Building on my gambler or scientist post… One of the most rewarding parts of leadership is carrying the accountability for your team’s work. Accountability isn’t good or bad, it’s simply the responsibility for outcomes; the wins and the losses. On balance, it’s hugely rewarding. But it also means you’re the one delivering bad news to the … Continue reading Not all experiments succeed
The Bowling Alley One of my strongest beliefs as a leader is that I want to create an environment where everyone has the chance to excel. Over the years, the best way I’ve found to explain this is through the bowling alley analogy. This is one of two analogies I've come to depend upon, the … Continue reading The Bowling Alley
It had been a while since I last went to a tech conference, and within minutes of the opening keynote (which included washing potatoes in a washing machine), I regretted the time away. I’d forgotten how good these events can be. Conferences create space. Space to think, to hear new perspectives & ideas, to learn, … Continue reading Agile on the Beach 2025
In early 2024, I likened our platform and Tech Strategy at The Collecting Group to a Singer 911. It made sense at the time: take a solid base (the Porsche 964), iterate on it with care and craft, and transform it into something beautiful, powerful, exclusive, and meticulously engineered. Something rare. A halo product. A … Continue reading Evolving Our Tech Strategy: Singer to Raptor
I’ll admit to overusing two analogies: bowling alleys (a post for another day) and icebergs. Tech initiatives, especially the ones I refer to as Momentum Builders, Debt Paydowns, and Risk Reducers (see: Gambler or Scientist), often resemble icebergs. Only the part above the waterline is visible to the business. This makes selling and celebrating them … Continue reading Shipping Icebergs: The Quiet Triumph of User Merging
Win or lose? I prefer experiment and learn. 3 things occurred: 1. CTO Coachings on “Bets” – Learning to break work into plays (business cases) that I can sell to the business. Every initiative falls into one (or more) of four categories: Momentum Builders (iterative improvements, process gains) Debt Paydown (tech debt, foundational work) Revenue … Continue reading Gambler or Scientist
A team member asked if our strategy and approach was lifted from the Phoenix Project. They wondered if that’s why I split our engineers into two squads: one focused on features, owning our frontend repos, and the other on platform, owning the backend and cleaning up the “messy middle”. We have a learning budget at … Continue reading The Phoenix Project?
I’ve always been a strong advocate for remote work, especially in the tech world. It offers flexibility, allows people to work from where they’re most productive, and makes a lot of sense for our industry. With Amazon forcing everyone back to the office, I can’t help but disagree with a one-size-fits-all approach. That said, our … Continue reading Remote, first
Last night, I went to a talk by Oliver Burkeman, for the launch of his new book, Meditations for Mortals. It was a brilliant evening, and his ideas hit home. He made a point that stuck with me: we all have problems, and they never fully go away. Some people’s problems are a lot worse … Continue reading Problems & Finitude
Two years in feels like a good moment to reflect on the journey so far and the road ahead. Just after my 1-year on post, things escalated as I became Head of Engineering and joined the Senior Leadership Team (SLT) at The Collecting Group (TCG), Collecting Cars and Watch Collecting. I’ve survived my first board … Continue reading Changing Gears: Navigating the Road to Executive Tech Leadership
Olly Brand 