Oct 16, 2021 · 32m · saastr
Hyperscaling At Scale with PagerDuty's CEO, Jennifer Tejada | SaaStr Software Community
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr fireside chat, PagerDuty CEO Jennifer Tejada and Sameer Dholakia discuss scaling an enterprise SaaS business, executing a strategic IPO, and building a durable, human-centric organization. Tejada shares insights on forecasting rigor, platform expansion, executive bench development, and corporate social responsibility.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 5.0 Guest teaching 2.0 Guest disagreement 0.3 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:10 Direct critique of people-averse CEOs
Tejada recounts confronting another executive directly, telling him he was in the wrong job if he did not like working with people.
Hardest push from Jason ▶ 10:19 Emphasizing strict quarterly forecasting disciplineDholakia pushes the discussion onto public company rigor, reminding Tejada of the strict envelope test for revenue predictability.
Biggest teaching moment ▶ 15:12 Learning durable growth mechanics from crossover investorsTejada details how crossover investor Henry Ellenbogen took her to school on articulating multiple structural growth drivers rather than relying on market optimism.
Jason holds their own ▶ 2:00 Dholakia details SendGrid scaling track recordDholakia establishes his bona fides as an operator by citing his experience scaling SendGrid from $30M through an IPO to a $3B Twilio acquisition.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Opening Montage: PagerDuty's Vision on Digital Operations and Resilience | 6 | 1 | 0 | 0 | The segment opens with an introductory keynote clip from Tejada before Dholakia takes the stage. Dholakia establishes strong domain expertise by summarizing his 25-year career taking SendGrid public and joining Twilio, creating a warm, peer-level dynamic with zero friction. | |
| Timing the IPO and Transitioning to Enterprise | 5 | 2 | 0 | 0 | Dholakia asks Tejada about determining the right timing for an IPO and shares his own SendGrid M&A rationale. Tejada explains transitioning into central IT enterprise sales and establishing credibility for large contracts. | |
| Cultural Evolution and Public Forecasting Rigor | 6 | 2 | 0 | 0 | Dholakia brings up public market forecasting discipline with the classic envelope test metaphor. Tejada builds on this by discussing internal guidance rules like sandbagging appropriately and issuing the lowest believable number. | |
| Navigating Employee Sentiment and Post-IPO Compounding | 4 | 3 | 1 | 0 | Tejada explains educating employees on post-IPO stock volatility and recounts crossover investor Henry Ellenbogen tutoring her on proving durable compound growth drivers. Dholakia facilitates with supportive prompts. | |
| Operationalizing Customer Trust and Expanding Use Cases | 5 | 2 | 0 | 0 | Dholakia notes board-level observations on expanding use cases beyond DevOps into customer support. Tejada explains operationalizing trust and shares an unexpected use case involving corneal transplants. | |
| Executive Leadership Bench and Succession Planning | 4 | 3 | 1 | 0 | Tejada offers candid leadership insights, recalling how she told another CEO he was in the wrong job for disliking people management. Both speakers agree on the necessity of having tough leveling conversations and building a deep executive bench. | |
| Corporate Social Responsibility and Pledge 1% | 5 | 1 | 0 | 0 | Dholakia and Tejada champion the Pledge 1% initiative and discuss PagerDuty.org. Both emphasize how purpose-driven corporate philanthropy drives employee engagement without impacting the operating P&L. |
Statements from this episode (15)
Dholakia: 2021 software IPO pipeline is most robust in 25 years
“I don't think I've ever seen in my time in this industry a pipeline as robust of IPO worthy companies”
Tejada: Going public established PagerDuty's enterprise credibility with CIOs
“So a big part of why we went public in 2019 was really to demonstrate to the market that we were a viable long-term platform that could support large, largest enterprises in the world, the greatest,
Brands around the globe in their digital transformation, and …”
Tejada: An IPO is only an exit for private investors, not the company
“I think the IPO is a really important milestone, and sometimes in Silicon Valley,
We treat it more like an exit, but it's only an exit for your private investors. It's a really important milestone for the company”
Tejada: Scaling requires actively evolving culture rather than protecting early-stage habits
“And it's actually not about protecting the culture. It's about developing the culture, building the culture that you need for the future on the strong foundation that you had as a startup, as a smaller company.”
Tejada: Public companies must beat and raise guidance, not just meet it
“It's not enough to meet your guidance. You have to beat your guidance and you have to raise and you have to have Not only great instrumentation on your pipeline and confidence in your leadership, but you also have to have really strong fidelity in how you thin…”
Dholakia: Compounding revenue creates far more enterprise value post-IPO than pre-IPO
“There's so much more value that gets created after the IPO. And it's, to Jen's point, it's always thought of as this end destination, this exit event, but gosh, once you start compounding revenue numbers
North of a hundred million in ARR at 3040, 50% year ove…”
Tejada: Daily stock swings do not reflect employee intelligence or business quality
“Do not watch that stock price every day, because on a day when your stock's up 10%, that doesn't mean you were 10% smarter or 10% better, and the day your stock's down 10%, it doesn't mean you were 10% more stupid than the day before, and you shouldn't be writ…”
Tejada: PagerDuty raised an unneeded Series D to test investor narrative
“And so we did not need the cash, but we raised a Series D about, you know, six, eight months before we went public in order to test our story and our narrative and our performance out in front of a number of what we now call crossover investors.”
Tejada: PagerDuty serves over 65 Fortune 100 and 45% of Fortune 500
“PagerDuty now serves more than 65 of the Fortune 100, and more than 45% of the Fortune 500.”
Tejada: A non-profit uses PagerDuty to coordinate urgent corneal transplants
“We have a nonprofit that leverages PagerDuty to manage corneal transplants, and, you know, really, like, talk about a time-sensitive, mission-critical workflow. A cornea becomes available by a donor, and you have, you know, less than a few days that that corne…”
Tejada's board advised her to focus only on unique CEO tasks
“I got feedback in a three 60 degree effort with my board about three years ago, and one of the things they said is, Jen, there's a lot of things across this business that you've done before, that you're able to do, you've been in that job, you can make those h…”
Tejada: Public markets do not forgive executive leadership gaps
“You want to have people lined up in the dugout ready to take on the next job, and that is so much more important in the public market because The market's not going to give you grace if you have an open role or a leadership gap that you can't manage.”
Tejada acknowledges PagerDuty is not profitable
“And we're not profitable, so I'm kind of thoughtful about that, like what I do with our shareholders' money.”