The Unexpected Journey from Webmaster to CTO with Learnerbly’s CTO and Angel Investor, Katherine Spice - E12

All of Katherine’s roles have exhibited social impact, and beyond her CTO position at Learnerbly she’s supporting female-founders as an angel investor.

It’s a combination that gives her purpose-driven career a fascinating angle, and it’s a delight to delve further into it as she joins us for episode 12 of Great Software People.

This episode covers:

• Katherine’s jump from civil engineering to software

• The career development from small team work to Head of Development with a team of 17

• A journey with Learnerbly leading to the Angel Investor path

• How we need to balance the shocking lack of funding for female-founded businesses

• Growth outside of the comfort zone, particularly in management roles

Episode highlights

“I gradually built up a rep for being the person you ask about mail merges because I know how to use computers, and they ask me ‘Any chance you know HTML?’” - 2:40 - Katherine Spice

“Female-founded firms get less than 3% of venture-raised money - that got me thinking about my impact in the world.” - 18:15 - Katherine Spice

“The way I’ve been thinking about it most recently is understanding, talking about, and communicating why it’s a problem in the first place. If you don’t do that, then you don’t have a reason to solve it.” - 24:40 - Katherine Spice

“You have to be brave - if you’re not operating a little outside your comfort zone, then you’re not really growing.” - 35:45 - Katherine Spice

LISTEN HERE:

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[00:00:13]

Rich: Welcome to another episode of Great Software People! Today, I’m joined by Katherine Spice, CTO at Learnerbly and an angel investor. We’ll explore her unique career journey, lessons from leadership, and her work supporting female founders. Welcome, Katherine!

Katherine: Thanks, Rich! I’m thrilled to be here.

[00:00:39]

Rich: So let’s dive in—did you always dream of becoming a CTO?

Katherine: Not at all. Growing up, my peers were planning careers as lawyers or doctors. I decided I wanted to be a civil engineer, a pretty ambitious goal for a 14-year-old! I tailored my education around it—maths, physics, and computer science at A-levels—and enrolled in university. Unfortunately, I dropped out after one term. Fluid mechanics was tough, but there were also personal challenges. I was devastated; it felt like my dream was over. I started temping to pay bills and landed a receptionist role at a charity.

[00:02:20]

Katherine: This was 1999, and the charity had a flashy website but no one to maintain it. I became the go-to person for IT questions and was handed an O’Reilly book to learn HTML. That Christmas, they asked me about Perl, and I said, “I don’t know it, but I’ll learn.” By the new year, I was making small changes to their site, eventually becoming their webmaster. That was the start of my tech career.

[00:03:43]

Rich: Perl! A language we don’t often hear about these days. What was it like working with it?

Katherine: Perl was fascinating, albeit quirky. It allowed for incredible creativity, though some developers leaned into making their code intentionally hard to decipher.

[00:04:22]

Rich: You stayed in that role for about six years. What came next?

Katherine: I moved to Trinity Mirror Digital Recruitment to join a proper development team. Initially, I was a software engineer, but I later became a team lead and then head of development. We grew the team to 17 people across Bulgaria, Argentina, and the UK. It was a transformative time, learning to manage distributed teams and handle large-scale projects.

[00:06:49]

Rich: How did working in a team compare to your solo webmaster days?

Katherine: It was eye-opening. Pair programming, test-driven development, and shared coding standards revolutionised how I approached problem-solving. I learned so much from my colleagues.

[00:08:33]

Rich: Eventually, you became a CTO at CV Library. How did that happen?

Katherine: I hadn’t envisioned myself as a CTO, but the opportunity felt right. CV Library was in the same domain I was familiar with—online recruitment—and used Perl, a language I knew well. When I joined, the tech team was just five people, managing a codebase full of quirks from its co-founder, who was also its main developer for 13 years. We rapidly grew the team to 55 people, introduced best practices, and scaled to over 4.3 million monthly users by 2019.

[00:13:40]

Rich: That’s incredible growth! What did you do after CV Library?

Katherine: I took a 10-month career break. It was my first real pause since leaving university, and it gave me space to reset.

[00:14:32]

Katherine: I returned to tech as the Director of Technology at FutureLearn, an online learning platform. It was a chance to work closely with experienced product and design leaders, which helped me grow immensely. Their expertise raised the bar for me.

[00:16:48]

Rich: That brings us close to your current role at Learnerbly. How did that come about?

Katherine: Learnerbly approached me while I was at FutureLearn. They’re a VC-backed company, and I was keen to understand the venture capital landscape better. It was a natural step to return to an exec role while learning how VC-backed businesses operate.

Rich: You’ve also become an angel investor. How did that happen?

Katherine: Joining Learnerbly’s board meetings and preparing board packs piqued my interest in the venture world. Around the same time, I joined a women’s executive network, where I learned that female-founded companies receive less than 3% of VC funding. That statistic infuriated me. I decided to invest in female-led businesses, focusing on startups in areas I’m passionate about, like health tech. My first investment was in a company addressing endometriosis, a condition I suffer from. Supporting them felt personal and impactful.

[00:22:25]

Rich: That’s an incredible mission. What advice do you have for aspiring angel investors?

Katherine: Start small and join a syndicate to learn the ropes. You don’t need to invest huge sums initially—what matters is aligning your investments with your values.

[00:23:39]

Rich: Let’s circle back to tech and diversity. How can we support women in tech and ensure more female founders succeed?

Katherine: It starts with understanding why diversity matters. Without diverse perspectives, we create products that don’t work for everyone. For example, we need UX designs that accommodate elderly users or features in apps like Google Maps that prioritise well-lit walking routes. Supporting diverse founders is crucial. More representation leads to more breakthrough ideas and normalises women in leadership.

[00:30:36]

Rich: CTOs are uniquely positioned to mentor future leaders. What’s your advice for them?

Katherine: Flexibility is key—remote work and flexible hours make tech roles accessible to more people, especially caregivers. Also, standardise how you recognise and reward performance. Don’t let presenteeism or confidence bias dictate promotions. Finally, for aspiring leaders, take small, intentional steps to expand your skillset—whether it’s presenting in meetings or learning stakeholder management. Leadership is a skill you grow into, and you can always return to individual contributor roles if leadership isn’t for you.

[00:37:15]

Rich: Katherine, thank you so much for sharing your journey. Your insights into leadership, investing, and diversity are inspiring.

Katherine: Thank you, Rich. It’s been a pleasure to reflect on my career.

Rich: We’ll include links to some of the resources Katherine mentioned in the description. Thanks again!

Learnerbly