Todd Olson, CEO and Co-founder, Pendo

From buying startups to speed up roadmap execution to preserving founder autonomy post-close, Todd breaks down the real levers behind successful acquisitions. This episode dives into how Pendo thinks about M&A without a corporate development team, why it rarely buys for revenue, and how Todd’s team avoids common post-close integration mistakes by keeping culture, product, and people at the center.

Things you will learn:

Why speed and product alignment—not revenue—drive most of Pendo’s acquisitions
The cost of delaying integration and how Todd learned to fix it
How to retain founder energy post-acquisition without over-relying on cash

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Episode Chapters

[00:04:30] – Taking a buyer-led approach from day one
[00:05:30] – When is the right time to do M&A as a startup?
[00:07:00] – The real reason behind Pendo’s first acquisition (spoiler: mobile gap)
[00:10:30] – How the team visit to Tel Aviv sealed the deal
[00:15:00] – Why preserving a legacy tech stack was a painful mistake
[00:19:30] – Walking away from a $1M customer (and why it was worth it)
[00:23:00] – Choosing smaller, simpler teams over “obvious” targets
[00:27:30] – Why AI startups are attractive—but only with the right integration mindset
[00:33:00] – Deal structures that actually retain entrepreneurs
[00:50:00] – Post-close surprises, real value creation, and the “pink wash” trap

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