Ex-Google HR Boss & CHRO At Oura: Why Most Companies get People Completely Wrong!

19 May 2026 · 50 min · 24 chapters

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In short

Strategic HR and people leadership, told through Judy Gilbert’s career (Google, Zymergen) and her current role as Chief People Officer at Oura; includes how to evaluate CHRO/CEO fit, build “soul” via clarity, and approach AI governance in a regulated, personal-data business.

Guests

Judy Gilbert, Chief People Officer of Oura; former Google HR leader (joined shortly after IPO; 12 years; led recruiting scale-up, learning & development, performance management; later HR roles across YouTube, Google X, and Alphabet “Other Bets”). Jeff Markowitz is the co-host/guest on the show segment.

Key claims

Most companies get people strategy wrong by treating HR as order-taking; high-leverage people leaders must translate business strategy into people strategy and operationalize it. CHROs fail when they bring a transferable “toolkit” instead of adapting to the specific business and CEO relationship. “Soul” comes from mission/clarity, not HR manufacturing it.

Notable examples

Google scaling from ~2,000 to 100,000+; Zymergen “boxes”/infrastructure gaps; Netflix/Coursera HR lessons; Coinbase culture manifesto; AI guardrails for EU/personal-data risk.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introducing Jeff and Judy

0:45 to 2:00

Hosts Jessica and Jeff introduce guest Judy Gilbert, Chief People Officer at Oura.

“Welcome to another episode of TruthWorks.”

The Oura Ring Experience

2:00 to 4:40

Discussion about the Oura Ring, its features, and user experiences.

“know because then I'm like gonna obsess over my sleep and I'm gonna you know what I mean yeah Yeah.”

A Tool for Empowerment

4:40 to 5:40

Judy discusses how Oura empowers users with health data.

“You wear it on your finger and it provides you with constant tracking of what's going on with your body.”

Understanding Oura's Functionality

5:40 to 7:00

Judy explains what the Oura Ring tracks and its benefits.

“And of course, since I work there, they have to complain about it all the time and provide lots of feedback.”

Judy's Career Journey

7:00 to 10:20

Judy shares her fascinating career path leading to Oura.

“And sort of if my scores are not great, it's usually because maybe I had to drink.”

Life at Google

10:20 to 14:02

Judy reflects on her 12 years at Google and its rapid growth.

“It was just this thread of all these different people-related things.”

Transition from Google to Startups

14:02 to 15:40

Explore the transition from a large tech leader to a startup environment.

“And then that led to some other kind of HR business partner type roles with Google X and with some of the other parts of Google that eventually became the other bets once Alphabet morphed from being Google to Alphabet.”

Building at Zymergen

15:40 to 17:36

Discuss the challenges and learnings from building a team at Zymergen.

“I mean, I spent seven years at Google, obviously, later than when you were there.”

The Emotional Toll of HR Challenges

17:36 to 19:31

Uncover the emotional challenges faced when transitioning to smaller companies.

“Started going through these boxes and it was like people's immigration.”

Joining Oura: New Beginnings

19:31 to 21:22

Understand the motivations behind joining Oura after a brief retirement.

“And so I took, I told myself I was going to retire and, you know, maybe write a book or something because who doesn't do that?”
Show all 24 chapters

Navigating Time Zone Challenges

21:22 to 22:49

Learn about the logistical challenges of managing teams across time zones.

“So what was it like day one when you get there?”

Strategic HR in Growing Companies

22:49 to 25:15

Delve into the importance of strategic HR in scaling businesses.

“I'm fascinated with sort of this question around the nature of strategic HR.”

Interviewing for CEO Alignment

25:15 to 28:00

Discover how to assess a CEO's understanding of HR's strategic role.

“But if it's a pure order taker, you just miss opportunities to have high leverage discussions earlier.”

Understanding Founder Engagement

28:00 to 29:50

Learn how a founder's openness and willingness to work on HR issues can impact success.

“And, you know, when I went to Coursera, I think they did really want it, but the two founders just couldn't.”

Importance of Collaborative Debates

29:50 to 31:40

Explore the value of discussions and debates in shaping compensation strategies.

“We did a bit of a debate about about compensation plans and how do you think about using cash and equity and different mixes and, you know, what have they done so far and what's appropriate for the stage.”

Adapting HR Strategies

31:40 to 34:10

Discover why HR leaders must tailor their strategies to fit different company cultures.

“Jeff, I have a question for you because, and I think Judy will want to know this too.”

Navigating CEO Relationships

34:10 to 36:25

Understand the delicate balance required in relationships between HR and CEOs.

“If you've got somebody who comes in with a playbook and says, okay, I'm going to do this now, that's kind of the cranking the operational side.”

Creating Company Culture and Soul

36:25 to 39:44

Learn how to develop a strong company culture and soul while making tough decisions.

“Yeah, it's, I mean, one of the, I think of the job as being, it's like the emperor's fashion consultant and you got to be the one to constantly tell him he's got no clothes.”

Authenticity in Company Values

39:44 to 42:00

Examine the importance of authenticity and clarity in a company's culture and values.

“And I think, you know, I think that's absolutely right.”

Maintaining Company Culture Amid Growth

42:00 to 43:42

Learn how clarity and authenticity in company culture influence employee perception.

“And so because we were so clear, that actually kept the soul, if that makes sense.”

Navigating AI as a Chief People Officer

43:42 to 45:34

Explore the evolving role of CHROs in strategizing around AI integration.

“And I want to make sure that we get to an important topic because, of course, we have to talk about AI because, I mean, who is not talking about AI?”

Balancing Innovation with Risk Management

45:34 to 47:24

Discover how to foster innovation while managing data safety and regulatory risks.

“But the broader use, like, how does my team, does my team use these tools?”

The Power of Diverse Perspectives

47:24 to 48:08

Learn why seeking divergent viewpoints is essential for solving complex problems.

“We always ask our guest, we put you on the spot and we ask you to leave our listeners with a little inspiration, something to go off and think about.”

Final Thoughts on Oura Ring and Personalization

48:08 to 49:26

Engage in a light-hearted discussion about personalizing Oura Rings.

“And I'm so happy you came on the show and everyone should go buy an aura ring right now.”
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Transcript

Automatic transcript. May contain errors.

0:00When you're building a business that relies so much on problems that get solved by smart people, the human capital is just so critical. And if you're not thinking of HR in a strategic way, and if you don't have the leaders who are capable of doing that, you're just missing a trick.

0:20Jeff Markowitz:What would happen if we just told the truth? Welcome to TruthWorks, where we dig into the nitty gritty of leadership and work. and what needs to change. I'm Jessica Neal. And I'm Cattie McCord. Our journey together started in HR, but trust us, it's evolved into something wild, honest, and well, a bit rebellious. So throw out the handbook. We're here to redefine rules to work for us, not against us. Let's dive into another episode.

0:58Jeff Markowitz:Hi, everyone. Welcome to another episode of TruthWorks. I'm Jessica Neal, your host. I'm here with Jeff Markowitz. Hi, Jeff. How are you? How are we doing? Good. Coming back for more, I see. Yep. Okay. Well, we have a very cool guest today who I've had the opportunity to spend a little bit of time with before, and she's very impressive. So I'm glad she agreed to come on to the show. But I have, and I think a lot of people know this company very well. I'm going to, I'll have a little confession that I have to make in a minute, but I have Judy Gilbert, who is the Chief People Officer of Aura. Welcome to the show, Judy.

1:39Jeff Markowitz:Thank you. I'm so excited to be here. Yes, me too. And before we started recording, Jeff was holding up his Aura ring and you were holding up your aura ring and then they asked me if I had one and I don't have one and I'm going to tell them why now because I didn't want to tell them why before we started recording but I'm nervous to get one I don't want to know you don't want to know no like I don't want to know because then I'm like gonna obsess over my sleep and I'm gonna you know what I mean yeah Yeah. And I should know. I should know these things because it's probably good to know, but I don't know.

2:21Jeff Markowitz:I'm like the person who doesn't. I don't like to go to the doctor. I will go if I have to. Judy, is that common? Is that a common thing with people afraid to have the... Sure. Yeah. It's a common concern. You get people all over the spectrum. You have people who want every little bit of detail and the Oura Ring is just the tip of the iceberg. and they also want their blood pressure all the time and they also want the labs and they also want, it's part of a whole thing. And then you've also got people, we've got lots of people who are, I don't wanna know. And one of the, I mean, so now I'm gonna try and sell you, but one of the things that's great about it is it's this tiny little device.

3:02It is unobtrusive and you can look at it on your phone or you don't have to look at it on your phone. And so you can, it's there if you want it and it just gives you a little bit of information and you can decide how much of that is helpful for you so that you can make better choices. And if weeks go by and you decide it's not something you need to look at, that's okay. It's still there for you. Yeah. You know, it's interesting. Go ahead. Yeah. No, you go. So I'm a big tracker, although I do kind of go into these phases, like Jessica said, where it's like, you know, I'm not going to be looking every day.

3:33You know, my pitch for Aura, and obviously I'm not associated with the company in any way. I mean, I used Whoop and Aura, and Whoop is just way too detailed for me. Too much stuff. And Aura is just simply great.

3:52Jeff Markowitz:There you go, everyone. We love to hear that. There's the sell. It's a tool in the kit. I feel like I need to get one. I feel like women are a big customer of yours, right? Big demographics. Absolutely. Yes. And so I feel like I'm an outlier or something. I feel like I need to get with the plan. We would like lots more people to get with the plan. That would be very good for us, but also for them, because I think it is such an empowering thing to have easy access to all this data about what's going on with your body and with your mind that helps you make better decisions. I mean, you're always in the driver's seat, but it's information that you can use to help steer you.

4:34Jeff Markowitz:Yeah, no, it's true. And if the listeners don't know, Aura, do you want to tell them what it is, Judy? Yeah. We didn't really say what it is. It's the world's best smart ring. It is a tiny little device. You wear it on your finger and it provides you with constant tracking of what's going on with your body. It tracks your sleep. It gives you information about respiration, about activity. It's getting better all the time. We keep investing in both the ring itself and the software that provides the insights about it so that users can get information about what's going on with their body and their health.

5:11It is not a medical device, but it provides information that enhances those kinds of conversations that you can have with your doctor, that you can get this second opinion on, I feel a little funny, what's going on with that, and then it's more data to help inform the decision.

5:28Jeff Markowitz:Yeah. What do you use yours for? What's the thing you like best about? Yeah, I use it as a way to engage with my kids. So I've got two teenagers and they are both users. And of course, since I work there, they have to complain about it all the time and provide lots of feedback. But it's a nice way to have this baseline to talk about, like, gee, I didn't sleep very well. And what do we think is going on with that? And it's this entry to conversation for us about thoughts and feelings and bodies that is just kind of a little subtle thing that's there for us all the time. Yeah, I know. If I had an aura ring, you know, it would tell me last night I had to wake up at four in the morning because my six-year-old's little doggie that he sleeps with fell out of the bed.

6:17And, you know, and he was yelling, Ma!

6:20Jeff Markowitz:And he, like, he can't get out of bed and get it himself, you know. And I don't know about your kids, but when my kid ever wakes up in the middle of the night, it doesn't matter what the reason is. He's screaming my name. It's never, mom, it's mom. But yeah, I woke up at four. Or it would be like your son. Yeah. Well, you can tag that and then watch the patterns and say, oh, it's him again. It's him again. Anyways, I would sleep much better. And it's much better now that he's six than when he was little. Right. It does get better. It gets better. Yeah. So what do you use yours for, Jeff? I mainly use it for sleep.

6:58You know, I just look at my sleep in the morning and see how I'm doing. And sort of if my scores are not great, it's usually because maybe I had to drink.

7:08Jeff Markowitz:Yeah, a glass of wine. A little too late. Maybe I had a big meal, something. But it definitely correlates. Yeah. You know, I don't get as much fitness benefit like working out just because, I mean, I use it working out. but the data itself isn't as useful for me anyway. It's mainly for sleep. Yeah. A lot of people use it for sleep, but it's a great product and I'm going to get it. Okay. I will. But let's talk about you, Judy, a little bit because your background is really fascinating. And I think you started at Aura in 23. Is that when you - 23. Yeah. It's been about three years. Yeah. So you started there about three years.

7:48Jeff Markowitz:But prior to that, you had a very amazing career. You spent 12 years, I think, at Google and worked with Laszlo. And I don't remember what I read, but Google was like maybe 3 ,000 or something when you started. Yeah, I joined a few months after the IPO. So late 24, it was a tiny little place. Yeah. And how big was it when you left after 12 years? I mean, we were well over 100 ,000 employees. I kind of lost track. I mean, it was, yeah, every year was our biggest hiring year ever for over and over and over again. And we just kept scaling it and getting into bigger things. And it was a real rocket ship.

8:32Jeff Markowitz:Yeah. Well, tell us about your career. How did this all happen for you? Because I know at least most folks that end up doing what we do, they don't set out to do it in the first place. No, there's no like HR Barbie that you grow up playing with that sets that path. No, I didn't know what I wanted to be when I grew up. And when I went to college, I wanted to keep those options open. And I've always liked learning about different things and making connections between things and finding interesting patterns in how the world works. And that led me to management consulting because it was a way to continue to kick the can down the road and not really have to pick a career.

9:18So I joined McKinsey right out of college, ended up going to business school, ended up going back to McKinsey, and really had some wonderful opportunities to work across a lot of different industries, see companies at different stages, see different management styles. And one of the things that I noticed through a number of years doing that kind of work was that a lever that was not really getting pulled was the people stuff. And, you know, this was the mid-late 90s and people operations was not yet a thing. You know, HR was kind of off in the corner and most companies, we weren't really being strategic about it.

9:57Even things like, you know, I looked at studies that we implemented. We did all the good analytical work at McKinsey. We put it in a big blue document. And when you went back six months or a year later, excuse me, to see, well, how did that go and what got implemented and what kind of change has been driven? Often, if there wasn't the change that we expected to see, there was some people-related thing that was underlying. It was like we were telling people to do one thing, but the incentives were set up for something else, or we haven't really done the change management, or the leadership wasn't right, or the skills weren't right over here.

10:30It was just this thread of all these different people-related things. And I thought that was interesting. And I thought, well, where could I go to do more of this work? And at the time, there weren't so many strategic people leaders you could look out in the world and see. There were a few, but it wasn't a thing. So I thought, well, where is people stuff a line job? And it's an executive search. And so I had the opportunity to join Egg On Sender for a few years during the dot-com boom, which was a tremendous learning experience and a way to, again, get exposed to a lot of different things and kind of help leaders through some of these transitional periods.

11:09And then you went to Google. Well, and then, yeah. And so it turns out I'm not very good at executive search. And so that was an important learning experience. So I have tremendous respect for people who are great at it. And I love working with them, but it was not the place where I was going to add the most value. What does that mean, actually? Yeah. How did you figure that out? I mean, it turns out that I tend to introversion. And so if you have a job that is fundamentally about getting on the phone and connecting with dozens of new people every day, that is going to not be a great way to manage your energy.

11:45And for a while, the learning from it was such that that brought energy to it, but it just wasn't going to be a long-term thing. And it just wasn't going to be the thing that I was best at. So that was, yeah, that was good to learn. Yeah. But then I had the opportunity to join Google. So it was summer of 2024. And actually, one of my colleagues from Egan Sender was doing some work with them through a set of conversations. because it wasn't, you know, Google was like 2 ,000 people. They grew really fast even over that summer, just getting things in place. And they needed some people with more business expertise to bring a little bit of structure to it.

12:25And so I had the opportunity to join in the HR department, which I don't think we were people operations quite yet. But my first job - Was Laszlo there? He wasn't there. He came on, I don't know, a bit after I did, but I, you know, he wrote my performance reviews for 10 years. So we were super closely together. Yeah. But, but, and, and Arnon Ghashuri came on at about the same time I did. And so he and I were kind of in a two in a box situation to scale up this enormous recruiting machine that Google needed to build in order to do all the things that they wanted to do. And so Arnon had all the recruiters reporting to him and I was leading the kind of more programmatic work.

13:06So things like college recruiting and systems and process and the diagnostic and the analytics of the whole staffing machine to build it up and be able to feed the engineering beast with amazing high quality engineers. And it still is an engineering beast. Yeah, it sure is. Yeah. Right? And you left how many years ago? So I left in 2017 and I, you know, in the, yeah, that's right. And in the, in those years, I had the chance to do a lot of different jobs and kind of Google grew, it evolved. There were a lot of different things that needed over time. And so I went from being very recruiting focused to different times I led learning and development, led performance management, went over to be the head of HR for YouTube after they were acquired and trying to figure out what the interaction between YouTube and Google was going to be.

14:02And then that led to some other kind of HR business partner type roles with Google X and with some of the other parts of Google that eventually became the other bets once Alphabet morphed from being Google to Alphabet. Again, you got to see a lot of different things and participate in driving a lot of that growth. Yeah. Wow. Amazing experience. Fascinating, I'm sure. Yeah. Yeah. Yeah. And then you go to startups. It's a super hard place to leave. But around 2017, my younger kid was getting ready to graduate from the Google preschool, which was sort of a funny moment for us thinking about, gee, what would life after this be like?

14:47And there were a lot of really interesting smaller company and some larger company opportunities at the time and just really thinking about what's that next chapter going to be. And I chose to join a small company. I was really excited about the idea of building something again and getting into that complexity and being part of a leadership team. The company was called Zymergen, and it was kind of biotech adjacent with some manufacturing and just a really interesting combination of business problems. Had some wonderful experiences there, built up a team, acquired some companies, did some things, took it public, sold it, shut a lot of things down.

15:26It happened during the pandemic. I mean, just what an amazing... Well, what a learning, though.

15:31Jeff Markowitz:IPO to selling to, you know, I mean, even though it's sad to kind of close things down, I mean, that's all learning. What were the big adjustments coming out of Google going to a company like Zymergen? I mean, I spent seven years at Google, obviously, later than when you were there. So it was a very different organization, I'm sure. But the learnings must have been stark between the two. Yeah, for sure. I think, you know, Zymergen was a few hundred people when I got there. So it was even smaller than Google had been when I joined. But that whole idea of how do you build things basically from scratch and how do you do them at a scale that makes sense for where you are right now, but future proofs it a little bit so that you benefit from some of the things that you've learned from having seen the movie before.

16:19But how do you find that right balance so that you're not overbuilding for the 10 ,000 person company when you're only 300? And by the way, the technology is changing in the background all the time. So the tools that you have available to use to do that scaling are also changing. And so staying on top of that is critical.

16:40Jeff Markowitz:I remember, I don't know if you had a similar moment, but I remember when I left Netflix for the first time. and was the head of HR at Coursera. And Coursera was like... I remember that. Yeah, yeah, yeah. I think we were like 70 people or something. It was small. And it was my first week and they ended up, they wanted to fire the office manager and she missed payroll. And I was like, okay, well, we can probably do that. And then I was, you know, they had nothing, no infrastructure. no nothing. And they had kind of made her pseudo HR, the office manager. And I let her go and I was cleaning out her desk and I was just going through, I didn't know why, but I started going through them.

17:31Jeff Markowitz:There were like these boxes all behind her decks, just like stacked up box after box. Started going through these boxes and it was like people's immigration. I didn't think she didn't know what to do with any of this stuff. And she just put it in a box and put it behind her. and none of it had been addressed. And I just remember I started crying. It was like 10 o 'clock at night and I was like, what have I done? Because you don't realize the luxury that you have at an organization like a Netflix or a Google that is established and things work. Information, you don't have to like look in a box.

18:08Jeff Markowitz:You can look it up in a HRIS. But did you have a moment like that when you? Absolutely. And I knew what I was getting into. I mean, you always ask the questions and sort of know what you're getting into. But there are always surprises. There are always things that look shinier from the outside. And then you get in there and you realize that there are those boxes filled with immigration stuff. Yeah. In our case, it was a file cabinet full of lab notebooks that nobody knew what to do with. And I think there are two figuring out, all right, what are the things where you need to get something that is formal and you need to get a person who's a subject matter expert to do it.

18:47And what are the things that you can sort of hack through by putting together some spreadsheets and finding that right balance of how do you make progress in a way that's sort of age appropriate for the company? And I also think a lot about that idea of you're juggling a lot of balls and it's okay to drop the rubber ones sometimes, but try not to drop the glass ones. And so figuring out in a new company, sometimes what's rubber and what's glass is not going to be the same as it was in the last setting. And so figuring out pretty quickly what are the things that are really going to cause the biggest problems that they break.

19:22Jeff Markowitz:Yeah, that's good advice. So let's see. So then you close the company down and then you go to Aura. Yeah. So I tried to retire briefly. I needed a bit of a break. And so I took, I told myself I was going to retire and, you know, maybe write a book or something because who doesn't do that? That's a good task. Well, it's not out yet, but it's almost done, the book. You know, yeah, you got to write a book. You got to have a podcast. You got to write a book, you know. You're living the dream here. I am. I am. Yeah. But, and that was great. And it was a time to think about what are the things I like?

20:02What are the things I want to do more of and less of. And it turns out I missed being on a team that was trying to do hard things and build. And one of the opportunities that came my way was, and I had been interested in the product and sort of interested in the company and knew it from a little bit of a distance. And the more I found out, the more I felt like the company was really at a moment where I would be able to do some good. And the reps that I've had at both early Google and then through Zymergen were going to be things that would, you know, things that this company could actually use.

20:37And also a lot of things I was going to have to learn and get to learn at the same time. So here I am. That's turned out to be true. And how it's played out that way? It has played out that way. I mean, I think, you know, you never, you never know what the growth is going to be like. You never know how the business is going to develop, but we've got, You know, we've got a product that people really do love. Very strong technology, very strong science behind it. And as we put the other pieces in place to make the business as strong as some of the product has been for a long time and allow us to scale, that's a great opportunity for people like me because it's the business side of things.

21:15And we can bring those skills to bear on this and really make the opportunity real. Yeah. So what was it like day one when you get there? Yeah. I think day one is when I really started to realize the time difference between San Francisco and Finland. And people had talked about it during the interview process. It's like, this is really hard. I was like, yeah, yeah, yeah. I've had teams in India. I've had teams in Singapore. I've had teams in Europe. This is going to be fine. But the reality of having most of the company in two different time zones that are 10 hours apart from each other is it's just extremely inconvenient.

21:56And I think there are some things that we've been able to do over time to turn that into a little bit of an advantage instead of a challenge. And if you're organized properly and if you've got people in different places and if you've got clear standard operating procedures and communications channels, you can do a little bit of follow the sun stuff that is not available to you if you're just in one time zone. So that's, you know, we got more work to do there, but that was an early one of like, oh, I see, I need to be on calls at six every day so that I ever get to see anybody. 6 a.m. or 6 p.m.?

22:37Yeah, it's 6 a.m. And like, okay. So fortunately, I have this ring that helps me know how my future is working and turn me into a morning person. So that works. Yeah, go ahead, Jeff. I'm fascinated with sort of this question around the nature of strategic HR. And Jessica and I have spoken about it in the past. I was a career kind of consultant before I went into venture capital. And then venture capital is not an operating role. It's just venture capital. And going to Google was sort of the first time I'd ever worked at a company. The way I saw HR at Google was it was very much a service provider, not strategic, wasn't viewed as strategic.

23:26It never reported to the CEO. And so whether it morphed into this or it was always the case, I don't know. But it was always the HR org always battled this being a strategic business partner versus just being an order taker implementer. And so how do you view that within Aura and how have you sort of polished that way of operating? Yeah, yeah. I think it is when you're building a business that relies so much on problems that get solved by smart people, the human capital is just so critical. And if you're not thinking of HR in a strategic way, and if you don't have the leaders who are capable of doing that, you're just missing a trick.

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24:17And there's other companies out there that your competitors are going to do that. And so, you know, you ought to take advantage of it. I think that looks very different at different scales. And if you get to the scale that Google's at right now, the biggest lever might be, how do you just make all this work as smoothly as possible? And it does become much more operational. But I think for companies that are in building stages, if you've got too much brainpower on what's our benefits platform going to be and how do you do that, you're not focused in the right place. And you want people who are on the CEO staff and or whatever those seats of decision making are, who are in the room and are not just focused on the people questions, but are really engaging on what are we trying to do as a business and why are these the choices that we're talking about making?

25:10And then how do we translate that into people strategy? And then how do we operationalize it? But if it's a pure order taker, you just miss opportunities to have high leverage discussions earlier. Yeah. I was curious. I have a question for both of you because I've never been in the HR leader seat. When you're considering an opportunity like an Aura or, Jessica, you're working with Reed, how do you interview the CEO to make sure that they understand the value of the people organization and how you think it works best? What do you look for?

25:51Jeff Markowitz:Do you want to go, Judy? Go ahead.

25:56I have some questions that I always ask myself and make sure that I get answered during the process. I mean, when I think about, is this a company I want to join and is this a role I want to take right now? My first thing is about the business. Is this a business that has potential to grow? Is it going to be interesting? Like, are we solving something that is fun and that is important and I can get excited about. Because I know I'm going to spend a lot of time on it. I'm going to spend a lot of energy on it. And it better be something that I feel like is worth doing. So that's thing one. Thing two is, does the business require a miracle for the technology to actually work?

26:35Like, are we at a place where this is actually about operations rather than about science or inventing? Because for me, that's a better stage to be at. And the third thing is, is the CEO somebody who is going to take my advice at least some of the time? And having those conversations during the interview process and getting into a little bit of sparring about like, oh, you think that's how that works? Well, let's talk about that. And have you thought about this perspective? I can find during those interview processes, both with the CEO and then also with members of the leadership team, I can get a pretty good sense of what is that dynamic going to be like?

27:11And I just, you know, I wouldn't be interested and I frankly wouldn't be that good in a situation where what they want me to do is do a really good job of like running payroll and throwing parties. Like God bless the people who are good at that. It's not me. I'm going to, you know, I'm going to, I'm not good at that either. I'm going to be all involved in what

27:28Jeff Markowitz:the business plan is. I hate, I don't know, but I hate the parties, right? I don't know. Everybody like them and I, but I hate them. I'm like, I don't want to go to another party. Just get some work done. I don't know. I'm, but I'm old and bitter, but, um, but I think you're, I think you're right, Judy. I think, um, you know, and I, I, I knew this, you know, I knew cause I worked at Netflix and I grew up there and it was a place where HR was part of the strategy. And, and so I knew if I was going to leave there, I wanted that to be the case. And, you know, when I went to Coursera, I think they did really want it, but the two founders just couldn't.

28:14Jeff Markowitz:They just weren't capable. So I think I got much better at digging into not just the desire, because you're not going to meet a founder or a CEO that says these things aren't important. They're all going to say that they're important. I think the difference is that, to your point, are they going to be open to your advice and your feedback, but also are they going to be willing to do the work? Because part of your success is that they have to do these things. They have to live these things. They have to be these things because if they aren't, then nobody else is going to do them. And then you're the HR lady coming around saying, come on everybody.

28:57Jeff Markowitz:And we talked about context, not control, but nobody does it at the senior level. So nobody else is going to do it. So I think I got really good at like doing that sparring and sort of seeing what it would be like in real life, but really kind of pulling that thread to really get down to the core of, well, what, when, when you say that, what do you actually do? How do you do it? How does it play out in your day to day? How does it play out in your meetings, in your agendas and your strategy? Because, again, be it like it or not, they're a big reason of you being able to be successful in your role.

29:32Jeff Markowitz:And they have to be an amazing partner to you. How did you test for it, Judy, at Aura? Yeah. A lot of conversations. And, you know, Tom and I got into a discussion. Argument is too strong a word, but. Debate. We did a bit of a debate about about compensation plans and how do you think about using cash and equity and different mixes and, you know, what have they done so far and what's appropriate for the stage. And it was and for me, it showed me that he I mean, he was digging in on this stuff in part because he didn't have an HR partner at that time because they'd already had a transition. But so that showed me, OK, this is a guy who's willing to get into the details.

30:20He is willing to learn this stuff. He's also willing to listen. And, you know, we're going to, we're going to, you know, we're not really making a decision here, but, but that, that discussion showed me he cares about it. He's thinking about why it's important. He's doing the legwork. He's thinking, he's willing to think a few moves ahead about not just how do you band-aid it now, but what might be the long-term implications of picking one path versus another. and you know something else that came out during that was uh and you know jesse he talks he goes and seeks out other opinions and i think that is so important and that's how i met you for all yeah

31:00Jeff Markowitz:we talked about compensation so i think uh woody uh tcb connected me with tom and and then tom brought judy into the the conversation and we had a wait three of us had a little chat about compensation. Nice. Yeah. Yeah. I mean, you can learn from your own experiences and your own scars, but you learn so much faster if you can get other people's scars and experiences into the mix as well. And so having that community is so useful. Yes. But what I love about that, Judy, and I think it's something that I tried to do, but you were sort of simulating what it would be like to work through a problem together.

31:38Jeff Markowitz:Yeah. Right. And not an obvious problem and a hard problem and an important one. And so I think that for the listeners, that's an important thing to do no matter what role it is, whether it's CHRO or others, because the more you can simulate what it's really like to work together, the better sense you're going to have of what it's going to be like in reality. Jeff, I have a question for you because, and I think Judy will want to know this too. You have seen many companies hire chief people officers, CHROs, whatever you want to call them. And there is a very high turnover in these roles, right?

32:18Jeff Markowitz:What is your theory on that? I want to know. That's pretty general because it's so company specific. Yeah. But the organ rejection on these roles is pretty high. So, you know, I did a client many years ago that you learn a lot from all of your clients in terms of how they do things, I found this person had hired a senior HR leader. They didn't work out and they came to us for help. And I said, so tell me why it didn't work out over different kinds of questions. And they said something which I see is fairly common around people leaders is that this person brought their toolkit with them and they felt that their toolkit would work.

33:07it was transferable within different organizations and maybe parts of it were, but it really, it wasn't in this case. And I see a lot of that where I've seen a lot of that. It's like, well, this is how we did it here. And this is our toolkit and we're going to do the same kinds of things. And then the people function, you can't be that. You have to be adaptable and you have to be willing to grow your own skillset, your own toolkit. Well, yeah.

33:35Jeff Markowitz:And I think you have to think uniquely and critically about whatever business you're in. And you're building for that, not for this other thing. I mean, it would be silly to think that the Netflix culture is that we could just do that in any company. It worked because it worked for us. It doesn't mean that all of those things are going to work for everybody else. And you just can't have the playbook approach. You got to really learn your business and build things that are going to solve problems for your company, for your people. Yeah, go ahead, Judy. I think that's the strategic HR point. If you've got somebody who comes in with a playbook and says, okay, I'm going to do this now, that's kind of the cranking the operational side.

34:20And if you're in a situation that's not exactly like the one that you were in before, you need to be able to read the room and you need to be able to understand what are the business problems we're trying to solve here? And so which parts of this toolkit do I need? And which things do I need to find somewhere else? Because I don't know how to do them yet. I think there's another one too, which is, and it's back to the questions that you ask coming in the door and really trying to understand the simulated conversations that you talked about, Jessica, is I find that sometimes people leaders want that relationship with the CEO to be something that maybe the CEO, is just where the organization just doesn't want and they think they see it and they think they can turn it once they get in, but then they're not able to for maybe not their own fault, but then they keep trying and it's just a misfit.

35:27Yeah.

35:28Jeff Markowitz:No, the chemistry between the CEO, founder and this role is just, I mean, it has to be there. And when it's not, it just is very short-lived. And it doesn't mean either person's not great, right? I mean, it could be that the CEO is great. It could be that the CHRO is great. It just doesn't mesh. And this role, I want to know your thoughts on this too, Judy, because this role has such a interesting element to it because you really are telling the CEO, the founder, the things that nobody else is going to tell them. And there's just this delicate, you know, balance of being the mirror and the bearer of that and carrying a lot of the weight of all the things that maybe you should tell them.

36:19Jeff Markowitz:Maybe you shouldn't tell them today, but, you know, maybe you're going to tell them tomorrow. But how do you navigate that? And how do you think about that? Yeah, it's, I mean, one of the, I think of the job as being, it's like the emperor's fashion consultant and you got to be the one to constantly tell him he's got no clothes. Yeah. But, but it's a repeated game. And so how do you build that relationship and how do you, like, what do you ground that in? And I think it's really important to have it grounded in, we want the same things. We want this company to be a smashing success. And I think, especially for this role, being able to honestly be low ego.

36:56And it is not about me. I actually, like, I just want this thing to be successful. Let's figure out how to make that happen. And so being able to have that, it's a funny balance because you've got to have the confidence of, I've seen these things. I've got a big toolkit. I know how to use it. And also I'm super low ego about it. Like that can be a hard balance to carry off. But I think it's tremendously important. And again, that goes back to, this is not about, you can't have a people strategy that's separate from the business strategy. This is all about what do we need to do short-term and long-term to enable this business to be successful?

37:36And how do we do all the people things in service of that?

37:40Jeff Markowitz:And sometimes, you know, they're just not ready for it, you know? And, you know, you got to know No one to hold them, no one to fold them. And I think that's part of the toolkit too. How do you, how do you care? Is this one where you carry it through what is going to be just a little bit of a rough patch? Or is this one that's not going to be winnable? And how do you make that decision? Yeah. And you got to pick the hills you're going to die on. Because there's so many and you can't die on them all. Yeah. How do you both create? I'm fascinated by the way businesses well Silicon Valley tech has transformed and it's everybody always has to be on their best behavior you have to be really careful walking around organizations there's a lot of sensitivity in organizations how do you create a soul for the company while making tough people decisions and running a business and it's not going to be

38:44Jeff Markowitz:just rainbows and unicorns like an overly sensitive place like you're running a business it has it's a business yeah so how do you create soul while running a business i mean it helps a lot if there is a soul when you start i don't see it as i don't see it as the people team's role to create the soul i think we can and the and the leaders that can can nurture that you can help it grow. But if you're looking to the people team to create the soul, I just don't think that's the structure that's going to do it. It sure helps to have a company that has a mission that people care about and that people see as something bigger than themselves that they want to be a part of.

39:26And that makes people willing to make little trade-offs around the edges to be part of this bigger thing. So I think, you know, join a company where that is already true and then help to and help to build it. That's a much faster way to it than trying to create a soul where there isn't one.

39:44Jeff Markowitz:Yeah. And I think, you know, I think that's absolutely right. And I think, you know, Jeff, you're kind of alluding to like, I think the pendulum swung, you know, especially through the pandemic to this kind of place where it was very sensitive and things were very heightened. And I think leaders really backed away from being as candid as they wanted to be and, you know, being direct. And they didn't want to hurt people's feelings because they didn't want to, you know, they didn't want to jeopardize losing someone. And also they were afraid that they might get in trouble for what they say and do, right?

40:20Jeff Markowitz:And so I think the pendulum has swung back to a more balanced place. But I also think the companies that navigate this well and continue to have their soul, right, if they had one in the first place, and let's face it, not every company has a soul, or they do, it's just not the kind of soul you want to be with. But I think that what companies that struggle with this are not clear about who they are and why they are this way. And then once they're clear, they then behave that way. Right. And so it's like employees can decide. Right. If they if that's what they like. Great. If that's not what they like.

41:06Jeff Markowitz:I think it was like. Was it Coinbase? They you know. Yes. But I mean, it was it actually, you know, was brilliant. And if you talk to the people that work there, you know, a year from that time that they kind of put out that manifesto of like, look, we are this. We are not that. We are this. This is what we care about. This is what we don't care about. If you care about these things, get on the train. If you don't care about these things, get off the train. I think it was incredibly helpful for them. Now, you may say as an employee or somebody that that's not me. That's not what I, you know, want to sign up for.

41:42Jeff Markowitz:But that's your decision. And I think that that was one of the things that we did very well at Netflix was that we were very clear. This is who we are. And, you know, average performance gets you a nice severance check and exceptional performance doesn't get you a raise. You get to keep your job like that's, you know, that's the goal. And so because we were so clear, that actually kept the soul, if that makes sense. And then people could decide. And I think many businesses are not very clear, especially on who they are and why they are that way. And so that's just confusing to folks. And when people come into a company, they've read your culture because everybody has a culture deck.

42:23Jeff Markowitz:Everybody has a manifesto. They read it, and then as soon as they start, they're looking around for it to be real or not real for the hypocrisy, right? Yeah. As they see it, they're like, yeah, you said you were transparent, but guess what? You're not. You're not transparent at all. You said you really value high performers. Well, there's a bunch of crazy people running around here who aren't very good at what they do, and so that's not true. So I think, you know, the clarity and then as much as you can, because everything's aspirational, but be that as much as you can. And things can change over time, too, right?

43:03As companies, it can be different to maintain what is that soul and what does that culture feel like as you keep adding zeros to your numbers of employees. And so I think leadership teams, and this is a place where I think in roles like ours, you can have a lot of influence, is noticing what are the shifts that are happening in the leadership and kind of asking questions like, hey, how are we going to make decisions like this? And so that you can kind of signpost that and be the guardian of some of that as it does evolve. It doesn't mean you're driving the direction of it, but you're paying attention to it and making sure that others see it as well.

43:38Yeah.

43:40Jeff Markowitz:We are kind of running out of time. And I want to make sure that we get to an important topic because, of course, we have to talk about AI because, I mean, who is not talking about AI? And we probably talk about it on every episode. So sorry, listeners. But as the chief people officer, and this is something that I think a lot of leaders in general are thinking about and struggling with, but especially chief people officers, CHROs, they are now the chief AI strategist for the company, right? So congratulations on that promotion, everyone. They don't all know how to do this, right? And nobody's like cracked the nut on how to figure this out.

44:21Jeff Markowitz:And there's a bunch of dynamics of, you know, robots are going to take our jobs and everybody's, you know. So how are you thinking about that at Aura? And what are some of the things that you are doing to strategize around AI being part of how the company operates? Yeah. I mean, it's complicated. I'll disclose that we don't have it all figured out. So sorry. Well, nobody does. So there you go. Exactly. Yeah. But I mean, I think there is tremendous opportunity with it. I wish the robots would take parts of my job and I'm trying to train them to do that more. Right. And I think we have a, but in the last year, we've really opened things up to encourage more experimentation.

45:00I think with a lot of companies, especially ones who work in kind of medical adjacent or personal data involved environments like we do, and especially ones who've got a lot of EU interaction, like the regulatory environment is so scary that I think for a while that caused us to be not broadly adopting. Yeah, you were. Tools and processes. It's a big risk.

45:27Jeff Markowitz:And I mean. Yeah. Yeah. Yeah. And so, you know, we've certainly had teams in a focused way, taking advantage of the technology and learning about it for a long time. But the broader use, like, how does my team, does my team use these tools? We've gotten a lot more comfortable in the last six to nine months with what might be possible. And I think it's so important. We've got teams set up within the company to put guardrails out there, to just help people make good decisions in an environment where there's so much information and so much change and also so much risk. And so just basic things like here is a safe place that you can put this kind of data.

46:05Here is data that you should never use in a system like this. And, you know, we're constantly reviewing to make sure that we are going as fast as we can, because that's really important, but never putting member data at risk or going where we shouldn't in a medical way. So it's a tough balance, but it's very much on everybody's mind. For sure.

46:26Jeff Markowitz:And then is this like, just internally, is this like a shared sort of strategy between like you, the chief product officer, CTO? So it is. And we've got a heavily, we were just meeting earlier today, but we've got a heavily cross-functional team that includes several members of the top leadership team, including me. And our head of IT, head of product, head of commercial, lots of areas represented, software certainly. And then supported by folks with more focused mandates to learn about this, learn about the regulation, and really be the subject matter experts so that we can make informed decisions as a leadership team based on that knowledge.

47:09Data-driven decisions. Who knew? Who knew?

47:12Jeff Markowitz:Those are generally good ones. Yeah. Use some data. With a soul. With a soul. Yeah. Well, data without a soul is, you know. Not always helpful. So Judy, we have to wrap up. I apologize, but it's been so lovely. We always ask our guest, we put you on the spot and we ask you to leave our listeners with a little inspiration, something to go off and think about. And so what would you like to leave the listeners with today? I think the idea that to solve complex problems, you need divergent viewpoints and it's just such a powerful tool. And so for any kind of problem that you have to solve, seeking out people who you know are going to see it differently to have a little bit of a debate, to hear what they know, it's going to make you smarter.

48:02It's going to make you better. And it's actually a lot more fun. So that was my advice.

48:07Jeff Markowitz:I love that. That's good advice. And I'm so happy you came on the show and everyone should go buy an aura ring right now. Judy, I do have one question about these or rings and the other confession I didn't make because I didn't want to be offensive is I want them to have like a bit more diamonds on them like you know I want them to be a little more you know you are not the only one and we actually there are um there are people out there who have solved that problem so they're actually jewelry makers who will make ring covers that laying out your aura ring. Okay. Because I just, yeah, I want it to like, if I'm going to have it on every day, like I want it to, I like want to look down and I want it to like sparkle.

48:56Jeff Markowitz:Yeah. I like the bling. Yeah. Okay. So I can get bling. You can get bling. Okay. Well, now I'm going to buy one. Yeah. There you go. I need to get a rubber cover for mine for when I pick things up. That's a good thing too. Oh, does it get scratched? You can do rubber cover. A new one doesn't. All kinds of things. Yeah. Yeah. Yeah. Well, Well, everybody buy your Oura Ring and follow Judy on LinkedIn. Thank you again, Judy. You've been a delight. And Jeff, get your rubber cover for your Oura Ring, okay? I'm going to do it right now. It has been such a pleasure. Thank you both. You're welcome. Thank you.

49:28Jeff Markowitz:Thanks, Judy. Thanks for listening to TruthWorks.

From the publisher

This week on Truth Works, my co-host Jeff Markowitz and I sit down with Judy Gilbert, the Chief People Officer of Oura, the company behind the Oura Ring.

Judy is not a typical HR leader.

She started her career at McKinsey, moved into executive search at Egon Zehnder, and then spent 12 years inside Google's People Operations team, helping scale the company from roughly 3,000 employees to 70,000.

Along the way she ran learning and development, ran performance management, and served as head of HR for both YouTube and Google's moonshot factory, Google X.

After Google, she became Chief People Officer at the biomanufacturing company Zymergen, where she helped build the team, took the company public, and then navigated its sale and wind-down.

She tried to retire. It didn't last. The pull of being on a team trying to do hard things brought her to Oura.

In this episode, we get into the difference between HR as an order-taker and HR as a genuine strategic partner, and why so many chief people officers get "organ rejected" within a year of joining.

We talk about the danger of arriving with a fixed playbook, the chemistry that has to exist between a founder and their people leader, and why the job is really about being the one person willing to tell the emperor he has no clothes.

Judy also shares the exact questions she asks before taking any role, how she pressure-tested Oura's CEO Tom Hale by sparring with him over compensation philosophy, and why a company's soul has to already exist before anyone can help it grow.

In this conversation, we discuss:

- The "I don't want to know" fear that stops people tracking their health
- Whoop vs Oura, and how much data is actually useful
- Why strategic HR is a competitive advantage most companies waste
- The three questions Judy asks before joining any company
- Why chief people officer turnover is so brutally high
- The "toolkit" mistake that gets HR leaders fired
- Being the person who has to tell the CEO he has no clothes
- Glass balls vs rubber balls, and what to drop when you're building
- How to protect a company's soul while running a hard business
- Why clear cultures keep people and confused ones lose them
- Why every CHRO is now the company's AI strategist

This is a candid look at the work behind the work, from someone who has built the people function at three very different companies and seen what separates the ones that scale from the ones that stall.

If this conversation changed how you think about culture, leadership, or the people who quietly hold a company together, share it with someone who needs to hear it.

Full episode of Truth Works with Judy Gilbert out now.

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