like ‘SkillGain’ with a straight face,” he explains. “We’re all big fans of bad puns. One of us came up with ‘Skiller Whale’ and it stuck.”
The shared love of bad ocean puns is something that bonds their team to this day.
Postpone building until you find fit
Despite being a software engineer, Hywel decided to postpone building any technology to begin with. He began running sessions with some clients he was consulting with.
“For the first 10 sessions I printed out the entire curriculum for each learner and cut it up into sections,” he remembers. “I would literally just push pieces of paper across the table to people.”
The initial sessions were written with an adventure game narrative, inspired by his love of board games. “With hindsight it was quite cheesy,” he says sheepishly. “After the first two sessions it became very clear that some people were just not going to buy into that.”
Participants would follow along with ideas, and were given some code to edit. In the first sessions, they were able to go very much at their own pace. Originally, he thought that this was a positive thing. “But I realised what we missed out on was the conversation.”
He explains how he came to see what really resonated: “Imagine a table with me at one end, and five or six developers each with their laptop. I'm sliding bits of paper. I would be looking over people's shoulders at their code editor and answering questions, giving them hints. There'd be a conversation that I'd have with someone. And someone else would be listening in. They’d say ‘Oh! I went past that, but I didn't really get that at the time.’ And that’s when I thought, ‘Ah… being able to go at your own pace, is not a good idea. The learning is worse for everyone if someone can bomb to the end.’”
He says that it became obvious that the experience was better with someone who's treating you like a peer, “rather than pretending that we're all part of this grand adventure story.”
So he redesigned the sessions for small groups working at the same pace, to enable a conversation. Dave joined him and they began to gradually build a platform, but still ran the sessions in person so they could really understand the dynamics going on in the room.
Then, in the run up to Christmas, Hywel turned up to deliver a session only to find two of the team were away in Argentina and Pakistan.’ I said, ‘Don’t worry, get them to join on Google meet,’” he recalls.
“We got the feedback that they thought they'd had just as good an experience as if they were in the office. And we thought, ‘OK, we are ready.’” Only now did they build video conferencing into the app. And from the start of the following year, they were fully remote.
They’d found a way to solve the problem in a way that worked. Now the challenge was how to sell it to others experiencing similar challenges.
Don’t compete, position yourself as different
This was the moment Hayley came properly onboard. Hayley had also spent time at BridgeU and with another EdTech, the social learning platform Aula.
In previous companies, Hayley had been competing for an existing budget and needed to solve the problem better than the competition. With Skiller Whale the challenge was a different one.
“It felt like all of the competitors were not trying to solve the same problem we were trying to solve,” she remembers. “Or they weren't positioning themselves that way. They weren't in the same headspace for our customers.”
“CTOs weren’t using the learning libraries like Udemy or Pluralsight to transform their teams. Instead, those platforms were very much seen as a ‘perk’. People like to have them, very much like people like to have a gym membership.”
They began playing around with the narrative that Udemy is like a gym membership. But Skiller Whale is like a personal trainer. “If you’re a sports team coach, you’re not buying everybody a gym membership and then, just say I'll just see you on match day,” says Hayley. “You are expecting people to exercise in their spare time. But you also need to coach them.”
This became the starting point for their product positioning. “It became clear to me that we needed to differentiate by being clear that we're not even competing. We're saying, you already know that those things are not solving this problem. But this problem can be solved with learning.”
Unlike self-paced learning platforms which have notoriously high drop out rates, Skiller Whale has a consistent completion rate of 94%. “It's not just a bit better than online courses. It's a completely different world.”
“People attend Skiller Whale sessions because there's someone waiting for them,” she says. “There's a human involved who is an expert in a thing that you are working on, and they are waiting for you to show up.”
She contrasts this with platforms that feel more like a library card. “It gives people the opportunity to go and explore. And so you end up with lots of things being started but never completed.”
At the other end of the spectrum, many of the CTOs they spoke with who were wrestling with transforming the skills of their team were considering bringing in consultancies like ThoughtWorks or feeling the need to hire someone. “We were trying to introduce this third way that no one had been thinking about. A skill injection that doesn't have to take three years to work.”
They realised that they needed to position themselves as a new category and find a short hand that would help them explain this differentiation. They initially tried the phrase ‘live team coaching’.
“We wanted to have something that would communicate really quickly the things that were different. It's live and it's with the team. The problem was that ‘coaching’ just has too many other associations,” says Hayley.
Their second iteration was ‘Micro Workshops’. “‘Workshops’ suggests live, rather than self-led learning.” This way of describing the proposition clicked and they continue to use it today.
Finding a channel that worked for CTOs
Despite the clear advantages of competing in a different way, creating a new category presented them with a growth challenge. “There's no budget line for it. There's no one Googling for us,” says Hayley.
This was compounded by the characteristics of their buyer. “There's a little bit that we can do with outbound, but for the most part, CTOs are phenomenally good at avoiding somebody they don't know,” says Hayley.
Hywel concurs and adds the CTO perspective: “I get so much inbound from dev agencies, recruiters. Is it trying to sell me engineers? Is it trying to sell me dev work? If it feels like either of those, you don't get to the second line because you would just spend all day reading those emails. Standing out in the middle of that is really hard.”
Hayley carries on, “We have to find other ways to reach them: through people that they do know.”
Their answer is community. “We're very visible in CTO communities,” says Hayley. “We run dinners and events that bring CTOs together and then they get to know us.” They also encourage their existing customers to do talks and share the impact they’ve seen by using them. “It's very community oriented, grassroots marketing.”
Some of Skiller Whale’s most vocal supporters, such as Meri Williams (ex-CTO of Monzo, current CTO of Pleo) have given talks where the developer productivity metric graphs they use are shown as evidence of the power of this kind of upskilling.
However, it took time to come to this realisation. “My biggest learning has been to trust myself in terms of what's working,” reflects Hayley. “Everyone says try Google ads or LinkedIn. That's how you get meetings, that's how you get leads, and it's a numbers game. Nothing in my experience was telling me that it was, but wasn't trusting my instincts.”
“Focusing on community emerged really early as a good approach, but it was lots of work. I was tempted by, what if there was an easy way? It turns out, the answer is there isn’t.”
Consider how to scale early
Once the community ‘flywheel’ was spinning, they needed to consider how to scale their highly hands-on learning experience. Fortunately, this was something they had deliberately thought about early on.
The inspiration had come from an unexpected source: the live experience of the classic UK TV adventure game show, The Crystal Maze. In the original, contestants are led around various challenges by Richard O’Brian of Rocky Horror Show fame. Hywel had taken part in an Escape Room-style recreation with some friends.
“Each group gets taken around by a different person and all of the characters that they play are different,” he grins remembering. “They are actors playing a part. We had someone who went by the name of Tex playing a Texan gun slinger. Someone else had had a Southern Belle. They all had their own spin on it: they weren't trying to be Richard O'Brien.”
This became their model for scaling: “We provide the same structure, curriculum and deeply thought-through exercises - and each coach brings their own style and set of experiences to share.” They now have a network of freelance software engineers who provide the coaching alongside their other work.
Scaling the curriculum
“Curriculum is expensive in terms of time to build. It's hard to do well, but that's our moat,” says Hywel. “It's taken a really long time to scale that. Now we are in a position where it would be very difficult to replicate what we have.”
Early on, they had realised that a fortnightly cadence worked well for the live sessions. The fortnightly ‘sprint’ cycle matched how engineering teams often approach learning and development and it also worked in terms of price: the cost-per-learner wasn’t too onerous.
But the other benefit was that they could build out the curriculum just-in-time.
“It was just a long enough time that we could write the next module of a curriculum. You’d always have a session coming up. You’d finish one and then need to start the next one straight away,” says Hywel. “But the second time we’d get a team that wants the same curriculum, it was there and we’d just have to deliver it.”
Alongside teaching specific technologies, they have also introduced more universal cross cutting skills like API design, domain driven design and pair programming. “It has really alleviated the problem of curriculum, because we now have something that we can sell to any organization,” says Hywel.
For a long time, they believed that management and leadership skills were well catered for but they kept being asked if they could offer training to support these skills too. “We're talking to an audience that is very quick to reject business jargon and is very quick to kind of judge someone as not technical and therefore not worth listening to,” says Hywel, reflecting on the need they are meeting.
Hayley has also noted another interesting dimension to this: “there are estimates that roughly 60 to 70% people who work in technology have some kind of neuro divergence. It often isn't catered for,” she points out. “If you have ADHD, an experience that includes videos that you can play at a faster speed, and where you can have multiple things open at the same time, makes it really hard to actually complete anything or to take it in.”
By finding a solution that plays to the distinctive needs of software engineers, they are starting to find new adjacent opportunities.
AI and future growth
Which naturally leads us on to the omnipresent topic of AI.
“An industry that needs to get good at using an entirely new set of tooling is a really big opportunity,” says Hywel. “We’re releasing a new curriculum on GenAI for software teams in June 2025 and already have a pretty good wait list of people who are eager to roll it out to their teams.”
He also notes that there is a big gap between what boards think is going to be possible with AI and what the reality is. “We think helping people appreciate the value and to know when and when not to use AI is a nuanced position. That is what we are planning to help educate people about.”
As well as what they teach, they have also been experimenting with the potential role AI might play in helping them to deliver it. However, they don’t believe the current tooling can compete with a human.
“It has made me realise that the need for what we offer is going to get greater over time,” says Hywel. “We need humans with deeper understanding, as the tooling gets more powerful. The skill of the person wielding the tool needs to increase.”
He believes that in future, developers will need stronger higher level and abstract skills. “The idea that you can just have a career where you're churning out code using the same ideas for 10 years in a row, doesn't exist anymore. I think the kind of the increase in skill that we need as an industry is pretty steep,” he says. “And we are already seeing that increase in demand from our customers. I think it’s going to be the biggest area of growth for us.”
Profitability and the right co-founders
Skiller Whale is now profitable having taken only £3.5m in funding.
“It feels like a phenomenal achievement in the current market. There have been so many tech layoffs and so much learning investment cut,” says Hayley, reflecting on the challenges of securing more funding as teams were cut. “Weathering the storm of the tech recession as a company providing the thing that is the first to be cut - learning - and coming out of it in the place we are I think shows that we really have Product-Market Fit.”
The pair reflect that key to navigating this tough environment was having the right co-founders around to support you. “We are always pro-conflict. We are always in favour of discussing things and thrashing things out,” says Hywel. “It’s important to trust the thing that the person has told you and you’re not left second guessing.”
This bond was formed a long time ago, whilst still at university. They tell a story about when they took part in a challenge to get as far as possible from campus without paying for transport. “We ended up being driven along an autobahn at over 100 miles an hour, in the middle of the night, thinking we were going to die and got to some small town near Essen. On the way back we had our passports confiscated, and were arrested at Calais.” Hywel grins. “I think our conclusion from that was, we're a Dream Team! We can do anything!”
Summary
We finish by reflecting on their journey and the key points that would be useful to others.
Gaining a deep, authentic understanding of the problem your customers have will help you find true product-market fit. Skiller Whale intimately understood the challenges CTOs face because two for their three cofounders had first-hand experience of the problem.
Postpone building as much as you can until you’ve really understood the best solution to the problem. They began by pushing pieces of paper around in face-to-face sessions where you could read the room and understand what resonated.
Don’t compete, be different. They deliberately positioned themselves as different from existing solutions to win more valuable business.
Find a short hand to describe a new category. They used ‘micro-workshops’ as a way of simply summing up their core differentiators.
Find a channel that works for your audience. Community was far more successful for Skiller Whale than outbound or paid marketing because it played better with their highly sceptical, hard-to-reach audience.
Start simple but have a plan for scaling. They started on paper with a single coach but knew how they would ultimately scale the experience: a structured curriculum with coaches able to be themselves.
Be open to adjacent opportunities where there is demand from your audience and you can have a distinctive take. They are finding new demand in universal topics, management and leadership skills as well as AI because they unique meet the needs of their community.
Build high levels of trust by being ‘pro conflict’. This will help you navigate challenging times like a tech recession.
“I would say number one is build stuff as late as possible. Product discovery through engineering is super expensive and slow,” says Hywel. “Postpone that as much as possible until you are sure you're going to be building the right thing.”
Hayley nods in agreement. “And if I had my time again, I would have doubled down on the community stuff earlier. Getting the CTOs, who love us, to tell their stories and enable that kind of connection to happen.”
If you would like to see a demo of Skiller Whale or get access to free technical assessments, book a slot in here.
And if you need support to find product-market fit, check out my coaching programme.