Groundwork Podcast – Episode 1

Kelli Dragovich (Pendo, GitHub, Looker)

Kelli Dragovich started out as an HRBP at Intuit. She moved on to Yahoo!, and from there, found herself in the world of rocketship startups.

Kelli Dragovich

A show about Chief People Officers from the world’s fastest-growing companies.

An HR Podcast about how these leaders guide organizations through the turbulent times of hypergrowth by investing in human beings.

They lay the groundwork that makes the impossible, inevitable. Join Lingo Live CEO Tyler Muse for conversations on how they became the leaders they are today, how they’ve navigated their toughest challenges, and how they envision the future of work.


Kelli Dragovich (Pendo, GitHub, Looker)

Kelli Dragovich started out as an HRBP at Intuit. She moved on to Yahoo!, and from there, found herself in the world of rocketship startups. Her background says it all: SVP of HR at GitHub, SVP of People at Hired, Chief People Officer at Looker, and now Chief People Officer at Pendo. If there’s one thing Kelli knows how to do, it’s how to build the plane while flying it.

In this episode, Kelli talks about the biggest mistake she sees leaders make as they’re scaling from 200 to 3000 people. We’ll hear about her time as an amateur boxer and the magic words by a professor that changed the course of her career.

What We Cover:

[0:04] Introducing Groundwork

[1:25] Introducing Kelli

[2:17] Real talk about her Bay Area upbringing

[6:41] Growing up LGBTQ and the power of authenticity

[9:30] Kelli’s time as an amateur boxer

[11:34] Reconciling competitiveness and being true to yourself

[13:33] Starting in Pre-Med, then shifting away from it, in college

[17:03] The magic words by a professor that changed the course of Kelli’s career

[19:35] The painful experience of job searching during the 2008 financial crisis (and how it informs how Kelli shows up today)

[23:47] Why Kelli continues to gravitate towards hyper-growth companies

[27:48] The biggest things hyper-growth companies get wrong

[30:14] The rapid and dramatic transformation of the Chief People Officer role

[35:16] What people want from their work experience nowadays and why black-and-white HR policies will fail to deliver it

Tyler  0:04  

Hello, and welcome to Groundwork, a show about Chief People Officers from the world’s fastest growing companies. I’m Tyler Muse.


Tyler  0:18  

I grew up in Dallas, Texas and London, England, and in 2012, I founded Lingo Live, a one-on-one skills-based coaching company that helps people gain the skills they need to transform the way they lead. I’ve spent the past decade meeting Chief People Officers who guide organizations through the turbulent times of hyper-growth by investing in human beings. They’re the ones who lay the groundwork that makes the impossible, inevitable. On this show, we get to know them on a human level, and explore how they became the leaders they are today, how they’ve navigated their toughest challenges, and how they envision the future of work.


Tyler  1:07  

Today, we’re featuring my conversation with Kelly Dragovich.


Kelli  1:10

I like a lot of things going on at once and to bring things together and create, you know, simplicity and clearness out of chaos and complexity. I think it’s so fun.


Tyler  1:25

Kelli started out as an HRBP at Intuit. She moved on to Yahoo!, and from there, found herself in the world of rocketship startups. Her background says it all: SVP of HR at Github, SVP of People at Hired, Chief People Officer at Looker, and now Chief People Officer at Pendo. If there’s one thing Kelli knows how to do, it’s how to build the plane while flying it.

In this episode, Kelli talks about the biggest mistake she sees leaders make as they’re scaling from 200 to 3000 people. We’ll hear about her time as an amateur boxer and the magic words by a professor that changed the course of her career.


Tyler  2:10  

Kelly, thank you so much for joining us. We’re so excited to have you on the show today.


Kelli Dragovich  2:15  

So happy to be here. Thank you.


Tyler  2:17  

I want to start with, so you grew up in the Bay Area. Is that right?


Kelli Dragovich  2:21  

I did. I’m one of the, I guess I’m told, rare, born and raised in the Bay Area. Natives.


Tyler  2:28  

I know you must have seen so much change. I can’t imagine. I mean, obviously I just moved back home to Dallas, where I grew up after spending some time in LA and New York. But you know, it’s changed. But it’s got to be nothing like what’s happened to San Francisco over the past 30 years.


Kelli Dragovich  2:42  

Yeah, it’s a little, it’s a little nutty. I’ll be honest with, you know, remembering back at middle school, which my kids now go to the middle school I went to and so it’s very strange.


Tyler  2:53  

Yeah. What was that like growing up in the Bay Area?


Kelli Dragovich  2:57  

It was good. I mean, I, you know, I’m told I’m really energetic, like, high energy person. And I just remember always going and I guess now that I’m an adult here, I guess that’s, that’s kind of par for the course around here is just kind of busy and go. And sometimes that’s good. And other people don’t like it at all. So I was just always really busy. A lot going on a lot of friends, a lot of sports, a lot of activities. So it was it was fun. I mean, there’s tons to do here, that’s for sure.


Tyler  3:30  

Yeah, it’s so funny. I feel like people have this stereotype of the West Coast life being a lot more laid back and relaxed, and not as much going on as maybe on the east coast. But I have certainly not experienced that. I can’t imagine what it was like growing up there with a kid with all the energy you have as a kid.


Kelli Dragovich  3:48  

Absolutely. I mean, I get told a lot, “you’re, you’re from the West Coast? You don’t seem like a West Coast person. So I think there is definitely some, some stigmas. But you know, Santa Cruz is right over the hill from where I live. And that’s definitely more laid back, so.


Tyler  4:02  

That’s awesome. Well, what were some of the most formative moments in your childhood that you feel like really shaped you as an adult?


Kelli Dragovich  4:10  

Yeah, I mean, I think one, you know, the Bay Area can be intense. And there’s, there’s there’s a lot again, a lot going on. I think if I think about my my high school years, and just the the friends I made there and kind of the values that shaped us, we’re still all actually very close from high school days. There’s always this, this feeling of being real, you know, and being authentic, and it’s hard. I will admit, you know, growing up in a privileged way, just to be honest, I’m well aware of that privilege. And I went to high school and Atherton where there was a lot of privilege, even though I didn’t grow up in Atherton. And you just kind of see a lot of that taken for granted or this or that and so I would say those four years were pretty formative for me. I knew I’d never leave the Bay Area. But I knew I didn’t want to kind of take that mold of a lot of the stereotypes around here, if that makes sense.


Tyler  5:09  

Mm hmm. Yeah, no, it totally makes it a very similar my childhood also grew up in a very, you know, privileged bubble, frankly, and but the realness you talk about is really unique. Because that’s not something that I experienced where I grew up. What did you mean by that, like being real was something that you learned as a value early on?


Kelli Dragovich  5:29  

Yeah, I mean, there’s just there’s a lot of, I don’t know, I just noticed a lot of posturing, right? A lot of how can I get this? How can I win? How can I get ahead, sometimes at the expense of others, and just kind of this fascination about status and this and that, and I am a competitive person, but I just kind of, I saw that. And I think just being genuine to other people, you know, kind of healthy and being down to earth is something that’s always been super important to me. You know, I think a little bit of another angle on that just, you know, in full transparency is just growing up LGBTQ. So just growing up gay in the Bay Area in the 90s. And just what that what that’s like, and just again, being true to others, being true to yourself, has always been super important to me.


Tyler  6:21  

Did you have people that you could rely on that you felt like were going through a similar journey to you? Because I think, you know, a lot of people assume being gay in San Francisco, you know, is one of the best places one of the most accepting inclusive places, but you mentioned there in the 90s was a little bit of a different story. Could you share a little bit more about that?


Kelli Dragovich  6:41  

Yeah, sure. I mean, it’s, first of all, full support, you know. I think it’s interesting, it’s, it’s more what you put on yourself almost, and the assumptions you make, you know, and how your family will react or this or that. And so I think that’s, that’s really interesting to me, is kind of the self, you know, boundaries we impose, you know, usually on ourselves, but no, it’s it was it was definitely full support. My best friend actually came out when she was 16. I didn’t until I was about 21. So very interesting. And we’re still close to this day, we actually have twin boys each who are 10 weeks apart. That’s story, oh, my gosh, yes, story for a different day. But we like to tell them, they were friends when they were zero years old. That’s a good one. But just yeah, a lot of support. And it’s just it’s just funny how these things parlay because I owe the tech see now and just my role in the industry, that it’s in, it’s almost it advantage in a weird way, you know, based on kind of just all the really good inclusion efforts that are out there, and diversity, equity inclusion, and it’s, it’s been really, really fun and driven a lot of change in that area. So, again, a lot of support, but it’s important to let kids know early and no matter what they are straight, gay, other, it’s okay. And I think a lot of homes just don’t do that. Not for bad intention. They just don’t think about it proactively,


Tyler  8:11  

Right. There’s so much fear about, you know, how you’re going to be perceived or what you need to be accomplishing. That concept of authenticity and being your authentic self is… That’s pretty amazing that that was grounding for you in your childhood. I mean, I feel like most people, that’s a very different experience that’s like they get to their late 20s their 30s before they realize like, man, I have just been pre-conditioned to live this certain type of life instead of just being real and being myself and wanting to really explore and, and share that person with the world. I was so anxious and neurotic about the scene that I was in, or the people I was surrounded by. That’s pretty awesome that you were able to have that type of a childhood.


Kelli Dragovich  8:52  

Yeah, I mean, that’s, I mean, believe me, I had my own neuroses here and there. We all do. But it’s it’s pretty crazy how powerful those things can be. If they’re not, you know, they’re not addressed. I mean, we have, you know, these kids committing suicide over crap on social media. I mean, that’s insane. There’s something wrong with that. So, again, just trying in practice, and you know, my sons are almost 11, and one of them was like, Maybe I’m gay. And I’m like, maybe you are, like, let’s talk about it. And so it’s, it’s really cool. Just to have that open environment where, you know, people feel like they have choice and it doesn’t really matter.


Tyler  9:30  

Yeah, yeah. That’s so awesome. You mentioned your competitive streak. I want to talk about that a little bit. So I know I’m a boxer. I’m not an amateur… I wouldn’t consider myself an amateur boxer. I would in the descriptive form, not the noun of amateur boxer. I’m quite amateur at it. But I love boxing. I love sparring. I want to talk a little bit more about that. Where did that come from for you? Where did when did you get interested in boxing?


Kelli Dragovich  9:54  

Yeah, I think it’s my dad used to say it’s always been in our blood. I mean, he was an athlete. He still has records at San Francisco State in track and field, so I think some of it was probably genetic. But I just I just loved it. I love the adrenaline of being physical, I still, you know, pride myself on being physically healthy and strong, it gives me it just gives me energy and confidence personally. So I will, you know, often cancel meetings or take a half day to go on a six mile trail run, it’s just it’s always been very important for me. So just growing up just loving loving those sports and loving that camaraderie at the same time. And just that that rush so was always in year round sports, this or that played in college, you know, and then we get we graduate college, and we’re like, oh, the real world and a job and you don’t really have time to play anymore. And you miss, I was like, what can I do now? Like, how can I be competitive if I’m not gonna do the usual stuff? And that’s where the boxing came in. It’s something you can do, you know, on your own after work. It’s still great workout. So I had an amateur career when I was 25. What am I now? 43. And I still, I still box, I got a bag in my garage. Do it often. It is it is amazing. But yes, a crazy feeling when you can play, a, you know, 90 minutes soccer game and run eight miles. And then you can’t actually do three two minute rounds. And you feel like you’re just, you know, your arms and legs are rocks, it’s very strange.


Tyler  11:29  

It is. It’s bizarre. And the adrenaline is a big part of the exhaustion too.


Kelli Dragovich  11:33  



Tyler  11:34  

So that’s interesting. So it’s so you’re painting this picture, which I feel like, speaks to how dynamic maybe you are as a people leader in an organization, because you have this embedded in you this value of authenticity, really want people to show up as their authentic selves, so important when you’re leading people function. And then but you also have this competitive streak as well, where it’s not just about, you know, the the individual, it’s about competing and under promising and over delivering. And obviously, there’s a high performance culture and a lot of these companies that you’ve been at some starting to see how these things probably played a big role in you being successful as a people leader.


Kelli Dragovich  12:15  

Yeah, I mean, it is, it is crazy. And sometimes those things don’t reconcile, well, competitiveness, and then, you know, being true to yourself and making sure you’re taking time, I think, you know, and I’ll be honest, I mean, for those of you who are out there, I’ve gone back and forth, probably four times now in the past six years of taking a break, you know, from this role from tech slowing down, it’s to the point where now or anyone who knows me is like your crying wolf, it’s a joke, no one believes me anymore about taking a break. So I struggle, you know, with those two things, because it’s been 100 miles an hour since I was 21. When I started into it, and it hasn’t stopped. And I love this role. I love building I love you know, entrepreneurial businesses, which is why I joined companies like Pendo and Looker and GitHub and Hired and it’s, it’s just fun. And it’s hard. And it’s great when you win and have great outcomes and you know, change change the world. But it definitely takes a toll. So, you know, again at 43 I’m in that space, where how do I balance these things and start thinking about the next, the next chapter? Because I don’t think the next 20 years can be like the former.


Tyler  13:33  

Yeah, no, it’s tough. I mean, I, obviously, you know, I’m nine years into building this company. And it’s, it’s nonstop, it affects… You know, there’s no such thing as time off, even when you’re taking time off, you’re thinking about work, you know, you’re thinking about the next thing that you’ve got to go out and get. So I want to talk a little bit about how you got into the field of people and HR, because I read somewhere that you… So you went to Santa Clara University, and you did Pre-Med for the first two years. And you you discovered right that that’s not actually the field you wanted to go into you wanted to go into psychology. Can you share a little bit more about that?


Kelli Dragovich  14:11  

Yeah, absolutely. I mean, I, you know, my story’s interesting. I ever since I was little, I wanted to be a doctor, it was just, you know, one of those things I want to be a doctor over and over I love science and math and was pretty good at it. So that continued and I was pre med for almost two years at Santa Clara. And it’s it’s one of those things where that that that work and that path. I mean, you have to love it, like more than you love anything to keep going through that. And I think I mean, I didn’t I didn’t sleep and it was so stressful. And it turns out I’m pretty good at science and math, but I think the thing that broke me was the organic chemistry. O-Chem class and…


Tyler  14:55  

Chemistry broke you.


Kelli Dragovich  14:57  

Organic Chemistry, not regular chemistry, because that’s pretty fun. But organic chemistry broke me and I, I went back to Santa Clara to speak on an alumni panel and just, you know, sharing some things about a year and a half ago around the career aspect. And I said, I literally just passed, you know, walked by the room that was like my fall, the science building. And we have like a final and it took three hours. And I remember I turned out… I have a pretty good sense of humor. I just walked up to my teacher and I turned it in. I said, Yeah, I don’t think I’ll be seeing you next year. And she laughed. But yeah, it was fun. But it also turns out that I, I’ve always had an entrepreneurial streak, too. So I’d be the strange kid that would like do science and do all these things, and then go out and be like, “hey, let’s spin up a lemonade stand, make some money, and go, you know, hustle and do all these things.” So I always loved, you know, building taking risks. And I’ve been pretty persuasive with with people and this and that and just enjoyed it. So naturally, when you fail out of your, you know, first choice, you go into psychology, everyone does that.


Tyler  16:04  

Like, well, that’s what I was gonna ask, like, why psychology? Okay.


Kelli Dragovich  16:08  

It’s the, it’s the fallback, right? I mean, everyone loves psych. So I did that. And I can’t tell you enough how I just couldn’t handle clinical psychology in the, you know, the couches and the Freud. Interesting but it just wasn’t me. It just wasn’t excited, entrepreneurial enough or action oriented enough. So just slowly took a couple other courses, like, you know, organizational behavior, and like, you know, economics and just basically, fast forward into this really unique, perfect blend of people and business without getting too deep into either. Yeah, that makes sense. Yeah, it wasn’t clinical psychology. And it wasn’t like tax accounting.


Tyler  16:50  

Right. But I love what you’re saying that it’s action oriented, you felt like, okay, the theory of a lot of this stuff is really fascinating. But at the end of the day, I want to put this into practice. How do we actually make is it about behavior change? Or what do you mean, when you say action oriented?


Kelli Dragovich  17:03  

Just getting stuff done. Building things, changing people’s lives. Just seeing, seeing things change, and doing it with other people. So you know, it goes back to the sports days, and just the the importance of friends and family, just that camaraderie has always been important to me, it’s still important to me. So I struggled with going into, you know, independent consulting for a while, just because it just doesn’t give me as much energy. So it was this concept of like, how do I put together business and people and like, build stuff at the same time? Like, does that even exist? I mean, I don’t know, I was a junior in college in 1998, or 99. Like I didn’t know, up from down, I didn’t know what a PowerPoint slide was, I mean, nothing, right. But one of my professors just basically said, the magic words to me one day, and she said, “Have you ever heard of industrial organizational psychology?” And I had no idea what that meant. I had no idea. It was a job or a major. And we talked about it for like three months. And I’m also extremely decisive. Like, that’s what I want to do. That’s it. looked into all these schools, she’s like, “Well, maybe you should work a couple years and then go…” No, I’m going to grad school, like immediately, because this sounds, this sounds really fun.


Tyler  18:21  

That’s amazing. But some people we talked to, they have this plan in place already. And they stick with the plan. And they kind of look out 10 years, and they can speak to like 10 years later, I actually got all this things done. And then other people are a little bit more spontaneous. But you typically don’t see the spontaneous folks being as decisive as what you just articulated, the ones that are more, you know, they would call themselves rudderless. I would call them open to new things are less decisive. Whereas it seems like you kind of you have both you have this, like open exploration, but when you find what you want, you go after it.


Kelli Dragovich  18:55  

Yeah, no, absolutely. And I, you know, you hear a lot of HR people, right? It’s like, it’s like “the” statement: “oh, I fell into it, right? I fell into HR”. And, like, I guess you could say I did, but not really, because I think about even my school or what interests me or even personal life and just my personality. I mean, all these things built into this, like, very unique blend of people in business, you know, with a competitive edge, which if you think about it is like this role in tech right now.


Tyler  19:25  

Yeah, absolutely. And how do you end up so you you end up getting your Master’s in Organizational Psychology? How do you end up at Intuit of all places?


Kelli Dragovich  19:35  

Yeah, that’s a funny one. So I got my master’s degree when I graduate like 2002, went down to San Diego for that. Amazing, by the way, still surf. My brother lives in Santa Cruz, so I’ll go over there and surf badly but I’ll still do it, which is you know, that’s all that matters. And I was in San Diego and came back, you know, after, right after I graduated he like why’d you come back by, why’d you leave San Diego so fast? And like, look, there’s only so many happy hours, right? Every day is happy hour in San Diego every day is 70, breezy and sunny. Like you got to… the point. You know, come back, so came right back. And the job market was terrible, Tyler. I don’t remember 2002. But yeah, it just wasn’t great. And again, you know, if anyone wants to talk, very strong point of view of well, you don’t have experience. So no, like I couldn’t find, I couldn’t find a job in HR at companies around here. And I’m not lazy. I mean, this was like eight hour searches. This was thousands of emails. This was this was like trying. And so to this day, because of that experience, like, if anyone “LinksIn” me, I will always answer it. Like, if someone randomly pings me on LinkedIn, you know, whether they’re in college, or they got laid off, or they want to switch careers, and they’re like, I don’t know what to do. No one’s helping me. I’m like, let’s talk.


Tyler  21:00  

So this is so awesome, that combination, I’m not just trying to make, you know, blow up your ego here, that combination of the competitiveness of like, I’m going to get this job, I’m going to make it happen with the empathy that then comes as a result of having gone through those trials. Like I went through the same thing. So I entered the workforce in ’08 in the middle of the financial crisis. And it was like nonstop head against the wall. But at no point do I look back and think, oh, man, I really should pay it forward. People are going through that. That’s awesome. That that, that that was where your brain went was I’m now going this is stuck with me such that 20 years later, I still do this and support people who are looking for a job. That’s that’s a huge undertaking. There’s a lot of people out there LinkedIn, people like you, I’m sure looking for a job.


Kelli Dragovich  21:49  

Yeah, it’s the worst feeling, you know, when you’re actually trying and just no one gives you a break. I was like, jeez, this sucks. I don’t want anyone to ever feel like this. So yeah, it’s been fun. And a lot of them have have been, you know, Santa Clara, juniors and seniors. And they’re like, “What did you do? Like, I want to be this one day, like, how do I do that?” And there, there isn’t a path for this. You can’t like be 20. And someone says, here’s how you become a Chief People Officer at unicorn company, pre-IPO companies like there just isn’t. Maybe there should be, maybe that’s what I should do next. But like engineering, sales, marketing, like, finance, like there are steps like you know, what you do I go to investment bankers, I go here, there is no clear path. And I think that’s something you know, that I experienced, and I just, you know, trying to help but but yeah, that empathy is important comes back, it comes back around a lot. I mean, someone ping me the other day who I talked to, I think it was like eight years ago. And they were like, I’m here. Just want to say thank you if you ever need anything? And I was like, “yes, I need you to hire me as a consultant in about three years.” [Laughs]


Tyler  22:59  

Well, that’s where that authenticity, I think comes into play too, right? You, you know, oftentimes, if you are successful, which you have been, you can lose some of that core that realness and feel like, oh, I don’t have time for these people anymore, right? Like, I’m super busy. I’m Chief People Officer at Pendo. I’m focusing on this consulting thing in a few years to try to figure that out. Like, it’s so easy to tell yourself that story instead of being real and saying that, wait a minute, you’re not, you know, you’re no better than these people to help these people out that you were in their shoes once. That’s, that’s awesome.


Kelli Dragovich  23:29  

Yeah. I mean, it’s all connected. You know, it all. It all like comes back around. So I think on my team now, I think there’s like, there’s at least seven people I’ve worked with in the past on this team. So it’s, it’s really important, especially if you’re in tech, you know, in Silicon Valley type companies.


Tyler  23:47  

So why is it that you gravitated towards and have continued to, towards hyper-growth companies? I mean, I’ve heard you say this before you like the versatility, the chaos, the intensity of building the business and the teams at the same time, but that’s a that’s a unique thing. A lot of people think hyper-growth, they think, “oh, this is gonna be sexy, it’s a unicorn, this is gonna be so much fun.” And then they get in and realize that chaos and intensity and are going, “wait a minute. This is not what I signed up for.” What is it about that type of environment that that you find so thrilling?


Kelli Dragovich  24:19  

Yeah, it’s it’s not easy. Like very, very draining, actually. But, but again, so so fun. I think it just depends on your temperament. You know, I like to say my, I don’t know if you gamble, Tyler, I like to gamble. But my favorite game is craps. Because it’s like insane. There’s like six games going on in that game at any given time. So I don’t know. I don’t know if it’s just, I have high bandwidth or maybe some attention deficit, like, I don’t know what it is. But I like a lot of things going on at once and to bring things together and create you know, simplicity and clearness out of chaos. In complexity, I think it’s, I think it’s so fun


Tyler  25:03  

So was there a moment? You know that that makes sense in theory? Can you give us an example? Was there something where you were able to make sense of the chaos and complexity and simplify and take clarity? And you saw that happen as in your role as a people leader and said, wow, this is this is my drug. This is what I want to keep doing.


Kelli Dragovich  25:21  

I mean, yeah, I mean, so I mean, the most, there’s, there’s a lot of them, but the most recent one, I guess, would be Pendo, you know, just decided to come in and do the usual well, I’ll take, you know, a month off, and I’ll start in January. And then, you know, it’s hard to do that. Because these, these companies are growing so fast and changing every minute. So you start to kind of dabble like, well, what do we need? You to try to get ahead of it right before you start. And I will say there was so many things that just weren’t even, like touched, let alone built a little bit. I mean, the people function and the organizational side of Pendo, probably was a year behind the company. And I think the team was about nine people. And we knew we had to hire at least 25-30 people this year, let alone hire into the company, at least 450 people. So I’m kind of looking at this tsunami, a lot of people like they would paralyze like, what do I do? And it was like, nope, like, put me on a consulting gig before I start. Ship me a laptop. Let me start kind of making sense of this and kind of think about, right, it’s kind of like, it’s back to the doctor motif, not intentional, but kind of like surgery. It’s like, you know, trauma. It’s like, where do I start? Where do I start?


Tyler  26:40  

Kind of like a game of Craps? It sounds like for you, yeah, look at all these games.


Kelli Dragovich  26:43  

Yeah, now we’re back to being a doctor? It’s all working. I really am a doctor. But it’s trauma. You’re like, where do I start? What do I do? And so it’s, it was just fun to be like, Look, let me just take this time, let me think about, you know, back, you know, my organization first, like, you can’t write help the kid in the plane unless you put your own mask on. And I got to build this team very quickly. And how do I do that? How do I rally them around a strategy? How do I bring the company along? Well, executing on things that are just broken or on fire? I mean, that that’s really fun to me. So I think, you know, where I can understand people are like, oh, geez, nevermind, like fight or flight. Like I lean into those things. Because once you crack those codes, and once you kind of get through that, it, there’s no better feeling. You know, and I think in this role at companies that are, you know, growing 70%, year over year, if you can figure out that recipe, not that it’s a playbook, every company, but if you can figure out like the trick, or the secret sauce on how to get through those first six months and come out the other side, it’s the best job in the world.


Tyler  27:48  

And you’ve been through this so many times, what are some of the common trends you see in these hyper growth companies when you come in some of the biggest things they get wrong or underappreciated?


Kelli Dragovich  27:58  

Yeah, I mean, I talk to a lot of Founder/CEOs, I love this, this stage, I love this job. But the stage I’m kind of your 200 to 3000 person, which I think is some of the most difficult, but rewarding kind of phases and building. And I talked to them a lot like, well, when should I hire an HR person or this or that. And I always, I always talk about one of the biggest, you know, misses is usually when these companies are super successful, and they’re just kicking butt because they’re focusing on revenue and more clients and product and more revenue and more clients and product. And that is great. But I talk to them kind of like a, you know, have you played Jenga, Tyler?


Tyler  28:41  



Kelli Dragovich  28:41  

You’re building this tower, right? If you think about the blocks, you’ve got, like business growth blocks, and then you have organizational or people blocks. And when you get a taste of that success, and you’re a, you know, co founder, and your company is finally moving, you have an inclination to like take the business growth blocks only. And just stack them like as fast as you can upward. But I always talk to them about like, be careful, because you’re not infusing in any of the organizational people, culture blocks. And this is like your architecture like this, this will allow you to keep building the business side aggressively without slowing down or falling. And you see it I mean, 150 is the first magic number 150 employees, things start to break or change 300 The next one. And if you don’t do this proactively and well by 500 people, you’re lucky if your business is just stalling, because internally you’re a hot mess, and like I don’t know what’s going on and everything’s all over the place. But I’ve seen a lot of companies have to stop, do layoffs, reset, and then and then they’re toast because the market just catches up.


Tyler  29:56  

Right. Yeah. So you’re you’re seeing this under appreciation or these blocks that are missing, typically are folks bringing you in when the fire’s already, they can see it and smell it, or are they more proactive these Founder/CEOs to say, look, I get it already, and I want to bring you in to get ahead of it.


Kelli Dragovich  30:14  

Yeah, well, it’s funny because I don’t you guys have probably seen this too. It’s, it’s changed, like, extremely dramatically in the last, I would say, five years. I think five years ago, even which is pretty recent, you know, it was like, oh, God, we have fires everywhere, we have to hire an HR person to put these out and keep putting them out. It’s like this insurance policy role.


Tyler  30:37  



Kelli Dragovich  30:38  

You don’t like you know, they don’t, they don’t buy the insurance policy until like, you know, things break. But this rule now is one of the most sought-after competitive, like, comp packages for this role have just gone crazy. One of the most sought-after roles. And if you’re, you know, a really good CCPO and entrepreneurial and great to work with, right, you’re focused on guidelines and bending rules versus setting them in black and white. I mean, if you’re, if you’re literally have the same makeup, as these Founder/CEOs, you think about it, they want to work with you, and then why to help build these companies. And so it’s the future of this role, I wouldn’t be surprised in 10 years if there was like, you know, majors and Masters, you know, courses and caught like a digital different focus on this than when I was in college.


Tyler  31:27  

Absolutely. And what do you think changed over the past five years? That’s so interesting, right? Because the HR functions existed for 100 years. So what what is it about the last five years and maybe not 100 years, but you get where I’m going.


Kelli Dragovich  31:39  



Tyler  31:39  

What is it that has happened over the last five years that you think made such a sea change in how people think about this?


Kelli Dragovich  31:47  

Wow, I mean, it’s a lot of things, whatever you think of just off top of my head, if you think about software, you know, like software companies, enterprise SaaS, companies, the term is kind of old now. And I feel lame saying it but like, “software is eating the world,” every company is a software company. But it’s true. Like, you know, academia to like John Deere, out of Idaho, wherever they’re based, to, like, your San Francisco-based tech company. They’re, they’re all tech companies. And so if you think about that, that type of talent, people are bringing in the type of products that are being able to be built. You have venture money, just all over the place. Like that’s been crazy to write all these companies going public, all this money being raised. I mean, there’s just, there’s a maybe it’ll crash one day, I don’t know. But there has been an increasing number of rapidly-growing successful, money-backed software companies out there over the past five years. And when that happens, you have more people, you have more issues you have, like, the more an abundance of like organizational things these companies have to focus on. People are waking up to like, that’s, that’s an important part of it. It’s not just the revenue and the product.


Tyler  32:59  

Right. So it’s not just a rising tide lifts all boats, like every function is coming in higher demand. There’s been, we’ve all heard the stories of the Zenefits. And the we work so the world that, you know, we’re growing super fast, but didn’t maybe didn’t think as much about this as they should have.


Kelli Dragovich  33:14  

Yeah, well, that goes to the you know, the Jenga tower. People say, “well, what do you what do you do at Panda all day?” I’m like, I’m making sure that this thing, or like stacking them appropriately, so we can build up, and it’s all supported, and we can keep going?


Tyler  33:28  



Kelli Dragovich  33:28  

I think, look, I think it’s no secret that diversity, equity, inclusion, instances, events, focus that, I think that really started it, right. I mean, if I think back to my start in 2014, GitHub, you can look it up on TechCrunch, it was kind of like write the big investigation and the boys clubs and the harassments. And all that, you know, was it was a big push. And I’ll admit, like, if I’m, you know, a Founder/CEO, I’m looking at that, like, oh, gosh, we need to hire insurance policies, look at all these companies, like, all this bad stuff is happening. And I think that was probably some of the impetus, you know, for people wanting HR people earlier and companies. But it’s, it’s, it’s necessary, but it’s not sufficient. Like anyone can hire an HR person that’s rule based and can do investigations. But these companies now are realizing if you want to, you know, be a $250 million public company, and you want to do that as quickly as possible. You need someone at that table that can focus on the business and also articulate the people side of it and build that tower together very quickly.


Tyler  34:33  

And they appreciate the tower for what it is because they’ve seen the Jenga towers fall already, which may be one of the differences five years ago.


Kelli Dragovich  34:41  

They’re like terrified right? Founder/CEOs are like I don’t know what to do or say like, Well, what do we do? It’s yeah, great.


Tyler  34:47  

Yeah. Well, what about the future so this is kind of the time we’re living in now. A lot of people talking about the future of work and I’m always like a roll my eyes at that. Like what does that mean when you say your work, like, let’s get down to brass tacks. I’m curious when you think about where this is all going hypergrowth companies the way that we work, distributed work all this stuff. What are things that excite you about the future of work and things that scare you about it?


Kelli Dragovich  35:16  

Yeah, I mean, I’m happy to I mean, you have the usual answers, I’ll just, I’ll get to brass tacks, right usually answers distributed and this and that. But again, I’ll just, I’ll just tie this back in, we’re almost at a wrap back to the authenticity thing of it. And the realness thing of it, I think the future of work is that people literally want to like, enjoy their lives and enjoy their jobs at the same time, and they want to work for a place doesn’t feel like the nine to five. And it’s just so funny. It’s because there’s been movies forever, right? Think about movies, or sitcoms, or whatever it is, like, people hate their jobs, and they bitch about their boss. And they, you know, on Sunday barbecues complain that they have to go to work on Monday. Like, I think there is going to be this incredible push to be real, and be yourself at work. And I that’s all I care about now, you know, is creating these teams that can just speak freely and feel feel comfortable, feel safe. And, you know, just kind of call it for what it is and not create these environments to go I’m at work, I have to kind of sit up taller, or watch what I say. I mean, people just want to be happy and enjoy work and enjoy their lives, I think we’re gonna see a lot, a lot of push towards, and we’re already seen it, people are leaving companies where there’s terrible leadership, or they’re, they don’t believe leadership is transparent. The mission of the company is sucks and isn’t good for the world. I mean, we’re seeing people making these choices already. And so for me, whether that’s flexible work, distributed this, that whatever it is, people just want honesty, and they want to have fun, and they want to enjoy their lives because it’s short, and the world is changing. And this whole COVID, all the other stuff that’s going on, it’s getting people perspective. And that’s what I’ve seen is people have more perspective than they did five years ago, when they would kill themselves to be unhappy for a payout.


Tyler  37:08  

Yeah. It’s a pretty optimistic future to look towards. And it’s also so simple and something you think about our grandkids, like looking back on this and being like, why was it that way before? Why did you do that to yourself? It makes no sense, you know.


Kelli Dragovich  37:23  

Yeah, it’s so simple.


Tyler  37:24  

Like smoking on an airplane, like when you see video that you’re like, why did you think that was a good idea?


Kelli Dragovich  37:29  

Even kicking off a team, something so simple as kicking off a team meeting and being like, well, this day sucks, like anyone else, what’s going on out there? I mean, it’s just a different vibe. It doesn’t mean that people don’t want to work hard. People want to work hard, but they also want to make sure that they’re not, you know, giving up really important stuff, either within the work walls or whatever walls or not walls, but at home and their lives.


Tyler  37:54  

Amazing. Yeah, I love, I would love to say that the future of work is one where people are able to feel much more authentic at their workplace and feel like it’s a integral part of their lives instead of a paycheck that’s supporting what they care about.


Kelli Dragovich  38:08  

Yeah, I think just to sum it up the Venn diagram of like, work and personal, you know, like, 10 years ago, they were separate circles, like, no, we don’t, you know. And now they’re like, it’s almost like an eclipse. Like, they’re, they’re almost like 80% overlap.


Tyler  38:25  

Anything scare you about that?


Kelli Dragovich  38:28  

Ah, yeah, yeah. I mean, we I’ll see, you know, I’m sure there are other CPOs on the call. It’s challenging. I mean, we have conversations weekly about like, geez, like, this is a blurred line, like, how do we, you know, deal with this with the company with with personal stuff. And there’s just there’s a lot of challenges that come with that, because it’s not as black and white anymore.


Tyler  38:49  

Kelly, thank you so much for sharing your story today and your thoughts as well on the role of people function at hypergrowth companies in the future of work. I’ve really enjoyed the conversation.


Kelli Dragovich  38:58  

Same here. This is fun. Thank you, Tyler.


Tyler  39:05  

That was Kelli Dragovich.


Tyler  39:10  

It’s refreshing to talk to someone who keeps it real like Kelli. One of the things that struck me about what she said was the point she made about early-stage startup environments, that kind of getting in right at the ground level, and they’re at 200 employees, maybe even 100 employees. And she talks about the chaos and the disarray of that environment and how she really wonders why she keeps putting herself in a situation where she’s walking into that chaos and disarray. And she wonders why it is that she finds such a thrill from being in that type of environment. And I can totally relate to that. I think, you know, I oftentimes wonder the same thing myself. Why do I do this? Why do I build a company from scratch? Why do I enjoy, you know, making all the sacrifices that come with working in that type of environment. I mean, even right now, it is nine o’clock on a Tuesday night. And I’m recording this in my closet. You know, instead of playing with my kids and my wife like this is just something that I get thrill off of something I enjoy and to a lot of people it doesn’t make sense and I can’t explain why but that totally resonated when she talked about that I can I can definitely empathize with that unique feeling


Tyler  40:32 

You can find us online at I’m Tyler Muse.


Tyler  40:39  

Groundwork is produced by Mike Giordani at Flowship, audio engineering by Alex Roses, production assistance by Casey Miller, music by Aaron Sprinkle, Adrian Walther, and Corolina Combo. Special thanks to Pedro Matriciano and Natalya Krimgold.

Until next time, thanks for listening.

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