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  3. The 3 archetypes of the future people team & Jessica Zwaan's first 4 Months in New Role
The Modern People Leader: Forward-Thinking HR

18 Aug 2026 · 43m · 16 chapters

Episode artwork

The 3 archetypes of the future people team & Jessica Zwaan's first 4 Months in New Role

In short

The episode discusses (1) why “speed” expectations for new leaders can backfire and why early shipping matters, and (2) Jessica Zwaan’s first ~4.5 months in her new role at Leapsome, including her 12-week onboarding sprint and her vision for future people teams shaped by AI.

Guests and backgrounds

Jesse (host) and Daniel (co-host) interview Jessica Zwaan. Jessica is new to Leapsome as VP People Strategy & Ops (after being COO at a ~500-person company). She previously worked at Talentful for ~3.5 years and has long experience across people operations, product strategy, marketing, and advocacy/community work. She also references prior founder relationships (e.g., Jenny and Kytan) and a forward-deployed engineer on her team.

Key claims

30/60/90-day plans are “dead”; if you’re not shipping in 3 weeks, it’s a red flag. People ops will grow fastest through AI, and people teams will develop three archetypes: (a) advisors/coaches, (b) architects building systems/workflows, and (c) “physical experience” owners (events, socials, L&D days).

Notable examples

Leapsome’s fully transparent compensation framework and calculator; leveling; an org-network-analysis-based performance review process; an interactive leveling tool; a dynamic promotion/merit increase coaching portal; and an AI “calibration pre-read” tool that flags discrepancies between feedback/scoring. She also cites her first HR job as filing paper contracts as an example of how HR work has changed.

Written by AI. May contain mistakes.

Chapters

0:00

The Need for Speed in Leadership

Leaders are pressured to act quickly and decisively in today's fast-paced environment.

“And I don't think, I think every single company in the world right now is feeling like we have to move quickly, we just have to make decisions, we have to be making progress.”
1:00

Exciting Developments and Good News

Hosts share their personal good news and recent experiences.

“Jesse, welcome to the Modern People Leader again.”
2:56

Jessie Zwaan's Transition to LeapSim

Jessie discusses her new role and experiences in the first months at LeapSim.

“Well, last night the offer was accepted.”
6:18

Building a Community for Modern People Leaders

Daniel shares thoughts on creating a community and engaging with listeners.

“Like literally we have a channel called build what you do.”
7:35

The Role of People Ops in the Future

Jessie highlights her strategic focuses and the evolution of HR functions.

“And so pretty good conversion rate so far.”
14:00

Introduction to HR Philosophy

Explore LeapSim's evolving HR approach and the shift towards people operations.

“This is how we work at LeapSim and have been kind of building off that.”
15:00

The Future of People Ops

Understanding the changing landscape of people operations and its potential.

“And I also really genuinely believe that I want the people that are kind of at the front of that change not to be VC tech bros and finance people.”
17:10

Emerging Archetypes in HR

Discussion on three new roles that will shape the future people teams.

“Maybe working with a forward deployed recruiter like we have here at our team at Leapsim.”
18:50

Jessica's Early Months at LeapSim

Jessica shares her initial strategies and initiatives in her new role.

“So we did a retro, we did our goal planning.”
21:00

Building a Transparent Framework

Insights on launching a transparent compensation and performance review system.

“The first thing I look for is someone that actually cares about people products in some way.”
Show all 16 chapters
23:00

Hiring the Right Engineers

Jessica discusses the profile and attributes of a forward-deployed engineer.

“And within the actual experience of onboarding, I realized like, wow, okay, some of the things I thought were true, in fact, are true.”
25:30

Navigating New Roles and Challenges

Jessica reflects on the challenges of onboarding and managing expectations.

“what's like, you like feeling like you know things and you didn't feel that way.”
28:04

Navigating Leadership Challenges

Explore the complexities of leadership in a fast-paced environment.

“And prior to that, I have been part of the founding.”
33:16

Understanding Leapsome's Vision

Learn about the strategic vision behind Jessica's role at Leapsome.

“I'd be curious to hear what Leapsom's perspective was like, why, like, why it was so clear for them to bring you on board.”
35:04

Innovations in HR Technology

Discover the future trends in HR technology and its impact on operations.

“When you look back at the work you accomplished, like, what do you think is going to be the one thing that y 'all are doing that other peers are going to be like, we got to do that?”
39:58

Jesse's Insights and Takeaways

Reflect on Jesse's key insights and the future direction of HR.

“you know, I've had the fairly unique experience of working in a commercial role as well.”
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Transcript

Automatic transcript. May contain errors.

0:00Every leader that's coming into a business, actually anybody, but you know specifically like leaders and people that are coming in with experience, the first thing they're being told is like speed, speed is our advantage, like get in, get stuff done, we don't have time to waste. And I don't think, I think every single company in the world right now is feeling like we have to move quickly, we just have to make decisions, we have to be making progress. Okay, so that, yes, I agree. That's fair. But if you're bringing someone in that has experience and then giving them the remit of like, you need to be moving with speed and urgency, that then puts you in a position where you have to be like, okay, well, there's gotta be a limit to that.

0:32I think these old days of 30, 60, 90 day plans, where you spend 60 days talking to everyone and 30 days, you know, finally like scoping out the things you're gonna do, those days are dead, they're gone. Like if you're not shipping something in the first three weeks, like it's a question mark on the fire. You're listening to the Modern People Leader podcast, where we go behind the scenes with today's top HR leaders and work experts. We talk to them about how they've gotten to where they're at, what they do every day, and what they see coming next for the future of work. Hope you enjoy.

1:05Jesse, welcome to the Modern People Leader again. This is like take 10 or 11. I don't know. I wish i had the actual 100 yeah something like that how's life time is better than the last so good yes how's i mean i think we all like we have so much good news stories so it feels like we all missed the whole hour just to do good news like a good news episode there's so much good news i like that jesse you go first i'm excited to hear what you have going on okay oh wait i feel like i need to send a picture we should put it in the show notes i'm gonna send it to our group chat because I don't think there's a way that I can describe my good news without you seeing the image.

1:49I think you can screen share if you want to share it. Oh, shit. I think I can. Okay, wait, wait, wait. Oh, yeah. We've never tried this, but... You can descript. Come in and clutch. We're like... Okay, this is like... Okay, I'm just... For those listening, I'm sure this is going to be cut, but I'm getting my screen share prepared. Okay. Share. Dio screen. Okay. You ready for this? I kind of want to be able to see you, but let's just do this. Ooh, Matrix.

2:19Jessica Zwaan: Oh, my God. Is that you summoning your eagle powers? This is me riding a horse while holding an eagle in Kyrgyzstan. This looks like an AI-generated image. This is not an AI-generated image. and i've got like i actually have here is the eagle hunter to demonstrate get out of here i know that is insane i know this is so for those watching or listening um we're gonna put the pictures in the show notes i'll send them through to you guys on text i just got back from kyrgyzstan one of my best friends is kyrgyz and while i was there i had the joy of meeting a kyrgyz eagle hunter which is a thousand year old tradition where people get eagles raise them from babies chicks and then teach them how to hunt those these eagles see humans as like their parents and then they take them back into the wild after 20 years to not decimate the eagle population but what they do is they ride around on horses with an eagle on them and then the eagle flies away and goes hunts rabbits and things and then brings the eagle back and brings the the hunt back in in winter and when I was in Kyrgyzstan I was allowed to sit on a horse and like summon an eagle it was so good that's my good news I don't know if I can top that Stephen do you have anything I definitely cannot top that I'm just like geeking out here so I like of course go immediately google like where is Kyrgyzstan and I funny enough was obsessed with this cooking show I think it's called like wilderness cooking and it's a youtube and i got like caught in this funnel of this guy i think he's from because i was like god that that landscape looks really familiar i think he's from uzbekistan or he's one of this from one of the stands and i'm like absolutely obsessed like go go and he ends every episode by going stupid and it's a trip and so the fact that you were in that part of the world riding horses you know unleashing eagles is pretty sick i'm not i'm gonna lie i feel like we need a custom slack emoji of you on the horse releasing the eagle like any triumphant that also needs to be your profile picture on all of the accounts now yeah exactly like all of them so my good news we could be homeowners we've uh made an offer on a home and I was, we just had a pod yesterday and I was like, I like we made an offer.

5:01Jessica Zwaan: Well, last night the offer was accepted. Uh, so that's cool. In addition to that, I'll give a quick Joaquin update. I haven't really talked about him in a minute. He got his first tooth in the last week and he started waving and asking for milk and man, he is just like growing and growing and growing. So that's good news also. And I think that's all I got. We were just crushing it all over the place. We have five pods this week and I log into LinkedIn and I'm like, CHRO of Hilton Hotels is shouting out Daniel and I about our podcast together. It's kind of surreal sometimes. I got to be honest with y 'all.

5:45Jessica Zwaan: What we've done, what we built, it's just super cool. So that's my good news. I mean, on that note, we had an intake call with, I don't know if it's Katerina or Katrina, Katerina Berg, who used to be at Spotify, who's now at On, and she's going to be doing We tried so many times, Jessie, to get her, she was the CHRO of Spotify for years, and like everyone, she probably was the most recommended guest that we never got on until now. So that's pretty exciting. i'm actually meeting up with the lovable cpo on monday next week i'm really excited yeah absolutely i mean their team is so wicked they're super super lovely uh marianne is her name and i've been talking a bit about building so i'm gonna when i meet with marianne next week i'm really excited maybe i'll maybe i'll drop the word and say like we need the people of modern people leader the listeners need you we need you we need her yeah yeah she needs to join us at a minimum, like join build and talk about the, let's talk about the stuff y 'all are going to talk about.

6:51Jessica Zwaan: Like literally we have a channel called build what you do. All right, Daniel, what's your good news, babe? My good news is, well, behind the scenes have been thinking about building a community for modern people leader. And phase one is just doing the research interviews and validating whether or not this is worth something pursuing. And we haven't done this. I haven't gone through this motion in a few years. This is how we started the podcast. It was through a similar process. And we have a very loose idea of what this community would look like. And out of the eight people that I've talked to, we've gotten four commits.

7:37So people saying that they're in. And so pretty good conversion rate so far. and I'm just getting a lot of energy from these chats. I'm hearing things. I'm hearing what's going on behind the scenes and I feel like sometimes that's lacking on the podcast because people can't just share everything. Maybe we should talk about what's going on

7:59Jessica Zwaan: behind the scenes, Daniel. That sounds like a juicy podcast episode. We'll save that one for the next one. I think I'm going to process all of the notes and see what some of the themes are. but all that to say i'm excited to keep building yeah awesome guys fun what a good start we got eagles we got new new ventures we've got new houses and speaking of speaking of new beginnings and new jobs for you jesse you're what the four months in to your role at leapson for three months April, May, June, July, a little bit of August. Yeah, so four and a half months. Let's just start there. What have the first four and a half months been like?

8:46Really fun. Wicked. I think, so if you know me and you guys both do, I kind of hate being, let me phrase this, frame this positively. I love feeling like I know things. You know a lot of things. And I love feeling helpful on my shit and I know what's going on. And I'm like, you know, I love feeling embedded and capable. And that is a feeling that you don't really get when you start a new company. Like, I think everyone starts a new role and you feel a little flailing and helpless. It's just tough, right? So there's been parts of that, but overall, I've really, really enjoyed this really kind of special role I have, which is doing product strategy and marketing and people ops and a bunch of cool stuff, which is in some ways really new to me, but also some ways like the stuff I've been doing for the past 15 years just boiled into one job.

9:53So that's exciting.

9:53Jessica Zwaan: And so what's your formula? What's your playbook? you haven't moved around a lot. Like I, you know, you've had several jobs, but I don't feel like you've moved around a ton. And so like when you have made, but the moves you've made have been pretty big. This is, I would think this is a pretty big move. And so what is your like game plan, playbook for transitioning into the new roles? Is it like the traditional 30, 60, 90? Like, you know, what's Jesse's, Vaughn's like playbook for onboarding into new work? You know, we hear all kinds of stories in the podcast, and I'll never forget the story that was told about a Mexico Beach FMLA backfire.

10:38One of their employees was out on approved medical leave, and then somebody spots them on Instagram. Feet up on the beach, looking a little too okay for someone supposedly recovering. So cue the call from the CEO wanting to pull their leave and all of the panic that followed. but here's the thing. There's actual legal precedent that says a photo isn't proof of anything. You can't just yank somebody's protected leave because of how a vacation pick looks. You need real evidence. And that's a trap a lot of HR teams fall into. Making a compliance call based on gut instinct instead of actually knowing the law.

11:14And that's exactly the gap 650 is built to close. 650 helps teams manage compliance across the full life cycle, from handbooks and policies to agreements, legal updates, and research. And their AI-powered research center gives you a way to ask employment law questions in plain English so you can better understand what applies and where. Because compliance calls shouldn't be made on gut instinct. They should be grounded in real legal clarity. For those of you that want to learn more about 650, go to the link in the show notes and let them know we sent you. You feel like I'm a 30-60-90 girlie? No.

11:47Is that it? Why am I giving off? Please, offensive. Absolutely not. Yeah, great question. I think I, you're right, I haven't moved around a lot. A lot of the jobs that I've had, I've been there for like three, four years, try to stay places for a long time, or at least like, you know, long enough to really see things come to fruition. I really like to have a very clear kind of like, I guess I kind of like vision about why I'm making a change, like why I'm moving to a new role, like what job is it doing for me? But also like, what am I really there to do for the company like what kind of mutual value exchange is coming out of this is a plan and not just like I want more money and I want a big bigger title and in fact actually Leapsim is not a bigger title and I think that's actually a really interesting thing that maybe is worth talking about today is like I've had so many people ask me like why would you go from being the COO of like a 500 person company to being the VP people strategy and ops at a 120 person company and I think that's a kind of a separate think about but for me I think really clear thing is like having a very clear like kind of like point of view of when I'm coming in like what am I here to do like what am I being asked to do and what am I really hoping to get out of it and for me the for leaps and like the big thing that was really exciting was that I could really work at the intersection of like product strategy marketing and advocacy so like talking more about my book doing you know more stuff like what we're doing on this call like podcasts and speaking to the communities and then also running people ups and of course running people up as a product team is a big part of this as well so for me the most important thing or like basically i set myself a kind of 12 week sprint of this is something i want to deliver the 12 weeks that has demonstrated that i've i've made groundwork on all three of those things and that was effectively an internal document of like how we hr at leapson that we could then start turning into messaging and positioning about our product and how we work, but also start turning into like content for people to read and understand like, well, if LeapSim is building the best platform for HR and recruitment and performance management, what are they doing as a team to make that actually valid?

13:56So that's what I did. Like I think on like week nine or something, I published like an internal doc being like, this is our point of view. This is how we work at LeapSim and have been kind of building off that. Tell us more about this, how we HR doc, like what are some of the highlights for you? Great question. It's funny. Cause there are some things that's like changed a lot from built for people, but it's like built on the same kind of fundamentals. Right. So one of the first things that's in there is actually, let me go back and go to exposition. The thing I mentioned before, like why would I move from a COA role into a VP people role or VP people strategy and ops?

14:32Like, You know, obviously my role is more broad. And my answer to that question is, I, first of all, it was like writing the purpose of work gave me like a bunch of perspective about what was making me happy. And I realized that spreadsheets just weren't the thing. It was like people and spending time with human beings. And the second thing is I was watching the world change and I genuinely believe that the function that's gonna have the biggest growth. So the most shift from where they are now to where they're going to be is people ops through AI. And I also really genuinely believe that I want the people that are kind of at the front of that change not to be VC tech bros and finance people.

15:17And I say this with the most love. Like I ran the finance team for the last, what, seven years. But I think that there's a huge bank of incredible talent that's been working in people operations for a very long time that really genuinely know how to run a people function. that at the moment need as much inspiration and collaboration and ideas and momentum as possible. So for me, I think it's a really exciting time to be in people ops and we'll see a huge amount of really exciting stuff being built. And we already are. So that's that. So that was where I got kind of my thesis coming in. And then the doc basically starts with like, I think the world of people operations is rapidly changing.

15:58I think the way that we build teams is changing. manager to employee ratios are going to start degrading in a very very interesting way the role of manager i think might even completely devolve into kind of like almost like squads being run much more fluidly with an underpinning of like enablement that maybe is you know people operations trained people or uh trainers or who knows right like there's this whole new org structural kind of like reality that might come out and for me i think the people team that supports these potential new realities is first of all, people ups as a product. Absolutely.

16:33I think there's never been a better time to make that argument. And the second thing is I actually think there's kind of like three profiles that are going to emerge in people teams and definitely in how I'm thinking about my team. One profile, which is going to be around taking care of people. So that is like advisory, coaching, mentoring, this enablement type role, right? That maybe replaces managers to some degree. The second role is going to be architects. So people building the systems and our ways of working and interacting with each other electronically. So that could be setting up our HRAS, our workflows, our integrations, our tooling on things like Lovable, like building things and being kind of tech enabled.

17:11Maybe working with a forward deployed recruiter like we have here at our team at Leapsim. Forward deployed engineer like we have at our team at Leapsim. And the final role that I imagine emerging is someone that is there to basically take care of the physical experience. so running off sites the office parties socials learning and development days like really like this like i would say this person could even come from like hospitality right like thinking about denny myers books like setting the table um is a great example so my my thinking is like the people team is going to emerge i think with these kinds of archetypes working within it and that's how

17:44Jessica Zwaan: we're building the team at leapsome as well and so now that you've had a chance to kind of understand like the architecture that was already in place, you know, established like what, what you're going to be focusing on, how you're supporting the business. Have you started to form? Like, are you actually now, you know, four and a half months in like aligning the things and OKRs? Like, can you walk us through how far like in four and a half months does, you know, the Jesse's Vaughn get into kind of setting the agenda? yeah well first of all is like basically the first thing i did even before i joined i was like talking to jenny who's the founder here about things that i would love her to start kind of like setting the groundwork for before i started so like explaining like sharing to the team like what's product sprints are getting the team to work with more with product and have them like begin to understand people's as a product then when i got in the first thing i did so i joined in April, right?

18:45So the very, very end of Q1 and beginning of Q2, which is great timing if you work in the way that I work, because it means that you can go straight into like planning and retro. So straight away, we did that. So we did a retro, we did our goal planning. And I did that the same way as I've done pretty much every company, which is focusing around like, what's the problem statements? What's the data to support that problem statement? What's the impact you want to have? Picking our initiatives, building out our roadmap, and then assigning and delegating tasks within that. So we work as a squad. And straight away, the first thing we focused on was compensation.

19:15and we launched our fully transparent compensation framework and compensation calculator in Q1. So straight away when I started. And then we also launched leveling. So we had leveling, we had compensation come out very quickly. Now we're launching, there's so many things that we've got coming out this quarter. We're like shipping as quickly as our product team almost. We have launched a fully organizational network analysis based performance review process, which has a really sick leveling tool I talked to Adam Horn today about which is like a fully interactive leveling framework tool that helps you assess other people on your team and give feedback we've launched a dynamic promotion and merit increase coach which is like a portal you can go into put your team member in a pulse from the leapsome mcp pulls different feedback it pushes back on you and helps you create a packet then you can submit to the people council that can review them.

20:09We've just been shipping. And part of this is also because we've hired a forward deployed engineer in our team. So I'm able to take ideas from pretty much user research to scrappy execution. And then he will take them and finish that off and make it sure it's properly deployed, it's secure, it has SSO if necessary, and that it's launched in a way that is appropriate within our tool stack so that my team can focus on problem, user research, improvements, and then he can really take over the work that I don't need them to do, which is like security, deployment, and all of those bits and pieces. I feel like we've been hearing a lot about four deployed engineers.

20:53If you're a people leader that's like, I need one, I need one on my team, who are you looking for? Like what's the profile of your four deployed engineer? was this somebody who was already on the Leapsome team that was already an engineer okay so you found we found them yeah so I have I'm this is the first time I've had an engineer into my team I've hired an engineer into my team in two different roles now and I think that gives me the insight of like kind of knowing a little more about what to look for things that I look for that I think I want to give you like the kind of like broad answer and then I'm going to give you some like, hey, you're out there listening and you want to go and recruit someone, here's some search terms, things to think about.

21:34The first thing I look for is someone that actually cares about people products in some way. So an engineer that actually wants to understand the use case and a product focused engineer. So I don't need this to be the most incredibly architected system that's robust for 10 million users. This is a system that is very much focused on usability, simplicity so if someone is like really motivated interested in like having like kind of a really nice simple contained product that's what I care about I do not need like the world's best technical engineer at all what I found has worked really well has been engineers that would like to be managers but maybe don't have the path to do that that are really interested in people management so like maybe they're more of a junior engineer and there hasn't been the path to move into management and for them this is like a good opportunity to get to know the basics of like what it looks like to manage because they're the people team right so they get to like understand the frameworks and methodologies and how to build them and doing these research and those kinds of things and engineers that want to get out of like the kind of technical day-to-day ticketing part of engineering and maybe a little bit more focused or interested on like building things hands-on

22:45Jessica Zwaan: with a customer if that makes sense I want to switch gears just a little bit like what in my experience every time I've joined a new organization, there were like things that I knew to be true and things that I believe to be true. And within the actual experience of onboarding, I realized like, wow, okay, some of the things I thought were true, in fact, are true. And some of the things I thought would be true are not. I'm curious, like, what are some things that were like some nice surprises some things that you thought to be true and were actually true like in in your role in the product just like in the entire experience yeah wow cool question so I knew Jenny for a while I think I lost like seven or eight years something like that and I I feel like as a people leader like people listening out there is gonna probably gonna be like nodding furiously at this but like it is like one of the most founder exposed roles I think like I think maybe sales has it sometimes as tough because lots of founders are doing founder-led sales and then their first CRO or VP sales comes in and they just get absolutely thwombed but like the VP people has the same kind of level of friction and exposure to the founder but just like never-ending the founder has like usually a lot of very strong opinions about what they want the culture to be but not very great experience executing on those things they can be you know sometimes really challenging they can sometimes be really like incredible and inspiring and it's really sometimes very difficult to tell the difference between those two things during interviews so glad I knew Jenny for a long time I spent a lot of time kind of like vetting founders before I joined companies and knowing them like my previous founder I worked with Chris I knew him for like 10 years before I joined talentful and Phil as well same deal and the team before that like I you know spoke to the board I asked for the P &L like I was like I really want to understand who I'm getting in with and I was really really glad when I joined Leapsome to see that like Jenny was the person that I knew her to be and Kaitan as well and honestly like their ambition and motivation to build a really incredible platform is a it's coming from a place of like extreme empathy and like really wanting to build the future of work in a way that's like thoughtful and two is like they're just really good nice people like they're just good people to work with They take feedback well, they're kind and inspiring.

25:16So yeah, that's been a really nice relief to know that that vetting was beneficial. And so you've mentioned a couple of times how in these first few months, you've often felt dumb or these are your words, not mine, saying that you felt like you didn't know what's like, you like feeling like you know things and you didn't feel that way. when I hear you talk through your 12-week sprint and how you put together this How We HR document and have a pretty visionary outlook on the different archetypes of what it's going to look like being in people and how it's going to change. You started with the problem statements and you started building and now you have this forward-deployed engineer that you're working with.

26:01It doesn't sound like you're struggling. I guess just help me out. In what moments have you felt that thing that you're describing where it just feels hard the vulnerability question yeah hit me i think no matter how capable you are right no matter how like much experience you have when you start somewhere new you're not just learning about it doesn't really matter right for a little bit because your job is to figure out like who are the people i'm working with how they want to be influenced what's where do i find information how do i not piss people off if i have really big ideas and need to move quickly and that process it is really important right like you have to do all of that to like make sure that you end up being effective but i'm used to after being in a company like talentful for like what three and a half years i just was having impact every day i was just doing things every day and i was capable to move things forward every day and now i'm in a place where I'm like oh my job today is to like talk to someone for an hour and make sure that they know that I'm a human and I have like you know a sensible brain part of me is like screaming and I hopefully don't want to listen to this and like wait a second that's me but like part of me is screaming because I want to just be like let's just do it let's just do the thing like like my bias to action is so strong that it really although I love working with people I I really don't like feeling like I can't just cut through the noise.

27:32Right. And I think it's like probably like a floor I need to talk about my therapist, but I just want to like, I want to just do stuff and build stuff and have fun on the ground. And like, I think the kind of more political things and the influencing and getting people to get to know me, all of that feels, it does feel to me like a bit like walking through mud. Like it's not my favorite thing about the job.

27:53Jessica Zwaan: I really relate to that. I've been doing some work, advisory, strategy and operations advisory work the last six weeks, eight weeks. And prior to that, I have been part of the founding. I've either been the CEO, I've been part of the founding team, but I have been at the company essentially from the beginning and for easily 12 years going back. And so to come in with an expectation that I'm bringing experience and knowledge, but also internally knowing and recognizing as an experienced person that I can't, I need to be able to work within the framework and the existing foundation that has been built.

28:45Jessica Zwaan: And, you know, I have like some guiding principles that I that I, you know, have to implement with myself, like whatever I'm recommending cannot create any drag on anything that is like existing unless that thing is like, you know, creating a massive risk for the business or, you know, there's certain conditions where I would interject myself. and I have found that that can be difficult. It can be difficult to kind of measure or meter or like tap the brakes, however you want to think about it for like founder Steven and for like sales leader Steven or sales exec Steven to like come forward. Like it's an interesting kind of mental exercise for me and so I really relate to what you're sharing.

29:37Jessica Zwaan: That is like a skill, like a really difficult skill. And like what I've had to rely on is like talking to the people, talking to my people and getting advice and, you know, sharing what's going on. And it feels like, you know, the flip side there is like, should I know the answer to some of these questions? And the answer is like, yeah, I think intuitively I know the right answers. but like again when there are parts of me that i'm not withholding but i definitely need to scale that back a little bit because you know i can be a bull in a china shop i don't know i don't know if any of this is making sense but like i find that to be tough no i think it makes a lot of sense like the bull in the china shop like i mean i say this a lot i'm like to kind of like if you think i'm being a cowboy and i'm just ruffling ruffling feathers and frustrating people let me know like i don't want people to be frustrated by me but i think as well like at the moment every leader that's coming into a business actually anybody but you know specifically like leaders and people that are coming in with experience the first thing they're being told is like speed speed is our advantage like get in get stuff done we don't have time to waste and i don't think i think every single company in the world right now is feeling like we have to move quickly we just have to be making decisions we have to be making progress okay so that yes i agree that's fair but if you're bringing someone in that has experience and then giving the remit of like you need to be moving with speed and urgency you that then puts you in a position where you have to be like okay well there's got to be a limit to that like so then what i've just been saying to kaitan and jenny is like if you see me doing something that you're like whoa hold on just know that i'm like i'm not putting a cap on the speed like you're telling me move quickly i am moving quickly if you pull me back i'm ready to be pulled back but i need you to tell me to pull me pull me back because i have an unlimited capacity just to do things and i'm not prioritizing maybe like deeply understanding all of the motivations of you know every team before shipping something like i'm just seeing the problem in shipping up based on my experience and based on the data i have and i think that that's the only way to move these days like i i think these these old days of 30 60 90 day plans, but you spend 60 days talking to everyone and 30 days, you know, finally like scoping out the things you're going to do.

31:57Those days are dead. They're gone. Like if you're not shipping something in the first three weeks, like it's a question mark on your hire.

32:03Jessica Zwaan: I literally said earlier today, I feel like in the time that we have spent talking about this, I could have built something that we could be reacting to and implementing. And like Daniel knows that to be true because I've worked with Daniel for a very, very long time. And he trusts that, you know, I will operate with guardrails. But like, you know, I yeah, I do feel like the stakes feel really, really high. I do think that it is that like there needs to be, you know, a desire to push forward and kind of a hesitancy or like desire to also make it like on brand and right. And I like that. I like that recommendation of like, hey, I'm going to you brought I believe based on our conversations that I was brought here for, you know, a very specific reason.

32:56Jessica Zwaan: And I am going to pursue that like to its fullest extent. And so if I need to pull back, like, you know, your leadership and your role, I think is going to need to, you know, to give that to me. So Jesse, so the beginning you, you, you explained this clear vision that you had for why this was the right job for you. I'd be curious to hear what Leapsom's perspective was like, why, like, why it was so clear for them to bring you on board. There's like no way of answering this question without me to send like a massive wanker.

33:31Daniel, I think... What did they bring you in to solve? I guess that's the better question. Like, what did they think you were capable of coming in and doing? Yeah, I think what Leapsim was really looking for is, you know, Jenny and Kytan aren't the HR people. They are incredibly smart and have built a great product, but they haven't lived the pain the way that, you know, I have. and I think having a person who has a very articulate point of view not just around like what it means to be in HR but also like what the future should look like how we can get there is like really really helpful for product strategy but also the fact that I want to go out and I love going out and talking to the community and understanding their pain points and bringing that back like I'm not just building my point of view in a vacuum I think is really helpful for them because the credibility of what they're building needs to be I think really centered and built in a foundation of like we have a very articulate and clear point of view what the future is going to look like and this thing we're building will help you get there and I think the team had a lot of those things and has a lot of those things but lacked I think that like the kind of like stamp of approval a seal of approval of like yes I'm a practitioner and I've been doing this for a very long time.

34:53And I have a bunch of people I talk to all the time that leads me to believe that we're on the right path.

34:58Jessica Zwaan: And so let's fast forward, you know, seven months feels like an eternity. When you look back at the work you accomplished, like, what do you think is going to be the one thing that y 'all are doing that other peers are going to be like, we got to do that? Well, I'm not going to let all my trade secrets out of this podcast. You guys are going to just go off and build a HRIS, aren't you? It seems like I'm currently on Lovable right now. He's not recording it. He's like, who is before I get straight in? Well, no, I would have had a totally different answer. I was like, my answer was simple. Like, I think they brought Jessie in because she's a genius.

35:35Jessica Zwaan: And I've said that before. And I believe that to be true. And you look at, we know Jenny pretty well. We know Jenny pretty well. And she is also a genius. and like I'm super excited like to see what what y 'all create together and the Leapsome team is like so deep so strong and so so yeah from that I mean you are the secret weapon in my mind like and there's only one of you so like that's like the secret's out but what are some some concepts that you think others might be envious of seven months from now yeah great question I think the Bigger things for me that we're really focusing on at the moment is like, let me try and break this down in a kind of simple way.

36:15It's like, first of all, we're really focusing on HR agents that you can trust, that are doing the work you want them to do and you need them to do and not removing HR. Like, you know, before I give you those three archetypes, right? There is an archetype, which is building systems and infrastructure. There is an archetype, which is working with people, being a coach, being an advisor. and I really genuinely believe that that very human role will not go anywhere and that a lot of people people are already in that archetype we're probably going to be hiring in to the other two if I'm honest with you I think there's a lot of like authentic work that needs to go into things like that just honestly like you know I've given this example in like a bunch of podcasts before but like my first HR job was like scanning physical printed contracts I thought the job ruled at the time which is fucking crazy to think about now but at the time I was like hell yeah I I love this job.

37:07And literally filing paper documents in filing boxes. If you remember those big kind of cardboard filing boxes, you had to like pile on top and put them into the filing room. That was my first job. That job does not exist anymore. Thank God. And now we have a completely different world. I think the future world that we see is going to be things like, you know, manually cross checking and running detailed payroll reports is not going to exist in the same way anymore. I think building calibration pre-reads is already a world we're not living in. like Leapsom just released our calibration pre-read tool, which I use today in our calibrations in our team, that automatically went through and flagged like discrepancies between feedback and scoring and more lenient managers and more hard managers.

37:47So that all we needed to do was go back through and like manually start pulling out examples that we thought were relevant and like cross-checking the AI calibration. Crazy change in the way that, you know, people operations team can work so we can spend more time in the room talking to managers about the calibrations. So a big part of this, I think, is Agentech and building agents. And that means both like leapsome agents that are built through our very opinionated background, like, you know, 2000 customers and 10 years of experience, but also people being able to build their own agents. If I wanted to build an agent that was unique to me, that did like a very specific task, like Jesse reach out to everybody in sales and decide whether or not they need a one to one based on whatever agent, then great, I could build that too.

38:29So kind of like a kind of, yeah, this kind of like HR delegation agentic kind of workflow. The other one is really like a kind of ability to kind of what I call like a plastic HRAS, which is building a HRAS that is like malleable and fully customizable and pretty much kind of narrow playpen. I don't think anyone should be vibe coding a full HRAS. And this is a, this comes out of like being one of the biggest vibe code champions in maybe the HR world is like I don't think you vibe code your HRS I think you vibe code your off-site planning documentation and like sign up pages I think you vibe code your leveling framework like interactive tools I think you vibe code a really fun little assistant that helps people like move through a specific process that already happens once a year your HRS you do not vibe code but how annoying has it been that for a very long time you wanted to build like a specific workflow there was only so many things it was like if and statements you were kind of limited in what you could do well what if you could kind of remove all those guardrails and instead just vibe code a full workflow from end to end which we've just launched or vibe code a organizational network analysis report to see if you should implement organizational analysis based on all of your old data which is something i did two weeks ago or three weeks ago like being able to like malleably use your HRS in ways that it wasn't designed for per se, I think is a future that I'm really excited about.

39:56And the final thing that I think is really interesting is like, you know, I've had the fairly unique experience of working in a commercial role as well. Like I've managed operations, I've managed customer success and customer support. And I have seen firsthand how sick some of these commercial tools out there have been. Like really, like you think Clay, HubSpot like there's so many great tools that exist for the commercial world for a really long time HR was getting the kind of secondary tooling very web entrepreneur very clicky I'm really excited about seeing the future where HR is being given as much high quality analysis insights tooling that a commercial team is receiving because we're finally able to demonstrate the same kind of ROI that like brand marketing is able to demonstrate.

40:47Man, I think that's the perfect way to end our episode, Jesse. Every time you join us, I feel like you drop like a Jesse bomb on us. And I'm gonna kick us off on our one word or phrase close. I'm gonna say limitless. Like you took your limitless pill this morning.

41:03Jessica Zwaan: I'm gonna go with brave new world. I like this world where we get the same value driving tools that everyone else gets in the people space. That's the dream. that's all we've wanted well we've wanted other things but that is a big thing we wanted yeah i'm gonna break the mold i'm gonna say eagles guys and you've got birds behind i forgot never hashtag never forget oh my god yeah the one i already like created got as far as creating like the sticker of it but i haven't sent it to us like yet so so fun y 'all this has been a blast can't wait for our next one when is our next one i love these why we i feel like it's my fault like i'm never i'm never around we'll figure it out we'll have to do another one here in a few weeks yeah yeah i love that i love that exciting times guys exciting yes i'll see you around good luck on the house text me let me know how you go um we'll shout out to you guys later all right bye thanks for tuning in to another episode of the modern people leader We really, really appreciate it.

42:12And if you enjoyed the show, please leave us a five-star rating. It would mean the world to us. And connect with us on LinkedIn. We want to know what you think about the show. And you can find links to both of our profiles in the show notes. Thanks again for listening and see you on the next episode.

From the publisher

Jessica Zwaan joined us on The Modern People Leader. We talked about her first four months at Leapsome, why HR needs to operate more like a product team, and how AI agents, forward-deployed engineers, and flexible HR systems could reshape the future of people operations.

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(11:40) Jessie’s 12-Week Sprint and the “How We HR” Document

(13:10) Why The Purpose of Work Changed What Jessie Wanted Next

(14:10) Why People Ops Will Change the Most Through AI

(15:30) The Three Future Archetypes of People Teams

(17:35) Starting With Retros, Problem Statements and Roadmaps

(18:15) Launching Transparent Compensation and Leveling

(19:10) Building a Dynamic Promotion and Merit Increase Coach

(19:30) Why Leapsome Added a Forward-Deployed Engineer to the People Team

(20:15) What to Look for in a Forward-Deployed Engineer for HR

(22:30) What Surprised Jessie After Joining Leapsome

(23:20) Why Founder Fit Matters So Much for People Leaders

(31:20) Speed, Urgency and Knowing When to Pull Back

(32:25) Why Traditional 30, 60, 90 Day Plans Are Dead

(35:10) Bringing Practitioner Credibility Into Product Strategy

(37:35) Building HR Agents People Can Trust

(39:20) AI-Powered Calibration Pre-Reads and Better Manager Conversations

(40:35) The Idea of a Plastic HRIS

(41:10) What HR Should and Should Not Vibe Code

(42:00) Why HR Deserves Commercial-Grade Tools and Better ROI

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

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