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Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation

March 21, 2025 / 34:00

This episode features Jennifer Tejada, CEO of PagerDuty, discussing the company's role in helping organizations manage their digital operations, the importance of technology reliability, and her leadership journey.

Tejada explains that PagerDuty is a software as a service platform used by major companies to ensure their technology services are reliable and available. She highlights how businesses increasingly depend on technology for their operations and brand experiences.

Tejada shares her insights on leadership, emphasizing the importance of thinking like an owner and adapting to the changing landscape of technology. She reflects on her experience at Procter & Gamble and how it shaped her management style.

The conversation also touches on the evolving landscape of AI and its implications for businesses. Tejada discusses the challenges organizations face in adopting AI and the need for rapid experimentation to stay competitive.

Finally, Tejada offers advice to young professionals about navigating their careers, encouraging them to embrace diverse experiences and remain open to new opportunities.

TL;DR

Jennifer Tejada discusses PagerDuty's role in tech reliability, her leadership journey, and career advice for young professionals.

Episode

34:00
00:00:00
Speaker: This podcast is brought to you by Knowledge at Wharton.
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Patti Williams: Jen, it's so nice to have you here. Thank you for coming to
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the Wharton School, and thank you for our conversation. I'm so, so pleased.
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Jennifer Tejada: Well, my pleasure. It's great to be back to
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Wharton. - Awesome. So I thought we would just start and maybe
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set the ground with, what is PagerDuty, right? So I've read
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that half of the Fortune 500 and nearly 70 percent of the Fortune 100
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use PagerDuty. Tell me a little bit about what PagerDuty is, and
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what are you doing for these organizations? - Sure.
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So PagerDuty is a pure software as a service platform that
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exists to help the largest and most innovative companies in the
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world deliver reliable and highly available technology
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services. And if you think about how any business runs that you
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interact with as a consumer, all of those businesses are running
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on software and increasingly data and AI today. And the
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challenge is you become really reliant on the convenience, or
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the 24 by seven on demand availability of something, and
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when suddenly your brand experience isn't available to
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you or doesn't work effectively because of a technology
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challenge, you don't blame the technology, you blame the brand
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as a consumer. And so, as the world's been, so to speak, eaten
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by software and become more technology driven, reliable and
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available technical infrastructure, software
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services, applications, and increasingly, LLMs and agents
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have become mission critical and important. And software, like
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human beings, is imperfect, and we're also deploying an
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unprecedented amount of software and technology into the
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ecosystem, and now new technology in the form of LLMs,
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agents, applications, integrations, APIs. All that
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complexity leads to the storming of breakdowns, or what we call
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incidents. And so the way our customers think about us is we
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help them manage their digital operations. And increasingly,
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whether you're a financial services business or online
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travel and hospitality, a tech company, you know, a ride share
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platform, all of these platforms increasingly deliver the vast
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majority of their brand services, their experience, they
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drive their revenue, driven transactions, all through
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technology. And so it has to work, and it has to work
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perfectly all the time. - Yeah,
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it's amazing. I think for so many organizations, a lot of
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that was back office, right? It wasn't solution critical. - For sure.
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- And that's a real change in, I think, the importance of this,
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and how sort of the center of the strategic sort of value
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proposition it really is for many of these companies.
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- Yeah, the way I think about it is you would never think of
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NASA's mission control as back office, but that is kind of how
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this works. You have a combination of technology, people,
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and AI watching how a very complex technology organization
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operates, and giving you an early read on, you know, where are some
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things that are looking like they're acting outside of their
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traditional operating boundaries? Or, where do you see
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an early sign that something bad is about to happen? And so the
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goal for us and for our customers is not to just help
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them respond more effectively when things don't work the way
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they're supposed to, but to help prevent big issues from
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happening, and likewise, to learn from every challenge that
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runs on the platform. And so we've been in the AI business
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now for almost 16 years. We've been collecting a significant
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amount of proprietary data since the very beginning of Pager-
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Duty. We started with machine learning and algorithmic AI,
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analytical AI, and in the past year and a half, have added
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generative AI, and just yesterday, announced agentic AI
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in our platform.
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- Amazing. We're going to come to that in just a minute. I want
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to -- you've been at PagerDuty since 2016, I think. -Yeah.
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- As CEO, right? - That's right.
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- Eight years is a pretty long time. - It's unusually long for our industry, for sure,
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particularly for somebody who isn't the original founder.
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- Yeah, amazing. And I think you took the company public in 2019?
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- That's right. - As you think about your leadership over those eight
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years, what are some of the biggest lessons you've learned
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about leading an organization and leading this organization in
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particular? - That's a great question. You know, in my early
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days at Procter & Gamble, in probably some of the first
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management training that I received there, and they did
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this tremendous job of putting you through an academy of job
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specific coursework. And one of the things they would say is, "Act
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and think like an owner," which goes a little further than, "Spend
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the company's money like you would your own," right? Some
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people don't spend their money wisely, right? So that might not
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actually be a good metaphor. But acting and thinking like an
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owner isn't just about, you know, trying to drive the share
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price or the share value up. It's, if you were running this
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job, or your team like it was your very own business, and
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that you owned all the investment in, all the outcomes,
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all the growth, all the challenges, like, how might you
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think differently? And I think so much about being a CEO,
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particularly in a culture of innovation, in a high growth
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startup, in an early public company, is about having that
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ownership mindset. And in some ways, you know, the company
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was founded by three co- founders. I sort of became the
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re-founder or the adoptive parent. And what's interesting
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about that in the early days, is you're raising that child
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with the other parents sitting nearby, looking on, right? And so
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there's a very high standard for how you adapt the
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company over time, how you develop new capabilities
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on an existing foundation, how you drive disruption, even when
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you may be attacking somebody's sacred cows, so to speak. And
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probably the most exciting thing for me has been how you first
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to reinvent yourself. We've been through many chapters and many
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transitions as a company. We were very small. You know, 30
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million in ARR when I joined, less than 200 people. And now
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we're over 1,000 people, and close to a half a billion in ARR.
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And so -- and we went from being this private, you know, series
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A backed startup, to being a public company traded on the New
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York Stock Exchange for now almost six years. And so
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through all those chapters as a leader, it's never boring,
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right? You're always having to anticipate, like, what
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does the next leg of the journey look like? How do we need to be
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prepared for that? And as you get bigger, those preparation
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cycles take longer. You need to be further out in front of kind
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of what's coming. And one of the things I'm really proud of is, we
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did, I think, quite a good job of future proofing our platform
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for big data, for AI and machine learning, and now generative. We
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rallied around one of our core value propositions, which is
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trust. So you know, PagerDuty's core reliability engineering
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is critically important, because if we have to be up when the
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rest of the world is down, and our customers hold us to a much
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higher standard than most technology and SaaS platforms.
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And so in the 16 years of the company's existence, we've
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never had a maintenance window. A maintenance window is when you
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log on to something and it says, "Sorry, we're not available.
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We'll be right back." Can you imagine if you were undergoing a
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major technology incident, a ransomware attack here at
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Wharton, and the one platform that is supposed to help you
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detect that and manage it and resolve it and remediate is like
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not available for that hour? So that -- our ability to keep
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innovating and expanding our product set and our platform,
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while at the same time, delivering the level of fidelity
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and reliability and trust that our customers, some of the most --
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I think,
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like most critical and
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highest standard holding customers out there in
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the marketplace, to live up to that ongoing standard, as the
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bar keeps getting higher because the technology gets more
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complex, has been a really big challenge. And we've done it
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while delivering very high gross margins, while continuing to
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grow, and, you know, while becoming a profitable company
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and a company that produces a lot of cash flow. - Amazing. One
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of the things that I think is particularly interesting is that
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you don't have a typical tech CEO background. - No.
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- Could you talk a little bit about your background, how you got here,
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and how do you think that makes you a better adoptive parent?
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- Yeah. Well, I grew up in small towns across the Midwest. I went
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to the University of Michigan on a scholarship. I got a
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liberal arts degree in organizational behavior and
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business management, which was basically psych for groups, you
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know, is the way I would think about it. And going to a big
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university like Michigan or like Penn, one of the benefits is
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you don't just learn how to learn, you learn how to navigate
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a complex system, and you learn how to advocate when you're,
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you know, a small speck in a really big universe. And I felt
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like my experience at Michigan prepared me for the world in a
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lot of ways, coming out of a, you know, smaller city, into
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this very diverse environment where I had to fight for
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classes, I had to kind of choose my own major, and at the time,
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like I was a 19 year old kid that felt very stressful. But
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when I look back on it, like the opportunity to choose my own
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adventure and just spend four years just discovering what was
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interesting to me, what I thought was going to be
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important in the world, like that was a very strong
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foundation. And I didn't really know what I wanted to be when I
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grew up. I still am trying to figure it out actually. I was
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originally going to go into healthcare administration, and
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the industry was deregulating at the time, so I decided to just
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go to work for a couple of years and learn how to adult and just
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get some experience under my belt, and by the grace of God,
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got a job with Procter & Gamble, and they had this
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phenomenal leadership rotation. So from the very early days of
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my career, I had -- I was taught, I think, important basics and
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foundations of what makes a great leader. How to find your
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own leadership voice, how to think about how to surround
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yourself with the kinds of other leaders or people that have
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skills that complement your skills and experience. And so as
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early as in my very early twenties, I was already thinking about, how
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do you compose a great team? You know, what makes the collective
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of a team better than just the sum of the individuals? So some
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of those really early lessons stuck with me for a long time.
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But when I -- you know, I showed up in the tech industry
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in the mid to late '90s, because it was moving fast. I
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could see this innovation happening, and I -- not only did I
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not want to be left behind, I didn't want to be a simple
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participant. I wanted to be a part of leading, you know, that --
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leading that disruption and that innovation from the front. And
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so I took a very big risk and went to work for a supply chain
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automation software company called ITU, and I leveraged what
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I learned at Procter & Gamble and what Procter & Gamble was
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known for, which was brand and marketing and go to market, and
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to some extent product, because product management at P&G is
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really brand, and kind of leveraged that to get my first
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job in tech. And I didn't send out any resumes, I met a guy on
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an airplane. And so, you know, I always remind my daughter, who's
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a college sophomore right now, like, "You've always got to be
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ready to give your elevator pitch." And sometimes you're only
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going up two floors, right? Sometimes you might have the
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Sears Tower to work with. But when someone asks you who you
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are and what you do, like, make sure you put your best foot
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forward in an authentic way that makes someone want to learn
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more. And I think that liberal arts degree, I think
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having an undergraduate education was really all about
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identifying complex problems and figuring out how to pick them
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apart, but then make the solution accessible to lots of
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different kinds of people, prepared me really well for
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general management, right? And then I'd also say, I come from
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like a really hard working family, so I have a sick work
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ethic, sick in a good way. And I also came from a family that
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really expects you to contribute to your community and to not
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wait to be asked. To take initiative, to think about how
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you serve the community around you. And I think that mindset of
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like looking out into the community and figuring out where
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you can add value is really important in the CEO job right
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now, because we have such a diverse stakeholder community
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now, much more so than even five years or 10 years ago in the
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role.
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- That's really interesting. So you know, as a marketing professor,
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one of the things that I have appreciated, besides the fact
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that you came from a marketing background at P&G, and you
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have this sort of branding mindset that you bring, that
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I've heard you say that you spend about half of your time
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with your customers. - I do. - I'm not sure most CEOs, even in
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marketing driven organizations, spend half of their time with
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their customers. Talk a little bit about why you do that, how
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you think it gives you advantages as a leader.
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- Yeah, I mean, part of it was just choosing a perspective that
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enabled me to devote time to sort of understanding our users,
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but also the economic buyer, the CEO the CFO, the CIO, who makes
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a decision to sign a multi- million dollar, multi-year
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agreement with us. I mean, that is a long term material
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partnership for a lot of the companies we serve, and they
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have lots of choices. And so part of it was figuring out how
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to get inside the minds of both our users and our buyers, and
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really understand what was important in their business.
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Because I think it's easy to become sort of tunnel vision
00:14:06
about like what your product does, and focusing purely around
00:14:09
the use cases that your products support. And that's how you miss
00:14:13
pivots. That's how you miss opportunities to move into
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adjacent areas. It's more how our customers' jobs are evolving.
00:14:23
Like, what is keeping them up late at night? And I mean, what
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are the big problems that they worry about, not for this
00:14:30
week or for this month or for Friday's payroll, but like, what
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are the big problems that are keeping them up 18 months
00:14:36
from now, three years from now, five years from now? And what's
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getting in the way of them positioning themselves and their
00:14:41
businesses for success? And can you be part of moving those
00:14:45
obstacles out of the way, or addressing those obstacles, or
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even changing the way the company operates? And so digital
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transformation has been like a playground. You know, somebody
00:14:56
said that, "If you love what you do, you never work a
00:14:58
day in your life." And I mean, I really -- I love the study of
00:15:02
different businesses. I get to look at businesses across
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industry and find patterns in terms of where there are some
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common challenges or common threads, where there are
00:15:11
emerging threats or opportunities, and use that
00:15:14
pattern recognition to inform our product roadmap, to think
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about the pace and speed with which we invest in innovation,
00:15:21
and where we might decide to say no to something. And I feel like
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my ability to anticipate what's coming really comes through
00:15:30
the the sum of all the conversations I have with our
00:15:34
customers and our prospects. And it also helped me approach
00:15:39
networking. Like, I've never been somebody who likes to network. I
00:15:42
don't like to just go to a thing and stand at the cocktail table
00:15:46
with my name tag on and meet people. But when I shaped it in
00:15:50
the perspective of, this is my market research, and you know,
00:15:54
these are people that need to be part of my community that
00:15:59
informs how we allocate capital, how we think about our future
00:16:03
roadmap, how we even think about our vision and mission as a
00:16:06
company, it made it not feel so much like networking, and made
00:16:10
it a much more, I think, tactical learning pursuit that
00:16:17
delivers a really strategic outcome in the end. And it's
00:16:20
funny, because I think a lot of people in the industry have
00:16:24
given me feedback that I have a really strong, deep and wide
00:16:28
network, and I always giggle inside when someone says that to me,
00:16:31
because I don't like networking. I don't really love going to
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conferences. I'm really picky about, like, which events I'll
00:16:36
attend and who I'm going to invest my time speaking with,
00:16:39
and what I'm trying to learn. Like, what are my goals in that
00:16:42
hour and a half, or the 16 minutes I'm going to have with
00:16:45
that person? Is there one thing I want to try and take away
00:16:49
from that? But the thing that surprised me the most is
00:16:52
just how much pattern recognition emerges, and how
00:16:56
helpful that can be. In the early days, when we were really an
00:17:01
amazing app that developers loved to use themselves, I could
00:17:06
see this pattern around, you know, data pattern recognition,
00:17:12
like being able to action analytical insights very quickly
00:17:16
when time really mattered. So you know, if you're a trading
00:17:19
platform in the financial services industry, and you
00:17:23
somehow can't manage transactions, because your
00:17:26
transaction environment goes down, like, not only are you
00:17:29
losing significant money every second, but you're also in the
00:17:33
risk of, you know, compliance breach, regulatory issues,
00:17:37
fines, even, you know, being prevented from continuing to
00:17:40
operate in certain jurisdictions, and that can
00:17:42
happen in minutes. And so the need to move fast really
00:17:45
matters. And so, you know, as I've gotten to know my
00:17:50
customers, I've also gotten to -- been able to identify patterns
00:17:53
in certain verticals, new use cases that I see that are common
00:17:57
across a vertical, and that usually comes from talking to
00:18:00
the CIO, the CTO, the CEO, not the user. Like, not somebody who is
00:18:04
is down, you know, hands on keys, so to speak, phone in
00:18:07
hand, using your actual application. I think that's
00:18:10
sometimes hard for people to distinguish, right?
00:18:13
- Yeah, absolutely. I mean, so first of all, as a professor, I
00:18:15
think we love people who love to learn, and it sounds like you're
00:18:18
bringing that growth mindset to the -- you know, to the experience
00:18:20
of networking, but also to thinking about how you're
00:18:22
leading your organization, so that's amazing. I wonder
00:18:25
if you can tell me a little bit about some of that pattern
00:18:28
recognition as we're thinking about AI. You know, you've been in
00:18:32
the space. The company's been in the space for a while. But for
00:18:35
many organizations, it's maybe a year old. They are just
00:18:38
trying to figure out something that moves so fast it's hard to
00:18:43
keep up with, figure out what the use cases are. And you know,
00:18:47
here at Wharton, we're really lucky, we have this base
00:18:49
of faculty who have been in the space for a long period of time,
00:18:52
and so we're able to share our expertise. But I think, what
00:18:55
does it look like to -- what are the kinds of patterns you
00:18:58
see across organizations when it comes to understanding and using
00:19:03
AI? - Yeah,
00:19:03
I mean, I think things often happen in stages or phases. And
00:19:08
you know, what I initially saw was a very big hype cycle. Like,
00:19:11
a lot of our large enterprise customers, knowing that AI was a
00:19:15
thing, recognizing quickly that it was going to be important and
00:19:19
disruptive, but then falling into one -- well, two camps, or in
00:19:24
some cases, both. This fear of missing out. Like, I need to be
00:19:28
doing something, my board is demanding I do something, I must
00:19:31
do something. Like, we have to do something. We have to get
00:19:33
started, or start starting. And then also this fear of getting
00:19:37
in. Oh my gosh, this is scary. This could be really dangerous.
00:19:40
You know, we could ruin our brand reputationally by doing
00:19:44
the wrong thing and not knowing, like, how to start and how to
00:19:49
start in a safe way. And the challenge when you're going
00:19:52
through a disruptive phase or a disruptive cycle in the
00:19:57
technical industry is, if you -- it's very easy to use risk as an
00:20:01
excuse to innovate gradually or incrementally, and generally,
00:20:05
more slowly than the disruptive players that have a, you know,
00:20:11
stronger risk profile and are willing to make bigger bets,
00:20:16
right? And that is often how, you know, captains of industry
00:20:19
can be left behind, right? And we've seen this prior to AI.
00:20:23
We've seen this in like the payments space, for instance.
00:20:26
Who would have thought that like our children would not have
00:20:30
cash and would use things like Venmo and CashApp, you know?
00:20:33
When we think about just how that particular sub
00:20:37
segment has disrupted traditional financial services
00:20:41
and their access to consumer assets, right? Like, it's just a
00:20:44
pretty interesting example, where those startup payments companies
00:20:48
had nothing to lose, right? And the incumbents are trying to
00:20:53
protect, you know, their current incumbency, but
00:20:57
also figure out how to move faster and do things that are a
00:21:00
little scary. I think we've moved past that, like,
00:21:03
just try and figure out how to get started, and now we're in
00:21:06
this evaluation and judgment phase, where our customers are
00:21:09
trying to understand, like, where is the real value? And
00:21:12
what's hard about that, to your point, it's moving very fast,
00:21:15
but it's unclear where the value in the AI stack is going to be.
00:21:20
Is it in the data center processing? Is it in the
00:21:23
LLM? Is it data ownership? Is it the application
00:21:26
sitting on top of it? Is it agents? And you just see this
00:21:30
kind of trend jacking that's happening as technology
00:21:35
providers, consultants, and enterprises are all trying to
00:21:39
figure out how all this comes together. I think the one really
00:21:43
strong pattern that has emerged for me is, whoever experiments
00:21:47
the fastest and most efficiently wins. And by setting up
00:21:51
experiments where you can pair domain experts, so subject matter
00:21:56
experts, in important parts of your business or customer facing
00:22:00
areas of your business that matter to you with either easy
00:22:03
to use technology or the technologists or researchers
00:22:07
that can help them apply the technology to those domain
00:22:11
specific problems that they deeply understand, that's where
00:22:14
you start to see these eureka moments. Like, oh, this could be
00:22:17
very valuable.
00:22:19
There's, again, a lot of experiments getting run. And
00:22:23
so I think it's very, very early days. And what I'm sure of is
00:22:30
there's a lot of work that humans do. Drudgery. You know,
00:22:35
tactical, sometimes repetitive, sometimes interrupt work that
00:22:39
won't need to be done by humans in the very near future, and we
00:22:44
shouldn't be afraid of that. We should embrace that, because in
00:22:47
every other industrial cycle where automation has been a
00:22:51
big part of the transition, humans have just found more
00:22:54
interesting, high value, innovative things to do with
00:22:58
their time. And I think that will be the case with
00:23:01
generative AI and AI more broadly.
00:23:03
- Yeah, super interesting. In addition to being a CEO, I know
00:23:07
you are a board member. One of the things that we have seen is
00:23:10
that sometimes boards aren't quite sure what their job is in
00:23:14
this AI space, right? And what do board members need to know,
00:23:16
and how do you think about this as a board member versus as the
00:23:19
CEO of
00:23:20
an organization? - Sure. I mentor a lot of operators and executives that
00:23:24
are making the transition from being an operator, and, you
00:23:26
know, being in the business to being a board member and having
00:23:29
oversight of the business. And one of the things I try and
00:23:34
remind them of is, a big part of their job is to ask the
00:23:38
questions that may not be obvious to someone who's in it,
00:23:42
right? And sometimes that means to step back and look at the
00:23:45
long term. Like, and sort of try and think through the game
00:23:49
theory of, if we do this, and our competitors do that, and
00:23:52
customers then do this, like, what will that mean for us? Or
00:23:55
even testing, like, is this decision a one way door or a two
00:23:58
way door? And helping management sort of size the scale of some
00:24:03
of the strategic decisions that they're making, and help them
00:24:06
sort of identify blind spots, right? Or fill talent gaps.
00:24:11
Or just anticipate, because I think when you're in
00:24:14
it every day, there is a tendency to be near term
00:24:17
focused. You know, the public markets drive this in the
00:24:20
90 day quarterly performance, which is super short term. Like,
00:24:25
nothing really happens in 90 days. And so also, the board's
00:24:28
job is to keep the long term viability, growth, and value
00:24:34
of the company in mind. And then helping management think about
00:24:39
how you're serving your stakeholders effectively.
00:24:43
There's a lot of coaching in board work. There is -- there's a
00:24:48
lot of, outside the board meeting, consideration. Like,
00:24:52
I often leave a board meeting and two days later is when I sit
00:24:56
down and think, "Oh, I need to reach out to Stefan, the CEO, and
00:25:00
talk to him about this." Or, "Oh, this might -- this could be
00:25:02
helpful." And sometimes it's as simple as, like, I sent a couple
00:25:06
of our board members the CEO book that was helpful to me,
00:25:08
right? And the book keeps coming up. It's kind of funny.
00:25:11
Sometimes it's just like a tactical, simple thing, like,
00:25:14
how can I help you find a shortcut? Because I've made this
00:25:17
mistake before, so you don't have to learn it the hard way.
00:25:20
And I think we, often as leaders, think of our boards as judges,
00:25:25
approvers, you know, our bosses. And we need to think of our
00:25:29
boards as coaches, experts, professors, maybe therapists,
00:25:34
mentors, like emergency response, etcetera. And so I also
00:25:40
think that businesses can sometimes be a little short in
00:25:47
their thinking about how you build board culture. How do you
00:25:50
think about the unique role of every board member in a board? In
00:25:56
my own head, with my board at PagerDuty, like I have different
00:26:00
roles for every single one of my board members, I give them,
00:26:02
whether they know it or not, you know, homework, or I ask them to
00:26:05
help on certain things. And I'll even -- if they're interviewing
00:26:08
someone for me, I'll even brief them specifically on what I want
00:26:10
them to cover versus another board member. So we get the
00:26:14
benefit of that complement of skills and experiences. And the
00:26:19
last thing that I would say is, one of the reasons I think board
00:26:23
culture is so important is because transparency is so
00:26:27
important. Like, you need to feel confident as a management team
00:26:33
that you can share the big decisions and the big challenges
00:26:36
with your board in a transparent way, and give them the
00:26:39
information they need to support you in making the best possible
00:26:42
decision for the business. And likewise, as a board, you want a
00:26:46
no surprises environment. Like, you do not want to be -- there
00:26:50
should never be a surprise in a board meeting. You should -- the
00:26:53
board should always be pre- briefed that something's
00:26:55
happening. They should be briefed incrementally on the
00:26:58
milestones and where you are against things. And I'm not
00:27:01
perfect at that, but I do work really hard to make sure nothing --
00:27:04
I don't sneak up on my board. I don't even like surprises in
00:27:08
terms of flowers and jewelry. Like, I'm very specific about
00:27:10
what I want. I think board members are the same. - What's the
00:27:13
book that you recommended? - Oh, I recommended <i>Working Backwards</i>,
00:27:16
which is a book that Bill Carr and his partner, who were
00:27:19
executives at Amazon, wrote about sort of the Amazon way of
00:27:23
starting with the end in mind. Writing a press release and the
00:27:26
frequently asked questions that you think you're going to get if
00:27:29
you're successful in delivering this thing about, really, people
00:27:35
call it memo writing, but it's really the skill of
00:27:40
summarizing the critical insights that you want your
00:27:46
reader to focus on, and distillation of a lot of complex
00:27:50
information that gets to higher quality decision making and
00:27:54
higher quality execution. And so I shared that because it's,
00:27:59
a template, and often getting everybody to use the
00:28:02
same practice creates simplicity in and of itself. Like, just
00:28:05
getting everybody on the same page will drive a lot of
00:28:09
efficiency and simplicity and clarity, even just a vocabulary.
00:28:13
Clarity is everything right now. - So I know that you
00:28:16
are here today to speak to some Wharton students, and you
00:28:19
mentioned that your daughter is in college at the moment. What
00:28:22
advice would you give young people about navigating their
00:28:25
own professional careers, maybe especially at this moment? I
00:28:29
just came from lunch with some MBA students who are finding the
00:28:32
job hunt a little daunting at the moment. Whatdo you tell them? - You know, I
00:28:37
felt this way as a -- in the early years of my adulthood, and
00:28:42
I hear this from my daughter and her peer group, and it's
00:28:45
like, "Well, I should be doing X." And it's this -- like, we're often
00:28:52
given these paths that feel a little bit like a salmon
00:28:57
run in a river, you know? Like, the current is going one way.
00:29:00
Like, you must go into investment banking and get the
00:29:03
investment banking internship, and then do your first two years
00:29:05
as an analyst. You must go into consulting. You must do this.
00:29:09
You should do X. If you don't do Y, you might never be able to do
00:29:13
Z, right? And I just think so much of that is BS. Like,
00:29:17
investment banking is a very small part, an important part,
00:29:21
of the business world, but there are lots of other ways to build
00:29:25
financial acumen, to build management acumen. And that's
00:29:27
not to take away from the wonderful programs these
00:29:31
companies deliver and the opportunities they create for
00:29:34
young people. But I just wonder if the mindset could be, "What if
00:29:37
I could?" As opposed to, "I think I should." Because I just
00:29:42
find so many kids that are like, "Oh yeah, I did that because it
00:29:45
was what my B-school, you know, kind of pointed me into that
00:29:48
direction, and I missed this opportunity to just discover what
00:29:52
I would really be passionate about." You know, when you're
00:29:54
really passionate about something, you tend to be better
00:29:56
at it than when you're just grinding through a checklist or,
00:30:01
you know, working your way up a ladder. The other thing, you
00:30:05
know, I try and even get my leaders and people to think
00:30:07
about, is that it's not about the career ladder. It's more about
00:30:11
the architecture and the tapestry of all the different
00:30:14
ways that you could go in a business in service of having a
00:30:19
steep learning curve, of building a diverse set of
00:30:22
experiences. And, you know, as generative AI becomes more
00:30:27
and more a part of our daily work lives and our lifestyles, a
00:30:31
lot of the time that we spend on, you know, more tedious tasks is
00:30:34
going to go away, and we're going to have the opportunity to
00:30:37
learn faster and apply new learnings more effectively, more
00:30:40
quickly, with the benefit of technology. And so the more
00:30:44
context you have, the better you're going to be able to
00:30:47
leverage that technology. If you stay in a narrow lane, you know,
00:30:51
if you're that wild salmon going down the Copper River, like
00:30:55
you're only seeing one view of the world. I always say to Sam,
00:30:58
my daughter, like, "Be the bear. Jump into the river every now
00:31:01
and then, get a salmon, have a splash, and then get back out
00:31:03
and go wander around in the woods, and sort of see
00:31:06
what's going on around you." So the last thing that I would say
00:31:11
is, we have such this finite period in our lives where only
00:31:15
jobs are really to discover what's important to us, right?
00:31:19
It's that period of education, whether it's
00:31:21
undergraduate or, you know, your graduate program. And that's
00:31:26
just, when you look back in your fifties and forties and thirties at that
00:31:30
time, you will never say to yourself, "I tried too many new
00:31:33
things. I discovered too many new things," right? And I
00:31:38
think that pursuit of getting on the path, the approved
00:31:45
grade A, five star, whatever the path is, sometimes means
00:31:50
that you're too focused on the destination and you miss the
00:31:54
journey, right? You don't -- not only do not get to enjoy the
00:31:57
ride, you don't get to stop off at the different places along
00:32:00
the way, which could change the course of your life, you know?
00:32:03
And so it's, how do we sort of stop and
00:32:07
reflect on that every now and then so you feel like you're in
00:32:10
that current? You go, "Wait a minute, like, could I just take
00:32:13
an elective that has nothing to do with, you know, my core
00:32:18
program, that's an area that I just want to discover, I don't
00:32:21
know anything about? That's maybe with people I don't have
00:32:23
anything in common with. And, you know, what might I
00:32:26
learn?"
00:32:27
- I love that, and I love the idea of just making yourself open to
00:32:30
serendipity, and not only as a young person maybe in an
00:32:33
undergrad or an MBA program, but I love your idea that that
00:32:36
serendipity throughout your career is also where you find
00:32:39
maybe the things that you care most about. - For
00:32:41
sure. One of the challenges we have in the tech industry right
00:32:43
now is that people tend to specialize early. And so a
00:32:47
marketing person will, you know, sort of take the elevator
00:32:50
straight up the marketing shaft and be a CMO, and they may have
00:32:54
ambitions to be a CEO, but they don't have the financial acumen.
00:32:57
They haven't owned the product roadmap. They haven't carried
00:33:00
the revenue bag, so to speak. And so then all of a sudden,
00:33:03
you're trying to find ways to give a senior executive exposure
00:33:06
to these things so that they can capably run the business as a
00:33:10
general manager. And I think the more leverage we get from
00:33:14
technology, the more some of these general leadership skills
00:33:18
are going to matter, because the big, hard calls are going to be
00:33:20
around judgment, ethics, you know, regulations, you know,
00:33:25
data usage, privacy. Like, some of these areas that are
00:33:28
becoming more and more important because of how technology can
00:33:31
leverage them so rapidly. - Yeah, it leaves us to answer the big
00:33:34
questions. - Yeah. And those big or the hard questions are,
00:33:36
that's where the fun stuff lives, you know?
00:33:38
- Yeah, I agree. Thank you so much for our conversation. I really
00:33:41
enjoyed it. Thank you. - Oh, it's my pleasure. Thanks for having me.
00:33:43
- Such a pleasure.
00:33:47
- For more insight from Knowledge at Wharton, please visit
00:33:50
Knowledge.wharton.upenn.edu.

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Episode Highlights

  • PagerDuty's Mission
    PagerDuty helps organizations manage their digital operations, ensuring reliability and availability of technology services.
    “We help them manage their digital operations.”
    @ 02m 06s
    March 21, 2025
  • Leadership Lessons
    Jennifer Tejada shares insights from her eight years as CEO of PagerDuty, emphasizing the importance of an ownership mindset.
    “Act and think like an owner.”
    @ 04m 44s
    March 21, 2025
  • The Importance of Customer Engagement
    Tejada spends half her time with customers to understand their evolving needs and challenges.
    “I spend about half of my time with my customers.”
    @ 13m 13s
    March 21, 2025
  • The Value of Experimentation
    In the fast-evolving tech landscape, the quickest experiments lead to success. 'Whoever experiments the fastest and most efficiently wins.'
    “Whoever experiments the fastest and most efficiently wins.”
    @ 21m 43s
    March 21, 2025
  • The Importance of Board Culture
    Building a transparent board culture is crucial for effective decision-making and support. 'You do not want to be surprised in a board meeting.'
    “You do not want to be surprised in a board meeting.”
    @ 26m 50s
    March 21, 2025
  • Career Advice for Young People
    Navigating professional paths can be daunting; embrace serendipity and explore diverse experiences. 'What if I could?' instead of 'I think I should.'
    “What if I could?”
    @ 29m 37s
    March 21, 2025

Episode Quotes

  • Act and think like an owner.
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation
  • If you love what you do, you never work a day in your life.
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation
  • Whoever experiments the fastest and most efficiently wins.
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation
  • Be the bear. Jump into the river every now and then.
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation
  • You will never say to yourself, 'I tried too many new things.'.
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation
  • How do we stop and reflect so you feel like you’re in that current?
    Jennifer Tejada CEO of PagerDuty on Leadership, AI, and Digital Transformation

Key Moments

  • PagerDuty Overview00:23
  • Leadership Insights04:23
  • Customer Engagement13:03
  • AI Disruption19:11
  • Fast Experimentation21:43
  • Board Transparency26:50
  • Career Exploration29:37
  • Embrace Serendipity32:30

Words per Minute Over Time

Vibes Breakdown

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