Technical debt rarely arrives in a support ticket labeled “technical debt.” Customers experience something simpler: the product is slow, unreliable, or the same problem keeps coming back. Kristin Isaac, Co-Founder and CEO of Strudel, joins Robby to look at software maintainability from the customer and product side of the organization. Kristin shares how her background in customer success, sales, and support shaped the way she thinks about reliability and why engineering teams often lack the business context surrounding the problems they’re being asked to solve.
That disconnect becomes especially important when engineers need to advocate for work customers may never directly see. Kristin and Robby explore why talking about technical debt alone often fails to persuade business leaders, and how engineers can instead connect maintenance work to customer experience, renewals, revenue, reliability, and risk. They also discuss the danger of letting the loudest customer determine priorities, the tension between urgent roadmap work and important foundational work, and why engineers shouldn’t quietly absorb the trade-offs that come with shipping faster. Kristin argues that better storytelling, shared metrics, and stronger relationships with customer-facing teams can help engineering make a much stronger case.
The conversation also turns to AI and the growing gap between generating software and understanding it. Robby and Kristin consider what happens when engineers increasingly ask AI for help instead of their teammates, and what that might mean for collaboration, onboarding, and learning. Rather than keeping that experimentation inside engineering, Kristin sees an opportunity for engineers to become educators across the organization… helping colleagues understand where AI works, where it falls short, and how teams can experiment with it together.
Episode Highlights
[00:00:49] Measuring Well-Maintained Software: Kristin shares practical measures around alert volume, detection time, recovery time, and confidence in frequent deployments.
[00:02:26] What Strudel Does: Kristin explains Strudel’s focus on bringing engineering, support, customer, and business context together around technical customer issues.
[00:07:35] What Customers Actually Experience: Robby and Kristin connect technical debt to the problems customers notice, including slow, unreliable, and broken software.
[00:12:39] Prioritizing With Business Context: They explore competing incentives across engineering, product, sales, support, and customer success, including the danger of relying on the “squeaky wheel.”
[00:21:14] Different Teams, Different Versions of the Problem: Kristin explains why no single department necessarily has the complete picture and why shared context matters.
[00:23:29] Who Owns Reliability?: Robby and Kristin consider where responsibility for reliability sits across engineering, product, and the broader organization.
[00:24:32] Making the Case for Technical Debt: Kristin explains why technical debt is easier to ignore when engineers can’t connect it to measurable customer or business impact.
[00:26:21] Advocating for Invisible Maintenance Work: The conversation turns to foundational improvements, the tension between urgent and important work, and partnering with customer-facing teams to build a stronger case.
[00:33:25] Engineers as Storytellers: Kristin argues that engineers can become more effective advocates by learning how to communicate technical concerns in terms the rest of the business understands.
[00:34:54] AI and the Understanding Gap: Robby and Kristin discuss whether software is becoming faster to generate than it is to understand and maintain.
[00:37:20] What Happens When Engineers Stop Asking Each Other?: They explore AI’s potential effects on collaboration, learning, onboarding, and the social dynamics of engineering teams.
[00:46:20] Engineers as AI Educators: Kristin makes the case for engineers sharing their AI experiments with product, sales, marketing, and customer-facing teams instead of keeping that knowledge inside engineering.
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