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Founder conversationUnicorn $50m+

The $100m Pendo Story

Pendo's CEO on flying out to close an early deal, interviewing nearly every hire and the CSM ratios behind $100M ARR

Todd Olson · Pendo

Published September 1, 2022
About this resource

Todd Olson, CEO and Founder of Pendo, shares:

- Crazy one-off projects we did early on

- How I maintained culture as we added offices

- Pendo’s CSM to customer ratio

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What you’ll learn

Pendo founder and CEO Todd Olson explains why doing unscalable things helped Pendo pass $100 million in ARR. He covers flying out to close an early deal himself, staying close to customers through support tickets and NPS follow-ups, interviewing hires and holding 90-day check-ins, and signing large customers before the system could handle their scale.

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Key moments

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Closing a 60K ARR deal in person

“It was a 60 k deal ARR when our largest deal previous was about $1,500 ARR.”

Learning from a single user

“So this is the value of doing unscalable things is by going direct to the user, direct to the customer, you derive all sorts of learnings that inform new feature developments.”

Pick up the phone with customers

“if you find yourself like trading emails with a customer, like pick up the phone.”

Interviewing nearly every hire

“I interviewed nearly every person at the company up until 500 employees.”

Let scale break, then fix it

“Sometimes things have to break and fall over to actually see what you need to fix.”

2005, My Garage in Seattle

“2005, My Garage in Seattle”

Crazy one-off projects we did early on

“Crazy one-off projects we did early on”

CD Rom I used to build all

“CD Rom I used to build all my computers to save money”

Unscalable People things

“Why I interviewed nearly every person for the first 7 years of Pendo”

… before you can scale

“You must do unscalable things at every stage”

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Resource files

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  • The $100m Pendo Story - Slide Deck

About the speaker
Todd Olson

Todd Olson

Co-Founder and CEO · Pendo

Todd Olson is the co-founder and CEO of Pendo, a platform that accelerates and deepens software product adoption. Before Pendo, Todd served as VP of Products at Rally Software where he served through its public offering. Todd joined Rally via its acquisition of 6th Sense, a company he founded and led as president and CTO.

Company revenue
$130M
Team size
1000

Slide by slide

Each slide with a short explanation of what it shows. Open the slide text for its exact wording.

20 passages

Pendo growth premise

  1. Slide text

    Founder500 Sept 2022 Todd Olson CEO, Founder of Pendo The $100m Pendo Story … and the crazy unscalable stuff we did at every stage

  2. An early company chapter

    A full-bleed travel photograph marks a transition into Pendo’s early story; the slide labels the moment as 2005 in a Seattle garage.

    Slide text

    2005, My Garage in Seattle

Unscalable work before scale

  1. Do unscalable work at every stage

    The central claim is that companies must take on work that does not scale before they can scale. The message applies this principle at every stage of growth.

    Slide text

    … before you can scale You must do unscalable things at every stage

  2. Revenue growth accelerates

    The chart shows Pendo revenue rising across the displayed years, with much larger increases in the later bars. The pattern illustrates growth accelerating over time.

    Slide text

    Pendo Revenue Growth

Early customer experiments

  1. Customer and people practices

    The talk will cover early customer projects and support alongside founder-led hiring and culture work. Examples include interviewing nearly every hire, maintaining culture across offices, and using talent reviews.

    Slide text

    Crazy one-off projects we did early on PEOPLE CUSTOMER What insane customer support looks like Our CSM to customer ratio My calendar when I interviewed nearly every person How I maintained culture as we added offices The talent review template we use today Over the next 20 minutes: I’m going to show you unscalable things we did at each stage to be ready for scale:

Insane customer support

  1. Customer work changes with scale

    The customer agenda progresses from running alongside early customers and providing intensive support to swarming on NPS and using higher customer-success coverage. At the largest stage, it shifts toward product-led customer-success experiments.

    Slide text

    Unscalable customer things Running at key early customers Insane customer support I’m going to show you $0-10M $50-100M $100M+ What it looks like to swarm NPS High CSM: customer ratios Product-led CS experiments

  2. Build around a customer

    An open office photo and a customer portrait accompany the call to build for a specific customer. The example makes customer focus concrete by putting one person at the center of product work.

    Slide text

    Building for Amy @Invoca

  3. A payment from an early customer

    A photographed check and its remittance detail show a payment to Pendo. The artifact gives a tangible glimpse of the company’s early customer work.

    Slide text

    CD Rom I used to build all my computers to save money 2005, My Garage in Seattle Full bleed image template

  4. Support can include a workaround

    A customer-support exchange explains a workaround for a missing feature and says a change was added to the product board. The example presents direct follow-up as a way to help a customer get unstuck.

    Slide text

    Provide insane customer support

  5. Pendo’s Series A financing

    A news clipping reports that Battery Ventures led an $11M Series A financing for Pendo. The article describes the company as making software for product managers to gather customer feedback.

NPS and customer focus

  1. Read customer feedback closely

    A customer response pairs a score of 6 out of 10 with detailed praise and implementation concerns. The conversation beside it shows the team following up on the concerns and tracking whether the cases were resolved.

    Slide text

    Obsess over NPS

  2. Scale customer success through three practices

    The diagram links scaled customer success to product-led programs informed by data, one-to-many communication across channels, and refined use of human effort. Together, the three practices form a cycle around customer success.

    Slide text

    What maniacal focus on the customer looks like today

Unscalable people practices

  1. People work changes with scale

    The people agenda moves from interviewing nearly every early hire to preserving culture through regular office visits and conducting detailed talent reviews. The columns connect each practice to a company stage.

    Slide text

    Unscalable People things Why I interviewed nearly every person for the first 7 years of Pendo I’m going to discuss: $5-10M $50-$100M $100M+ How I preserved culture by visiting every office quarterly The importance of detailed talent reviews.

  2. A founder’s calendar is fragmented

    A time-insights panel overlays a crowded weekly calendar divided among meetings, travel, interviews, personal events, and other work. The dense schedule illustrates how many kinds of commitments compete for a founder’s time.

  3. Colleagues prepare food together

    A group gathers around a kitchen counter to prepare food together. The image conveys colleagues spending time together away from individual desks.

  4. Assess talent with a detailed framework

    A career-level matrix pairs expectations for product designers with a private manager assessment. The assessment prompts managers to review performance, potential scope, retention risk, and promotion readiness.

    Slide text

    Conduct detailed talent reviews

  5. Extend the talent framework

    This build reveals more of the career-level matrix, extending the comparison into a higher-level design role. It emphasizes that expectations and development criteria vary by level.

    Slide text

    Conduct detailed talent reviews

  6. Do unscalable work at every stage

    The deck returns to its central principle: unscalable work comes before scale. The repeated statement closes the argument across both customer and people practices.

    Slide text

    … before you can scale You must do unscalable things at every stage

  7. Customer activity grows over time

    The chart compares event totals for Pendo’s largest customers in 2017 and 2018. Every 2018 bar is taller than the displayed 2017 bars, and WebPT appears in both years.

  8. Thank you from Todd Olson

    Todd Olson closes the talk by thanking the audience and identifying Pendo.

    Slide text

    Sept 2022 Todd Olson CEO of Pendo