EP 9. Getting Started with Product Thinking with Jenny Rudd
In this episode I’m joined by Jenny Rudd — founder of Dispute Buddy, and a natural product thinker with a non-traditional path into tech.From turning her home into a top-tier Airbnb through clever customer research, to scaling a regional magazine and now building a legal tech startup from personal experience — Jenny’s story is all about deep empathy and smart product instincts.We talk about staying in the problem space, running lean customer discovery, and building products that truly solve painful, emotional problems — even before writing a line of code.
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41:23
Ep 8: Bridging Product and Developer Experience: Lessons from Xero and Beyond with Hannah Eickmeier
Create one-click bug reports with Dummi.In this episode, I talk to Hannah—a seasoned product leader and platform product expert at Totara Learning, with prior experience at Xero and as a fractional CPO—about:Her transition from learning & development into product leadership.Lessons from bringing product thinking into technical teams at Xero.How to empower platform teams and define a clear strategy.Metrics that matter for platform teams, including internal satisfaction and time-to-release.Why developer experience directly impacts product quality—and how to improve it.Building strong product cultures in both startups and enterprises.Creating alignment through one-page strategies and async communication.How leadership differs between startups and larger orgs—and what remains constant.
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1:02:11
Ep 7: From MVP to Global Markets: Building, Localising and Scaling Products Internationally with Christina Baldarelli
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In this episode, I talk to Christina Baldarelli—Entrepreneur-in-Residence and Operating Partner at Ministry of Awesome, as well as a 1-1 Product Consultant and Fractional CPO—about:
Her unconventional journey into tech and product leadership.
Lessons learned from scaling Mobi during New Zealand’s COVID-19 lockdown.
How to navigate product challenges when expanding into international markets.
Balancing growth, retention, and prioritization during hypergrowth.
The importance of iterative product development and validating early.
Common pitfalls for startups and how to avoid overspending on MVPs.
Building adaptable product teams and fostering cross-functional collaboration.
Key strategies for aligning product, business, and market opportunities.
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58:32
Ep 6: Product Strategies that Win: Insights from Drift's Zero to $1.2B Journey with Matt Bilotti
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In this episode I talk to Matt about:
Matt's lessons from scaling Drift to a $1.2B acquisition.
Insights on rapid iteration, product-market fit, and moving from SMBs to enterprise.
Strategies for aligning product and growth with user personas.
Advice on joining startups, spotting red flags, and staying flexible.
Takeaways from AngelList on high-autonomy teams and compliance.
Tips on avoiding perfectionism, validating early, and learning from failure.
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51:58
EP 5: Engineering Lessons from Slack and Vend with Rowan Oulton
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In this episode I talk to Rowan about:
His journey as one of the first engineering hires at Vend, helping it scale from 5 to 200 employees in just four years.
Key lessons from his seven years at Slack as a Staff Engineer, including tackling tech debt and building a product users love.
What it takes to secure a tech role in the US.
How investing in developer experience can motivate and transform your engineering team—and practical ways to apply this to your company.
The valuable lessons Rowan is carrying forward as he builds his new startup, Prosaic.
Product Tales takes you behind the scenes of software development, where we sit down with product experts to discuss the challenges and successes that shape the products we all rely on. From creating exciting new features to unravelling complex issues, Product Tales uncovers the stories behind every build.
New Zealand