The Blue Anchor Sessions is a behind-the-scenes look at the real-world wins, failures, and turning points that define the journey of product leadership in financial services. In this 9-part series, veteran product strategist and fractional CPO Steve Jackson shares raw, insightful stories from the trenches — from rescuing billion-dollar misfires to standing up for what’s right, launching under pressure, and saying no when it counts. Whether you’re a product professional, executive, or founder, these episodes reveal the practical lessons, ethical dilemmas, and tactical breakthroughs that drive real impact in high-stakes environments.
Podcasts coming soon
EPISODE 1: “The $1 Billion Misunderstanding”
When over $1 billion quietly walked out the door of a flagship investment product, the company guessed at the cause. I didn’t. Focus groups revealed the truth: nobody — not clients, not advisors — understood the product. We rebuilt it from the ground up and reversed the flow, pulling in $1 billion in new assets in just six months.
EPISODE 2: “The Policy Said No — I Said Yes”
A decades-old insurance product failed a client when she needed it most — because the policy language hadn’t kept up with reality. I fought the case all the way to the board and won. This episode explores how doing the right thing sometimes means going against internal systems — and winning buy-in at the top.
EPISODE 3: “My First Product — And My First Failure”
My first solo product launch ended in a thud. An imported investment idea from Ireland bombed in Canadian focus groups, and I warned leadership. But I was told to launch anyway. It failed — and then I got promoted. This one’s about learning through failure, and why sometimes owning the flop earns you more than playing it safe.
EPISODE 4: “White Label in 90 Days — With Two Companies That Don’t Like Each Other”
Two firms. No trust. No traction. Just a high-stakes deadline to launch a white-labeled Home & Auto insurance product across Canada. I didn’t know the space — but I led the build, negotiated the deal, got regulatory approvals, and hit the target in 90 days. Here’s what it takes to launch when the clock is ticking and the room is cold.
EPISODE 5: “Doing the Right Thing — When It’s Easier Not To”
This one is personal. When I uncovered misconduct and serious ethical violations at a major FI, I couldn’t look away. I investigated, documented, and sent a letter to the board. It ended careers — and ended my time at the company. Here’s how to lead with integrity, even when the personal cost is high.
EPISODE 6: “Too Many Band-Aids”
Ever walked into a department where every problem has a patch — but nothing actually works? This episode dives into what I learned about root-cause analysis from a NASA advisor and how decades of bandaids can strangle output, culture, and innovation. Process isn’t sexy — until it breaks everything.
EPISODE 7: “Find All the People Who Know More Than You”
You’re only as good as the people you trust. In this episode, I talk about how to gain momentum by finding the experts in your organization — IT, Legal, Ops, Sales — and building with them, not around them. Product leaders need humility, access, and collaboration. Here’s how to build it.
EPISODE 8: “Saying No — When You Own the Bottom Line”
Everyone has ideas — especially the people who don’t own the P&L. This episode is about the hardest part of being a product owner: saying “no.” Not dismissively, but with logic, transparency, and empathy. I share how to bring others along when killing bad ideas — and finding the gold in the rubble.
EPISODE 9: “Analog Wins: When Tech Says No, Build It Anyway”
I needed $100K to build a mutual fund tax impact tool. I got denied. So I built it myself — in Excel — and got it rolled out to 1,200 branches. When tech roadblocks pile up, product people need to improvise. This one’s about grit, hacks, and delivering real value even when the system says “no.”