#371 The Real Reason Your Product Team Needs a Feedback Loop with Todd Olson, CEO at Pendo

Software teams are shipping faster than ever, but speed hasn't solved the oldest problem in the industry: most software still isn't very good. AI coding tools have lowered the barrier to building something, yet they haven't lowered the barrier to building something worth using. As more people who aren't trained software creators start shipping products, a new question is forming across product, design, and engineering teams: if AI can build almost anything, how do you make sure it builds the right thing, and builds it well?

Todd Olson is co-founder and CEO of Pendo, the product experience platform he started in 2013. Before that, he held product and engineering roles at Rally Software, Red Hat, Cisco, and Google. He's the author of The Product-Led Organization and has led Pendo through raising over $356M in venture funding while growing to 2,300+ customers.

In the episode, Richie and Todd explore why bad software still gets built, how much context AI coding agents need before they can be trusted, using behavioral data and "rage prompts" to catch what's actually frustrating users, the shift toward headless and agentic software design, how product, design, and engineering roles are splitting apart, managing one-way-door risk during AI transformation, and much more.

Links Mentioned in the Show:

• Jeff Bezos’s one-way door / two-way door decision framework: 2015 Amazon shareholder letter
• HubSpot’s 2024 terms-of-service backlash
• Ramp
• Stripe
• Fin (Intercom’s AI agent), recently announced to be acquired by Salesforce
• Anthropic / Claude Code
• Connect with Todd
• AI-Native Course: Intro to AI for Work
• Related Episode: The Data Team’s Agentic Future with Ketan Karkhanis, CEO at ThoughtSpot

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