“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

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This month, we chatted with Jennifer Tejada, CEO and Chairperson of PagerDuty, the digital operations management platform trusted by over 33,000 customers worldwide. Jennifer joined PagerDuty as CEO and Chairperson in September 2016 and has led the company through its IPO in 2019 and significant growth in the digital operations space. Jennifer has three decades of leadership experience - from marketing consumer products to delivering disruptive cloud and AI -centric software solutions. She has a successful track record in product innovation, optimizing operations, and scaling public and private technology companies. Prior to her role at PagerDuty, Jennifer was CEO of Keynote Systems, where she led the company to profitable growth before its acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading its global strategy, product and marketing  orgs up to its acquisition by ABB. She has also held senior positions at Procter & Gamble and i2 Technologies. Jennifer currently serves as a board member and the Nominating and ESG  Chair of The Estée Lauder Companies Inc. (NYSE: EL).

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1. You joined PagerDuty as CEO in 2016 when it was primarily known as an alerting tool for developers. How did you approach expanding the vision to become a comprehensive digital operations management platform, and what were the biggest challenges in that evolution?

When I joined PagerDuty in 2016, we were in high-growth mode with under 200 employees and 8,000 customers who often graciously appreciated us for saving their sleep, sanity - and even their relationships. Today, we’re an AI-centric enterprise platform supporting mission-critical operations for more than 33,000 customers around the globe and across every major industry. Nearly half of the Fortune 500 and the Forbes AI 50, and approximately two-thirds of the Fortune 100, rely on PagerDuty. 

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One significant challenge as we scaled - and frankly, a fun one - was expanding our vision without eroding the magic of our original incident response experience. We doubled down on reliability and resilience while building toward what was clearly coming: AI-driven operations at scale. That meant investing in platform capabilities, launching the PagerDuty Operations Cloud platform, releasing our generative offering and first agents and educating the market without compromising developer love. 

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2. Taking PagerDuty public in 2019 was a major milestone. What were some of the behind-the-scenes challenges of preparing for the IPO, and how did you maintain company culture and focus on customers throughout that process?

An IPO is like preparing for a wedding. There are a lot of people, plans and opinions, and meanwhile you have a day job to manage. You’re under a microscope with bankers, lawyers, auditors, lining up six quarters of guidance while driving innovation, keeping customers happy and overcommunicating to employees.

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The roadshow itself was an 11-day blur: San Francisco to Chicago, King of Prussia, Baltimore, Boston, and New York. Twilio’s Jeff Lawson sent us a karaoke machine, to release some energy. In Boston, our CFO Howard Wilson and I riffed on a “Shallow” duet (Lady Gaga would cringe), and the IPO team would cycle through their favorite hits from Eminem and Queen to  “American Pie” on other stops. You learn a lot about a person from their karaoke “money” song. In fact we covered a lot of ground together, including a heated debate in Baltimore on the “risk management” merits of eating oysters pre-pricing day.

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The unsung hero of our IPO team was a Morgan Stanley analyst at the time, Michael H., who somehow always anticipated that a protein shake, soy latte, or honey-lemon tea was exactly what I needed, when I needed it, as well as a fresh bottle of sanitizer after every 30 handshakes or so. 

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After full days of investor meetings, we shared photos and videos with the team, and held weekly all-hands to explain the why, the plan, and what wouldn’t change: customers first, roadmap intact. The culmination was ringing the NYSE bell with 130 Dutonians, customers, board members, and our mascot, an animated green “Pagey” who garnered their own IPO coverage from CNBC. 

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The travel triggered an old back injury from my college golf days. And frankly the biggest personal challenge was having untimely back surgeries between roadshows. It was a wake up call. Since then, I’ve made meaningful changes — protecting my sleep, insisting on exercise, being intentional about nutrition, and preserving regular time to recharge with family and friends. 

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3. What’s your approach to AI transformation and what are some of the ways PagerDuty is specifically using AI to transform its own operations? 

AI is the defining opportunity of our careers. It’s both a little scary and incredibly invigorating. Unlike prior waves of innovation, like mobile or cloud, everyone has access to hugely powerful tools with low barriers to entry, and we are all learning and applying this tech at a faster pace than I have seen. 

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At PagerDuty, we have been investing in AI, starting with machine learning, since late 2016. We understand the power of well-engineered data and automation. With the advent of generative AI, we invested early in a secure, internal-only environment where every employee could safely experiment with multiple tools. Engineers using AI-assisted coding tools have increased throughput 25 percent on average. Employees report saving at least two hours a week on average and share experiments and wins in Slack channels to quickly scale what works. We are moving from experimentation to transforming our operations as a company, and there are no sacred cows. 

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We are using code assistants across development to augment our building. In our latest innovation release, we shipped more than 150 platform improvements and a suite of new AI agents that have already helped some customers resolve incidents up to 50 percent faster. But it wasn’t AI that made this release special, it was the efforts from our team to kick off a Customer Love sprint to attack some of the most popular requests we get from customers and ship them. People make the magic. AI helps you magnify and scale it faster than ever.

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Maybe the biggest lever is process redesign. AI and automation gives us the power to revisit everything we do that is manual and high friction, empowering subject-matter experts to move faster. As AI changes the work, we’re evolving the organization to match. 

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4. What do you wish startups knew about doing business with your organization? When startups fail to get PagerDuty as a customer, why and where do they typically fail?

PagerDuty is a public company with a startup soul. We were founded by three Amazon engineers to solve a very real pain point. Our people are highly empathetic, earnest and can-do. 

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If you’re a startup selling to us, show that you value trust as much as speed. We’re building an enduring, sustainable business and we expect the same from our partners. Come in curious, with a crisp value proposition, a clear understanding of our business and a willingness to collaborate. Don’t tell us and sell us, show us how you can help us achieve our mission better, smarter and faster.

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And a few tips: No slides. I hate slides. ;-) Concise memos? Yes please. Random cold emails, no thank you.  

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5. You've been in the CEO chair at PagerDuty for nearly a decade and at Keynote Systems for a few years before that. What have been some of the ways you’ve evolved as a leader in that time? 

There’s no “next promotion” for a CEO. Instead, you learn from each chapter and every stakeholder as the company stretches to meet new opportunities. You are constantly reinventing the company and yourself.

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The last five years brought a lot of chapters: pandemic, remote work, social upheaval, interest rate and geopolitical instability, macro uncertainty. Many CEOs will tell you they’ve seen more crises in five years than in the prior twenty.

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I’ve had to get even more comfortable making decisions with incomplete data and adjusting quickly. Now is the time to kill bureaucracy and move quickly and intentionally. And to leave your previous playbooks behind because there are new ways to attack old problems. 

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6. What's the best advice you've received - or given - about how to manage people?

Hire people who hate to lose, and flourish on a team. Hire people who are so smart they scare you and don't get annoyed when they challenge you. Lean in. 

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People want clarity on where they’re going and why it matters. Set clear expectations. Holding a high bar as a sign of respect. Make sure your teams have the tools and support to do their best work. 

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Lead with curiosity, not judgment. Often, what looks like a performance gap is actually a clarity, resource, or support issue that you can solve together. Active listening helps. You have two ears and one mouth for a reason.

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Create an environment that supports efficient risk-taking. The most expensive experiment is one that never ends in a rigorous evaluation and (if warranted) implementation.

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For newer managers, remind them that if the members of their teams are successful, then they will be successful too. 

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And never underestimate the power of a simple thank you. Celebrate the small wins along the way - building a company is hard work, and people need to feel valued and recognized for their contributions. Written or short thank yous go a long way. 

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7. Describe one pivotal moment in your career that was truly defining for you - an opportunity that changed your life, or a moment where you recognized defeat and changed course.

I am a CEO because a sponsor said, “Jenn, why aren't you a CEO?” I thought I liked being a strong number two, handing all the hard stuff up and going home to put my baby to bed. He pointed out that I never brought problems, only solutions. He started giving my name to recruiters. 

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Soon after, I assumed my first CEO role. It was frightening every day and exciting at the same time. I am convinced I was pretty terrible at it at first but like my sponsor told me, I was actually more ready than I thought I was. Being pushed towards this role crystallized the difference between mentorship and sponsorship for me. Mentors advise and sponsors advocate, putting their reputations on the line to open doors. 

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8. What's a piece of advice you would give to yourself 20 years ago, if you had the opportunity?

No matter how talented and ambitious you are, you cannot succeed alone. Build a peer network with intention. Surround yourself with people you respect and admire. It’s not optional. 

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Raising a child an ocean away from my family, with a supportive partner who also had a busy career, meant I was heads down in my day job while at work. After returning to the United States from Australia, I shifted my approach to make networking part of my job. 

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Now I dedicate a set portion of my time to engaging with other CEOs. These relationships are critical to the success of my company - whether for commercial business sponsorship, raising capital or guidance for new challenges. And for learning, sharing ideas, and sharing empathy. It can be a lonely job but only if you let it.