Triangle Tweener Talks

What drives someone to leave a cushy corporate role, start (and sometimes stumble at) multiple tech ventures, and finally build one of the Triangle’s most iconic unicorns?

On this episode of Triangle Tweener Talks, we sit down with Todd Olson, Founder and CEO of Pendo—a leading product analytics platform now powering hundreds of the world’s top software experiences.

Todd pulls back the curtain on his early days coding in a bank at age 14, his near-miss exits that fueled an enduring chip on his shoulder, and how he and his co-founders built Pendo into a 900-person juggernaut. Along the way, Todd dives into the heart of “Founder Mode,” evolving your culture (when everyone’s giving you a million reasons not to), and why relentless customer focus might just be the ultimate growth hack.


Tune in to hear:
  • Todd’s Unlikely Start in Tech: How a 14-year-old data-entry temp turned into a Unix-wielding problem solver at a major bank.
  • Roller-Coaster Beginnings: The heartbreak of Todd’s first ventures, what went wrong—and why he kept going.
  • Building Pendo from Scratch: The aha moment that sparked a mission to help software companies measure adoption and drive true customer value.
  • Scaling to 900+ People: How Todd keeps the magic of a small startup culture alive while serving a global enterprise customer base.
  • Customer-Obsessed Leadership: Why Todd personally calls customers with less-than-stellar feedback and how it’s created a near-cult following among Pendo users.
  • Founder Mode & Culture Shifts: Hear Todd’s take on revamping core values mid-flight, returning to in-person collaboration, and leaning in on product.
  • Raising Capital vs. Growing the Pie: Practical wisdom on why picking the right investors (and not sweating ownership percentages) is a path to real success.

Where to Find Todd Olson:
  • Linkedin: https://www.linkedin.com/in/toddaolson/
  • Pendo: https://www.pendo.io/
  • X: https://x.com/tolson
Where to Find Scot Wingo:
  • Linkedin: https://www.linkedin.com/in/thescotwingo/
  • Tweener Times: https://www.tweenertimes.com/
  • X: https://x.com/scotwingo
In this episode:
[00:05:03] Ringing the Gong & Celebrating Deals
Todd shares a big customer win, the excitement around “gong moments,” and why team collaboration fuels success.
[00:07:48] Bank Life at 14: Todd’s Early Tech Origins
Hear how Todd’s mom bragged to the right person at the right time, launching him into a data-entry job turned accidental programming career.
[00:12:55] First Startup Heartbreak: Cerebellum
Todd recounts his early venture, the near-miss acquisition, and the board drama that ultimately shaped his “chip on the shoulder.”
[00:18:06] TogetherSoft & 250 Engineers in Russia
Managing a global dev team while hopping planes monthly—Todd explains the pressure cooker that taught him real product management.
[00:25:45] M&A Lessons at Borland & Working with Frank Slootman
Todd gets a front-row seat to high-powered leadership under a now-legendary CEO and learns what high growth really looks like.
[00:31:20] Sixth Sense & the 2008 Crunch
Diving into Todd’s second startup, nearly running out of money, and how radical transparency pulled the team together at the eleventh hour.
[00:39:10] Rally Software’s IPO & the Enduring Chip
Writing parts of the S-1, standing on the NYSE balcony—yet realizing it wasn’t truly his company, pushing Todd to keep going.
[00:44:45] Founding Pendo & Picking Co-Founders
Why Todd returned to Raleigh for his next venture, how the early Pendo crew came together, and the story behind the name.
[00:52:15] Choosing the Right Investors
Todd recalls how a single “yes” check started the seed round—but why aligning with good humans is even more critical than a big valuation.
[01:05:05] The Power of Customer Obsession
From personal phone calls to instant problem solving, Todd reveals why old-school “MBNA-style” service still wins hearts in SaaS.
[01:08:10] Entering ‘Founder Mode’ & Betting on AI
Todd opens up about reinvigorating Pendo’s culture post-COVID, re-committing to product, and the looming wave of AI-driven software.


In the news:
  • Pendo CEO talks ‘founder mode,’ going public and his Raleigh software firm’s first profit: https://www.newsobserver.com/news/business/article293725529.html
  • How Todd Olson of Pendo Got His First Customers: https://www.inc.com/alexa-von-tobel/todd-olson-pendo-customer-journey.html
  • Olson’s ambitious journey: https://www.bizjournals.com/triangle/news/2022/04/08/todd-olson-leads-pendo-ambitious-journey.html

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.

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Triangle Tweener Talks is sponsored by:
  • Atomic Object: https://atomicobject.com/

What is Triangle Tweener Talks?

A podcast for builders by builders in the Triangle. We explore the startup journey and stories with local Triangle founders, from the idea to the exit and everything in between. Hosted by serial entrepreneur and founder of the Triangle Tweener Fund Scot Wingo, and produced by Earfluence.