From Engineering to VP of Product: A Career Chat With James Hill
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We chat with James Hill, VP of Product at Buildkite, about his career journey through tech—from engineer to product leader—and what it takes to build fast, aligned, and impactful teams.
Please introduce yourself
Hi, I’m James. I live in Bowral and have worked in tech for 20+ years now! I’ve spent most of my life learning and working in Sydney and London. I’m a proud dad and a keen sailor when time permits! I love exploring new things and getting out on the water to have an adventure.
What do you do for work today?
I’m the VP of Product for the emerging products group at Buildkite. We focus on identifying, incubating and scaling the next generation of impactful and complementary opportunities to Buildkite’s best-in-class Pipelines product. What I love about emerging products is that we have to be hyper curious, and balance speed and risk to learn quickly!
What do you do outside work?
My daughter loves sailing competitively, so we spend a lot of time talking strategy, competing at regattas, and fixing equipment. It has Moneyball qualities: You look to invest in areas where you get outsized returns (education and second-hand equipment).
I’m incredibly fortunate to share that passion with her at the moment. You never know how long a connection like that will last, so we’re making the most of it and collaborating on a sailing website too, which is a fun way to introduce her to how the web works behind the scenes.
What did you study?
Computer Science at UNSW
Can you briefly describe your career journey to date?
After Uni I jumped straight into product engineering, not that it was called that at the time 😆…. I was working on data-warehousing and data visualisation problems for a B2B SaaS product.
I didn’t know that Product Management was a thing, but in hindsight I was doing a lot of PM shaped things and just really lent into understanding the customer problem and identifying where we could deliver value faster than our competitors.
My first decade was largely IC product engineering, I was always very close to the customer. The teams I worked on didn’t have PMs but we had great delivery and a fantastic iteration culture so we could validate ideas very quickly.
I was also always looking for opportunities to optimise team processes, I would explore whatever I could do to drive down delivery time to validate ideas.
In 2016, I started leading teams. At first, it was largely just filling gaps that existed in organisations at the time. I wasn’t intentionally looking for those roles, I just saw that things needed to get done and would end up doing them. My manager at the time was swamped and I just said “How about I do XYZ so you can focus on ABC?”.
After managing people through COVID I was mentally exhausted and wanted to get back to IC work, but I was looking for a force multiplier role. By then I’d worked with quite a few PMs and felt that I had a lot of the skillset to take it on if I found the right company.
I’d been a long time customer of Buildkite and knew the product well, meanwhile Buildkite were looking for someone in engineering leadership they could flip to a PM to help scale-out the product offering. It immediately felt right and I’ve been helping some of the biggest engineering teams on the planet ship code ever since.
Transitioning from hands-on technical roles to leadership positions, what key takeaways or unexpected challenges did you experience, and what advice would you give to someone navigating a similar shift?
I don’t think they’re unexpected, but here are two challenges which I’m sure most will encounter on a daily basis.
The first is alignment. It doesn’t take long for people to be misaligned. You need to look for ways to foster that alignment all the time.
The second is dopamine. Every time you shipped to prod your brain gave you some dopamine and it felt great. However, you can’t rely on shipping to prod for dopamine any more, if you are then you’re probably not spending enough time fostering alignment. Instead you’ll get your dopamine when someone else ships the thing.
You get warm and fuzzy when your teams are firing on all cylinders, aligned and delivering on company objectives.
Read JML’s Alignment > Autonomy if you haven’t already.
You went from Technical Lead to Head of Engineering at The Conversation. That must have involved a significant shift in focus from technical problem-solving to strategic thinking. Any resources or mentors that helped you along the way?
There was definitely a shift in the day to day work, but problem solving is still core to any job. So you take that problem solving ability and apply it to strategic thinking. Andy Jassy has a great quote “there's no compression algorithm for experience“ that said reading the experiences of others is the next best thing. Speed running those lived experiences (through reading or audiobooks) helps you pattern match along the way.
Most books typically only have a couple core concepts, so you can probably pick up a lot from ChatGPT or summary services like Blinkist. That said here’s a 3 great books if you haven’t read them already:
- Good Strategy Bad Strategy: The Difference and Why It Matters by Richard P. Rumelt
- Unreasonable Hospitality by Will Guidara
- The Manager’s Path by Camille Fournier
What inspired you to take on a product management role at Buildkite?
I (professionally) grew up on the gospel of speed as a competitive advantage. Every insight you gain today has a compound effect on tomorrow's outcome.
As an EM, I’d look for ways that my teams could ship faster with minimal risk so that we could learn quicker. Not only would the compounding knowledge help drive the product but the engineers would be happier with the momentum they were building.
As a PM at Buildkite, I felt that I could apply the same thinking but instead of just one team, I could work with some of the very best companies in the world to make their delivery processes faster, and it hasn’t disappointed!
How does working in media/publishing compare to software development? What were some unique aspects of the work culture, skills, and challenges you experienced at The Conversation vs. Buildkite?
Now that I think about it there’s a lot of overlap in the culture and challenges faced by both organizations.
The Conversation prides itself on fact and evidence based journalism delivered in the same news cycle as the incumbents. Ultimately that means the content has to be right and it has to be delivered quickly, which is not too dissimilar to Buildkite.
That said, The Conversation felt like it has more cache invalidation challenges 🤣.
From your experience so far, what are the key elements of a successful product team?
I’ve interviewed countless extremely high performing teams from the most iconic product companies and if I had to pick one thing it would be the cycle time. I.e. time from ideation to production.
The shorter the cycle time, the more rolls of the dice you get. This is why GenAI is so crazy good, coupled with great testing and delivery, it can collapse your cycle time down to minutes.
Do you miss being more hands on? Do you still code?
I still code things here and there, primarily to test features and taste the product.
But, holy moly, AI is crazy good these days. I vibecoded an app into existence in a couple hours and had it validated by 100+ strangers within seconds. Amazing.
Coding was always a means to an end for me, to create a solution to solve a problem. If it’s possible to do via generative AI then I feel like that’s scratching the itch.
Have you ever taken an extended break from work, and what effects did it have on your career and personal growth?
When our daughter was born, my partner Alexia had a photographic series to complete. So I took about 18 months off and helped her produce her works.
Once we decided I’d go back to work it took at least 3 months to get a suitable role. At the time I thought it’d be way easier to pick up a role than it was.
Sure, it undoubtedly slowed my career, but likely accelerated my daughter’s development, even if I had a do-over I would do the same again.
Was there ever a 'road not taken' in your career that you wonder about?
I've jumped on most opportunities that came my way, so I don’t have too many “road not taken” moments.
What's the best piece of advice you've ever received and often pass on?
I don’t have a single best piece of advice, but I often remind people of compounding knowledge.
Like compound interest for money, knowledge also compounds over time. It’s why learning a third language[1] is often significantly easier than learning the second. You’re leveraging everything you’ve learned going from 1 to 2.
I often think about this when my daughter watches The Simpsons, I’ll laugh at 90%+ of the jokes and maybe she’ll laugh at 10%. She doesn’t get all the cultural references yet. As her knowledge compounds over time not only are things easier, but they’re funnier, richer, deeper, everything becomes more enjoyable.
[1] depending on the language.
Where do you see yourself in the future? Any particular roles or challenges you’d like to undertake?
Over the past 2 years I've spent more and more time learning the go-to-market sides of enterprise sales, spending significantly more time in both the marketing and sales organisations. While I’m not chasing a role in those disciplines I’m loving the learning about the challenges they present. What’s that saying: First-time founders are obsessed with product, second-time founders are obsessed with distribution.
What legacy or mark would you like to leave in the tech industry, and why?
I think like most humans I want to leave something better than I found it. On a local level I strive to help my team, company and community think critically about the challenges we face and the solutions we’re exploring.
Generative AI has already unleashed a tidal wave of new opportunity. As the models rush to store more context and reason about more complex scenarios, I often wonder how we’ll manage these systems which are responsible for extremely critical processes.
Any podcast you are currently listening to, or a book you are reading?
- I’m a fanatical long time listener of Acquired, there’s something there for everyone (tech, sport, luxury, history)
- Lenny’s Podcast
- Lex Friedman’s Podcast
What is your favourite tool or resource, and why?
Loom + AI. It’s a massive alignment multiplier, doesn’t matter whether it’s a customer or someone on the team, a quick loom + the AI notes means you can validate an idea that much quicker.
Lovable. OMG, Prototyping an MVP in hours with Lovable is truly amazing.
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