44 min read

Episode 2: People operations

Today, we're drilling down into one of the most important parts of operations—the people! And, specifically, the people who take care of our people.
An Asian woman is super imposed on a yellow background. Headline reads, "Opsy: a podcast for ops professionals".

We talked about operations more generally in the first episode of the podcast—what it is, what areas of responsibilities are and aren't included, and how ops has changed in the face of a global pandemic and the rise of remote work.

Today, we're drilling down into one of the most important parts of operations—the people! And, specifically, the people who take care of our people.

Human Resources, or People Operations, has been a crucial business function for decades but the speed at which startups often grow has made Recruiting, or Talent Acquisition, a specialty in its at own right.

So how do these functions work together? What does a Head of People do exactly? And how does one juggle all the people-related hats at a rapidly growing startup?

That's what we're going to dive into today!

About Our Guest

Our guest is Jennifer Kim, a consultant, coach, startup advisor, and the founder of Startup Recruiting Bootcamp.

Jen is probably best known as an early employee of Lever, where she worked as Head of People and helped dramatically scale the organization in its early years.

She's open sourced a lot of her best practices (and hot takes 🌶️ ) on LinkedIn and Twitter in an effort to help us all get better at the people stuff.

About this Episode

In this episode, we're discussing people operations and recruiting. Specifically:

  • The importance of People Ops/HR at a growing company
  • Whether you can really rely on one person to be Head of People and Recruiting... and how these new Head of Remote roles fit in, too!
  • The best practices Jen learned at Lever for scaling an early-stage company's people processes and how to prevent burnout in the process.
  • Why HR has such a bad reputation—and what to do about it.
  • A simple program that Jen started to support middle managers at Lever

... and so much more!

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More Info


Caro Griffin  0:03
Welcome to Opsy, a podcast for people doing opsy work in tech. I'm your host, Caro Griffin. And every month I dig into what opsy work really is by talking to an operations pro who has something really cool to teach us in a traditional part of ops like HR or finance, or a newer specialty, like no-code ops or marketing ops. Thanks for listening!

Today, I'm here with Jennifer Kim, badass recruiter, startup advisor, founder of Startup Recruiting Bootcamp, and the possessor of many a hot take. Jen is probably best known as an early employee of Lever, where she worked as Head of People for years and helped dramatically scale the organization in its early years.

A lot of the work she did there has since been open sourced via LinkedIn and Twitter, where she's super prolific and sharing best practices that move our whole industry forward. This is initially how I came across Jen. I learned a lot from her in the early years of my people ops career by reading what she wrote online. And then I was lucky enough to learn from her directly when I joined a cohort of her Startup Recruiting Bootcamp last year. Where I learned so much!

Recently, she found herself in Mexico City for a few months and we got to talk even more about tech and people ops, and how the industry is changing in the face of even more remote work. And we did it all over tacos and board games. And is there really anything better than that? I think not! All of this to say, pop you some popcorn and get ready for some tea. This is going to be a good one.

Thanks so much for joining me today, Jen! Super excited to chat with you about all of the things.

Jennifer Kim  1:40
Yeah. Thanks so much for having me.

Caro Griffin 1:42
I think most people on the internet know you as @jenistyping— I love that Slack reference and always have—or as the former Head of People at Lever. And so, for those of you who don't know, Lever is a really popular Applicant Tracking System that's used at a lot of startups. And you were a really early hire that basically built the whole people org. I think that was your first role at a tech startup, right?

Jennifer Kim  2:01
Yeah, I'd been in a startup before, but that was my first foray into the wild, wild world that is tech startup.

Caro Griffin  2:07
Yeah. So what made you transition into tech? And what appealed to you about that role, specifically?

Jennifer Kim  2:11
Yeah, so some background - I've always been interested in the kind of like people problems in the business. I think there's just so much, well, opportunity. I was going to say inefficiency.

Caro Griffin  2:23
A little bit of both!

Jennifer Kim  2:25
You know, there's all these cool ideas and entrepreneurs trying to like, you know, get things off the ground. And what do we actually ended up spending all of our time on? It's like, people problems. And, if we were all just like, you know, 5% better at hiring, I really do think we would just be like such a better world.

So, I've been a recruiter, I've been in career counseling, and I got to kind of hungry for more impact. Like many people, I think I really looked at tech as like, "Ooh, that seems very exciting over there. Where can I go insert myself?" And yeah, really learn, grow, but hopefully make a lot of change outside of change.

I specifically wanted to work in a recruiting software company, and got, you know, really lucky and timing in terms of finding the really great team that I aligned with, coming in really early. And, you know, in the beginning, as most kind of early stage, non-technical roles are, it was pretty broad and undefined in a lot of ways. I actually came in as the first customer success manager, supporting the product and kind of like the scaling of customers, and soon moved into Chief of Staff, but then really ended up doing pretty much every role under the sun.

I mean, there was a point where the engineers were like, "Well, if you just do a coding bootcamp, you can then like, check off that box." And I was like, "Oh, that sounds like a lot of work. I think I'm good with like eight out of ten."

Caro Griffin  3:47
Yeah, that seems like eight more than is probably needed. [Laughs] So yeah, definition of wearing all the hats then.

Lever went on to win lots of workplace awards, and many former employees have said that working at the company was a life changing opportunity. So, what do you think contributed to that?

Jennifer Kim  4:04
Oh, wow, thanks for the, you know, opportunity to brag a little bit...

Caro Griffin  4:07
Absolutely! All about that here.

Jennifer Kim 4:10
I think, for me, it's becoming maybe a little bit cliche, but I truly am so passionate about  community. And I think a company, especially like an early stage one where people are really getting to know each other, but also work with this like, very, like, intense sense of shared purpose. It creates for an environment that I think you can really not just make a working environment not just about the performance, but about the people as well. It's really putting an emphasis on culture. So, you know, part of my job was definitely kind of figuring out the baseline. "Okay, what is it that you need to do to lay like the like— turns out like no one had paid taxes for like, a couple years, you know, when I—

Caro Griffin  4:48
Whoa! Gotta love discoveries like that.

Jennifer Kim  4:51
Yeah, I mean, you know, when you put a bunch of engineers in the room, they're just like, whattt? We were supposed to do what now? And set up you know, some basic systems, information systems, and so on.

But the challenges that I ended up getting most drawn to were around like communication. Like, how do we do our own internal hiring? So, even as I was working with customers and the product, I just found myself really drawn by, you know, how can we really like, walk the talk? We want to help our customers do the best hiring possible. We should be modeling that. So that means we should be thinking about it, you know, critically, trying different ideas, questioning assumptions, because everyone knows, like, HR, recruiting, operations can be very outdated in terms of like best practices.

So, in terms of what actually made it a life changing opportunity, I'll give like a specific piece of feedback that I got, which was, you know, I think we were like 30-40 employees... and we had a kind of like a first burst of sales hiring. And quite a few of them are coming from Box because one of our sales leaders came from there. And Box was like +1,000 by then and employees would come in, go through the onboarding program that I designed, and they would say, how come, you know, at this, like tiny, 30-40 person company, the onboarding program is like, so much for what robust than what we came from? And my CEO gave me a lot of credit. She said, like, oh, people are just literally not used to an environment that has someone in an operations-like role caring so much. And it really was a combination of things. I do think it's some of like my natural abilities. But it's also the fact that I was supported to go do that. There were times I was overloaded, because oh, boy, there were—

Caro Griffin  6:35
I mean, you were only wearing eight hats, Jen. I'm sorry. You were overloaded by that? Come on, talk to me after you have nine.... [Laughs]

Jennifer Kim 6:41
Very strange, right? At a startup, who does that?

There were actually a couple times where I would talk to my team, like, hey, y'all, raising a flag.... I actually remember that there was one all-hands where I almost cry, because I was like, "You guys, like, I'm literally drowning." And, in hindsight, the fact that I felt safe enough to say it, and immediately my team would respond being like, "Oh, my gosh, let's jump in. Let's help Jen. What do we need to reprioritize? Do we need new head counts here?" So I do feel like it was really an ongoing thing.

The thing about startups is that, you know, whatever you set up now, you'll probably end up either tearing down or modifying in three months, maybe one month, anyway. So I do think it was like, really an ongoing effort between me and my team.

Caro Griffin  7:26
Yeah, totally makes sense. And onboarding is something I could... we could do a whole episode about it, because I feel like I ran into a similar experience in the past where it's just like, the bar is so low, but it's such a great investment of time, I will always make that argument because it just can go such a long way.

Jennifer Kim 7:41
Oh, yeah.

Caro Griffin  7:41
Yeah. So, we'll nerd out about that another time.

Jennifer Kim  7:44
Future episode

Caro Griffin  7:45
Future episode, for sure. Part two!

So, I talk to a lot of folks in the Opsy community who are really moving into that rapid growth phase that you saw firsthand at Lever. What advice do you give folks who, you know, join these early stage startups, who are taking on all these people processes?

Jennifer Kim  8:00
Yeah, there's a couple of things. I think, what's exciting about ops, and why I'm sure a lot of people are listening are attracted to these roles, is that it's so broad. So if you like variety, if you'd like learning, like you will probably not be bored.

The challenge, though, is that in a startup, in a fast growing environment, companies can scale exponentially, right? Like actually, that's their job. They're supposed to! But we as humans, cannot. We can pretend our bodies and mental health and, you know, all that is suited for it, but it's just not. We can't have biology that way. So, I do think there's a way that we have to be realistic about what you can take on, embracing change for yourself, not just like the task.

One of the best pieces of advice I got was, you know, when I was maybe a few months in, and someone told me that the thing that's really fantastic about startups is that you get to wear a lot of hats, as we were talking about. But, as the company grows, you also get to choose and specialize which hats make you the happiest, which, you know, give you the most fulfillment, and, if you don't choose it, someone else will choose it for you... I guess this is a me saying it now thing and not my not my friend. [Laughs]

Because my what my friend was saying... as the company grows, it is going to be part of your job to hand things off. To, you know, maybe you're the person that does like the zero to one, build from nothing to something, but then you hire someone or someone else on the team takes it from one to two. Something that you can do is really think about what kind of projects really give you joy, what draws you, what do you spend yourself thinking about... hopefully not in like a 'can't turn my brain off' high-pressure way but because it's intellectually challenges you.

For me, that's when I started focusing from like... yeah, when I was doing everything—operations, product—to the internal kind of like people side of things. I really found myself like wait, I like the hiring. I like the culture management, people management, performance. So, whatever you like, focus on that, because whatever you hand off, someone else in the world is perfect for that job. Like, what sounds boring to you, like compliance? Some, some person will be like, "Oh my God, give it to me"

Caro Griffin  10:17
Yes, absolutely!

Jennifer Kim  10:19
But if you're the one kind of like clinging on to it, like, "Oh but, I need these eights hats because like, I'm so important and like, I'm so good at them." That's how you burn out. That's actually also how you get in your own way of scaling your own impact. And you can actually carve out the career that you want, the specialty that you want. And I know that's a whole another topic that we can get into because, like, the whole, like, tension between being an ops generalist versus some specialty. I know some people could be like, "Don't make me choose!" But I think there's some value in choosing.

Caro Griffin  10:50
Yeah, absolutely. Or at least doing that T-shaped thing like, "Cool, I can do a little  of everything," but really having that specialization area.

So we've talked about your eight hats. You did a lot of things at Lever. What was most random hat you put on?

Jennifer Kim  11:03
I mean.... truly, so many random hats. And, you know what, I'm gonna take this in a maybe different direction, a little bit more somber, and a little bit more real note. I've never said this on a podcast before.... but there was a time when I was really struggling if I wanted to focus on HR/people operations or not, because I was like, "Well, I don't want to be like pigeon-holed, no one likes HR people." Like, we don't have a great reputation. I want to be liked. [Laughs]

Caro Griffin  11:30
Yes, I don't even know what—I'm like, yeah, it's rough. That's such a hard part of the job.

Jennifer Kim  11:34
Yeah, because I like it, and I'm good at it. But I don't like the way people look at me when I tell them I'm HR.

Caro Griffin  11:40
Totally, and I think recruiting gets that too, in like a different way. People are like, "ugh, a recruiter." Or, "Ugh, HR." And then, especially when you're at a company that... those are roles that are more likely to be undervalued and under-appreciated and underpaid. And it's like, "why am I doing this again?" Like, "Should I go to that bootcamp and become a technical person?" I think it took me a long time to—

Jennifer Kim  11:59
"Maybe people would finally respect me if I was technical."

Caro Griffin  12:02
I think it took me a long time, there were several years, of like, "should I go back to being a developer? Should I learn to code?"

Jennifer Kim  12:04
Yeah, and I think that's, like, so relatable for so many people in these roles. So, yeah, I've gone through that for years, kind of that conflict of like, I think this is a valuable career field. I'm good at it. But boy, it's challenging me every day. And, you know, something happens, and I just like, want to rage quit. "Maybe I'll be a PM after all!"

But the thing that actually solidified my decision was, unfortunately, like a really sad, tragic incident where one of our employees passed away in like, a truly like a freak accident.

Caro Griffin  12:40
Oh, wow.

Jennifer Kim  12:40
Very sudden, like, you know, very beloved person that everyone was really close to. And I just remember being like, what 26 or something at the time, and realizing we had this challenge of like... First of all, there are all these like logistics to get through around like health insurance, supporting his partner. Like, we don't have a policy for this, and we shouldn't, right? But also there was this like, emotional, support part of like, this shock and grief, of leading employees through it.

I just had this moment where, okay, like, weirdly, an opportunity that I would have never asked for, but I can step up here and really be part of the leadership team. So, for me to like really process my feelings, and like really step up, that will allow me to kind of take care of people around me. I got to see the difference of like people responding, you know, as like, sad as it was, they felt supported, the family felt supported in terms of like all the resourcing that we brought in. And I just remember thinking in that moment, even as I was also, like, stressed out and overworked at the time, I was like, "Oh, this work does matter." Because, if it wasn't for me doing it, I don't know who would have. I don't know who else could have stepped up.

Caro Griffin  14:01
Yeah, I think those that's such... Wow, such a tough situation to be in. And one of those things like you said, like, no one needs a policy for this, hopefully. I hope it's a freak thing that very few of us have to deal with, or definitely only have to deal with once. But I think so much of these roles is like, "Okay, we wrote the policy when we needed the policy," but then there are these moments like this where, yeah, it is such an opportunity to lead this community, as you called it, like through this tough time in a way that... Yeah, I never would have thought about their partners, health insurance, you know, and like, what can we do to really bring everybody through this in a way that like, we are setting the standard, right? We're saying that, like, you know, building teams and hiring people is what was what we're doing. Let's do this in a way that that measures up to that.

Jennifer Kim 14:40
I think it's like the responsibility of people work, right? It's not the same thing as I don't know, like coding, where, you build something and it's, you know, it might break but it's not gonna talk back at you. It's not gonna be like, "I'm going for a divorce. I can't work for a while."  You know, like, there's some reasonably reason predictability. But I do think, whenever you're working with humans, life is going to happen. There are just things that are gonna be uncontrollable by it. And as someone who is working in that space, like my customers are people, I will never be able to control outcomes. But the best I can do is to really try to enable the environment where everyone can do their best work. It's not just like the happy hours and, you know, like, all the little wins of hiring. It's like, real life stuff. It's all the toughness of what comes with, you know, especially these days, like political debates, and not even like harassment, disagreement, but also just like outside things going on... Covid response... All of this, I see it as an opportunity for all of us to kind of just like, raise some standards around here and just the world. Corporation, are not doing the best at it,

Caro Griffin  15:58
Really?! What a shocking thing to say. I knew you were going to have some hot takes.

Jennifer Kim  16:09
That's why I love startups, because we get to try different things, really work with humans on a human level. We're small enough to kind of like feel like it. And it's given me some of like, my most like, fulfilling moments in my career, for sure.

Caro Griffin 16:23
That's lovely.

So, shifting away from Lever a little bit, you still wear a lot of hats. You're a startup advisor and consultant and a coach and the founder of Startup Recruiting Bootcamp, which I definitely want to talk about. And, I guess, maybe we start there. Can you tell us a little bit about the bootcamp and what led you to found it?

Jennifer Kim  16:38
Yeah, you know, I mentioned earlier, I was drawn to Lever because I, in my naive, innocent, idealistic days, thought, "Oh, hiring is broken. Maybe software will solve the problem." Update: do not recommend such an idealistic point of view, while I learned a lot, and I'm very, very grateful, and actually very proud of what I helped build over there.

Caro Griffin  16:59
Yeah, it's like, great software is great. But you need the great software and the great people. Yeah, no, I definitely remember that, the days when you think a tool is going to solve every problem.

Jennifer Kim 17:08
"Airtable will solve all my problems!" It can help but, you know, probably not quite the silver bullet that we're looking for...

So yeah, because I only got more exposed to this, like, the opportunity in this space, it got me really thinking about what is the the vehicle that I want to impact change on. I started kind of doing, organically, two things on opposite ends of the spectrum. So one was, you know, consulting. Which, you know, most people are somewhat familiar with — like, I would work with companies one on one, coach the founders, coach the internal operations people—and I really love that because I get to go deep, I get to build relationships... But I felt pretty limited in terms of like, time, and, you know, there's only so many times you can explain how to write a job description without going insane.

On the opposite end, though, I'd have the writing. So, I do, yeah, as you mentioned, a ton of writing. A lot of hot takes. And that's really fantastic for reach, but I just didn't feel like I could get deep enough. There's so much you can say in 280 characters.

So I was on vacation in Bali, and I was just like sitting there

Caro Griffin  18:13
NBD. Casually laying on the beach in Bali.

Jennifer Kim  18:16
Yeah, I mean... isn't that what everyone does on vacation? Think about how do you solve recruiting?

Caro Griffin  18:20
Yeah, that's exactly what I'm gonna be thinking on my vacation next week.

Jennifer Kim  18:25
It's what I do because I have no life or hobbies, outside of recruiting.

Caro Griffin 18:30
Now, I know that's not true but I'll get it go. So, you're in Bali and you're thinking about recruiting...

Jennifer Kim  18:37
So I kind of figured out, okay, I want to do something in this middle, where I can work with groups and have the time to go deep enough, but really also build like a community and like a cohort based model. So that's really where Bootcamp came from. The goal for me for with Bootcamp is—I want to help train this, like, next generation of startups. You know, maybe it'll take five years. This stuff takes a long time, unfortunately, for it to be really visible in terms of impact. Not as quick as some of the other departments. But I want to be able to say like, you know, like, "Oh, this batch of like, these super cool companies that are becoming well known, especially, hopefully being good at hiring, what is the common denominator?" And hopefully, they can say like, "Oh, back in 2020 2021. They all took Startup Recruiting Bootcamp." And that ended up being a strong foundation, but they were able to really get hiring right from the start instead of trying to, you know, like, hire a bunch of people, make mistakes, and be like, "Oh, we did it wrong," and then trying to play catch up forever.

Caro Griffin  19:37
Yeah, I love that you have such a long term vision for it and a goal. I think, sometimes it's so easy to get caught up in like, I want to do this many people or this much revenue or like, I want to teach someone to do X but like really focusing on impact, I think is really cool. So I want to shout that out. But also, you know, I mentioned earlier I had like the privilege of going through the Bootcamp and I considered myself, like, pretty good... Like, I've never worked out at a Lever in that kind of hyper growth stage. I've always worked more in like, bootstrapped companies that are smaller and, even when we were growing a lot, we were never growing quite in the same way, but I was like, "Yeah, I've been recruiting for years. I've been like, a Head of People for a year, like, I got this. This is cool. This will be like a nice, like, you know...." and I still learned so much. And loved it and recommend everyone to do it. But who do you think it's best for? Because I think when I went through it, there was like, recruiters, but there's also some founders... Who would you love to see in sort of a boot camp?

Jennifer Kim  20:32
Yeah, I get this question a lot. And I have an answer, that's maybe a little unexpected. I  hear a lot of like, you know, founders or even repeat founders that are just like, "I thought I knew what I was doing. Turns out I don't." [Laughs] Experienced recruiters who've been doing it for years, they come in and get a ton of value. And that's why I think it's less actually about the role. We have had founders, recruiters, hiring managers, you know, from like, all backgrounds, all different roles. But, instead, what makes for a great fit is really like the attitude around hiring. There's still a ton of people for whom they look at... well, they have heard enough times about how important hiring is. So the awareness is there, but not necessarily the motivation. There are a lot of people who look at my program, they're just like, "Do you have a shorter one?"

Caro Griffin  21:19
Oh, my God. I bet.

Jennifer Kim  21:21
Or it'll be like, "I'm too busy." Because there's a lot of attitude around like, okay, hiring is important. But there's still dissonance around "but I don't want to do it." Who can I pay to get rid of this problem for me? And the core of Bootcamp is that this is a leadership skill. If you want to be building any teams, you can't just like, skip this and hope someone else will do it for you because it's challenging you in new ways. Just like, you had to learn how to code, just like you had to learn how to sell, if you're a leader, you're gonna have to learn how to work with people. And hiring is such a big part of that. So I think the biggest like filter for me has become people who are excited about this work and motivated to, like, truly learn it. And we don't do a lot of like, pushy sales. Because if they're coming at it with like, "I really want to take bootcamp but we're too busy hiring." I'm like, "Okay, I can't help you."

Caro Griffin  22:16
That's a bigger problem, yeah!

Jennifer Kim  22:19
Yeah, if you want to do the things that are inefficient and make you like, hate hiring, and I'm offering a solution that makes things easier. "Here's high ROI things, here's how to make it work for you." You know, you can take a horse to water, but you can't make a drink. Good.

Caro Griffin  22:36
Absolutely. And I think the idea of like talking to a founder, especially in tech, where hiring is such a huge part of like, the founders role. I used to talked to people all the time, yeah, who not only don't want to do recruiting, but I think I hear the same thing or similar things about management. They're like, "I just don't want to manage people. Can I outsource that to a CEO?" And I'm like, "You're in the wrong role." Like, you can be the boss somewhere without being a founder, who has to recruit and has to manage people, like, you can get smart people to help you do those things, but you can't completely outsource them.

Jennifer Kim  23:08
Something I heard recently, that really kind of, like stuck in my brain is that, you know, like, what is a founder? Who is a founder? And it's someone who like, just really does best learning on the job... And not everyone is going to be the best and that's fine. And what I like about that is, you know, I really appreciate seeing how much you got out of Bootcamp. And, you know, I hear that feedback a lot about how much it resonates for people. Because for some, not all, but some people like the content of Bootcamp or how he talked about like, you know, the context of like, the power dynamic shifts, and the psychological reasons for why hiring is hard. And the the structure that you just set up, like, all this is a leadership skill that, for a lot of people, it's intuitive, but we're just working in broken systems. So we hate hiring because it feels bad. Because it's done badly at most places.

So, what we think of hiring and management, you know, most of us think back to our personal experiences, right? Like the time you had a horrible manager, and you're just like, I hate management. And so I hate all managers. And you're like, well, actually, you know, I feel confident saying, everyone would love a great manager. It's just that they're so rare. So being avoidant of this challenge is not helping us collectively get better. So it really is an individual challenge that you can take. If you want to be a leader, do you want to be the type of leader that you know really approaches it from a learner mindset and tries their best? Or are you just kind of like running away and trying to avoid your past trauma? Which, like, I understand. Work trauma, so real. Past manager trauma, tech interviewing trauma, it's all there. But, if you want to be a leader, it's up to you to choose to kind of confront it and learn from it because you're going to be affecting other people.

Caro Griffin  25:01
Absolutely. What a pull quote. And I think that's, at the end of the day, one of the things I really appreciated about Startup Recruiting Bootcamp. It was not only like all of the tactile pro tips and strategies and like that kind of stuff, but also this like bigger picture, like, here's how to do it in a way that feels good, that candidates are going to feel good that you're going to feel good, and that also like, you're still going to drive results, right? It's not one or the other, like, these things can coexist.

So, shifting gears a bit, to talk more generally about the operation space, how do you think of or define People Operations? Especially, as you know, I think we've in this conversation used HR and people ops, kind of, like interchangeably. But I would love to hear your thoughts about if there's a difference, if that's just branding, or like how you define that role?

Jennifer Kim  25:45
Yeah, my field has such a branding new problem, because we get, you know, suh dirty looks from people, when we explain what we do know. [Laughs] But I do think like, generally, the words are kind of the same. There might be some distinctions.

But here's how I think about like operations and people ops - there's this quote out there that says, a business really comes down to two functions. There is product and then there's growth. So there's the thing that you build, some products, services, and then kind of like the business around it, which is sales, marketing, customer support.

I actually disagree with this gentleman. I think there's a third function that's really that operations layer that enables all this to happen. And I do think in most organizations, especially startups, that third layer, has really been neglected. It's kind of taken for as a luxury. Like, okay, as long as you build a thing, and you make money, everything should magically work out, but no. You need ops people, you need, people like us to actually focus on that third layer, just like you have engineers working on the product, and sales people working on sales.

So, to me, people operation is like a part of that. Everything is going to be people. It doesn't matter how great the idea is, you need someone to build it. And that's going to be humans. And humans are going to have certain needs and pesky things like health insurance. And if you don't, you know... it's like, very, like Maslow's hierarchy of needs, right? Like, if you're not able to set up the environment where people can do their best work, they're just not going to do it. It doesn't matter how brilliant this engineer is and how much you're paying, you have to take that as a very critical business functional. So that's what I imagine as people operations.

Caro Griffin 27:28
Great answer.

So, you call yourself a Head of People, but you obviously do a lot of work in the recruiting space. So how do you think those two functions work together? And, I'll be honest, I'm partially asking this question, because I want to hear your take, especially on these startups that try to put people and recruiting together, like do you think that those can coexist and how that works?

Jennifer Kim  27:49
Yeah, so I can say this as someone who's been on both sides. I was doing full time recruiting for a while, and then I shifted over to the HR side. Really, for me, what it comes down to is when we go back to like that T-shaped career function, my home, my anchor will always be in recruiting. It's where I started, it's what I'm obsssed with, but I can do a Head of People function in a startup.

So I think the, you know, maybe not the most helpful answer, is that it's gonna depend. In a startup, where you just don't have enough headcount for all the specialty roles, you are going to want generalists who can do multiple things. So I don't think that's necessarily like a bad thing if someone is trying to do both or multiple aspects of People Ops. I do think that, ideally, if you don't have that internal experience of someone who hasn't, you know, like done it themselves, you're pairing that person with some kind of outside expertise for like advising and that sort of thing. I really do think at an early stage startup, what's probably going to be more important is that kind of startup-y-ness. Maybe, well, the opsy-ness. Someone who can work broadly, wear multiple hats, try on different things, learn as they go, as opposed to, you know... You can pluck out a Facebook recruiter who's been doing it for years, but drop them into a totally green field, not everyone, some people will step up. They're like, "Oh, my God, I'm so excited to build and try things and—"

Caro Griffin 29:17
Yeah, and like develop the new skills and strategies that they need.

Jennifer Kim  29:20
Exactly, yeah, but not everyone will. So I think it is a kind of like a fine balance between like, sure, like, some natural proclivity for like people work, some experience, but also that kind of that startup x factor.

Caro Griffin  29:32
Yeah, that totally makes sense. And I think in my roles, again, because I've primarily worked at smaller, like bootstrapped and early stage companies, it makes sense to have that generalist. I've always done a little bit of both. It kind of goes back to like valuing that operations role and knowing at one point you can't have one person do all the things, you're gonna have to build out the specialist when you get the headcount and knowing what phase you're in.

Jennifer Kim  29:50
So just because like your ops person or your first kind of people person is so wonderful and can wear lots of hats... Does it mean they should keep doing it? In an ideal world, the founders or leaders are helping that person manage their workload and scale and not burning them out since that is so common.

Caro Griffin  30:07
Yeah, absolutely. I always go back to Molly Graham's Lego analogy of like giving away your Legos and building Lego towers. And you know, and part of a good manager at a scaling organization is someone who's going to help you realize that there's a shiny tower you can build over there, but you have to drop the Legos that you're currently hoarding right now.

Jennifer Kim 30:23
Yeah, that that article—and Molly's one of my mentors—I like paste that article everywhere.

Same! I reference that article so much and I've never met Molly so I'm like... Molly is your mentor?? You know, Molly in real life? Okay, we'll talk about this later.

No, so she's so amazing. And this concept was just like, unlock something, and one of the challenges I had was like, because I was teaching everyone also let go of their Legos and really, you know, trying to like, socialize a language around it, I realized no one was doing it for me. Right?

Caro Griffin 30:56
As is always the case, right? Like, put on your oxygen mask before you help other people! Yet, we never do.

Jennifer Kim  31:02
And I do think that's like really important for ops people to like, really advocate for themselves, because your job is inherently about like enabling others and facilitating this environment, make sure - one , you know, you can do it for yourself, but there's a limit to how much you can do it for yourself. It's gonna take the leadership, so they need to know about it. So you need to actually teach them how to support you.

Caro Griffin 31:25
I mean, that's great, because I was about to say something about how like, if your leaders aren't doing it for you, you need to figure out how to like build another support system, because like, I've relied on a coach and friends and peers and mentors and stuff to help me do that. And when I've worked at roles where I think the CEO really struggles to do that, in certain cases, but you just said, you know, you have to teach them how to do it. And I would love to hear your insight on any pro tips that you have for teaching them how to do that.

Jennifer Kim 31:50
I think it's both. I also love what you said about like creating your own support network, getting those external validations. And that's something I wish I'd done more. But even like teaching others how to do it. Yeah, also learned that the hard way. As most things are...

Caro Griffin 32:06
Those are the things we internalize the most right, though? The worst mistakes we've ever made, the really embarrassing moments like those, you know, like, the gift of those horrible cringe worthy things is that, you know, like, they're buried deep in the mind. You're gonna remember those lessons. I was talking to someone about this the other day and try to see them as a gift instead of being like, "don't think about it, don't think about it."

Jennifer Kim  32:29
Caro, are we about to go into work therapy?

Caro Griffin  32:32
I'm sorry, I thought that's what this was? I called that the calendar invite work therapy. Did you not see that?

Jennifer Kim 32:38
But it is something that was a really big challenge for me. The thing that you need to learn, the hardest lessons are going to be different for everyone. For me, it has been, as someone who you know, really identifies as getting a lot of joy out of helping, and you know, likes being the background person by nature, advocating for myself, and also teaching others around me to take care of me has been one of my biggest challenges. Because I approach things from so enthusiastically, like, you need help with that? Like, someone like vaguely mentions a problem, like I'm on it, just like chasing after it...

Caro Griffin  33:15
Same! Yes. Especially when it's like some like manual, ridiculous thing. And I'm like, "Oh, I can help with that. We can streamline that. We can write an SOP, we can automate it, let's do it."

Jennifer Kim 33:25
Yeah, and I love the feedback that comes afterwards. But when it comes to advocating for yourself, you know, learning how to draw boundaries, like that took a different type of skill, and challenged me in ways that I was not used to. It required me to be like, really vulnerable about, like, where I was coming at, be honest with myself, you know, really probably, like, confront some personal ego issues that I think, you know, we all have. Ask for help - the worst thing - but then you realize, you know, by making the ask and trying to come at it from the best way you can, which is the emotional honesty, you know, managing your own communication and emotions, and then seeing how people react to that. And sometimes they will be right there with you. They will thank you for drawing boundaries and letting you know what what's going on with you. Sometimes people don't, and that just gives you more information about what you want to do afterwards. There is a way that I was avoiding those conversations, because I just wanted to be the person that could do everything.

Caro Griffin  34:31
Yeah. Because as ops people, we're used to filling in gaps and being a superhero. And like, that's part of, I mean, being completely honest. Like, that's part of what I love about ops. I love being the superhero who can do all the things and who, you know, can channel that Legally Blonde GIF where she's like, "What, like, it's hard?" Like, I think about that all the time. Like when a founder comes to like me with a tough problem. And I'm like, I totally got this but you know, sometimes I don't and it's hard to admit that but also I think sometimes in the past—I can only speak for myself—but will say that like I didn't let people be there for me who ended up showing up and being great. And like, you know, I wasn't allowing us to, like reach that level of like, friendship or colleagueship or whatever you want to call it, you know, where we were like operating with like a wall or a boundary that wasn't necessarily, like needed or beneficial.

So, yeah, I love the idea of like giving people that opportunity to show up for you and to support you. And then, like you said, if they don't, you have more information. You can like, move on to the next step and plan accordingly.

Jennifer Kim  35:28
Yeah, I agree with all that you said, I would just add on like... because you're probably doing that for everyone else.

Caro Griffin  35:33
Absolutely. As a Head of People, so often we are. You know, we're putting on that oxygen masks for everybody. So, you know, we've talked a lot about people ops roles and HR roles. And you know, people ops has been around for a few years now. So we've seen those titles and recruiting, but a new title that we have definitely seen pop up, especially at these more established remote first companies is a Head of Remote role.

You and I have talked about this before, but these people are often in charge of setting up team members for success and fostering a productive work environment. And I'm like, isn't this People Ops? Isn't this operations in a remote environment? So I want your thoughts. How do you think this fits into the future of our organizations?

Jennifer Kim  36:14
Yeah, no, it's funny, because I started seeing a trend, maybe right before COVID, but then definitely ramped up after COVID hit - Head of Remote jobs. And I saw some similarities happening with Head of DEI, recently, too, which is why I think I recognized a pattern... but, in some companies, that role makes total sense.

You know, there's a few companies that were like, well known for being very remote. And they decided to invest in both the brand and also just like the way that company operates by carving out, you know, often a very visible person. Then I started seeing this trend where I would see tweets from like founders, or, folks, that would be like, "you know, when I start a company, I can't wait to hire like a Head of Remote to really, you know, facilitate, like, communication and information systems and performance in a remote setting." And I just remember being like... oh, yeah, that's HR. That is HR.

So I understand, on one hand, you know, I get where it's coming from. It could be excited about this new way of working and recognizing that investment could you know, go a long way. My slight issue is that by doing that we're actually devaluing the work that's already been been done, and also the people who have been doing it. Yeah, that's kind of like wanting to like, carve out the cool, exciting parts, and then continue to devalue HR. And I don't think it's a coincidence that you know, most HR roles are women. There is a gender discrepancy when you look at HR roles and HR leadership, of course, because... the world. But most Head of Remote jobs that I've seen are occupied by white men. So I have a theory that Head of Remote jobs are actually just Head of People jobs where they didn't want to call themselves HR sooo....

Caro Griffin  38:09
Yeah, and I think you just so perfectly put your finger on and summarize what I couldn't quite articulate when I saw these jobs. It's like what you said, it's carving out the fun, exciting parts. And I'm like, we've already rebranded from HR to People Ops. We can rebrand again, to like, remote operations and Head of Remote, but like, at some point, we're gonna have to stop retitling things and really address this undervaluing and shuttling to the bottom of the list of these people ops people who are really the glue in a lot of organizations, especially these fast growing ones. They're doing all the things, wearing all the hats, you know.

Jennifer Kim  38:48
Yeah, I get it. I mentioned, I got the dirty looks so I don't blame them for not wanting to be called HR. My CEO, a few years ago asked me like, "I think it's time for you to go from Chief of Staff to something else. Do you want to be Head of HR?" and I said, "Why do you hate me? Why do you want that for me?" I'm not kidding. I literally was like, "Oh, my God. Like, please don't make me." No, I literally was like, please don't make me do that. So we ended up coming up with like a euphemism, which is like head of employee experience that was really Head of People. So for me, I get it, like, girl been there. It's just that the rebranding is motivated from and leads to collective avoidance of the actual work. Right? So we keep trying to carve out and just pull out the fun parts. But really what needs to be done is everything I said about hiring and Bootcamp kind of still holds here. It's companies that need to step up and take this work seriously in a holistic manner, not just what's trendy and cool. Remote is very important. I do think it is the future, but not at the cost of neglecting kind of like those foundational people skills that the industry, the corporate world is still behind on.

Caro Griffin 40:03
Yeah, I think a related thing I see a lot is founders who are like, "Oh, I don't need a super senior. I'm doing all this ops work. But I don't need a super senior ops person, like I'm doing it all." And there's just this dichotomy of like, you're arguably like the most senior or time-demanded person at this company but like, you don't need a senior person to do it. You're doing it, but it's not valued. And just I think, yes, this perception, I guess, of HR and people ops, just really trickles through a lot.

Jennifer Kim 40:29
I think the biggest one of the biggest challenges in that is, unlike product or growth, operations results are hard to measure. They take a longer time. They are a lot more environmental and contextual. Sales, you see the sales leaderboard. It feels so concrete, you see the graph going up. Product, you can you can see it. You're like, ooh, shiny.

It's different with our work. And that's why it is hard to value. So when someone says to you, like, we don't need a senior person, like I can totally imagine because they don't know what's not there.

Caro Griffin 41:04
Yeah, yeah, exactly. Well, shifting gears a little bit... You said a few minutes ago that you are a background person, which like made my eyebrow go up. Because I hear this from like, all Ops people. And I do not share it. I'm not a background person. But I think it's really common in most people so I'm not surprised when I hear this. But I was very surprised when I heard you say this because you are an incredibly prolific writer and tweeter in the startup space and about people ops. So, what are the pros and cons of that? And is it hard for you to put yourself out there in that way? Like, how did you become this very public person?

Jennifer Kim 41:44
Listen, I aske myself that every day. Like, how the heck did I get here? It definitely wasn't on purpose. But yeah, no, I actually am very introverted. Like, you saw me in person! So there's a difference between like online and like personas.

What's funny is that like, one of the things I got to really learn and push myself on by the nature of being a hyper growth startup is how to really be a visible leader. Because for so long, I was comfortable being the background person. It's just that, when the company's growing that fast, there was a limit to how much I can just be like, I'll just be the quiet background person. When the company is small, people will still kind of see it and be like aw, I appreciate it, but not when the company's hyper growth. I just I realized that, you know, this is a whole other conversation for another day, but I was having a hard time claiming credit. I was having a hard time feeling appreciated, people didn't know the work I was doing. But, on the other hand, I also got to learn I was forced to get good at public speaking. When I was giving, you know, our weekly all-hands, you know, it started with like, 50-60 people, and I'm like, okay, I don't love this, but I can do it, because I know each person and we're all friends. And you know, every week, it's like, you grow... and I blinked and all of a sudden, there were 150 people in front of me and you know, I'm giving like a public talk every single week. And I remember I would black out. Literally, just like, every week, like I said things, I clicked through slides...

Caro Griffin 43:12
Aww, Baby Jen!

Jennifer Kim 43:15
I know! She was so little back then. The being forced to do it is what made me, you know, get good at it. To the point where now I'm very comfortable. But a similar thing happened with writing too. I used to be a Normie. I only actually started tweeting two years ago with like, I don't know, just a few hundred followers from like, very, like basic level of work. And I decided a couple things, one, to really kind of build up my personal brand because I was independent having Lever, and you know, that's what you do as a consultant.

Caro Griffin 43:49
Well, and then there's just so much career security in making yourself known and making your work known and building your network in that way.

Jennifer Kim 43:56
You're building an anchor that's like, not dependent on a company. So I realized I needed to do that.

But secondarily, I really wanted to genuinely like teach because I was so driven by like, oh my god, everyone is so bad at hiring. Let me talk about what I know. Like, I genuinely love sharing and I like open sourcing my work.

So, what's funny is that you know, people don't realize this but when I first started I literally had to have every draft like read by a friend. And sometimes they'll come back with like, is this English? What are you trying to say? Because it would be bad!

When you know you want to do like something like writing on the internet and you see all these cool people and like they sound so smart... You don't get to see their first drafts and everyone starts somewhere. No one is born a great tweeter as far as I'm concerned. And yeah, it literally took me like a year of getting comfortable. And I've only been comfortable for like, yeah, the last year and a half. And I can't tell you how many connections and opportunities I've gotten out of it, like you. I think we met on Twitter!

Caro Griffin 45:14
We did! Yeah, we met on Twitter. I wrote like a CDMX Guide, and you were like, Hey, I'm gonna be in CDMX...

Jennifer Kim 45:18
Yeah! Oh my gosh.

Yeah, so it's been this like, really incredibly powerful tool. And like, don't get me wrong, there's definitely some like weird downsides to it. For every, like, 20 comments that are just appreciative really thoughtful discussions, it takes like one dude being a jerk that makes me like, why am I doing this? Should I rage quit? Delete my Twitter?

Caro Griffin 45:42
I relate so much to what you're saying. Because I feel like it's been a muscle that I've like, worked and got better out of like writing and being public and whatever, both to build my career and also, because I was, you know, an early people leader at a remote company before remote was like, super common. And so much of what I did was through trial and error, and I was like, please, for the love of God, let me like, save someone else this trouble so that they're not like, you know, making this ridiculous mistake that I made. You know, ops person want to make it efficient for everyone. But yeah, that I still have a really hard time shaking off that one out of 20 tweets, where I'm like, arguing with them in the shower. So, I don't know, I guess maybe I'm just looking for you to tell me that, like, that's also a muscle and it gets better...

Jennifer Kim 46:24
It is! Just like how I used to blackout during every all-hands and then eventually you don't. Like you literally are just like, "Oh, I remember that one. I think I was breathing during that one." So there were times where like one comment, I'd be like, running it over in my head, and in the shower for like days. Now, I'm just like... oh, another one happened. Okay.

I do think you just get used to it. And the important part is like anchoring on the positive, like, the type of connections that you get to facilitate, the learning, hopefully, that you get to do. Because, yeah, I know, you have, like, so many stories and value that people are figuring it out in real time right now.

Caro Griffin 47:04
Yeah, and I think a secret agenda, maybe a not a secret agenda, of this podcast and the Opsy community in general, is to try to get more people to share their stories in a way. You know, to like, just talk to me sitting here in my closet, like about their stories. Or to write something or just put something out there. Because I have seen in my own experience, which is just like such a fraction of the reach that you have, you know, what benefits can come of that right? Both for you as an individual professional, but also like for the industry at large.

Jennifer Kim 47:36
Yeah, I think that's because you know this community and type of ops person that's really great at their job. But, as some of the themes that we kind of keep like circling back on are like, not maybe not the like, biggest self promoter. I don't mean that in like an obnoxious sense, but someone one who can like advocate for themselves and own their work. And, from that, comes like a type of leadership that you can teach others and share your work. And I didn't know that. I learned it the hard way, which is why I try to be open about it now.

Caro Griffin 48:07
Yeah, and, any awesome ops people listening, I will be your cheerleader. If you're a backstage person, you know, reach out with whatever cool thing you're working on. Jen and I will be your hype women. To move us all forward, right?

So I guess on a hype woman note, I want to be your hype woman! I like to end every episode with a little showcase, if you will, to help you show off something really awesome that you've done, that you're proud of. And so I would love to dig into a project that you that you are really proud of from your past or like an Opsy win that you've recently had.

Jennifer Kim 48:40
You know, we've been talking about how ops people can like scale their careers and maybe move beyond kind of like just being the efficiency person, but really like, think about how do you scale the environment.

So people ops in particular, is going to work very closely with the emerging management layer at a startup. And that's something that I wish I started tackling earlier, instead of being like, oh, no, I'm behind on that.

So this is a little bit less of an issue when middle management, like leaders who are maybe not the founder themselves, were just one or two people, because I could work with them really directly. But, as is common when, let's say you get another round of funding, and you get you hired 10 more people for the sales team and then you hire two more sales managers and, all of a sudden ,you have this new emergent middle layer.

I realized, "Oh, I can't support people individually as I used to." And a really great opportunity you can unlock is creating almost a sub community of middle managers who can learn and help each other. So things I would start would be a manager's monthly.

All you have to do as the facilitator or, you know, the ops person is do what you're good at—send out a calendar invite. You explain what it is, which is to support group learning and discussions for all these people that are in different departments. But they are the same layer, that middle management.

So what I would do is just like pick a different topic, or even just like a book or an article, and everyone should come in reading that, or, you know, maybe the topic is 1-on-1s, maybe the topic is performance management. We would just kind of go around, like, what are some best practices? What are your questions? I would always designate someone to take notes, like you can take turns, and then send that out to other people who weren't able to attend. And hopefully, like new managers can read up and catch up on those notes.

It's a really cool way of integrating both kind of like, best practices out there. But also creating the space for people to talk about it and figure out what's going to make sense in your environment. So, that ended up being a really successful project where, you know, pretty easy to start. You just send on a recurring calendar invite and pick a topic like, how to give feedback, communication, etc. And your job is just going to facilitate and let them talk and take notes.

Caro Griffin 51:05
I love that. How did you find getting buy in for this? Were the managers like, "Yes, this sounds great. Let's do this." Or did you have to like do some convincing

Jennifer Kim 51:14
You know, this is one of the very few products that required very little convincing. Because I think a lot of middle managers, whether they're first timers or veterans, it can be really lonely job. When it's just your department—let's say you're coming from like a Director of Marketing—everyone that is under your stewardship, like they need stuff from you. You don't always feel like like, well, I also need support. And I have questions and there are things I'm learning on the job. So I found that launching something like this, there was a very favorable response, people really wanting to attend, being excited to attend.

So, yeah, I would say if your company is at that stage, where you're working with that middle management layer, just try it out, if you have any inkling for it. I bet it'll be received better than you think. Coming from recruiting, I'm so used to being like a burden. Can you please submit this feedback form? Oh, but I'm busy... but when I really framed it as like, this is a space for you to like, get support on management as we're all learning. I just found to be a fantastic response.

Caro Griffin 52:22
Yeah, this isn't an ask. This is a gift with a bow on top. Enjoy.

Jennifer Kim 52:26
You're welcome.

Caro Griffin 52:28
No, I love this. And actually, I had started something like a much less polished version of this at a previous job. As you're talking, I'm like, yes, this is great. I love the taking notes. I love the having a theme. And even if it's people can't commit to reading a book, let's do an article. Let's just like talk about how we facilitate 1-on-1s. There's so much value in that. And also the fact that you're sharing this right now, I think, just goes back to that whole like, yes, if I had had this idea and didn't have to come to it and iterate on my own. Like, if I could have just jumped to, I'm going to start this and this is how we're going to run it. Like, it would have saved me time, right? And so the value of all of us learning from each other - I feel like this was a common theme in this episode. So this is a great place to wrap it up. I love it.

Jennifer Kim 53:09
Yeah, this was so much fun. I really appreciate the space to talk about it. I appreciate the space to talk about it with you, because I think that makes so much more fun. And I hope it's useful to the listeners.

Caro Griffin 53:18
Absolutely. So I'm sure everyone has already followed you on Twitter and LinkedIn after hearing this episode, but for those of them who haven't found you yet, where where should people stay in touch? Or should they reach out to you? Where can they find you?

Jennifer Kim 53:30
Yeah, so those two channels are at for me - @jenistyping on Twitter. I'm Jennifer Kim on LinkedIn. I try to post things that I hope will be helpful or slightly humorous in the strange, strange world that is operations and HR. Apparently, people like my posts. I hope they're useful.

Caro Griffin 53:51
We definitely do. I'm speaking for everyone.

And then obviously, you are running Startup Recruiting Bootcamp. I'll make sure I put a link to that in the show notes.

Jennifer Kim 54:01
If folks are listening and they're at all involved in hiring, or if your company is expected to hire they should definitely come because you'll get a lot out of it.

Caro Griffin 54:09
Yes, you absolutely will. I will promise it on Jen's behalf.

Well, everyone, thanks so much for listening. Until next time, stay opsy!

Thanks for listening to Opsy. You can find resources and links from this episode in the show notes at Opsy.work. And, while you're there, I hope you'll take a second to join our free community where we share resources and opportunities that help us all level up in our ops careers. Until next time, stay opsy, friends.