Aug 28, 2020 · 44m · 20vc
20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like
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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 episode of TwentyVC, host Harry Stebbings interviews PagerDuty CEO Jennifer Tejada about enterprise leadership, decision-making under uncertainty, and board management. Tejada shares actionable frameworks for managing risk, building high-trust corporate cultures, and driving long-term organizational strategy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 24.1% of the talking time here. How this is scored →
Harry as informed peer 1.6 Guest teaching 3.7 Guest disagreement 0.8 Harry pushing back 0.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 37:34 Frustration with tech industry diversity pace
Jennifer expresses direct frustration about being one of the few women leading enterprise software companies and calls out the industry for taking far too long to change.
Hardest push from Harry ▶ 37:55 Challenging corporate diversity hand-wavingHarry cuts in to challenge superficial company memos and mission statements, directly pressing the guest on what specific operational steps companies must take.
Biggest teaching moment ▶ 11:30 Reframing fast vs slow career progressionJennifer completely corrects Harry's framing of career pacing by explaining that progression is not about speed, but about intrinsic motivation and learning velocity.
Harry holds his own ▶ 37:55 Demanding operational rigor on diversityHarry demonstrates keen industry awareness by refusing PR answers on diversity, forcing the guest to explain PagerDuty's exact operational and metric-driven strategy.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jennifer Tejada's Career Journey to PagerDuty | 1 | 2 | 0 | 0 | Harry introduces Jennifer Tejada and asks a standard background question regarding her path to PagerDuty. Jennifer provides a comprehensive overview of her career from P&G to software leadership while Harry listens attentively. | |
| Career Strategy, Talent Development, and Leadership Skills | 1 | 4 | 1 | 1 | Harry asks for career advice for graduates. Jennifer explains the importance of general management experience and warns against young leaders taking the elevator straight to the top with narrow functional skills. | |
| Intrinsic Motivation and Re-evaluating Professional Risk | 1 | 5 | 1 | 1 | When Harry asks whether to go fast or go slow, Jennifer reframes the issue entirely away from speed to intrinsic motivation and learning velocity. She also details her practical framework for evaluating personal risk. | |
| Isolating Decision-Making and Personal Reflection Routines | 2 | 2 | 1 | 1 | Harry shares his personal reflection routine and asks how Jennifer isolates her decision-making. Jennifer outlines her outdoor routines and admits to using relentless probing in team meetings to process complex decisions. | |
| Addressing Vulnerability, Self-Doubt, and Data Analysis | 1 | 3 | 0 | 0 | Harry asks about vulnerability and self-doubt. Jennifer candidly discusses managing imposter syndrome through deep data analysis, asking the seven whys, and leaning on a strong team. | |
| Decisiveness and Making Calls with Imperfect Information | 2 | 4 | 0 | 0 | Harry notes they have completely departed from the pre-planned schedule to discuss executive decision-making. Jennifer teaches how board experience and crisis management train leaders to make fast calls with imperfect data. | |
| Building Trust and Fostering Constructive Team Debate | 1 | 4 | 1 | 0 | Harry inquires about fostering internal constructive debate. Jennifer references Patrick Lencioni's frameworks and shares how she pushed PagerDuty past its overly polite Canadian/Midwestern roots toward healthy conflict. | |
| Strategic Board Management and Board Member Excellence | 2 | 5 | 1 | 0 | Harry seeks mentorship on how to be an effective board member. Jennifer details how CEOs should treat boards as strategic partners rather than pure oversight, and advises board members to listen attentively and ask rare, insightful questions. | |
| Quick Fire Round, Tech Diversity, and Long-Term Vision | 3 | 4 | 2 | 4 | During the quick fire round, Harry interrupts and pushes past generic corporate memos on diversity to demand concrete actions. Jennifer responds with an operational blueprint for treating DE&I as a core business initiative with metrics and accountability. |
Statements from this episode (15)
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.”
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…”
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.”
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…”
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.”
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…”
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…”
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.”
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…”
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…”
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…”
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.”
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.”
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…”