Remember the SaaS playbook that built today’s tech giants? Well, it’s officially dead. The AI revolution is rewriting the rules, leaving companies without a roadmap for what comes next.
However, Pendo CEO and co-founder, Todd Olson, is mapping out a new playbook using insights from customers, other founders, and his own team, all of whom are either beginning and in the midst of their AI transformations.
In this episode, host Trisha Price and Todd unpack how leaders can thrive when everything they know gets turned upside down. This isn’t your typical founder interview - it’s an open, honest conversation about leading when there’s no playbook to follow.
Here’s what you’ll discover:
“There’s no AI playbook. …Even the AI-native founders are just experimenting like the rest of us.” - Todd Olson
The power behind an entrepreneurial spirit. Todd shares his thoughts on what the role of a CEO needs to be during a transformation. And why his majors and minors, along with his entrepreneurial mindset, are exactly what the company needs from him right now. Todd’s lesson: Have the conviction to show that your idea can work.
How Pendo went all-in on AI. Todd reveals the strategy behind acquiring AI-native companies over established players, and how injecting new DNA changed everything from engineering practices to innovation. He also shares how his role in experimenting with AI tools inspired the rest of the company.
How to balance AI innovation with enterprise expectations. Todd explains the balancing act he and his team face with enterprise customers who still expect familiar and compliant solutions, while simultaneously introducing AI agents and workflows to guide the company through an AI transformation.
Whether you’re a founder trying to reinvent your business model or a product leader tasked with building your company’s AI strategy, this episode reveals what it actually takes to lead with entrepreneurial conviction when the only certainty is change.
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Presented by Pendo. Dive deeper at pendo.io or connect with Trisha Price on LinkedIn.
