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Todd Olson on employee retention

From 2731: The Evolving Role of AI in Business: Perspectives from Pendo's Leader · · Neil C. Hughes

“I'm not amongst the leaders that think that the ultimate goal is zero attrition at a company. And that may be a controversial thing to say, attrition is super healthy. You know, we look at or it's like no one's left really, yeah, company's really different than it was and some people like that change but some people don't.”

Todd Olson
Cofounder, Pendo
Controversial employee retentionorganizational changeleadership

On , Todd Olson, Cofounder at Pendo, spoke about employee retention during 2731: The Evolving Role of AI in Business: Perspectives from Pendo's Leader on Neil C. Hughes.

2731: The Evolving Role of AI in Business: Perspectives from Pendo's Leader
Watch on YouTube at 25:58
2731: The Evolving Role of AI in Business: Perspectives from Pendo's Leader
Neil C. Hughes
Watch on YouTube at 25:58
In today's episode of Tech Talks Daily, I had the privilege of hosting Todd Olson, CEO of Pendo, for a fascinating discussion that traverses the realms of product analytics, AI adoption, and digital customer experiences. Todd's insights offer a deep dive into the evolving landscape where traditional companies increasingly identify as tech entities, requiring significant shifts in mindset and strategy. Todd elaborates on how enterprises are undergoing a paradigm shift, moving from project-based work to embracing the agility and continuous iteration technology enables. This transition necessitates shorter cycle times in software development, allowing rapid user feedback and influencing subsequent releases. Todd underscores the importance of transitioning from a 'project' to a 'product' mentality, highlighting that software demands ongoing care and nurturing. A critical aspect of our conversation revolves around the differing attitudes towards AI adoption in Europe and the United States. Todd points out that Europe tends to be more regulatory and cautious, particularly concerning privacy issues and AI accuracy, while the US often prioritizes innovation. He advises a measured approach to AI implementation, advocating for thorough testing and a gradual build-up of comfort based on proven results. Integrating new technological roles into existing structures is another challenge that Todd addresses. He emphasizes the importance of blending internal and external hires for effective knowledge transfer, highlighting that internal employees understand the company and product while external hires bring specialized role knowledge. Leadership communication around AI also emerges as a critical theme. Todd speaks to leaders' need to clearly articulate the 'why' behind AI to ensure middle management buy-in, a group often focused on executing current plans. Todd also touches on the crucial aspect of upskilling existing teams. He discusses the need to assess teams' willingness to embrace failure and change, acknowledging that some level of attrition can be healthy for company transformation. Lastly, we delve into the realm of digital customer experiences. Todd shares his belief in the power of empathy, achieved through self-use and observation, to ensure exceptional digital interactions. He provides insights into how observing user sessions can reveal critical pain points and drop-offs, ultimately enhancing the customer experience.
Todd Olson

About Todd Olson

Cofounder · Pendo

Todd Olson, co-founder and CEO of Pendo, delivered the opening keynote at the company's Pendomonium conference on March 31, 2026, where he discussed the impact of AI agents on software development and product management. Olson stated that "programming is unrecognizable now that AI agents actually work" and noted that "coding constraints are disappearing," making product managers more critical in determining what to build. He introduced several Pendo innovations, including Leo (a platform navigation agent), enhanced agent analytics, MCP integration for connecting Pendo data to external AI tools, and Pendo Predict for churn prediction. Olson also remarked that "Wall Street doesn't quite know what to do with the fact that now anything can be built," referencing a $300 billion drop in software company valuations, but added that he is "not a buyer of everything is going to go away" because software companies solve "hard important problems." In a March 13, 2026 interview on the Tech Talks Daily podcast, Olson discussed how AI is redefining product-led organizations. He argued that during the zero-interest-rate period, "so much funding created lots of software companies that likely shouldn't exist," predicting a "reckoning" for some businesses while asserting that "great businesses that solve really hard problems will be fine." Olson also emphasized that "originality is going to be the most interesting asset in an AI-saturated world," as people will increasingly crave "original, crafted work that feels like someone built it with love, care and an opinion." He noted that product teams can now move faster, with refactoring occurring "in weeks instead of months," but stressed that this does not replace "judgment, taste, or understanding your users."

Profile compiled from Todd Olson's verified public interviews and appearances. See all quotes & transcripts →

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