Hi everyone. I'm Maggie McGrath, senior editor at Forbes. On this episode of C-Suite Unscripted, we sat down with Jennifer Tejada. She is the CEO of PagerDuty, a publicly traded company that helps other companies manage their tech emergencies. We talked about how chaos is inevitable in the age of agentic AI, and also why she feels it's so important to get 8 hours of sleep and to say publicly why she does this. But, I think my favorite part of this conversation was the part where Jennifer talked about the time she used M&M's, the candy, to make a career decision. Let's dive in.
You have been CEO of PagerDuty for 10 years, almost. Your anniversary is later this year. I'm wondering, just to give our viewers a sense of what you do, can you kind of compare and contrast where the business was when you took over as CEO compared to where it is today, including there was an IPO in the middle?
Yeah, I mean, the business was very small when I joined. It was founder-led, venture-backed, private. It was less than 50 million in ARR. We were less than 200 people. And it was very much a self-serve, bottoms-up, developer solution that helped developers manage their products and services more effectively when they weren't working the way they expected them to work. And the idea was that you would get ahead of a technology emergency before it became a big problem for the business, and importantly for customers. What I found really interesting and compelling about that was so many companies that I've worked with, digital operations, digital transformation has been my playground from a career standpoint. We're going through these massive transformations from brick-and-mortar customer engagement, physical brand deployments to more of a digital brand experience. And there's a lot that has to happen behind the scenes to ensure that every digital brand experience is perfect and wonderful and has the consumer or the customer coming back over and over again. And PagerDuty was collecting a lot of data on why things break, how they break, where the dependencies are, what's required to diagnose them and fix them, but wasn't putting it to work with AI. So even back in 2016, I had this vision that we could take that proprietary data set and put it to work in service of automating a lot of the diagnostic and the triage, and ultimately the resolution of what we now look at as major incidents. So the business, we grew it over time. In the early days, people wondered if it could be a stand-alone business. And I think my perspective, having worked in a lot of other industries, both in software and on the enterprise business side, I just saw this massive total addressable market of large enterprises, the most important brands in the world, that are still going through digital transformation and now being asked to nearly overnight convert their businesses into AI-native businesses. So it's been a really interesting leadership journey, because it hasn't been just about growing the company and pivoting our strategy, but also about demonstrating that we have the enterprise resilience to serve the largest companies in the Fortune 100 and the Global 2000, as well as the most innovative AI-natives and startups. It's been about growing our leadership and providing grounded advice on how to make the leadership transition that has to accompany the technology transition. And now that every company is a technology company, what we do, digital operations and AI operations, is essentially enterprise operations. So it's been a rewarding journey, because my vision hasn't really changed, but the pace of technology has made it more interesting and intellectually challenging every year.
So many follow-up questions, but I want to dig into the technological emergencies that you referenced, or when things break. Yeah. Because we, for this series, have talked to cybersecurity CEOs. We've talked about malicious actors who are going after companies and demanding ransom and really wreaking havoc. How much of your job is helping companies guard against those external threats versus maybe it's just something breaks, as you said, when they're implementing a new AI technology and your technology then has to come in and disentangle an own goal, so to speak.
I think the most important thing for a large enterprise or mission-critical software provider to understand is that chaos is inevitable. These major issues where something doesn't work the way you anticipated it to work, which then leads to significant business impact, brand disruption, customer disappointment, these things are going to happen because humans are imperfect, software is imperfect, AI is imperfect, and the systems we use to run businesses and deliver brand experiences have become increasingly complex. They're not manageable by humans. They require a lot of telemetry, diagnostic, learning, and understanding to pick apart the driver. The PagerDuty platform doesn't discriminate between whether the genesis of an issue is from an external bad actor, an internal malfunction, or the collision of multiple events that become a major incident. We're all about identifying anomalies early, getting to a diagnosis quickly, and as automatically as possible resolving the issue before it impacts the end customer or the blast radius expands to financial or customer impacts. And it's also about learning. Every incident is a huge opportunity to learn. That chaos leaves us with phenomenal lessons that we can action to prevent more fragility in the future. Now boards, audit committees, and CEOs not only understand the importance of enterprise resilience, but they're prioritizing it. There's investment moving to these areas, and there's a leadership challenge because with enterprise resilience comes operational and leadership resilience. You have to be prepared for the unexpected and anticipate these emergencies, because how you respond demonstrates your commitment and care for your customers.
Whether you're talking to your customers or you serve on boards, you're an investor yourself, you kind of have a pretty wide purview on technology leaders and business leaders in the country. What's your sense of how attuned they are to these risks and the need to mitigate them? Are you still in the convincing phase when it comes to potential customers, or is all the interest inbound?
People generally underestimate the blast radius of a major incident. I think we're so used to customer forgiveness. A mobile network goes down, and after three days consumers forget. But what happens when their contract comes up for renewal? Do they have a long memory around that reliability? As barriers to entry in consumer products have come down, customers vote with their feet quickly. If their transaction gets stuck, they switch to another app. That switching cost is low for the consumer but high for the brand. I learned at Procter & Gamble that when a brand fails, the customer doesn't blame the supply chain or the technology vendor. They blame the brand. Trust is the new currency, especially as we release agentic agents and use more AI. Enterprise resilience drives trust. So CEOs understand it. I'm being asked by many CEOs how to operationalize trust and build resilience posture so that when things happen, they can ensure the best outcome. That's a proactive stance. Hope is not a strategy.
Now, you said earlier that chaos is inevitable when you're stacking technology or bringing in new systems. I want to tie that to the dollar value risk that you were just alluding to. Obviously, there is money lost when there is a technological breach or when something breaks. But as a consumer, I expect a certain degree of something going down. I'm resigned to it. But what do you place as the potential dollar value? Is there a maximum figure you cite when talking to folks about this could cost your company X billion dollars?
Well, in the last year, major incidents are up 43% across our platform, and we serve two-thirds of the Fortune 100, half the Fortune 500, and more than half of the Forbes 50 AI leaders. The average incident costs our customers $800,000. Multiply that by the number of incidents a year, and you're talking millions in initial disruption, not including the long tail. Every generation has lower expectations around data privacy, but there is an expectation of a delightful experience. In e-commerce, I pay attention to shopping cart abandonment due to slow processes. In fintech, transactional velocity slows, money doesn't move, trades fail. These are big financial issues. Having said that, humans are adaptable, but we need a vigilant, resilient posture because the bad actors have the same access to AI. Leadership must involve anticipation, scenario planning, practice with tabletop exercises. It's one thing to have a playbook, another to execute it under public scrutiny.
In talking about the way that PagerDuty has grown since you've become CEO, you mentioned AI when referring to the early days. Obviously, this technology wasn't invented just two years ago, but the rapid scale over the last few years is different. Was AI part of the business plan from day one of your tenure?
Absolutely. The reason I joined was to leverage that data set to automate. Initially we used machine learning and analytical AI to consolidate and correlate information. Then we used AI to automate workflows and help customers recognize similar incidents and resolve them. We graduated to generative AI and launched PD Advance quickly because our data was well engineered. Now you can ask the platform in natural language about past incidents, the best responder, duration, impact. This year we released five agents, including an agentic site reliability engineer and an agentic scheduler. We've reduced toil for human responders, who range from developers to CEOs. I've had CEOs call me after being paged during a major incident, or even complain that they weren't paged. So AI has been core to our product, helping customers detect and prevent major incidents before they have long-tail implications.
It's your job as CEO to be proactive. The pace of agentic AI development has surprised even me at Forbes. Is there anything you're surprised to say you're doing with AI?
I'm surprised at how quickly some employees have embraced AI to do magical things. The best ideas come from functional experts, not just technologists. They use AI for marketing content, customer engagement, research, simulations. We're seeing this across all departments. It's a little scary but exciting. There's a huge premium on good judgment. You can't just do whatever the agent says. We need guardrails and a culture of care for data security. AI is the new operational risk layer in business. We don't fully understand its potential or risks. Leadership requires a growth mindset. We're working with native AI startups and frontier LLMs to learn. We don't know the full potential. There's a lot of bluster out there. Is it real or just product marketing? Risk is two-sided: we have a responsibility to mitigate, but using risk as an excuse to go slow is losing. I have empathy for CEOs trying to balance moving fast with their boards, worried employees, and unproven ROI. Every CEO needs to understand compute costs and infrastructure. This is a business and financial problem, not just tech. I'm proud of our agentic SRE, but more interested in how we redefine business operations as AI operations and prepare leaders for a different reality.
As I listen to you answer, I'm struck by how much you mention learning and evolution. How important is it for you as a CEO to be curious or have a learner's mindset? Is that a fair conclusion about your leadership strategy?
Yeah, my team would say it's the best and worst thing about me. I'm constantly ideating and asking questions. I can go from 60,000 feet to six inches quickly. One thing I learned early is to understand what drives people. I like being on a steep learning curve. I enjoy being in the arena because every day is different. Learning is a currency you can constantly accumulate. Being in an industry that's always changing keeps me motivated. There's no shortage of things to learn, from financial services to AI natives to energy requirements. I'm always trying to figure out the biggest problems and how we can help solve or prevent them.
As you think about your leadership journey, you became CEO of a founder-led company, went through an IPO, and now we're in the age of agentic AI. You said learning happens within chaos. Is there a critical moment that shaped how you approach being a CEO?
In my first CEO role, I was afraid of making mistakes. I woke up every day fearing something I couldn't handle. I overprepared to cope with that fear. In my second CEO role, I realized I could never know everything. The emotional energy I gained by letting go of that fear and being open with my team was huge. Now I'm direct about what I don't know. That level of directness is jarring for some, but it's better than false confidence. It's not for everyone.
We'll get to your career history, but I want to ask about something I've heard you say: you will cancel workouts and hangouts for sleep. I don't hear many CEOs publicly saying they need seven or eight hours. Why is it important to not just get the sleep but to say it publicly?
I'm not like a lot of CEOs. I didn't fit the mold when I took a deep tech CEO role. I've learned that what works for peers doesn't work for me. I used to be proud of operating on four or five hours of sleep, but when I looked at the quality of my operation, I wasn't optimizing. When I became a mother and CEO, things changed. My health is the infrastructure of my performance. If my health fails, it's bad for the company. So I changed my habits. I organize around sleep, cancel meetings, prioritize workouts. I choose hotels based on yoga mats. Your health is the infrastructure of executive performance. Elite athletes don't treat their bodies poorly. I learned the hard way that sleep and health are not optional.
You're making me feel better about an email I sent earlier. Someone asked about a meeting at 6 vs. 9 p.m., and I said let's do 6 because I want to be in bed by 10. Then I second-guessed myself for being too candid.
If you're not annoying 10% of people, you're probably optimizing for the lowest common denominator. You can't please everyone. It's inefficient to perfect the last few percent. Focus on the most important customers, strategy, and talent. I remember Andre Iguodala saying, 'Do your job.' How you accomplish it is up to you. Block out the noise, reflect on what's important, and build a micro customized plan for yourself. There's technology to support that.
Well, I think it's interesting to see where people come from and what they learn. Was your first job out of college at Procter & Gamble?
Yes, it was a happy accident. I planned to go to grad school in healthcare administration, but the industry deregulated and opportunities dried up. P&G reached out because of my golf and leadership background. I had no idea what they did—I researched them via microfiche. But what struck me was the high quality and integrity of the people. P&G is one of the best leadership academies. I worked on Pringles and other brands.
I had some crazy jobs in my leadership rotation—working on Pringles, Folgers, Jif in inner-city Cleveland. It was unglamorous but taught me to never lose sight of the customer. Whether it's a dairy cooler in Cleveland or a CEO of an investment bank, your job is to understand their pain and prioritize how to serve them.
