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Nov 3, 2022 · 29m · top-founders

The $100m Pendo Story: The Crazy Not-Scaleable Stuff We Did At Every Stage

Todd Olson · 25m spoken Nathan Latka · 1m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Pendo CEO Todd Olson shares core lessons from scaling Pendo to over $100 million in ARR, detailing how deliberate, unscalable actions in sales, customer support, talent management, and system architecture drive rapid enterprise growth.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 6.2% of the talking time here. How this is scored →

Nathan as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Nathan pushing back 0.0
05100:0010:0020:000:59–6:09 · Nathan as informed peer 0/10 Todd Olson on Unscalable Sales and Early Growth Todd Olson presents a keynote on early unscalable tactics, recounting how he walked the Dreamforce floor with a free pass and flew uninvited to Salt Lake City to close a 60k ARR deal. Host Nathan Latka is not present on stage.6:14–12:59 · Nathan as informed peer 0/10 Customer Obsession, Support Queues, and NPS Follow-Ups Olson discusses extreme customer obsession, explaining how early founders should answer support tickets and personally reach out to every low NPS score. The segment is a solo keynote address without host interaction.13:02–15:16 · Nathan as informed peer 0/10 Founderpath SaaS Valuation Tool Announcement Nathan Latka delivers a mid-roll advertisement for Founderpath valuation tools before the recording returns to Olson describing manual customer success spreadsheets. No direct dialogue between host and guest occurs.15:17–24:25 · Nathan as informed peer 0/10 Scaling People: Hiring Discipline, Global Visits, and Talent Reviews Olson outlines his people management philosophy, including interviewing every hire up to 500 employees, running 90-day check-ins, visiting global offices, and conducting detailed talent reviews. The presentation format continues without host commentary.24:27–28:55 · Nathan as informed peer 0/10 Overcoming Corporate Filters and Scaling by Breaking Systems Olson concludes his presentation by explaining how bypassing management layers and letting systems break under enterprise loads like Zendesk forced company scale. Latka remains absent from the stage.0:59–6:09 · Guest teaching 0/10 Todd Olson on Unscalable Sales and Early Growth Todd Olson presents a keynote on early unscalable tactics, recounting how he walked the Dreamforce floor with a free pass and flew uninvited to Salt Lake City to close a 60k ARR deal. Host Nathan Latka is not present on stage.6:14–12:59 · Guest teaching 0/10 Customer Obsession, Support Queues, and NPS Follow-Ups Olson discusses extreme customer obsession, explaining how early founders should answer support tickets and personally reach out to every low NPS score. The segment is a solo keynote address without host interaction.13:02–15:16 · Guest teaching 0/10 Founderpath SaaS Valuation Tool Announcement Nathan Latka delivers a mid-roll advertisement for Founderpath valuation tools before the recording returns to Olson describing manual customer success spreadsheets. No direct dialogue between host and guest occurs.15:17–24:25 · Guest teaching 0/10 Scaling People: Hiring Discipline, Global Visits, and Talent Reviews Olson outlines his people management philosophy, including interviewing every hire up to 500 employees, running 90-day check-ins, visiting global offices, and conducting detailed talent reviews. The presentation format continues without host commentary.24:27–28:55 · Guest teaching 0/10 Overcoming Corporate Filters and Scaling by Breaking Systems Olson concludes his presentation by explaining how bypassing management layers and letting systems break under enterprise loads like Zendesk forced company scale. Latka remains absent from the stage.0:59–6:09 · Guest disagreement 0/10 Todd Olson on Unscalable Sales and Early Growth Todd Olson presents a keynote on early unscalable tactics, recounting how he walked the Dreamforce floor with a free pass and flew uninvited to Salt Lake City to close a 60k ARR deal. Host Nathan Latka is not present on stage.6:14–12:59 · Guest disagreement 0/10 Customer Obsession, Support Queues, and NPS Follow-Ups Olson discusses extreme customer obsession, explaining how early founders should answer support tickets and personally reach out to every low NPS score. The segment is a solo keynote address without host interaction.13:02–15:16 · Guest disagreement 0/10 Founderpath SaaS Valuation Tool Announcement Nathan Latka delivers a mid-roll advertisement for Founderpath valuation tools before the recording returns to Olson describing manual customer success spreadsheets. No direct dialogue between host and guest occurs.15:17–24:25 · Guest disagreement 0/10 Scaling People: Hiring Discipline, Global Visits, and Talent Reviews Olson outlines his people management philosophy, including interviewing every hire up to 500 employees, running 90-day check-ins, visiting global offices, and conducting detailed talent reviews. The presentation format continues without host commentary.24:27–28:55 · Guest disagreement 0/10 Overcoming Corporate Filters and Scaling by Breaking Systems Olson concludes his presentation by explaining how bypassing management layers and letting systems break under enterprise loads like Zendesk forced company scale. Latka remains absent from the stage.0:59–6:09 · Nathan pushing back 0/10 Todd Olson on Unscalable Sales and Early Growth Todd Olson presents a keynote on early unscalable tactics, recounting how he walked the Dreamforce floor with a free pass and flew uninvited to Salt Lake City to close a 60k ARR deal. Host Nathan Latka is not present on stage.6:14–12:59 · Nathan pushing back 0/10 Customer Obsession, Support Queues, and NPS Follow-Ups Olson discusses extreme customer obsession, explaining how early founders should answer support tickets and personally reach out to every low NPS score. The segment is a solo keynote address without host interaction.13:02–15:16 · Nathan pushing back 0/10 Founderpath SaaS Valuation Tool Announcement Nathan Latka delivers a mid-roll advertisement for Founderpath valuation tools before the recording returns to Olson describing manual customer success spreadsheets. No direct dialogue between host and guest occurs.15:17–24:25 · Nathan pushing back 0/10 Scaling People: Hiring Discipline, Global Visits, and Talent Reviews Olson outlines his people management philosophy, including interviewing every hire up to 500 employees, running 90-day check-ins, visiting global offices, and conducting detailed talent reviews. The presentation format continues without host commentary.24:27–28:55 · Nathan pushing back 0/10 Overcoming Corporate Filters and Scaling by Breaking Systems Olson concludes his presentation by explaining how bypassing management layers and letting systems break under enterprise loads like Zendesk forced company scale. Latka remains absent from the stage.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 31.9% · guest 68.1%0:00 · Nathan 31.9% · guest 68.1%3:00 · Nathan 0% · guest 100%3:00 · Nathan 0% · guest 100%6:00 · Nathan 0% · guest 100%6:00 · Nathan 0% · guest 100%9:00 · Nathan 0% · guest 100%9:00 · Nathan 0% · guest 100%12:00 · Nathan 28.6% · guest 71.4%12:00 · Nathan 28.6% · guest 71.4%15:00 · Nathan 0% · guest 100%15:00 · Nathan 0% · guest 100%18:00 · Nathan 0% · guest 100%18:00 · Nathan 0% · guest 100%21:00 · Nathan 0% · guest 100%21:00 · Nathan 0% · guest 100%24:00 · Nathan 0% · guest 100%24:00 · Nathan 0% · guest 100%27:00 · Nathan 0% · guest 100%27:00 · Nathan 0% · guest 100%
Sharpest disagreement ▶ 25:20 Debating scale with CTO

Olson recounts forcefully arguing with his CTO that customer acquisition must proceed regardless of whether technical infrastructure is fully prepared to scale.

 Hardest push from Nathan ▶ 13:02 Host commercial break framing

Latka delivers an assertive pitch for Founderpath, emphasizing how founders should leverage concrete comparables to prevent equity dilution.

 Biggest teaching moment ▶ 16:25 Critiquing generic interview questions

Olson educates the audience on why conventional interview inquiries are useless and demonstrates how to rigorously probe candidate track records.

 Nathan holds their own ▶ 0:10 Latka setting conference standards

Latka asserts his authority during the episode introduction by stating he required every speaker to show actual revenue graphs and primary business artifacts.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Todd Olson on Unscalable Sales and Early Growth 0000 Todd Olson presents a keynote on early unscalable tactics, recounting how he walked the Dreamforce floor with a free pass and flew uninvited to Salt Lake City to close a 60k ARR deal. Host Nathan Latka is not present on stage.
Customer Obsession, Support Queues, and NPS Follow-Ups 0000 Olson discusses extreme customer obsession, explaining how early founders should answer support tickets and personally reach out to every low NPS score. The segment is a solo keynote address without host interaction.
Founderpath SaaS Valuation Tool Announcement 0000 Nathan Latka delivers a mid-roll advertisement for Founderpath valuation tools before the recording returns to Olson describing manual customer success spreadsheets. No direct dialogue between host and guest occurs.
Scaling People: Hiring Discipline, Global Visits, and Talent Reviews 0000 Olson outlines his people management philosophy, including interviewing every hire up to 500 employees, running 90-day check-ins, visiting global offices, and conducting detailed talent reviews. The presentation format continues without host commentary.
Overcoming Corporate Filters and Scaling by Breaking Systems 0000 Olson concludes his presentation by explaining how bypassing management layers and letting systems break under enterprise loads like Zendesk forced company scale. Latka remains absent from the stage.

Statements from this episode (11)

Assertion Not checkable as stated
Olson: Pendo jumped from a $1.5k deal to $60k ARR
“It was a 60 K deal ARR when our largest deal previous was about 1500 dollars ARR.”
Todd Olson Nov 3, 2022 ▶ 4:48
Assertion Supported
Olson: Pendo reached $100M ARR while growing over 50%
“Announced that we crossed a hundred million dollars in ARR. Last year, we're growing north of 50%, so you can get a sense of where we are.”
Todd Olson Nov 3, 2022 ▶ 5:49
Prediction Not checkable as stated
Olson: Pendo will probably reach nearly $200M ARR by year-end
“We'll probably end the year just under two hundred million ARR, so and we've gone from basically zero to that in under eight years”
Todd Olson Nov 3, 2022 ▶ 5:57
Disclosure
Olson: I personally phoned every customer who emailed in early days
“In the early days of the company, I picked up the phone every single time a customer emailed me. Every time.”
Todd Olson Nov 3, 2022 ▶ 9:29
Disclosure
Olson: I still monitor Zendesk and work support tickets at Pendo
“Folks, I still am in the Zendesk queue, and actually, even this morning, I was communicating with my VP of support. We're looking at doing a sprint to burn down our backlog, and I volunteered to go into the tickets and burn down the backlog with our support te…”
Todd Olson Nov 3, 2022 ▶ 10:12
Assertion Not checkable as stated
Olson: Battery invested in Pendo after an Austin CEO recommended it
“We heard about us because an investor, Battery, was here in Austin, and they were meeting with a local company, and the CEO, they asked the CEO Who, who's the interesting company that you use, and that Liz Pinto thing is like pretty good, and it's, they got gr…”
Todd Olson Nov 3, 2022 ▶ 10:51
Disclosure
Olson: I personally read every Pendo NPS response every morning
“This morning when I woke up, I read every Every single MPS response we got this morning from the last time I looked, which is last night when I got off the plane and got to the hotel”
Todd Olson Nov 3, 2022 ▶ 11:31
Disclosure
Olson: Personally interviewed nearly every candidate until Pendo reached 500 employees
“It is a fun fact that I interviewed nearly every person at the company up until 500 employees.”
Todd Olson Nov 3, 2022 ▶ 15:54
Insight
Olson: Corporate layers sanitize frontline data shown to top executives
“The fact is you've got a lot of layers, and they all want to look good, and they all care about how they're perceived inside the organization, so if there's a presentation to someone high in an organization, you're gonna get three people's filter on what that …”
Todd Olson Nov 3, 2022 ▶ 25:20
Insight
Olson: Startups must let systems break to know what to fix
“Sometimes things have to break and fall over to actually see what you need to fix.”
Todd Olson Nov 3, 2022 ▶ 28:15
Assertion Not checkable as stated
Olson: Pendo processes over 100 billion events per week
“We now get over a hundred billion a week, and this is when we had a hundred billion cumulatively. This is probably back in that 20 17 range. We have tens of trillions of events now.”
Todd Olson Nov 3, 2022 ▶ 28:25
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