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.

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

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.

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. 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.

Hello and welcome to Groundwork, a show about chief people officers from the world’s fastest growing companies.

I’m Tyler Muse.

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 envisioned the future of work.

Today we’re featuring my conversation with Kelly Dragovich. I like a lot of things going on at once and to bring things together and create simplicity and clearness out of chaos and complexity.

I think it’s so fun. Kelly started out as an HRBP at Intuit. She moved on to Yahoo and from there found herself in the world of rocket ship 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. There’s one thing Kelly knows how to do it’s, how to build the plane while flying it. In this episode, Kelly talks about the biggest mistakes 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.

Kelly, thank you so much for joining us. We’re so excited to have you on the show today, so happy to be here. Thank you. I want to start with so you grew up in the Bay Area. Is that right? I did.

I guess I’m told rare, born and raised Bay Area natives. 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 it’s changed, but it’s got to be nothing like what’s happened to San Francisco over the past 30 years. Yeah. It’s a little nutty.

I’ll be honest, remembering back at middle school, which my kids now go to the middle school I went to. And so it’s very strange. Yes. What was that like growing up in the Bay Area, it was good. I mean, I’m told I’m a really energetic, high energy person, and I just remember always going and I guess now that I’m an adult here, I guess 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 it was just always really busy a lot going on, a lot of friends, a lot of sports, a lot of activities, so it was fun.

There’s tons to do here, that’s for sure.

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.

Absolutely. I get told a lot. You’re from the West Coast, you don’t seem like a West Coast person. So I think there is definitely some stigmas, but Santa Cruz is right over the Hill from where I live, and that’s definitely more laid back. That’s awesome. What were some of the most formative moments in your childhood that you feel like really shaped you as an adult? Yeah. I think one the Bay Area can be intense.

And there’s a lot again, a lot going on. I think if I think about my high school years and just the friends I made there and kind of the values and that shaped us were still all actually very close from high school days. There was always this feeling of being real and being authentic. And it’s hard, I will admit, growing up in a privileged way, just to be honest, I’m well aware of that privilege. And I went to a high school in 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.

Yeah. No, it totally makes sense. Very similar. My childhood also grew up in a very privileged bubble, frankly. 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. Yeah.

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 saw that. And I think just being genuine to other people kind of helping being down to Earth is something that’s always been super important to me. I think a little bit of another angle on that just in full transparency is just growing up LGBTQ. So just growing up gay in the Bay Area in the 90s and just what that’s like, and just again, being true to others, being true to yourself has always been super important to me.

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

First of all, full support.

I think it’s interesting. It’s more what you put on yourself almost. And the assumptions you make on how your family will react or this or that. And so I think that’s really interesting to me. It’s kind of the self boundaries we impose, usually ourselves. But no, it was definitely full support. My best friend actually came out when she was 16.

I didn’t till I was about 21. So very interesting. And we’re so close to this day we actually have twin boys each who are ten weeks apart.

Oh, my gosh. Yes. A 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 a lot of support. And it’s just funny how these things parlay, because the tech scene now and just my role in the industry that it’s in.

It’s almost an advantage in a weird way based on kind of just all the really good inclusion efforts that are out there and diversity equity inclusion. And it’s been 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, 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.

Right. There’s so much fear about how you’re going to be perceived or what you need to be accomplishing that concept of authenticity and being your authentic self.

That’s pretty amazing that that was grounding for you and your child. But I feel like most people that’s a very different experience. That’s like they get to their late twenties or 30s before they realize, like, man, I have just been preconditioned to live this certain type of life instead of just being real and being myself and wanting to really explore 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 childhood. Yes.

Believe me, I had my own neuroses here and there. We all do. But it’s pretty crazy how powerful those things can be if they’re not addressed. We have these kids committing suicide over crap on social media. I mean, that’s insane. There’s something wrong with that. So again, just try and practice.

And my sons are almost eleven and one of them is like, maybe I’m gay, and I’m like, maybe you are like, let’s talk about it. And so it’s really cool just to have that open environment where people feel like they have choice and it doesn’t really matter. Yeah, that’s so awesome. You mentioned your competitive strike. I want to talk about that a little bit. So I know I’m a boxer. 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? When did you get interested in boxing? Yeah. I think my dad used to say it’s always been in our blood. I mean, he was an athlete, still has records at San Francisco State and track and field.

So I think some of it was probably genetic. I just loved it. I loved the adrenaline of being physical. I still pride myself on being physically healthy and strong.

It just gives me energy and confidence personally. So I will often cancel meetings or take a half day to go on a six mile trail run. It’s always been very important for me. So just growing up just loving those sports and loving that camaraderie at the same time. And just that rush. So was always in year round sports this or that played in College and then we graduate College and we’re like, oh, it’s the real world and a job. And you don’t really have time to play anymore.

And you missed. I was like, what can I do now? How can I be competitive if I’m not going to do the usual stuff? And that’s where the boxing came in, something you can do on your own after work. It’s still a great workout. So I had an amateur career when I was 25.

What am I now 43 and I still box. I got a bag in my garage do it often. It is amazing. But, yes, a crazy feeling when you can play a 90 minutes soccer game and run 8 miles, and then you can’t actually do three, two minute rounds and you feel like your arms and legs are rocks. Very strange. It is. It’s bizarre.

And the adrenaline is a big part of the exhaustion, too. Yes.

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. You really want people to show up as their authentic self. So important when you’re leading a people function.

But you also have this competitive streak as well, where it’s not just about the individual. It’s about competing and under, promising and over delivering. And obviously there’s a high performance culture at a lot of these companies that you’ve been at. So I’m starting to see how they think probably played a big role in you being successful as a people leader. Yeah, it is crazy. And sometimes those things don’t reconcile, well, the competitiveness and then being true to yourself and making sure you’re taking time.

And I’ll be honest 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 from this role, from tech slowing down, it’s to the point where now where anyone who knows me is like you’re crying Wolf. It’s a joke. No one believes me anymore about taking a break. So I struggle 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 entrepreneurial businesses, which is why I joined companies like Pendo and Looker and GitHub and hired.

It’s just fun and it’s hard, and it’s great when you win and have great outcomes and change the world. But it definitely takes a toll again at 43, I’m in that space where how do I balance these things and start thinking about the next chapter? Because I don’t think the next 20 years can be like the former.

Yeah. No, it’s tough. I mean, obviously, I’m nine years into building this company and it’s nonstop.

There’s no such thing as time off. Even when you’re taking time off, you’re thinking about work. 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 in HR because I read somewhere that you went to Santa Clara University and you did premit for the first two years, and 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? Yeah, absolutely.

My story is interesting. Ever since I was little, I wanted to be a doctor. It was just one of those things. I’m going to be a doctor over and over love science and math. I was pretty good at it. So that continued. And I was premed for almost two years at Santa Clara.

And it’s one of those things where that work and that path you have to love it more than you love anything to keep going through that. And I think 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 chemistrym class.

Chemistry broke you.

Organic chemistry, not regular chemistry, because that’s pretty fun. But organic chemistry broke me.

I went back to Santa Clara to speak on an alumni panel and just sharing some things about a year and a half ago around the career aspect. And I said I literally just passed, walked by the room. That was like my fall, the science building. And we had, like, a final and it took 3 hours. And I remember I turned 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’m going to be seeing you next year.

And she laughed. But yeah, it was fun. But it also turns out that 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, makes money and go hustle and do all these things. So I always loved building, taking risks. And I’ve been pretty persuasive with people and this and that and just enjoyed it. So naturally, when you fail out of your first choice, you go into psychology.

Everyone does that. That’s what I was going to ask. Like, why psychology. Okay. 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 and the couches and the Freud.

Interesting. But it just wasn’t me. It just wasn’t entrepreneurial enough or action oriented enough.

So just slowly took a couple of other courses, like organizational behavior and economics and just basically fast forward into this really unique, perfect blend of people and business without getting too deep into either.

If that makes sense. So it wasn’t clinical psychology and it wasn’t like tax accounting, 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 Orient, just getting stuff done, building things, changing people’s lives, just seeing things change and doing it with other people. So it goes back to the sports days and just 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 independent consulting for a while just because it doesn’t give me as much energy. So it was this concept of, like, how do I put together business and people and build stuff at the same time? Does that even exist? I don’t know. I was a junior in College in 10, 00, 19, 98 or 99. I didn’t know up and 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. 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 of years and then, no, I’m going to grad school immediately because this sounds really fun.

That’s amazing. Some people we talked to, they have this plan in place already, and they stick with the plan and they kind of look out ten years and they can speak until, like, ten years later. I actually got all these 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 they would call themselves rudder less. I would call them open to new things are less decisive, whereas it seems like you have both. You have this open exploration.

But when you find what you want, you go after it. Yeah. No. Absolutely. And you hear a lot of HR people, right? It’s like the statement. I know. I fell into it, right.

I fell into HR. 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. All these things built into this very unique blend of people in business with a competitive edge, which, if you think about it, is like, this role in tech right now.

Absolutely. And how do you end up? So you end up getting your Masters in organizational psychology? How do you end up intuitive of all places? Yeah, that’s a funny one. So I got my master’s degree. What did I graduate in 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 all that matters.

And I was in San Diego and came back right after I graduated. People like, Why did you come back? Why did you leave San Diego so fast? I’m 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 some point come back. So it came right back. And the job market was terrible. Tyler, I don’t remember 2002, but it just wasn’t great.

And again, if anyone wants to talk very strong point of view of, well, you don’t have experience.

So no, 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 like trying. And so to this day, because of that experience, if anyone links in 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.

That’s just so awesome. That combination. I’m not just trying to 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. I went through the same thing. So I entered the workforce in eight 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. If people are going through that, that’s awesome. That that was where your brain went.

This has stuck with me such that 20 years later, I still do this and support people who are looking for a job. That’s a huge undertaking. There’s a lot of people out there Linkedining people like you. I’m sure looking for a job.

Yeah, but it’s the worst feeling when you’re actually trying and no one gives you a break. I was like, Jeez, this sucks. I don’t want anyone to ever feel like this.

It’s been fun. And a lot of them have been Santa Clara juniors and seniors, and they’re like, what did you do? I want to be this one day. How do I do that? And there isn’t a path for this. You can’t be 20. And someone says, here’s how you become a cheap people officer at Unicorn Company, pre IPO companies. There just isn’t. Maybe there should be.

Maybe that’s what I should do next. But, like, engineering, sales, finance.

There are steps like, you know what you do. I go to investment bankers or I go here. There is no clear path. And I think that’s something that I experienced, and I just tried to help, but, yeah, that empathy is important.

It comes back around a lot. I mean, someone pinged me the other day who I talk to. I think it was like, eight years ago, and they were like, I’m here. I 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.

Well, that’s where that authenticity, I think, comes into play, too. Right? Oftentimes if you are successful, which you have been, you can lose some of that core. That realness and feel like 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. It’s so easy to tell yourself that story instead of being real and saying, no, wait a minute. You’re no better than these people to help these people out that you were in their shoes once.

That’s awesome. Yeah. I mean, it’s all connected.

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

So why is it that you gravitated towards and have continued to towards hyper growth companies? 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 unique thing. A lot of people think hyper growth. They think, oh, this is going to be sexy. It’s a unicorn. This is going to be so much fun.

And then they get in and realize that chaos and intensity are going, wait a minute. This is not what I signed up for. What is it about that type of environment that you find so thrilling? Yeah, it’s not easy, like, very draining, actually.

But again, so fun. I think it just depends on your temperament. 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 if it’s just I have high bandwidth or maybe some attention deficit. 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 simplicity and clearness out of chaos and complexity.

I think it’s so fun. Was there a moment 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 into clarity? And you saw that happen in your role as a people leader and said, wow, this is my drug. This is what I want to keep doing.

Yeah, there’s a lot of them. But the most recent one, I guess, would be Pendo, decided to come in and did the usual, well, I’ll take a month off and I’ll start in January, and then it’s hard to do that because these companies are growing so fast and changing every minute. So you start to kind of dabble like, well, what do we need? You try 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, they would paralyze, like, what do I do? And it was like, no, 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 trauma. Where do I start? Kind of like a game of craps. It sounds like for you.

Yeah. Look at all these games. 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 was just fun to be like, look, let me just take this time. Let me think about back my organization first. You can’t help the kid on 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 while executing on things that are just broken or on fire? That’s really fun to me. So I think where I can understand people are like, oh, Jeez, never mind, like, fight or flight. I lean into those things because once you crack those codes and once you kind of get through that, there’s no better feeling. And I think in this role at companies that are 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 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. 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 under appreciate? Yeah. I talked to a lot of founder CEOs. I love this stage. I love this job at this 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 talk to them a lot. And they’re like, when should I hire an HR person or this or that? And I always talk about one of the biggest 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 products and more revenue and more clients and product.

And that is great. But I talk to them, like, Have you played Jenga Tyler? 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 CEO founder and your company is finally moving, you have an inclination to 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 your architecture. This will allow you to keep building the business side aggressively without slowing down or falling. And you see it.

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 don’t know what’s going on and everything is all over the place. But I’ve seen a lot of companies have to stop do layoffs, reset and then their toes because the market just catches up, right? Yeah. So you’re seeing this under appreciation of these blocks that are missing typically, are folks bringing you in when the fires 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. Yeah. Well, it’s funny because you guys have probably seen this, too. It’s changed extremely dramatically in the last I would say five years.

Well, I think five years ago, even which is pretty recent, 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.

They don’t buy the insurance policy until things break. But this role now is one of the most sought after competitive comp packages for this role have just gone crazy. One of the most sought after roles. And if you’re a really good CPO 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 literally have the same makeup as these founder CEOs, if you think about it, they want to work with you and they want you to help build these companies. And so it’s the future of this role. I wouldn’t be surprised in ten years if there was majors and courses and just a different focus on this than when I was in College.

Absolutely. And what do you think changed over the past five years? That’s so interesting, because the HR functions existed for 100 years. So what is it about the last five years? Maybe not 100 years. But you get where I’m going. 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? Well, it’s a lot of things. But if I think of just off top of my head, if you think about software like software companies, enterprise, SaaS companies, the term is kind of old now, and I feel lame saying it. But like, software is in the world.

Every company is a software company. But it’s true, like academia to like John Deere out of Idaho, wherever they’re based, to your San Francisco based company. They’re all tech companies. And so if you think about that, the 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. That’s been crazy, too, right. All these companies going public, all this money being raised.

I mean, 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 more, an abundance of organizational things these companies have to focus on. People are waking up to like, that’s an important part of it. It’s not just the revenue and the product, right? So it’s not just a rising tide, lifts all boats, like every function is coming in higher demand.

We’ve all heard the stories of the benefits and the WeWorks of the world that we’re growing super fast, but maybe didn’t think as much about this as they should have. Yeah. Well, that goes to the Jenga Tower. People say, well, what do you do at Penda all day? And I’m making sure that this thing or stacking them appropriately so we can build up and it’s all supported and we can keep going, right? I think it’s no secret the diversity, equity, inclusion instances, events, focus.

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 the big investigation and the boys clubs and the harassments and all that was a big push. And I’ll admit that if I’m a founder CEO, I’m looking at 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 for people wanting HR people earlier in companies, but 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 be a $250,000,000 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. 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. They’re, like, terrified, right? I don’t know what to do or say. Well, what do we do? It’s great. 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, roll my eyes at that. What does that mean? When you say future of work, let’s get down to brass tacks. I’m curious when you think about where this is all going. Hyper growth companies, the way that we work, distributed, work, all this stuff.

What are things that excite you about? The future, work and things that scare you about it.

You have the usual answers. I’ll get to brass tax, right? Usually answer is distributed and this and that. But again, I’ll just tie this back. So now 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 enjoy their lives and enjoy their jobs at the same time and they want to work for a place. It doesn’t feel like the nine to five. And it’s just so funny.

It’s because there’s been movies forever, right? If you think about movies or sitcoms or whatever it is, people hate their jobs and they bitch about their boss. And on Sunday sailing, barbecues complain they have to go to work on Monday. I think there is going to be this incredible push to be real and be yourself at work. And that’s all I care about now is creating these teams that can just speak freely and feel comfortable, feel safe and just kind of call it for what it is and not create these environments. 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 going to see a lot of push towards and we’re already seeing it. People are leaving companies where there’s terrible leadership, where they don’t believe the leadership is transparent. The mission of the company 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 giving people perspective. And that’s what I’ve seen.

People have more perspective than they did five years ago when they would kill themselves to be unhappy for a payout. 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 yourself? It makes no sense. It’s so simple driving on an airplane, like, when you see video of that, you’re like, why did you think that was a good idea, even kicking off a teen? Something so simple is 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 giving up really important stuff either within the work walls or whatever.

Walls are not walls, but at home and their lives.

Amazing. Yeah. 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 an integral part of their lives instead of a paycheck that’s supporting what they care about. Yeah, I think the vent just to sum it up the Venn diagram of work and personal.

Ten years ago, they were separate circles. No, we don’t. And now it’s almost like an eclipse. They’re almost like 80% overlaps.

Anything scary about that? Yeah, I’m sure there are other CPOs in the call. It’s challenging. We have conversations weekly about, like, Jeez, this is a blurred line. Like, how do we deal with this with the company with personal stuff? And there’s a lot of challenges that come with that because it’s not as black and white anymore. Kelly, thank you so much for sharing your story today and your thoughts as well on the role of people functioning at hyper growth companies in the future of work. I’ve really enjoyed the conversation. Same here.

This is fun. Thank you, Tyler.

That was Kelly Dragovich.

It’s refreshing to talk to someone who keeps it real. Like Kelly, 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 talked 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 I oftentimes wonder the same thing myself.

Why do I do this? Why do I build a company from scratch? Why do I enjoy making all the sacrifices that come with working in that type of environment? Even right now? It is 09:00 on a Tuesday night, and I’m recording this in my closet instead of playing with my kids and my wife. 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 definitely empathize with that unique feeling.

You can find us online at Groundwork Show.

I’m Tyler Muse.

Groundwork is produced by Mike Giordani at Flowship Audio Engineering by Alex Roses Production Assistants by Casey Miller Music by Aaron Sprinkle Adrian Walter Coralina Combo Special thanks to Pedro Matriciano and Natalia Krimgold until next time. Thanks for listening.

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