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
1 year ago, I left my 22 year IBM career to join a startup. Everything changed and nothing changed. I've learnt a lot about myself.
Observe * Reflect * Make For 2-3 hours investment, there is a lot to be gained from the badge. Even for experienced Agile practitioners. The common language and practical application of agile practices would benefit all. https://www.ibm.com/design/thinking/ My top 5 takeaways: 1. WHY, iteratively Asking why three or more times evolves the answer with … Continue reading Design Thinking Practitioner Badge
Olly Brand 