Jennifer Tejada

Executive Chair, PagerDuty · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

executiveinvestor@jenntejada ↗LinkedIn ↗pagerduty.com ↗

Tejada served as CEO of PagerDuty from 2016 until 2026, leading the digital operations platform through its 2019 New York Stock Exchange IPO and global enterprise scaling. She previously served as CEO of Keynote Systems through its acquisition by Dynatrace and serves on the board of directors of The Estée Lauder Companies.

15statements → 3claims → 1claims resolved → 3.67/5average certainty → 2.2/5average debate potential → ≈4.5/5argument clarity, estimated → 4said about them ↓

0 supported 1 partly supported 0 contradicted 2 not checkable as stated how the 3 claims stand · each chip opens the sources

1 prediction · 2 assertions · 12 insights · every statement was checked. The prediction and assertions are the 3 claims: statements the public record can support or contradict. 1 is resolved, and 2 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Jennifer argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

How they sound: speaking style how? →

219 words/min while actually speaking · 0.2 um and uh per 1k words

No argument clarity score for Jennifer Tejada: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 20 exchanges on the produced feed is ≈4.5/5, shown at half point precision because the sample is small and produced tape scores higher.

Measured by listening to 6,551 words across 1 episode, but every recording we have of Jennifer Tejada is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →

How the interview went all their pushback → series average →

Across 1 rated episode:

host pushback ▾ 1/10

pushed back at the host 1/10

setup questions received 85%

host pushback: the hardest questions Harry asked, tap to play ▶ 23:09“How did you get comfortable making fast decisions with imperfect information?” ▶ 20:17“did you ever doubt yourself in the role? And how do you think about dealing with vulnerability and self-doubt?” ▶ 14:19“How do you think about risk assessment yourself?”

What they said15 What others said4 Episodes1

Everything Jennifer Tejada said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight

Going public forces executives into fear-based, short-term decision-making

“Since I've taken the company public, you're actually kind of trained and modeled to constantly be managing risk. Like, you know, if you do this, what will the street think? If this happens, then how will that impact the stock price? And it's a lot of short-ter…”

Jennifer Tejada Aug 28, 2020 ▶ 15:03 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Fast decisions made with limited information outperform slower, data-heavy ones

“If you look back on decisions that you've made in the past, ones where you've had a lot of information, ones where you've had very little information and kept score, I think you would find that the quality of the decisions you made with less information is jus…”

Jennifer Tejada Aug 28, 2020 ▶ 25:18 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Prediction Not checkable as stated

Tech industry faces executive talent shortage within 20 years, predicts Tejada

“And they're in a hurry, but I think we could end up 20 years from now without really well-trained executives leading businesses, because the foundational companies that used to do that for the industry are not anymore.”

Jennifer Tejada Aug 28, 2020 ▶ 7:48 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Leaders without self-doubt exhibit concerning levels of arrogance and narcissism

“I think anybody who runs a meaningfully sized company or is responsible for the employment of hundreds of people or has a duty of care in a leadership role is going to doubt themselves. It's natural. And frankly, if you're not, I'd be nervous about the level o…”

Jennifer Tejada Aug 28, 2020 ▶ 20:55 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

CEOs must understand every corporate function before leading, says Tejada

“When you're the CEO, there's not a ton of time for on the job training. You really need to understand what you have in front of you and what you're working with. And that includes having some wherewithal and understanding of what each function is meant to deli…”

Jennifer Tejada Aug 28, 2020 ▶ 10:24 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Professionals must feel slightly scared to remain open to possibilities

“If you're not a little bit scared in everything that you're doing, you're not being open enough to the possibilities that are out there.”

Jennifer Tejada Aug 28, 2020 ▶ 14:36 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Walking one-on-ones yield more candid conversations than video calls

“I find when we're walking, we have a more candid Conversation. More emotion is leveraged in those conversations than when we're on video going through to do lists.”

Jennifer Tejada Aug 28, 2020 ▶ 18:02 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Uncomfortable team accountability is a muscle that must be built deliberately

“Like you have to build that muscle to be able to have an uncomfortable conversation within a team and being comfortable and holding each other accountable to goals and commitments that we've made. And that's a muscle that doesn't just come naturally. You actua…”

Jennifer Tejada Aug 28, 2020 ▶ 22:35 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Corporate board members operate on only 10% of executive management data

“When you're a board member, you're asked to approve Or advise on the basis of having about 10% of the data you're used to having as an operator.”

Jennifer Tejada Aug 28, 2020 ▶ 23:22 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Assertion Not checkable as stated

Early PagerDuty meetings were overly polite and unproductive, says Tejada

“And what I found was that everybody was being very careful not to get in anybody else's backyard, not to get in anybody else's grill. And it was a very nice conversation. Meetings were very pleasant, but they weren't terribly productive. And we tended to be fo…”

Jennifer Tejada Aug 28, 2020 ▶ 27:51 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

High-growth companies almost never reach team norming due to rapid scaling

“In a high growth company, you almost never get to norming. Like there's just no stasis because the company is changing so fast because of the scaling. And so you're kind of constantly pivoting back and forth between forming and storming. And if that's uncomfor…”

Jennifer Tejada Aug 28, 2020 ▶ 28:57 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Bad news never improves with age, requiring full board transparency

“So I think part of good board management is transparency. We have a no surprises policy in my team and my board because bad news doesn't get better with age.”

Jennifer Tejada Aug 28, 2020 ▶ 30:59 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

The best board members ask few but highly insightful questions

“I mean, I think the most phenomenal board members I work with are the ones that ask super insightful questions in the right moment.”

Jennifer Tejada Aug 28, 2020 ▶ 33:54 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Insight

Diversity must be managed like a core business initiative with explicit goals

“Treat it like a business initiative as opposed to a box checking exercise or something that HR owns. And with any important business initiative, you set explicit measurable goals with explicit milestone timing, timeframes, and you allocate resources and leader…”

Jennifer Tejada Aug 28, 2020 ▶ 38:12 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Assertion Partly supported

PagerDuty shifted from mostly male to gender-balanced across most departments

“We were a deeply technical company that was mostly male when I got there, and our team is balanced across the board in most cases”

Jennifer Tejada Aug 28, 2020 ▶ 39:01 20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

The other half of the tape: Jennifer Tejada's own voice is left out of every number here. Other people bring the name up 4 times in 3 episodes on 20VC. every mention, with the transcript →

Who brings them up most Byron Deeter 2 Jason Lemkin 1 Harry Stebbings 1