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

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent? 2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally? 3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities? 4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this? 5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here? Items Mentioned In Today’s Show: Jennifer’s Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is the 20 Minute VC with me, Harry Stebbings, and I'm diving straight into the show today because all who know me know I love enterprise. And today I'm joined by one of the leading enterprise CEOs of our generation, Jennifer Tejada, CEO of PagerDuty, the company that provides a real time operations platform, ensuring less downtime for your digital services. And prior to their IPO in 2019, PagerDuty raised funding from some of the best in the business, including Excel, Andreessen Horowitz, Baseline, Bessemer and Harrison Metal, to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems, leading to their acquisition by DynaTrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at MinCom, leading to their acquisition by ABB. If that wasn't enough, Jennifer's also on the board of the Estee Lauder Companies Inc.

• 0:44Harry Stebbings?

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• 1:26Harry Stebbings?

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• 2:10Harry Stebbings?

  Relationship and there's nothing like meeting face to face and there's nothing like Zoom to make that happen. Zoom lets you connect and do business across town or around the world. Zoom ties together all your communication needs into one easy platform for video conferencing, for video calls, group chat, webinars and your conference rooms and connect easily from anywhere, your mobile phone, your laptop or conference room itself. Zoom is how business gets done today. Get your free account at zoom.com today. Meet happy with Zoom. That's quite enough for me though, so now I'm very excited to hand over to Jennifer Tard, a CEO at PagerDuty.

• 2:47Speaker 01

  You have now arrived at your destination.

• 2:51Harry Stebbings?

  Jen, it is such a joy to have you on the show. As I said, I heard so many great things from Ethan at Bessemer and from Samir at SendGrid. So thank you so much for joining me today, Jen.

• 2:59Speaker 02

  Well, it's my pleasure to be here, Harry. Thanks for having me.

• 3:01Harry Stebbings?

  I've been excited about this one for a very long time. So I do want to start this day with a little bit of context on you and how you made your way into the wonderful world of SaaS and tech. So how did you come to be CEO, the game changer and now public company that is PagerDuty in a very succinct three to four minutes? What an unfair question.

• 3:18Speaker 02

  Well, some of it was luck and some of it was hard work and some of it was having the right network and being really clear about what I wanted. I mean, I started my career right out of college at Procter and Gamble. So I have a consumer marketing and sales background, but I learned in that role how to work through partners because P and G really relies on channels to engage with their consumers. And at the time, the internet was kind of starting to happen and I wanted to be a part of the future as opposed to the past. And so I took a leap and went to work for a fast growing company called I2 Technologies. And it was supply chain automation, which is really odd place for a consumer marketing person to go. But what was really interesting to me was that it was a highly quantifiable value proposition.

• 4:01Speaker 02

  You go in and say, your supply chain costs this many million dollars. If you automate some of that with software, it can cost you 30, 40, 50% less. And I just really felt like that was a value proposition people would be able to get their heads around, even though you were delivering it through very complex technology. And I saw the opportunity to. leverage technology to be disruptive as well. And that was my introduction to tech and I sort of, despite living in a couple of different countries and moving around a lot, never looked back and have always felt at home here. PagerDuty was an interesting opportunity because I had just sold my last company and had been acquired by Compuware and Dynatrace. And I really wanted to get back into building and growth because I had experienced that at I2

• 4:43Speaker 02

  and I'd gradually gone to bigger and bigger companies and felt like I was improving things, but not really disrupting markets. And so I set out to meet as many of, I think, the most well-known investors in the market. And I think a lot of people think I've been around the valley forever. I was really kind of a valley outsider. I moved back from Australia in 2013, so I had to sort of build a network from scratch. And that allowed me to sort of look at the market very analytically with quite an open mind and kind of carve up the landscape to figure out where I thought there were the best growth opportunities that my skill set suited. And PagerDuty was a little bit unlikely because I was looking to move back more into maybe consumer or B2B2C.

• 5:27Speaker 02

  And what I loved about PagerDuty though is it's very platform-esque. It's designed to improve the lives and the work and manage time effectively for our users. And developers are so innovative in their own right. As customers, they're super influential in how our product ebbs and changes and evolves. And at the same time, we're delivering a platform that really helps enterprises deliver their customer experience to their end consumer, end user. And so very important, I think, place and role amidst we're seeing as, I think, seismic acceleration and digital transformation right now. So, you know, a little bit of right time and right place, a little bit of being really clear about what I wanted to do,

• 6:08Speaker 02

  knowing I wanted to go back into growth, knowing that probably the growth stage was a good stage for me. I'm like not so good in a garage. I like resources. I want teams, but at the same time, I wanted to build. And I think being really clear on that helped me to identify a lot of opportunities.

• 6:23Harry Stebbings?

  Can I ask, in terms of kind of growth and development for your skill set there, as you mentioned, and choosing PagerDuty, this is slightly unfair of me to ask. Well, but I'm intrigued because I get a lot of graduates who say to me, Harry, I'm looking at the ecosystem today. And I'm not sure whether I should join a startup, I should start a startup, or I should really learn at a growth stage company or a public company like PagerDuty with incredible employees. What do you recommend, Harry?

• 6:46Speaker 02

  I would recommend that graduate startup, PagerDuty.

• 6:50Speaker 02

  But there there's a reason for that, and that's that PagerDuty has an explicit strategy around growth and development. And we're making significant investments in training and educating not just our entry level people, but also our executive and senior management staff. And I learned that lesson from P and G, that if you want to build a phenomenal organization that really is customer centric and can continue to grow and evolve, no matter what the market throws at you, you have to invest in developing your people. And not just the technical skills, but also management and leadership skills, self discovery and self learning. Anything from speaking to problem solving, there's an opportunity to invest in people and help them develop their own capabilities

• 7:33Speaker 02

  and their careers within their adventure inside your company. And in our case, that's PagerDuty. I worry that a lot of organizations in the tech industry are not investing in growth because they hire people off the street and expect them to be expert and come in and do what they need to do. 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. As you said, a lot of graduates are choosing to maybe start their own company, to go to an early stage startup, etc. And these companies, you're going to learn a lot on the job, but you may not necessarily learn some foundational skills

• 8:12Speaker 02

  that you need to be a great leader, like how to attract talent, how to interview a new recruit, how to develop a human being, how to set goals and expectations for individuals and for your team, how to manage difficult performance conversation, how to set a vision, how to engage others in your vision. I mean, these are things that actually can be taught in a structural foundational way that can live with you for a long time. The other thing I would say is that we tend to be in such a hurry, in such a Fast paced world and one of the things I appreciate about COVID, if there is anything to appreciate, is it has kind of put us in slower motion at home and in our personal lives. We're not traveling and racing around the world.

• 8:52Speaker 02

  But the same thing is true for thinking about your career. I think young people tend to want to take the fastest form of transport up to the top, take the elevator straight up. And what I'm seeing in the market is a lot of people who come to us and want to be in senior executive positions, but have a very narrow functional expertise and skill set because they haven't worked across other functions within an organization. And part of that is because of the way technology companies are structured. They don't, they tend to be very functionally centric as opposed to having different BUs or different businesses where you could try your hand in owning and managing a P and L and really being in the general manager that runs that organization, which I had that opportunity in consumer goods and I think a lot of

• 9:37Speaker 02

  companies and industries in the world do offer that opportunity that where you see young employees going in and doing what we call management rotations or people taking assignments where they run divisions in other countries or they run business units where they can learn a different skill, whether it's supply chain and logistics or it's marketing and advertising or it's sales or it's product management, product development or customer success. And you just don't see employees being encouraged to cross train as much anymore because of that hyperspeed desire to get to the top as quickly as possible. And I think we're cheating the industry by not building leaders and developing and designing leadership roles that include that kind of rich experience that you get from

• 10:19Speaker 02

  working in different functions with different types of people with different types of skill sets. And I have to tell you that 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 deliver, how each function works, what are new ways of doing things, what are more antiquated ways of doing things so that you can help coach the executives around you. You by no means need to be an expert in every function, but you need to know what good looks like. And I think it's hard to get there when you're observing that functional discipline from a distance.

• 10:57Harry Stebbings?

  You mentioned that impatience and it's something that I've always struggled with. So I'm gonna ruthlessly use your knowledge and advice here for my own personal gain. But I've often and very likely been offered amazing opportunities throughout career, which is very, very grateful for. But I'm often stuck in the quandary of go slow to go fast, don't take on too much, don't be too aggressive. Make sure what you have now is working before you move on to the next thing or earn the right to do the next thing. Versus, hey, you'll always underestimate what you can do, run fast, charge. How do you balance between the two? And I guess, what would you advise me, Jen?

• 11:31Speaker 02

  Harry, I think it's not so much a fast or slow thing and it's more about being aware of what you're truly motivated by. Like what you intrinsically are inspired by in your life and in your career. And in my case, I learned pretty early on that the thing that gave me the adrenaline rush, that got me inspired, that got me excited in the morning was to see how much I could learn in the shortest time possible. I wasn't as driven by money or power and authority or title or even public exposure. I was more driven by how rich can the learning experience be? And how can I get opportunities where I can take on more things, where I can learn really quickly, but also demonstrate mastery in the form of value?

• 12:13Speaker 02

  Like, am I having a personal impact on my team? Am I having a personal impact on my customers? Am I having a personal impact on my company and my industry? And so that has sort of led my decision making on, do I feel like my learning is stagnating? Maybe I need to try something different. Do I feel like I'm overwhelmed and I'm actually not adding value? Maybe I need to slow down until I can really see some fruits of my labor. And by doing that, I'm really playing my own game and I'm setting my own pace. As opposed to letting all of the externalities, many of which are sort of vanity centric, as opposed to sanity driven, drive how I feel about my own growth and my own development in my career.

• 12:56Speaker 02

  And that's worked really well for me, but it really comes down to knowing what you're motivated by. And I can't tell you how many conversations I've had with leaders in my business or people that I've mentored. Where they wanna know, should I go do this thing? And the first thing I'm asking them is, well, what are the things that make you really happy at work? And make you feel that you have a sense of purpose and deeply fulfilled and inspired? And what are the things that you don't really like to do? And that sounds like a really mundane tactical question to ask, but I'm always surprised by how many people aren't able to answer that readily because they're so focused on what they should do, what they must do because other people have set those expectations for them. And this idea that it is a race.

• 13:39Speaker 02

  Honestly, you're gonna be hard pressed to find many tech CEOs, particularly in deep tech, who have as different of a background as I do. But I was a CEO in my early 40s, so I think I did okay. And I'm still learning and I still feel like there's so much more for me to do, even as I chalk up decades of experience. It feels funny to talk about that, but I do know what drives me, I guess.

• 14:03Harry Stebbings?

  You know, often something that is a limitation on people in terms of, they maybe know that they're really happy doing X, but the risk is much greater. It could be leaving a certain role, it could be pursuing their dream, whatever that is, but the risk is the thing that stops them. And that's with me. And Ashen, how do you think about risk assessment yourself?

• 14:22Speaker 02

  My younger sister gave a toast at my wedding and one of the things she referred to was me being the risk taker in the family. So I may not be the most balanced person to ask on this subject, but I've always taken the perspective that 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. And I grew up in a series of small towns and went to a really giant state school and then went to work for a really big company that moved me around the world. And as I mentioned, I've lived in a number of different continents and countries around the world. And I've learned to embrace the adventure that comes with risk and see that as a learning opportunity, as opposed to focusing so much on what can go wrong. What's interesting though is since I've taken the company public,

• 15:05Speaker 02

  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 term risk. Management and ultimately what that leads you to is kind of fear based decision making. And so I'm finding myself having to be really aware of that, trying to catch myself when I sort of fall into that trap. And really trying to continue to look at the long game because at the end of the day, I think trying to compartmentalize risk in a really manageable way can be super helpful to psychologically getting past it. So I often ask myself, what's the worst thing that can happen? Let's say I take this job and it goes terribly and I get fired.

• 15:47Speaker 02

  Like, will I be able to get employed again? Absolutely. Yeah, I'll be able to find another job. What's the worst thing that can happen if I take on this project and it fails miserably? Like, maybe I'm embarrassed for a couple of weeks, but will I find another project? Sure. And so working through in a really logical way, like, what's the worst thing that can happen? And how will you recover from that if that happens? On the flip side, like, what's the opportunity on the other side of that? And that's what I get really excited about. The other thing is, I think we often think that something is a risk when it really isn't. It may be conventional wisdom that to go off and not be an accountant or not be a lawyer because your parents were accountant and lawyers is really risky to go work in tech. But at the end of the day, I think everybody has their own individual path.

• 16:29Speaker 02

  And you have ultimate control over how you navigate that path and how you develop along that journey and what you gain from that journey, not somebody else. And so I really think it's getting increasingly important in such a noisy, media driven, now video driven world, that we all take a little bit of pause and start to reflect and self discover and learn for ourselves what's going to be best for ourselves instead of what the world wants for us. Because if I had listened to what the world wanted for me, I would have done the same job over and over again for the last two decades.

• 17:02Harry Stebbings?

  I totally agree with you. I guess my question to you is, what do you do to isolate your decision making from the world and from the externalities that affect it, be it Wall Street, be it pressures of investors, the team, you name it. But what, like, for me, you know, I go on a walk with my mother every morning, like an hour and a half. And I talk, and I basically just like ask her advice. And that's like the core process for me coming to a big decision. Do you have a process around which you just? You yourself from the world and and really isolate your own decision.

• 17:30Speaker 02

  I do. I really like to be out in nature. And when I lived in Australia, I liked to be out in the ocean. I did a lot of open water swimming and surfing. And now that I'm a little more landlocked, I do a lot of walking and hiking. And so I like to be near a mountain or an ocean or a hiking trail in some way, shape or form, because I feel like when I'm out in the open, my mind is open, my body is in a good, healthy position for my brain to work the best. And I do walk every single day and I do a lot of walking one on ones with my team. 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

• 18:11Speaker 02

  to do lists. So I do try and kind of disconnect myself from the world. My team knows that I have a penchant for skiing and water sports. I like jumping off of things. And so multiple times a year, I try and get away and hurl myself off the side of mountains and just feel that fresh air in my face. And I think while I'm taking on those activities, I also used to do a lot of deep thinking while I was traveling. And I do miss my flying time, to be honest, because I would be there in that cocoon of a seat, just kind of thinking through what I needed to be doing in the next coming months or the coming year. And so I've sort of replaced my flying time with additional walking time or just some quiet time to myself. I find a corner in the house and

• 18:53Speaker 02

  go think on my own. I'm an extrovert, though, and so a lot of my processing happens with other people. Sometimes they don't even know they're helping me process. I feel a little bit like I'm using them. They may think that I'm helping them with something, but I'm actually processing a challenge I've been thinking about for a long time. And I also like to instigate and be provocative with my team. It sort of poke them to think differently. Yesterday, I was particularly torturous in an executive meeting, really pressing them on how we're executing against our strategy and what we're doing well, what we're doing not well. And does that come down to alignment? Does it come down to capital allocation? Does it come down to conviction? Does it come down to COVID? What is it? And I was relentless, let's put it that way.

• 19:38Speaker 02

  But that's part of me processing, which is a little bit selfish sometimes, but I think good for the company that I'm thinking about the long game.

• 19:45Harry Stebbings?

  I mean, I would love to have been a fly on the wall in that meeting, but I I do have to ask, because we mentioned kind of the risk assessment there is one of the kind of decision making elements. The other is kind of doubt and insecurity, I I guess, in a lot of cases, certainly is for me. And again, you mentioned kind of using people and they maybe don't know that you've probably seen a pattern here in terms of my questions and advice. When you think about these decisions and it's natural to doubt yourself. And so I guess my question to you is, you know, it's easy to look at you now and CEO of a paid duty, public company. And the question that I have is like, did you ever doubt yourself in a role? And how do you think about dealing with vulnerability and self doubt?

• 20:22Speaker 02

  Yeah, all the time. When I first came back to Silicon Valley, everybody was talking about this thing called imposter syndrome. And I didn't really understand it because I've always been so open about how much self doubt I have that there's like no secret imposter thing. And I think being open about those feelings that you have, one helps you really come to terms with them because they're out there. Like you're not like sitting on a secret, you're not simmering this kind of hypothetical idea inside your head. You've actually put it out there. I'm constantly doubting myself. 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.

• 21:07Speaker 02

  And frankly, if you're not, I'd be nervous about the level of arrogance and narcissism in a person that isn't questioning. Are they prepared? Are they equipped for the role? Are they doing the right things? Are they making the right decisions? So yeah, I absolutely doubt myself all the time. And the way I manage that though is, and my team knows this, I like to have a lot of data around me. I like to do the analysis, understand parts of the business at a very detailed level, particularly if something's not going as well as I expected to, or if it's going better than I expected it to, I want to understand why. Simon Sinek has the five whys. I probably have seven. It's probably overkill. But I I like to really dig in and understand why something is the way it is, why it's working the way it is or not working the way it is.

• 21:50Speaker 02

  And just having the knowledge, like having the background, having the foundational understanding. Standing of a particular issue or a problem gives me a lot of confidence. I think the other thing that helps you manage self doubt is surrounding yourself by great people. Because I'm never in this alone. I'm surrounded by a phenomenal experienced team. A team that I trust, a team who each in their own right are very good at their jobs and expert in what they do. But also open to new challenges and not afraid, not going to make fear based decisions. As opposed to sort of taking a leap every now and again. And they're also a team that I think are not afraid of the truth, are not afraid to have a healthy debate.

• 22:32Speaker 02

  And that's been something we've had to work on. Like you have to build that muscle to be able to have an uncomfortable conversation within a team and be uncomfortable 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 actually have to build it.

• 22:49Harry Stebbings?

  I have to say Jen, I don't think I've ever done an interview where we've like totally ignored the schedule, but I'm loving this so much. I, I do have

• 22:57Harry Stebbings?

  to double click on, so to speak. And it's like you mentioned that kind of having data and how that supports your decision making and makes you a little bit more comfortable. Leaders today, and you often have to make very big decisions with very imperfect information. How did you get comfortable making fast decisions with imperfect information?

• 23:13Speaker 02

  Yeah, one of the things that's really helped me in becoming more decisive as a leader. There's actually three things. One has been board work. I've been a board director for the better part of 25 years. And 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. And so you get really good at consolidating the information that you have and making a call, making a judgment call, leveraging your experience and your instincts, whether things are going in the right direction or they're not, or the governance that's supposed to be there is or isn't. The management team is asking themselves the right questions, or there are some other questions they should be thinking about, et cetera.

• 23:57Speaker 02

  And so being on boards got me comfortable making decisions with little information. Also having experience working through crises and if you You're in business long enough, you're gonna manage a crisis or two, not the least of which the one that we're in right now. But in a crisis, it's usually time sensitive. There's usually a lot of emotional pressure to fix something. There are people, stakeholders, looking to you for guidance and direction and information that in some cases could be life or death. And you're all having to do this under significant time pressure with very little information. And so the truth about a crisis is it has a beginning and an end. And knowing that after having been through a couple gives you the peace of mind

• 24:39Speaker 02

  to, I think, be calm and weather that crisis as it's happening. And at PagerDuty, I mean, this is what we do for a living, incident response, and helping individuals detect issues quickly and early so that they don't explode into crises, but then manage those issues with cross-functional team members and quickly get to the bottom of them so they can protect the customer experience, protect their business, protect their teams and their reputation in the process. And I think in doing that, you do learn a lot about how to make quick decisions in service of getting the decision made and moving forward, as opposed to getting caught up in analysis paralysis. And then the last thing that has helped me in this is if you look back on decisions that you've made in the past,

• 25:22Speaker 02

  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 just as good and maybe better because you made that decision more quickly and were able to execute more quickly, which might have given you an advantage than when you got analysis paralysis. I think it's much harder when the decision isn't obvious. And that's where you go digging and looking for data. And at some point in time, making a decision is better than no decision at all. And as I've gotten older and a little bit wiser, hopefully, and a little more experienced, I've learned that making any decision so that you're technically running an experiment and can learn something is better than waiting for more information.

• 26:06Harry Stebbings?

  Yeah, no, I totally agree in terms of that, not waiting for more information. I do wanna ask, you mentioned also encouraging debate internally. And it's such a difficult thing to really foster that culture and environment internally where disagreements can be viewed in a productive way. How do you think about fostering that culture and what can one do proactively to say, hey, this is a free space? Bring all of your concerns, issues, problems to the table in a product. How do you do that?

• 26:31Speaker 02

  Yeah, it's not easy and I'm a big fan of Patrick Lencioni, who is famous for his book, The Five Dysfunctions of a Team. He describes an environment where in order to be able to have those uncomfortable conversations and have a, what I call a healthy constructive debate, you have to have a foundation of trust. So I think it starts with making the investments in time, in money, whether it's offsites, it's one on ones, it's thinking about who you hire and what your team needs, but making the investments to build a very strong foundation of trust in a team as a starting point. And then there's the, setting the culture and the values of those teams. So making it clear to the team that we actually do want to focus forward

• 27:16Speaker 02

  and we want to be progressive, we want to challenge ourselves and we also need to hold ourselves accountable. And if someone is not accountable to a commitment, you have to be willing to have enough trust as a team to call them out on that and figure out how to get that particular issue back on track. And then there's practice, right? There's just no substitute for practicing. And I will tell you, like, this did not come naturally to page your duty or to art. I'm from Minnesota and the company was founded by Canadians. I mean, you can't get any nicer and politer unless you added maybe some English people in there. 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.

• 27:59Speaker 02

  And it was a very nice conversation, meetings were very pleasant, but they weren't terribly productive. And we tended to be focusing on the things that were going well as opposed to the big challenges that we really needed to address. And I often felt like I was always the one that was pointing out like, well, what about this thing that's in red? And what about this thing that's in red? And what are we doing about this? Which made me feel like the nagging kind of fish wife in the team. And so we really started to talk about as a team, why we were where we were and what we needed to change to get to a different vision for our team. And that vision is one where we will have a healthy debate, where we can disagree, where we can have a debate in a room, but then even if we don't

• 28:41Speaker 02

  Don't all agree in the end, we align, we sort of quote unquote disagree and commit, I think that's a Jeff Bezos thing. And that has taken practice and every time you add a new team member, you almost kind of go back to scratch. I think about the sort of forming, storming, norming model and 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, forming and storming, forming and storming. And if that's uncomfortable, maybe a growth company is not a great place for you.

• 29:15Harry Stebbings?

  I totally get you and I love that kind of flip flopping back and forth. I do want to ask you, you also mentioned kind of the board management and how that helped your perspective in terms of getting comfortable operating within perfect information. Both sides of the table, if we start on kind of the operator side for you, I guess, you know, from the many years now of experience on the operator side, and I know you obviously sit as independent board member in other companies. But you know, with PagerDuty today, say, what do you think and what's been the big lessons in terms of what does great board management mean to you as a CEO?

• 29:43Speaker 02

  Well, I've had this awesome opportunity at PagerDuty to curate our board, which you don't always get as a CEO, and if you're a founder listening, it's something that I would take very seriously. Because I think of the board as being for the company and for management, where often people think about the board as being governance and oversight. And yes, that is part of their job, but at the end of the day, the board is part of your organization that is trying to set the right strategy, trying to help you execute effectively against that strategy, try to drive share and win in the marketplace. And so when you think about it from that perspective, you tend to think about your board members more as partners than as your bosses, so to speak.

• 30:25Speaker 02

  And in doing so, I think it enables a much more collaborative and engaging conversation on both sides of the table. I mean, there's nothing more boring for a board member than knowing that you're seen purely as oversight and the person that you've got to send reports to and someone that is in the position to manage governance and maybe just hire and fire the CEO or the team. Board members want to be engaged, they want to leverage their skills and their experience. Experience as well and they need reasonable transparent picture of what's going on in a business in order to do that. 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.

• 31:07Speaker 02

  And so if something's going down in the company that's not good or not what we expected, I want the board to know often and early. And likewise, the board gets significant transparency into the underlying drivers of our business and how the business is going. In exchange for that, I also expect from the board calm, cool-headed, empathetic leaders who will help us dissect some of these issues and come up with new ways to think about them, but not necessarily solve them. And I think that's a hard transition when you're an operator going to being a board member. Sometimes you come into that boardroom with your operating hat on and you want to be in decision-making, telling and doing mode

• 31:48Speaker 02

  as opposed to questioning and refining and really helping the management team look at the challenge from all angles. And I'm very lucky, our board is made up of a number of really capable, phenomenal operators who have very complementary skills. And so that's the second thing I would say is in addition to transparency and really having a clear idea of the role the board is going to play in your business and with your management team and frankly with you, also curating the composition of that board and being very thoughtful about what you need, when you need it. And also making sure that board members know, you know, why they're there. I get called, you know, there's been a really big push over the last couple of years

• 32:31Speaker 02

  to get women and people of color on boards. So I get a lot of inbound on boards. And one of the first questions I want to know the answer to is why me? What is it about my background or my skill set that you think could uniquely bring value to this board today? And if they can't answer that question, then I'm going to move on very quickly. Because I think that that means the management hasn't thought through the composition and the complement of the different skills and experiences and the diversity of the board they're trying to.

• 33:02Harry Stebbings?

  Speaking of the board that they're building, in terms of being like an independent board member or a board member, on the flip side, not as the CEO, you know, it's something that I've really tried to scale in terms of learning curves in the last few years joining my first few boards. What would you advise me in terms of what can I do to be the best board member to you, the CEO? What would that advice be, especially given kind of it being the first few boards?

• 33:24Speaker 02

  It's funny because after every board meeting I go to, I self-assess, how did I do today? Was I a good board member? You know, I would say the best board members are very good listeners. They're astute listeners. They're active listeners because they're not just reading the report you wrote them or the slides you're presenting, but they're watching the body language. They're getting a sense for how does the team look? Does the team look fatigued? Does the CEO look inspired? Where do I need to focus my time and attention? Good board members ask great questions, and they don't ask a lot of questions, to be honest. I mean, I think the most phenomenal board members I work with are the ones that ask super insightful questions in the right moment. And when that happens, everybody

• 34:04Speaker 02

  knows it because the whole room kind of stops, or the whole Zoom kind of stops in this case. And they really are provocative and insightful in maybe helping you find another lens to look at the business through, or to look at a problem through. I think great board members are great sounding boards. So without judgment, a CEO should be able to call a board member and really openly share something that's worrying them or concerning them. And unfortunately, like, that's a really, I think for some board members, that's a really fine line to play because you're also responsible for ensuring that the right leader is in place and you are essentially the accountability point for that leader. And so, creating an environment

• 34:47Speaker 02

  of trust where a CEO will call you out of the blue and say, I need help. I'm trying to think through something in confidence. I can't share it with my team. I'm not ready to bring it to the board. What are your thoughts on this? That's a one-to-one, trustful relationship that I think gets built over time, but it can be accelerated based on the behavior in the boardroom. It can also be delayed based on the behavior in the boardroom.

• 35:10Harry Stebbings?

  No, absolutely. And I think it's the job of the board member to really build that relationship and instantiate that level of trust. I do wanna move to my favorite, which as I said, I've never quite wholly glazed over a schedule as much as we have done today. But I've loved the conversation. So I would love to do a quick fire round. So I say a short statement and then you give me your immediate thoughts. Are you ready to dive in?

• 35:29Speaker 02

  I'm as ready as I'm gonna be, Harry.

• 35:30Harry Stebbings?

  Okay, so tell me, what's the favorite book and why?

• 35:34Speaker 02

  I read this book Tuesdays with Maury many years ago. And Mitch Albom is a sports writer for the Detroit Free Press at the time. He wrote the book. And I loved how he talked about spiritual security and how you can feel a sense of safety amongst your family that is very hard to replicate in any other part of your life.

• 35:52Harry Stebbings?

  Biggest challenge of your role with Page's Duty today?

• 35:55Speaker 02

  Staying focused on the paths to growth that we think are gonna have the biggest impact. You know, when you're a high-growth company, you have a lot of opportunities and it's easy to delude yourself in trying to do too many things. And we're always constantly trying to reprioritize and narrow our focus and it gets harder and harder with every quarter that goes past.

• 36:14Harry Stebbings?

  The best CEOs, the best resource allocators, agree or disagree with that being the primary characteristic?

• 36:20Speaker 02

  I'm not sure if it's the best, but I definitely agree it's an important characteristic trait.

• 36:24Harry Stebbings?

  Yeah, no, totally. Who's your biggest mentor and what's been a big takeaway for you from that relationship?

• 36:30Speaker 02

  I have many mentors. I tend to seek mentorship on specific issues as opposed to go to a specific person. Probably because I'm not very good at asking for help and I don't like to burden a single person. But I think my best mentors are the ones that challenge me as opposed to ones that are constantly cheering me on. And that's what I have my parents and my family for. And I like it when a mentor says, you're thinking about this all wrong, or stop feeling sorry for yourself, or snap out of it and focus on the stuff that really matters. I think it's really helpful.

• 37:02Harry Stebbings?

  When I say success, who's the first person that comes to your mind, Jen?

• 37:05Speaker 02

  Lately Scott Cook, I've been spending a lot of time with Intuit, they're a customer, I'm speaking to their leaders today, actually. Scott was at Procter and Gamble and then was the founder of Intuit. And he's created such an incredible legacy of leaders, not just in the valley, but across industries around the world. And still to this day is very involved in what his end customers need and building product. He's just an incredible person to observe and watch and know.

• 37:30Harry Stebbings?

  What would you most like to change about tech and the valley today?

• 37:33Speaker 02

  The diversity. I am tired of being one of the very few females in enterprise software, leading enterprise software companies. And I think we're taking too long and I'm glad the dialogue is much more advanced than it was a few years ago. But we're still way behind where we need to be in terms of creating access and opportunity for women and people of color. And frankly, just underrepresented people in general.

• 37:55Harry Stebbings?

  Sorry, can I, what can specifically be done? Cause I'm so with you and I'm kind of fed up of seeing all the kind of company memos and mission statements. And you're like, great, what now? What are you doing to follow up? Do you know, so what do you think the ecosystem and specific companies themselves can do very specifically to really move this forward at pace?

• 38:11Speaker 02

  Yeah, I think one is to 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 leadership and you go. And you execute a bunch of programs and you check the progress of those programs. And if they're not working, then you adjust. And I think there's been a lot of hand waving and to your point, a lot of talk about setting the tone from the top, but not putting the programmatic operationalization in place within the company to drive true measurable change.

• 38:55Speaker 02

  And that's something that we've been doing a pager duty in the time that I've been there. And the results speak for themselves. I mean, 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. And that came through intention, but also through diligent planning, programming, measuring.

• 39:15Speaker 02

  And constantly getting better and we're still not done. I still think we have so much more to do. But I think treating inclusion and diversity and access and equality as a business initiative as opposed to some cultural or HR or corporate responsibility activity that we need to undertake is part of driving change. And I think the more transparent the industry and companies can be around reporting their progress on diversity and inclusion and things like pay equity, the more peer pressure will create to move the entire industry forward. So PagerDuty is going to release some of that data later this summer to kind of try and help accelerate that process.

• 39:57Harry Stebbings?

  Totally with you in terms of that transparency and what it forces the ecosystem in terms of accountability. I do want to finish though with the final one. The next five years for you and for PagerDuty, obviously long-term horizon thinking, but it's a tough question, but next five years for you and for PagerDuty, what does the picture hold?

• 40:13Speaker 02

  Well, I hope I just continue to get smarter and better in myself and faster, but at the same time not have to do it in a hurry. I think PagerDuty is increasingly making this transition from having been a really well-known, to your point, game-changing product company to a true platform that really helps organizations manage real-time, unpredictable, unplanned and unstructured work wherever it turns up within an organization. So we started in dev, we've moved from dev into IT, into security, starting to see us in places like customer service. But increasingly, the common theme is there's a lot of work coming at people that happens unexpectedly, that's unstructured, but yet needs cross-functional collaboration

• 40:58Speaker 02

  and is time-sensitive and mission-critical because it's in service of the end customer. And that's really where our focus continues to be. I'd like to think that in five years' time, PagerDuty is not only delivered on that mission, but also on our commitment to improve time-sensitive global healthcare and access for people through pagerduty.org to create more equitable and sustainable communities around us by creating access for people who want to have careers in the tech industry. And that frankly, five years from now, we won't be having this conversation because there'll be so many other female and people of color who have reached the CEO role in enterprise that I'll be irrelevant by that point.

• 41:41Harry Stebbings?

  Jen, as I said, I've so enjoyed doing this. Rarely do we totally avoid the schedule. So thank you so much for joining me today. This has been so much fun.

• 41:48Speaker 02

  Oh, it's my pleasure, Harry. And thank you so much for your persistence. It's been a lot of fun and I really appreciate you including me.

• 41:56Harry Stebbings?

  I mean, I just so enjoyed doing that. I literally asked the first question, which was on the schedule. And then all the other questions you heard were not on the schedule at all. Jen was amazing and I couldn't be more excited for the times ahead with Page D C. If you'd like to see more from us behind the scenes, you can on Instagram at H Stebbings nineteen ninety six with two Bs. I always love to see you there. But before we leave you today, I'm sure you've heard about it, but my word, there is a product that I love, Carter. Carter simplifies how startups and investors manage their equity, track camp tables and get valuations. Go to Carter dot com forward slash two zero V C to get ten percent off. More than eight hundred thousand employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration. So you can see real time data in the Carter platform and work with Carter's team of experienced fund accountants.

• 42:41Harry Stebbings?

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• 43:22Harry Stebbings?

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• 44:05Harry Stebbings?

  As always, I so appreciate all your support and I can't wait to bring you a fantastic set of episodes next week.