Ep. #38, Wayfinder with Heidi Waterhouse

In episode 9 of Platform Builders, Christine and Isaac sit down with Manny Medina, founder and CEO of Paid, to unpack the tectonic shift happening in software. From the rise of AI agents that autonomously perform tasks, to the death of seat-based pricing, and why ARR and SaaS metrics just don’t make sense anymore—Manny makes a compelling case that we’re entering a new era. If you're building, investing in, or working with AI-native companies, this is essential listening.

In episode 38 of Generationship, Rachel Chalmers sits down with Heidi Waterhouse, co-author of "Progressive Delivery." They unpack what Progressive Delivery means as an extension of continuous delivery, focusing on the crucial role of user experience in software development. Discover fresh insights on user autonomy, the pitfalls of uninvited AI, and how to bring empathy back into the software lifecycle.

In episode 8 of Platform Builders, Christine Spang and Isaac Nassimi are joined by John Melas-Kyriazi, founder and CEO of Standard Metrics. John shares his journey from VC to founder and how he’s rethinking investor–portfolio company collaboration. From spreadsheets to vertical SaaS, and now to AI-powered platforms, John dives deep into building software that’s truly purpose-built for venture capital.

In episode 7 of Platform Builders, Christine Spang and Isaac Nassimi dive deep into the world of CRMs and SaaS strategy with Steve Oriola, CEO of Unbounce. Steve shares his insights on the historical shifts in CRM technology, the critical role of data in modern marketing solutions, and his approach to leading companies through significant transitions and acquisitions. Learn how focused product development and a strong company culture can drive success.

In episode 82 of o11ycast, Ken and Jess chat with Morgante Pell, the visionary behind Grit, an AI-powered agent designed to automate developer toil and technical debt. The discussion covers the evolution of AI in coding, the challenges of building and deploying AI agents, the future of combining code awareness with production awareness, and Grit’s acquisition by Honeycomb.

In episode 81 of o11ycast, Charity Majors and Martin Thwaites dive into a lively discussion with Hazel Weakly and Matt Klein on the evolving landscape of observability. The guests explore the concept of observability versioning, the challenges of cost and ROI, and the future of observability tools, including the potential convergence with AI and business intelligence.

In episode 80 of o11ycast, Ken Rimple and Jessica Kerr chat with Kent Beck about the emerging world of AI-assisted coding. Beck shares his experiences with "augmented coding," discussing the benefits, challenges, and the evolving relationship between developers and AI agents. They explore how these tools are changing software development practices and what it means for the future of coding.

In episode 79 of o11ycast, Hamel Husain joins the o11ycast crew to discuss the challenges of monitoring AI systems, why off-the-shelf metrics can be misleading, and how error analysis is the key to making AI models more reliable. Plus, insights into how Honeycomb built its Query Assistant and what teams should prioritize when working with AI observability.

Episode 78 of o11ycast examines the world of OpenTelemetry Transformation Language (OTTL) with Tyler Helmuth and Evan Bradley, the maintainers behind this innovative framework. Discover how OTTL enables powerful telemetry data transformations, its practical applications, and what lies ahead for OpenTelemetry's transformative ecosystem.

In episode 77 of o11ycast, Charity, Martin, Ken, and Jess welcome Jeremy Morrell to talk about OpenTelemetry, the future of observability, and how small teams can get started. Jeremy shares stories of debugging breakthroughs, adopting standards, and building tools that help engineers focus on what matters.