PagerDuty CEO Jennifer Tejada | Leadership Cross-Training

Hi everyone. Welcome to Grey Matter, the podcast from Greylock, where we share stories from company builders and business leaders. I'm Heather Mack, Head of Editorial at Greylock. Today we're featuring Greylock General Partner Sarah Goa's interview with Jennifer Tejada. Jennifer is a CEO of operations management company Pagerduty, which she led to a successful IPO in 2019. Prior to joining PagerDuty, Jennifer Jennifer was CEO of Keynote Systems, but she spent most of her career as a marketing executive at numerous companies and across several industries. In this interview, Jennifer talks about her experience leading PagerDuty through the last five years and how the company is working with a wide range of organizations today. She also talks about the increasing role of automation across industries and how her background in marketing has given her a unique edge in leadership and communication. The discussion is part of Greylock's Virtual Speaker Series I conversations, which you can hear more of by subscribing to our podcast on SoundCloud, Spotify, or wherever you get your podcasts. Enjoy.

Jennifer is the CEO of PagerDuty, the operations management company she took public in 2019. The company's successful IPO marked the first time in a decade that a female CEO has taken a software company public on the New York Stock Exchange. Being a CEO, while female, isn't the only thing that makes Jennifer stand out, of course, and I'm hopeful that being both of these things at once will soon stop being considered rare. Jennifer is a second time CEO, previously the CEO of Keynote Systems and a longtime tech marketing executive. I've long appreciated her unique ability to communicate in a real, direct, honest and understandable manner. She translates technology for the business world, she has a broad view of it, and she's also a board member at UiPath, Puppet Labs and Estee Lauder. Jennifer is a courageous leader and the measure of courage is not speaking out when others do, but when they don't. PagerDuty became one of the first tech firms to issue a statement against racial injustice following the murder of George Floyd and subsequent violence last year. PagerDuty is also a leader among companies pushing for diversity and inclusion in the workplace, an issue near and dear to my heart, and the company has an equality focused foundation. PagerDuty.org Real Talk is an all too rare quality in the competitive enterprise market these days, but Jennifer has set the Standard under her five year leadership. PagerDuty has grown considerably from beloved brand of tech companies to mission critical tool for business critical operations and its momentum has accelerated with the pandemic era shift to remote work. But I'm especially excited to host Jennifer because I think many still underestimate pagerduty's potential and ambitions. Thanks for being here, Jennifer.

Hey, Sarah. It's great to be here. How are you?

I'm great and we're really excited. It's almost exactly five years to the day since you joined PagerDuty and I remember speaking to you soon after you joined as CEO. A lot has happened in that time. The company had one of the biggest IPO pops of 2019. It's been a wild ride. But before we dive deep into the company, let's talk about how you ended up in tech in the first place because it wasn't your original plan. Can you walk us through the various paths you've taken that have brought you here today?

Sure. And I get this question a lot. I think people are interested in my career path because it is different. And what I hope it is symbolic of is the fact that there are opportunities in tech for all different kinds of people. I have a liberal arts degree from one of the best universities in the world, University of Michigan. But I graduated thinking I was going to move into some form of business management or even healthcare management, because that was what my dad did. The healthcare industry was deregulating at the time, so I decided to take a job to get some experience. And I worked for Procter and Gamble for just under seven years. And what I loved about my P and G experience was it's a company that drives its talent and promotes talent from within. So they invest heavily in leadership development and generally in career development. So I built a very strong foundation in a number of areas of expertise from leadership management, brand management, marketing, product strategy, et cetera. In less than a decade there. And that positioned me really well to look at big problems to become a general manager, but also positioned me well to be flexible. I've worked in a lot of different jobs. As soon as I left P and G, really the impetus for leaving P and G was to join the tech industry. I joined a supply chain automation company, which wasn't really obvious given I was a consumer marketer. But I love value propositions that are highly quantifiable. And it just made so much sense to me that if you start with a supply chain that has a lot of waste in it and use software to automate the system and all the players in that value chain, you can actually create demonstrable cost savings and value for customers. And so that was my first experience in software, was a high growth company Called itwo. I was the head of marketing there. I had terrible imposter syndrome and was way over my skis in terms of what I was doing. But I had that foundation of great leadership and how to build an organization, how to manage people effectively, how to think about positioning your brand. And from there, you know, the tech industry was just a part of who I am and you know, something that I've done for a long time. I did a short stint in private equity. I was the CMO of a public telco. I went in and became the number two in a private equity backed software company, the largest enterprise software company in Australia. Sold that to a large multinational engineering firm and decided I really wanted to get back into growth, I wanted to go back into building. And so I set out. I returned from over a decade in Australia to San Francisco and set out sort of looking at different roles. Keynote Systems was really interesting transition because it was private equity backed, it was a company I took private with Thoma Bravo. But a great way to sort of cut my teeth going from being the number two to the number one leader in a company. And yet I still found like it wasn't growing fast enough. It was an orientation around EBITDA and profitability and I wanted to build again. So I turned to the people who are funding all the building, the venture capitalists and started talking to different investors who I respected about which marketplaces were growing, where do they see emerging new business models and very quickly decided I wanted to be in something that was either B2B2C esque or this sort of emerging SaaS. Bottoms up SaaS market. So that's how DevOps came into play or a multi sided marketplace. And PagerDuty wasn't really an obvious choice. It's an infrastructure software company, deep tech, selling to technical people. Me and my little marketing degree had a pretty interesting transition to that. But actually I learned a lot about infrastructure in my last couple of jobs and I know a lot about enterprise software and most of I have a lot of experience in digital transformation. So the customer base for me has been the same across the board, even if the buyer has changed. What I love about PagerDuty is it leverages my consumer brain because our app is consumer grade. The way we engage with developers is the same way I learned to build products and market directly to consumers. And likewise you have this awesome sort of crossover from product led growth to enterprise which drives a lot of these explosion in your business. So it actually ended up being a really great fit and you know, five Years later, I think it was a good decision.

What an adventurous career in terms of just making those decisions. Before you came to pagerduty for many people who'd want to, you know, emulate growth and leadership the way you did, how did you decide? It clearly wasn't doing the same thing repeatedly. But how'd you decide? Like, oh, like private equity. Take private supply chain DevOps. Like, you know, many people as they build careers, they're trying to build depth of expertise in just one sector or one stage of company. You obviously thought differently. So what were you looking for each time?

Yeah, I actually think one of the challenges in our industry is an over rotation towards specialization. Because when, you know, when you look for a leader, a functional leader or regional leader or a business leader in a business unit, you want someone that has broad experience, that has actually seen how all the functions come together to build a business that understands product strategy and go to market and you know, how you get to Friday's payroll and you know, have see a path to profitability. And the challenge is if you're specializing, kind of trying to take the elevator straight up, you don't learn, you don't cross train and learn a lot of those capabilities which are really important in general management. So my first piece of advice is if you want to be a CEO, you need to move across organizations. You need to build a breadth of your skill set and you at a minimum need to develop strong familiarity of the role every function in a business plays together because you're going to own pulling those puzzle pieces together. For me, someone helped me discover very early on in my career that I'm motivated by a steep learning curve. I'm severely intellectually curious, I'm an extreme extrovert. I like to surround myself with smart people. My goal is always to be the dumbest person in the room, which is not the same as not wanting to have the answer. Like I suffer from that problem too. But I would say that it was great for me to be able to try different things and always would take one thematic thread. I took my marketing expertise and that's how I jumped into tech. Then I took my enterprise software experience to move from supply chain into more private equity. Then I took my leadership experience and moved into a public company CMO role. And then I brought in that to business and product and M and A and took that into my CEO role. And so I always found kind of one way to jump to the next sort of stepping stone in my career. But I have never done anything twice other than Being a CEO, I mean, that's odd. Like, I've tried to do new things and the two companies I've run are very different in terms of their profile and their growth rate and even their global distribution and everything else. And so I would say just don't be afraid to try things that are counterintuitive to you if you can see that they will help you build your sort of leadership toolkit.

I think that's super sage advice simply because there's such an emphasis on rapid progression right now that the value of this idea of, as you describe it, like business cross training, I think is not discussed very often. Just to pull on one other thread of wisdom from your experience is there are a lot of people building and leading companies who have not seen an economic cycle before. Right. And you work through the first.com bubble and the recession. How do you think that affects, like, your leadership today?

I think it just steals you for a crisis because, you know, you know from experience, you don't have to take someone's word for it that the pain might be deep and it might be broad, but it will have a beginning and an end. Right. And so you know how some people say, it's not my first rodeo, it's not my first recession, it's not my first crisis, like, and I've survived. I'm very hard to kill, apparently. And that gives you kind of the confidence to sort of seal yourself and sustain yourself for whatever period of time you have to sort of change and be in crisis mode. And so I also think as a leader, as you mentioned, this, this sort of rapid acceleration, the rapid progression of careers, and, you know, I'm going to sound like the old lady in the room saying this, but I think it's really important to remember that there's no replacement for experience. If you play a sport, if you play an instrument, if you do anything that's competitive, you know that all the experience that you get makes you a better player. You know, I golfed in college and what I learned is the more times you could play a course, the better your course strategy would emerge. The more, you know, issues that you had to manage on the golf course, the better you got in sort of keeping it together and keeping that low score at the end of the day. And I think sometimes we don't place enough value on just getting the miles under your feet and being able to trip a few times and learn that you can get back up, learn that you can run through an injury, learn that you can get through a crisis and so sometimes maybe think about before I quickly switch to the next thing so I can add a letter to my title or have a new project. Did I make the most of this experience? Did I fulfill my learning goals in this experience? And likewise, another one of my big motivators is how much value did I create? Like how much value? Was it incremental? Was it disruptive? Was it a step change? Because sometimes I see people not even staying in roles long enough to make a difference. To me, that's a motivator. Like, I want to know that I had an impact on our market, our customers, our products, our people, et cetera. And sometimes that takes a little time. So I'm not saying you have to be patient. I think all great CEOs are impatient by definition. But I do think that the way, you know, the yardstick with which you measure your success shouldn't just be how quickly you move from one title, one project, one job, to the next.

One thing that at least comes across as intuitive versus learned, though maybe it's learned with getting the miles, is that your leadership style from the outside seems highly empathetic. And I admire the fact that, you know, through many positions across different industries in your career, you've obviously been able to figure out how to quickly connect with people, learn, communicate with. I'm sure the execs at the Thoma Bravo back company were different from the execs you worked with at P and G, for example. Right. And figuring out how to build those relationships had to be really different. And I know you as somebody who genuinely desires to understand others. What shaped this mindset of just like being able to connect to different people and then like making that part of your leadership?

Yeah, I think the first example I had of what leadership should look like outside of school teachers was my father. And my dad was a hospital administrator. And this is a really interesting job because, you know, when you're running an 800 or a thousand bed hospital, like you're responsible for everything, not just patient care, but everything from janitorial services all the way through to, to neonatal healthcare outcomes. Right. And one of the things that I think made my dad a very special leader was that when he walked the halls of the hospital, everyone from an individual contributor on the janitorial staff and someone handing out food in the cafeteria line to the head of the medical staff felt like they knew him and he knew him. He had a way of connecting on kind of a level playing field basis with anybody that he came across in a business. And it always amazed me that as his jobs got bigger and as the hospitals got bigger, that connection that people felt to him kind of stayed the same. And if anything's been frustrating about the pandemic, it's that it's felt harder for me to connect with people when I'm stuck in this single zoom box, et cetera. So, like, I'm bursting to get out and run around the world and meet our new employees and reconnect with employees that have been with us for a long time and see, you know, some of my customer friends and, you know, just. Just my CEO peers, like, get out and get back into the world and make those connections because I do think they're super important. But I just remember him saying, like, everybody has a contribution to make, and you never know when somebody's going to make a huge contribution or when it may be, you know, really important. So you look for that opportunity in every person that works with you and works for you. And I'm not perfect. I mean, there have been times over the last 18 months when I've been stressed, we've been under pressure, when, you know, it's. There was a lot of lack of visibility in where the market was going. We had no idea. And I've been short and grinding my team and, you know, looking for us to build stronger muscle out of all this. So being empathetic doesn't mean you're always nice. It doesn't mean you're always perfect. It doesn't mean that you're not critical. Sometimes, you know, I'm working on coaching versus being critical because I'm really critical of myself, and I'm sometimes really critical of my team, and I can be a hard driver. But at the same time, with that intensity comes someone that I do think my team knows, really cares about them. Right? And really cares about our customers and how we show up as a company. And I often, I've been known to say, like, it's not just what we do, it's how we do that matters, because people will not remember what you said or what you did. They'll remember how you made them feel. And that's something that stuck with me for a long time.

So along this theme of connection and even working on the different styles of connection within your employee base and with your global community, one thing I know is that you've made some of your choices and created some of your own opportunities throughout, like, seemingly random connections. Right? Can you talk a little bit about that? Like, how you built that as a muscle and how you do it authentically.

Part of it comes from that intellectual curiosity. Like I'm interested in people's stories. Like I like to hear about what makes them tick. I remember being younger and hearing leaders say, I don't really like managing people. And I would think to myself then why the hell are you in that job? I still love developing people. I love the expression on someone's face when they do something that they didn't believe they could. When you asked them to do it, they looked at you like you were crazy. And then here they've achieved something huge. That transformation in a person for me is, you know, fills my cup. And so I've just learned to like, listen to people's stories and kind of understand what's important to them. My first tech job manifested from a conversation with a person on a flight. And it turned out we had just come from meeting with the same headquarters and I had screwed up a deal. They were trying to close by saying, you're not ready to do something, you know, so that was kind of touch and go there for a minute. There was cocktail involved in splitting that over. But, you know, this person had a really interesting story and it turns out he was leader at i2 and, you know, one thing led to another and that's sort of how that happened. I believe in the potential of most people and I think, you know, the minute you write somebody off, the harder it gets. I just. Adam Grant is someone who I really respect and we've done some work with him. And one of the things he recently posted was this idea that as you become more powerful or more senior in an organization, your ability to judge character is harder because you're further and further away from seeing how people behave when nobody's watching them. And yet some of the less experienced people in the room are watching that all the time. And so who you look to to sort of double check your instincts on people might not be your senior team. It might be that really observant individual contributor in engineering or that seemingly cynical person, but who's really analytical and paying a lot of attention to what's going on. And so I think just being open minded about, you know, who influences you, what influences you, and not creating such a hierarchy for the relationships that are important. Like we hear so frequently, you need to prioritize ruthlessly, et cetera. I don't know, I kind of think the color in life is getting to know different types of people and hearing their different perspectives. And that's how we imagine bigger things. It's how we solution big problems. It's how we disrupt markets.

This may be specific to venture, but perhaps not. I remember one of the first things I was sort of taught as part of the greylock culture coming in and not even thinking I was going to be a venture capitalist for a long time was invest in long term relationships. And I had a very recent example where somebody had introduced me to an engineering leader at like a big tech company as a friend. Right.

Just please be helpful to this person.

He is my friend probably six years ago. And that person just became the engineering leader of one of our like very promising growing companies. And like you build all of these connections where you're just trying to pay it forward, not assuming anything comes back. And like I've been shockingly surprised and like the ecosystem is actually smaller and far more connected than you think. And so I love being able to operate that way.

I always say to people, never burn a bridge. Like you just never know, you know, even if you have to let someone go because things aren't working out the way you do that. Right. Make that a win win for everybody because you just don't know where someone's going to turn up again next or what you're going to need in a different role or who's going to ask that person what they thought of you, et cetera. So I try and play the long game.

Yeah, well, and it sounds like that also requires some optimism about what everybody's capable of. Right?

Yeah. I don't think you can be a great leader unless you're optimistic and you think about what's possible for a person. And sometimes that does feel like it's in conflict with making a hard decision. Right. Like I think especially when we're hyperscaling or we're scaling a business and you realize that a business has outgrown someone. You know, can you coach them? I mean, first instinct is can we coach that person? If that doesn't work, my second instinct is, well, can we find a different role for them? Because there's institutional memory there, there's, you know, all kinds of history, their connections, their relationships. And then the third thing is, will they be better off trying something different and can we help them make that transition? Right. So there's a lot of options outside of show that person the door, give up quickly. Right. And sometimes when speed is so emphasized. Right. We can be biting off our nose to spite our face in that regard.

Okay, let's get back to what I'm sure feels like 90% of your brain. But getting back to where pagerduty Is today, right? Yeah, you've been there since 2016 and the company was, I don't know if this is acceptable to say, somewhat of a sleeper hit. For the first couple of years, nobody.

Had ever heard of pagerduty. It was like not a fun thing at cocktail parties to tell people where I took a job. I'm like, I'll take a job at pagerduty. They're like, well, what are you bringing pagers back? So yeah, it was a little bit of a cult sleeper. Developers knew what it was like. Any developer you asked absolutely not only knew PagerDuty, but they're like, oh my God, I love PagerDuty. Well, it was either like, oh my God, I hate pagerduty, but thank God for pagerduty. It's waking me up in the middle of the night, the whole thing. And it's really been fun to kind of reposition the company and sort of help this little baby grow up to be an enterprise grade platform that supports like, that has become critical infrastructure across the global 2000 and frankly support the most important brand engagements and operational environments in the world. And some of that has been a lot of hard work in the background that you don't see like investment and innovation in infrastructure, investment in innovation, in resilience at scale. Right. There's nothing sexy about shipping a new capability that, that helps you get from four and a half to five nines unless you are the last line of defense for all the revenue in the universe. Right. So there's a lot of blood, sweat and tears that have gone into really transitioning a single product company to a multiproduct platform that has ubiquitous application across just about every industry in the marketplace. And we've just been somewhat smart and somewhat lucky that digital transformation, DevOps adoption, cloud adoption, and more recently distributed working have all been phenomenal tailwinds for the company.

What have you heard from or learned from customers over the last year and a half that's different? What's new?

Some of the things that I think are new, which I love, are that customers now like sort of recognize the importance of the relationship with their strategic vendor partners. We went from in some cases having kind of a very transactional relationship. I've got software to sell, you need to buy some software, like, let's figure out how to go through procurement, make that happen. And one of the things that I think the pandemic shifted was this move to starting every meeting with like, hey, kind of a wellbeing check in, like, how are you Right. And just I think a much more transparent and open conversation about the challenges that we're facing. Like we're sort of all in this pandemic together. And that's led to some really strategic and more open conversations around what are some of their business challenges and their technology challenges that we can serve. So there's been kind of this relationship shift that I think is just much more vulnerable and much more interesting in my view. Another is that even though we've been talking about digital transformation for a long time, most of our customers are still on the very early end of the continuum and some of them are moving slower and some are moving faster than others. Many accelerated a lot of initiatives that you see on the front end. So they shifted to digital go to market models, they shifted to digital brand experiences, but they haven't necessarily caught up on the back end. And so we're still seeing a lot of plans for and future investment in transformational initiatives to modernize the technology stack that supports how the business shows up, how the company runs, how revenue is generated, et cetera. The third thing is that security and data management and just responding to unplanned issues, these have all become mainstays, not compliance boxes you needed to check. So my view is that more work is shifting from being predictable and planned and scheduled to being spontaneous and unplanned and mission critical. And that bodes really well for a platform that manages real time operations. Some of the other things I hear from companies is this problem of, there's lots of proclamations out there, but this problem of figuring out, like, how we all work best, how we're going to work in the future. There's a lot of experiments running. We're all part of one big experiment. And most of us in the business world are incredibly privileged and fortunate. And if you look around the globe, there are a lot of communities that are still in real pain. You know, no access to vaccines, little access to Internet, you know, it just. You've also kind of got to constantly remind yourself as a leader of where we actually are and how many communities around us still have such a steep climb to get to a place where they can take care of themselves effectively, they can reduce the risk of the pandemic. And frankly, until we solve that for everybody, we can't solve it for ourselves. So that's the last point I'd make, is that the responsibility of the CEO has really broadened. It's not just about running your company. It's not just about looking after your shareholders and your customers and Your employees. It's about actually leaving the community in a better place than it was when you got there, being the source of information to help people, you know, live and learn and work safely. There's just a heightened level of responsibility, and the job's a lot broader and in some cases trickier than it used to be. I mean, I think. You think, look at the social unrest that we've seen, the inequality and the conversation that's really, thankfully surfaced since the murder of George Floyd. I mean, none of those issues are easy. And there's no executive in the world who can sort of go past them without dealing with them. Because this is a dialogue we need to continue to have because we haven't solved the problem of systemic racism and inequality and social justice for everyone.

I think, like, your approach is clearly to recognize and to try to bring that into your leadership of pager duty, any of these difficult issues as CEO, without saying, like, we have solved them, because we have not. And then I think what you described certainly resonates in that for many leaders, like realizing, realizing or just being forced to see that any of these organizations we lead, they sit in a much broader context that's very interconnected. Right. We saw it across so many different dimensions over the past year, like health, community security, inequality.

Yeah, totally.

There's so much potential for pager duty beyond just the initial, like, developer on call use case that I think of as. I don't remember a period of time where, like, our companies at scale didn't use it. Right. I was like, well, I don't know. How's the service going to stay up otherwise? Right. Like, database went down. Obviously, pagerduty is the system, and I think more and more people see that. But if you go beyond that, what do you think most people don't understand about PagerDuty and what you guys are trying to do?

Well, I think the market is finally starting to get it, you know, I mean, they're starting to not only believe it, but see. But there is an infinite number of use cases for a platform that can use software and machine learning to detect a signal that's anomalous in some way, route intelligently, route that signal to the right handful of people who can diagnose the issue and start to solve that problem and then automate more and more of that solve. Like, generally speaking, what it is is a new way to think about workflow, right? A more autonomous way to think about workflow, really targeted at challenges that are unpredictable, that are unexpected, that are usually expensive, and like I said business critical, reputation critical, etc. So what we've seen is our customers take PagerDuty from the development community and engineers into other parts of the business. And there are some obvious adjacencies like IT and IT operations. Security response is another. And with the rise of ransomware attacks and phishing, et cetera, most of our Customers also use PagerDuty for security response. There are things though that are less obvious. Like we have a large enterprise software company that uses PagerDuty to manage its quarter close and has their legal team and their commercial teams working across the different business units to close out all the terms in contracts that manage pricing across different business units for single large customers. Right? And you're under a time crunch, it's time critical. You don't know when a contract's gonna come in versus another contract. And you have to orchestrate the efforts of a lot of different experts in the business to get that done. We have lots of healthcare organizations that use pager duty, lots of nonprofit organizations that use pager duty. Organ transplant is one of our favorite examples because we would have never come up with that as a go to market proposition. But the signal of an organ donor is available, starts an incident on the PagerDuty platform, and then PagerDuty orchestrates all the players necessary to find a recipient and to transport, you know, extract that organ, transport it, get it transplanted in the, you know, 36 or 72 hours of viability you have for that organ time. Critical, unpredictable, unstructured work, you know, so just think of some of these examples. That's what gets me excited about the business every morning. That's why I wake up. So we're taking more of a flexible approach and trying to make it easy for customers to leverage us in different circumstances like that. And one of the fastest growing today is customer service. Where there's a customer issue, you may find out about it through your social listening capabilities or through a customer calling into or chatting into a call center. And that customer service person today has no visibility to the product owner. And what's going on inside the product environment or the technology environment. It's a black box. It's a series of creating tickets, trying to search through email distribution lists, et cetera. And time really matters. I mean, we just launched a brand campaign and one of the taglines is uptime is money. Nowadays you have a second or two before a consumer will just totally give up on you. And so that's created lots of different use cases, even within customer service. I think the other thing that people don't really realize about PagerDuty is we are the center of all digital operations for the economy, not just a customer. We have over 560 integrations out of the box and there is a class of companies being born building businesses off the pagerduty signal. And so it's a really interesting environment to be able to build from because we see so much through that ecosystem and that's informing how we think about what the next product feature set is or where are customers really interested. I mean, we spotted customer service because we kept seeing the name of these incidents associated with customer service or we'll see a name of an incident and this is something to do with like accounts payable. Right. Or physical security. I think that's the sort of next step for PagerDuty is becoming the operations cloud for the modern enterprise and doing that by making the platform more flexible for all different kinds of users, more approachable for different users, but continuing to have really strong machine learning capability built on over a decade of data that allows you to automate more and more of that. And so we think of it as automation and service of people. You know, it's human in the loop automation as opposed to black box automation. And that helps us continue to build that heart and minds connection with the user who is the utmost importance to us.

As an analogy, when I joined Greylock, you know, we were lucky enough to be small investors in ServiceNow and like that company, I think had the hardest time convincing the market for a while that it help desk and service management would matter. Right. Because it's like I asked to reset my password or something. It is something that has become a backbone product in the enterprise. And so when you zoom out and you think of it as a more generic real time workflow platform, I think that really opens up the aperture of so many use cases that are exciting if you project forward and you think about your and the team's ambitions for PagerDuty, like what are the biggest challenges you face and what do you need to go build out and expand capability in to go meet those use cases?

Yeah, I mean one of the big challenges is awareness and preference and like how people think of you as a company and how people find you. Like our early growth days came through word of mouth. Like every developer chose us as kind of one of the five or six tools that they had in their sort of startup toolkit. Now as a platform you've got the challenge of continuing to build your relationship in those User communities, and at the same time having a viable and clear and interesting value proposition for CIOs and CEOs and CFOs. So there's that balance, which I think a lot of enterprise SaaS companies go through that transition. And then at the same time, I think it's also continuing to build out features and functionality, but at the same time make sure the app is super intuitive and super easy to use because our primary use case remains incident response. The difference is there are lots of incidents, there's lots of different kinds of users, lots of incident types. But if it's not easy to navigate the app and get done what you need to get done, automate what you need to automate in the most moments that matter, then the app loses a lot of its efficacy and its competitive advantage very quickly. And so we spend a lot of time on ux. We're really thoughtful about where we put a button or if we, you know, if we move something around, we get crazed, you know, calls and input emails in the middle of the night from people who are going through an incident and can't, can't find the button they use, the radio button they, they used to click. So, you know, we also constantly listening to the market, but also looking ahead at what's possible. And I see a world where pager duties on every handset, you know, every device in an organization and likewise like we're seeing, you know, some really interesting trends with industrials, you know, trucking companies, energy companies, oil and gas companies, energy grids, local governments, et cetera. So places that you historically wouldn't have seen us go because we started in software and the Internet and then moved into E commerce and kind of. So Those obvious for SaaS markets and organ transplant, apparently, organ transplant. But like all those investments that you make in things like SOC 2 and you know, moving towards Fedramp, et cetera, they become so important in expanding, you know, your addressable market. And that's, you know, those, those investments are paying off for us.

You mentioned machine learning and intelligent routing. What's the strategy for investment in that?

At pager duty you can never invest enough. I mean, one is how do you make sure you can continue to capture data that is important in a way that's efficient and well engineered, that allows you to leverage that data and in a way that maintains the trust of your users. So like, trust is one of our core value propositions, trust and transparency. And I think in this world where people are increasingly concerned around how their data is leveraged, how their Data is used like that. That's a high priority for us. The second is, you know, not getting caught up in, like, the interesting science and focus on solving the big messy problems. And some of those problems, some of the biggest problems in the world, are not very sexy. So you have to constantly kind of keep your eye on the ball of like, what are the big ugly problems that our customers need help solving and how do we help them solve them? I mean, another example I can think of, we have a retailer, and during hurricane season, depending on what's going on, they need to very quickly move inventory from one distribution center to another. And they use Patriot to connect their weather forecasting signal to their inventory environment so they can move fans and dehumidifiers to where it's raining and air conditioners to where it's hot and heaters to where it's freezing. And that sounds like that was all something that was done manually. But now if this particular retailer can't do that, well, maybe Amazon or someone else can. So in a very competitive world, being able to respond to the situational environment for your customers like this is super important, right? And so those are just some examples. But I don't see problem to solve.

I think that's really sad.

I mean, we don't help you make playlists, we can't help you get a ride, we can't help you deliver food. But all the people who do that use pager duty, right? Because you don't like it if you go out for your run and your playlist doesn't download or Starbucks can't get your coffee order or whatever. And we're sitting behind all of those experiences.

Do you change your relationships management style or how do you think about relationship management differently when you think about the pager duty, co founders, execs, other employees, so just the different constituencies within your org.

I have a huge amount of respect for the people who come before me in anything I do. Right? And so when I met our three co founders, one of the first things on my mind was like, wow. I mean, these guys basically came out of college and got a company to over 30 million in revenue, like with no experience. And I can count the number of people I know who did that on a, you know, few hands and toes, right? And so one just paying homage to that achievement and that accomplishment and keeping that in the back of your mind as you think about what's the next stage of growth? Who do you need for that next stage of growth? Just really respecting the foundation that was built for you. When I transitioned with our founder, I made a huge effort to make it a victory lap for Alex and the other co founders, make it a transition that everybody who had come before me, you know, blood, sweat and tears, had built. And likewise, an exciting new future for where we could all go together. So it's less about changing your management style and more about celebrating the successes of all the people that remote. I mean, just as recently as last week on a town hall I was talking about, I was just sharing some appreciation for our alumni. I mean, there's a lot of people who have been part of the pagerduty story that are no longer at pagerduty. And you know, in this really like, dog eat dog talent environment, it's easy to say like, oh man, why did that person leave? And instead I sort of try and think like, look at the amazing contribution that person made. I hope they take something they learned and the pagerduty culture into the tech industry and build something great. You know, I want all of our alumni to be super successful. And so I always say when people leave, like, let me know if there's anything I can help you with. And I mean it. When you think about management as you scale, it's really about one looking for people that can grow ahead of the company as opposed to people that are trying to catch up with the company or people who are just growing alongside the company. You really want a mix of hungry up and comers that are innovative thinkers and you want a mix of people who have seen around multiple corners and know not only what good looks like, because I always hear, oh, they've seen the show. They know what good looks like. You want people who knows what a shit show looks like and isn't like completely knocked off their feet when it comes, they go, oh, yeah, I remember when that happened. Three times. You know, sometimes my team will be like, you're not panicked? And then like, no, I sadly lived through this before. I really screwed it up last time. I think I have some better ideas this time. So you want that balance of youth, enthusiasm, innovation, invention and experience. Right? And that's less about management style and more about planning for the talent that you need to take the business where you want to go. I feel like there's always pressure from boards. They like, well, don't get too far ahead. Don't get too far over your skis when you're hiring. I've just never had that experience. As long as you screen for people who are entrepreneurial and willing to roll their sleeves up, you can hire somebody who is totally overqualified for a job that will pull you faster through that scale. As long as they are okay rolling up their sleeves and doing the work you need them to do. If they need a lot of staff, if they can't remember how to build, then they're not going to work out. And that's what boards are fearful that you hire someone who can't roll up their sleeves and build. They only know how to run up here. So make sure you're hiring people who like, know how to deconstruct something, know how to reverse engineer something, know how to build it from the ground up. Like, are not afraid to make hard decisions, are not afraid of the mess. I always, when you're scaling, I look for people who love the chaos, they love the mess. They, they pride themselves in being able to put systems and process into place alongside of, you know, the more glory generating work. But it's, it's a balance. And then the last thing that I'd say is as you're scaling, you're letting go of a lot of things. You're distributing your Legos, things that you traditionally managed yourself. You're distributing those Legos on an ongoing basis. And you know, the good news is you will never run out of Legos because there's new Legos falling from the sky as you're distributing more Legos out. But your job's gonna change and that's natural. Like the things that I focus on now, you know, as a public company leader versus the thing as I focused on five years ago when the business was less than 100 million in revenue. Like they're very different, but it's good different. Like I don't miss the things I used to do because I've replaced them with new things I've had to figure out. And then the last thing is you have to build a team that trusts each other no matter what. You have the best people in the world and you can be a great leader, but if that team does not trust each other, you're going to move slower than a team that does. You're going to hit a wall somewhere and it's going to become the finger pointing game or the stay in my lane game. And you're not going to be able to achieve the sort of, you know, big goals you've set for yourselves. So make the investment in team building, in trust building, in one to one relationships in the team. Don't have everything coming back to you because you'll become the biggest bottleneck in the company.

That has to work across the leaders in your team. But you also, multiple times have stepped into being a CEO, not as founder. It seems like the first step of that is also trust within the organization. And so how did you go about building that?

I'm the refinder, I'm the adoptive parent. You know, like, I come into an organization and when you work alongside of a founder, it's akin to like adopting their child and they have to stick around and watch you raise it right. So it is a partnership. You can never forget about the fact that there's an inextricable link between you and the founders as a leader, just like there's an inextricable link between you as a leader and your employees. And, you know, my job as a leader is to try and keep that trust gap as narrow as I possibly can because, you know, there will always be cynics. There will always be people who say, oh, you know, leadership is up there doing something that's not in our interest. It's in shareholders interest, or it's in their interest, or it's in customers interests, but they're not doing it, you know, on behalf of employees. And the best way to, you know, manage that trust cap is to constantly be talking and be transparent. I mean, I still answer questions in town hall that maybe my lawyers would advise against, right? Because I believe in transparency and trust. And, you know, I trust our employees to treat confidential information with the respect and the care that it deserves. And that allows me to have an open conversation, you know, even with nearly a thousand employees. So I think it's just really important to you earn that trust through action more than anything else you can do. You can. People will listen to what you say, but they will really care about and watch what you do. So every action you make, every, you know, step you take in a company or frankly, the things you don't do, your employees are keeping score. Right? And so I'm always trying to think about how do I stay on the positive side of that ledger? How do I. The trust ledger, let's call it. How do I stay on the positive side? Sometimes I get busy or, you know, in the old days I'd be traveling a lot or. And. And I wouldn't be as outbound and connected to employees. And that creates a communication vacuum. Like they suddenly not hearing my narrative, so they're going to fill it with their own narrative, right? And so making sure that I'm touching base. Like, we used a ton of just short form video over the course of the last 18 months to stay connected with our employee base. Right. I dropped into the San Francisco office this week and you know, reminded people of like all the reasons why they chose pager duty and all, how all those reasons still exist. But it is like fitness. Like you are always working at it and if you take a week off, you're going to pay for it later. Like, you got to continue to build that muscle.

It's clear that you get energy from exercising that muscle. If we just stand this topic of leadership and like, look at the other, another direction of it around the board, I think that's very relevant for many of the entrepreneurs. You know, in this conversation today, you've seen it on both sides and different scales. Like, how has your board work changed how you interact with your boards board members?

So I am a huge proponent of board work for executives at all levels because I think it develops empathy that you don't develop as an operator. So, you know, number one, like from a career development standpoint, I think if founders, if, you know, VP level employees want to participate in boards, they should because it just gives you a lens of a company that is more strategic, more high level, you know, balances risks and outcomes and also gives you context. You know, like over the years the boards I've been on are no longer on the puppet board. But even, you know, when I was on the puppet board, puppet was experiencing some things that pagerduty hadn't and vice versa. And just that relative context like, you know, help both the puppet team and me, you know, learn faster than we would have if we were doing it on our own. So I huge proponent of doing board work in general. But what I would say is by being a board member, it's helped me build empathy for what my board directors are looking for and expect from me. And likewise by bringing operators onto my board. There's a lot of operator empathy in that room. One of the early lessons that I learned, you know, that I'd love to help others not learn the hard way, is bring independent board members into your boardroom early. And often, like a lot of people say, I don't need independence till I'm getting ready to go public. You need experience. You need people who have seen the Ugly movie before, who have made the mistakes before you make them, who can be in that room and sort of balance the discussion, right? And there are great investors out there who are awesome mentors and coaches and have operational experience themselves, but they have conflict. They're there to get an exit and get a return from the investment that they make. If you bring in an independent operator into your board, their sole goal is primarily to make sure that you and the company are successful, that you go about that the right way, you know, provide obviously some oversight and have some fiduciary responsibility. But so bring in those independent operators early and get that operator empathy in the boardroom. I think the second thing that I've learned is I've never seen a good board surprise ever. Not good news, not bad news. Like, there's no such thing as a good surprise in a boardroom. Like, so we have a no surprises mentality and we are very transparent with our board. And like anything else, a board relationship is a collection of one to one relationships and then a set of many to many relationships. So you have to invest the time in building trust with your board members or with management if you're a board director, just like you have to build trust, you know, with your employees or your teammates. And sometimes I think that's overlooked because people say, I want to minimize the time I spend with the board. So I'm going to talk to them every quarter, you know, when I have to out of obligation. No, no. Like you should be touching base with your board members every month, you know, when you're younger, every week, kind of younger in your company's growth cycle every week. I do think it's also good to remember that the board is there for the company. Right? And sometimes we get that relationship mixed up and we over curate and control the messaging and the information that goes to the board, which limits their ability to be effective. If you're kind of all in it together and there's a lot of visibility and transparency, then the board can be, you know, more constructive in helping you work through the hard issues and the hard problems. It's your job as a CEO to curate which issues, which problems you really want the board to focus on. And I often say to my team, you know, one of our jobs is to prevent a board member from feeling like they have to bring help in an unsolicited way. Right? Because that means, that means we either didn't recognize the issue or we have not convinced them that we've got a handle on the issue or communicated your.

Prioritization like, no, these are the issues we really care about and we've heard you, but like, here's where we're going to focus. One thing that's actually a question of like genuine, you know, one to one advice from, from you. I love is I believe trust is earned as a board member. And graylock is very long term orientation. So we try to be as aligned as possible as we can be with our entrepreneurs. Right. The exit is 10 years from now and that looks more similar to what founders are doing than, than a year.

Right.

But all that being said, like, I recognize that and I am a huge proponent of independence as well, but I think one of the challenges I personally run into when suggesting this and trying to help companies build an independent board early is, is a sense of loss of control or, you know, fear of that. Right. What's your reaction to that?

Some of that is just inexperience. Right. And not having been around board members who know the difference between being a board director and an operator. So the best board members, in my view are phenomenal expert listeners. They're not proactively calling you every week, you know, to check your work or to get in your business. They're listening, they're helping you think of the questions maybe you should be asking yourselves that you haven't. They're applying pattern recognition and saying, you know, the last time I saw this set of information or this set of circumstances, here's what the outcome was like. They're helping you look ahead, look around the corner and I think you can screen for that. Right. I mean, one of the challenges with new directors, like first time board directors is they have this huge like natural to desire to want to add value. And I always tell new directors like, you don't have to add all your value in the first meeting. Like listen more, say less. It'll be three, four meetings before you even really understand the company. Even if you think you're a vertical expert in marketing, sales, product, you know, legal, pick your poison, finance, et cetera. And then the second thing is make sure that like your board understands what you expect from them. Now the reality is it's the board's job. The board's number one job is to hire and fire the CEO. So if you're not doing a good job, demonstrating you do understand the marketplace, you do understand the issues, etc. And they're asking you questions and you don't have good answers for them, well, then you're probably going to have something to worry about. But you'd be worrying about that anyway, right? So better you have people in your camp who can help you sort of navigate through those issues. I'm a huge believer in narratives. I'm trying to kill slides everywhere. I just think they're the most unconstructive, useless time wasters on the planet. And so I Write a board narrative. And I mean, the board narrative I wrote at the end of Q1 last year as the pandemic was really hitting, was pretty bloody, you know, and, and it wasn't to shock our board members. It was to just really level set everybody on, you know, where the world was. Because if you weren't sitting in a business, you weren't seeing it yet. It was sort of coming in a wave like a tsunami. And that's one of the best things I ever did. It developed a lot of empathy. The board hunkered down, they were super supportive. You know, we took a long term view, we made some decisions that, you know, have a huge long term upside, but at the time, you know, might have felt uncomfortable. And I think that's what you want, but you need to be able to have an honest, intellectually honest conversation with your board. And so it comes down to the people. There are board directors out there that are frustrated, retired operators that want to do that from up high without the responsibility. I try and, you know, filter those people out of the process.

Right. Well, perhaps part of the trust building exercise is just making sure people understand they can screen for what they're looking for and what can be helpful.

Before I hire a director, I talk to people they've worked for. I've talked to people who've worked for them, I've talked to their board members. And if they've sat at another board, I've talked to the CEO. So I have a really good sense of how they're going to behave. One of the questions I always ask is, what are they like when the shit's hitting the fan, like when things are not going well, what does it look like? Because you want somebody who's calm and steady and supportive and helpful. Right. And we often hear a lot about what people are like at their best in an interview process.

We are out of time here. Thank you so much for joining us, Jennifer. I'm looking forward to eventually getting to walk some miles together as well. Jennifer, thank you so much again for joining us. We appreciate your insights. I learned a great deal and thank you for being generous with your time.

Oh, thank you. It was great to see you, Sarah, and thanks to the whole Greylock team and best of luck to everybody.

That concludes this episode of Gray Matter. If you enjoy this interview and want to hear others like it, please hit subscribe. You'll get new episodes delivered directly to you and you can catch up on episodes you've missed. Like my interview with Greylock investor Christine Kim, who shared lessons learned from five years of scaling product at Uber. You can subscribe to greymatter@soundcloud.com greylockpartners. You can also subscribe on Spotify or wherever you get your podcasts. You can find new episodes and blog posts every week on greylock.com blog and and you can follow us on Twitter reylockvc. Thanks for listening.