The HRBP-as-Coach Model with Jen Paxton, SVP People & Talent at Roofr
Jen Paxton is SVP of People & Talent at Roofr, a high-growth SaaS company, where she reports directly to the CEO and owns both talent acquisition and HR — the full employee lifecycle. A three-time startup-to-acquisition People leader with more than a decade in startups, Jen has scaled companies to $50M ARR and built an HRBP coaching program at Roofr where every manager gets a dedicated HRBP as a personal coach. Her single biggest argument: HR should lead the AI transformation inside the company, not wait for it to land on their desk.
For People teams at 100–1,500 person scaleups, informal communication breaks down and no one has full visibility into what every department is building. Jen explains how HR's cross-cutting position — touching every department — makes it the right function to own AI change management, communication, and cross-team visibility.
For People teams at 100–1,500 person scaleups, informal communication breaks down and no one has full visibility into what every department is building. Jen explains how HR's cross-cutting position — touching every department — makes it the right function to own AI change management, communication, and cross-team visibility.
Challenges Addressed
- Siloed HR vs. cross-cutting HR: Jen Paxton argues traditional HR stays siloed while a strategic people partner understands how each department's work affects every other, making HR the only function that cross-cuts the entire business.
- Duplicative AI builds: At Roofr, where every employee has Claude access, Jen identifies the core risk of two departments independently building identical tools (her example: two pricing calculators) because there is no cross-departmental visibility.
- AI as change management, not just tech: Jen frames AI as a "hot potato" — it upends how people do their jobs, creating change management work and potential attrition that HR is positioned to own.
Actionable Takeaways
- Assign every manager an HRBP coach: Jen Paxton's HRBP program pairs each manager with a dedicated coach who teaches effective one-on-ones and runs live role-play for delivering difficult feedback. Build the foundation before expecting managers to grow.
- Replace flat "no" with options: When a manager brings a request, Jen recommends answering "this won't work, but what about X or Y." This frames HR and the manager as solving the problem together and builds trust.
- Monitor AI usage to surface and share high-impact builds: Jen tracks company-wide Claude token usage to find valuable AI builds, then makes them publicly visible. This drives social learning and cuts duplicative work across teams.
Questions This Episode Answers
- What's the difference between a strategic people partner and traditional HR? Jen Paxton explains that traditional HR is siloed and admin-focused, while a strategic people partner understands the inner workings of every department and how their work flows into each other. HR is the only function that genuinely cross-cuts the whole business.
- Should HR own AI enablement in my company? Jen argues yes. She compares "AI enablement" roles to the "head of remote" roles that proliferated during COVID and were later absorbed back into HR, predicting AI enablement will follow the same path under L&D, manager coaching, or HR ops. HR does not need to be technical — it needs the right partnerships and cross-departmental visibility.
- How do I build trust as an internal coach to managers? Jen builds trust through vulnerability, genuine follow-up questions, and framing herself as tackling problems alongside the manager rather than blocking them. She treats each coaching conversation as a two-way partnership, not a question-and-answer transaction.
Links & Resources Mentioned:
- Connect with Jen Paxton on LinkedIn
Daria Rudnik (00:02.58)
Welcome to Built by People Leaders. I'm your host, Daria Rudnik, and this show is for HR and L&D leaders, those shaping real impact from within and building AI ready organizations. Each episode, I sit down with people leaders to talk about how they build strong cultures and shape organizations around them. It's about HR being seen as a true business partner by leaders and by HR themselves. So let's dive in. Because today I have a very special guest.
Jen Paxton, she's the SVP of People and Talent at Roofr and she reports to and partners closely with the CEO to scale a high-growing SaaS company. A three-time startup to acquisition people partner, Jen helps executive teams build high-performing organizations through leadership development, organizational design, talent strategy, and performance management. She believes the best people leaders don't just support the business, they shape its trajectory. That is so true.
Welcome, Jen.
Jen (00:59.47)
Thank you so much for having me. I'm really excited to have a conversation today. Yeah.
Daria Rudnik (01:05.078)
well we had our previous conversation. I mean, I really like I have so many questions for you, but I'll start with the first one. How do strategic people partners are different from traditional HR?
Jen (01:18.54)
Yeah, well, I mean, I think the very first thing that would set a people partner that is more strategic up is really knowing kind of the inner working of the business. there's so many different complexities within each department. And so if you can understand how one department works with other departments and kind of that flow, that's actually only going to benefit you in the long run.
a lot of traditional kind of HR departments are very siloed. They only do their work and they don't remember how much their work can impact every other department and vice versa, how every other department's work can actually impact their department. So really having that kind of understanding that it is a two-way street, I think that really sets all the leaders up for being more strategic.
Daria Rudnik (02:11.977)
Well, I I do agree, but it sounds kind of unfair. Like marketing does marketing, finance does finance, HR knows everything. Is it fair?
Jen (02:19.828)
Yeah. So I don't think life is fair on that one. But I also think they, you know, our our role is so very unique that it does cross-cut all departments. Whereas you can't really say that about maybe like a marketing department or like a sales department. Like they don't really cut across every single one. They they're not, they're not having kind of those
Coaching conversations with managers because they are you know, building the top of the funnel for our company. Now, I'm not saying that a marketing leader shouldn't know the whole business as well. I think it's potentially even a little easier for them to know whole business because they're a part of how the business works on the kind of customer lifecycle, sales lifecycle, go to market lifecycle, if you will. but it is a little bit more challenging, I think, for the HR side to to get into that as well.
Daria Rudnik (03:15.401)
Yeah. That's true. That's true. Well, well tell us about yourself and your journey and path into HR leadership.
Jen (03:24.588)
Yeah, so I have been in startups for more than a decade at this point. I have loved seeing a startup, you know, scale. So from very, you know, very small to you know getting that first you know, 50 million in ARR as well. and honestly, there's so many fun challenges and problems that come my way that I don't think I would trade it at this point.
Daria Rudnik (03:54.517)
Yeah.
Jen (03:54.599)
like I I know that sounds I mean it it's definitely like chaos and sometimes you feel like you know you are in this like it's gonna be like this huge like circus where there's all these different like things going on at one time and you just kind of have to make sense of them. but I really I really love making yeah making sense of the chaos. and my role cross-cuts you know, all of talent acquisition and HR.
So I have kind of both teams reporting into me and that's been the case at a few of my startups I've been at. And I really love owning that full employee life cycle and journey.
Daria Rudnik (04:32.967)
Mm-hmm. Well, you are in startups, like building startups, helping startups grow into scale ups. And and these are the companies that actually I mean shape our future. And I'm curious, are there is there anything you see changing and how HR role and people leaders role is evolving now?
Jen (04:54.75)
I think this really started more when when COVID hit. And I haven't said I haven't said this actually in a podcast in many, many years, like since COVID, honestly. But I think that the reliance and like the the leaning on HR really kind of came to a head during COVID because there were so many kind of change management and
things that just touched employees' lives, that that was the perfect opportunity for HR to say, like to step up and say, I can be more strategic. I can think long term. I'm not just here to be a note take or an admin or like a benefits person. Like I can think about how you know, what we're doing on a daily basis affects employees, which affects productivity, which affects, you know, the bottom line of the company. So I think that
that was probably the pivotal moment for HR to to kind of step into the limelight, if you will, and and really, yeah, kind of flex those strategic muscles.
Daria Rudnik (05:55.989)
Mm.
Daria Rudnik (05:59.754)
Yeah. I well I agree. I remember like before COVID it was always like a okay, invite me. I I wanna be in this party. I wanna I wanna be in this meeting. I wanna join this conversation. What are you talking about? Let me join in. When COVID hit, it's just hey, we need a jar here now.
Jen (06:15.118)
please. Yeah. And yeah. And I think the conversations really you know, has switched. at least I'm I'm experiencing personally, where it's not me asking to come to these meetings. It's hey Jen, I really would like you to be in this meeting. Can you be there? and it's having kind of those advocates on the leadership side as well that have already started seeing kind of the value and the impact you're bringing. And so they're already inviting.
Daria Rudnik (06:17.597)
Yeah, exactly. Like help is
Jen (06:43.232)
inviting me into those conversations versus me like kind of clawing at the door. Right. And so I love that kind of, yeah, that pivot that's happened. At least again, for me personally, it's happened, which is nice.
Daria Rudnik (06:48.168)
Yeah.
Daria Rudnik (06:52.935)
Yeah. Yeah. Well, I mean, like I I I've seen that in many organizations. It just whether HR really can bring some value, whether they're ready for this kind of conversations and when they are ready, well, they are part of the conversation. When they're not, I mean they're just moving back to admin compliance stuff as they were before. That's true.
Jen (07:14.646)
Yeah. I think there also needs to be a bit of bravery as well in this because we're stepping out of our comfort zone a bit. and again, like getting into that limelight, I mean, there's a spotlight on you. And if things go well, it's great. But if things go wrong, obviously, you know, it it gets it it gets even more tenuous to continue on, right? So I think that's also a very big challenge that we have
Personally, as HR leaders, because you either are gonna step up to that challenge and and make it work, or you're gonna kind of go back into your shell and say, Nope, not for me. Thanks. I'll just stay over here in my little bubble. So and and it it really it it depends on the leader too. And I won't say like either one is bad. I will just say kind of what my path was, right?
Daria Rudnik (08:07.475)
And like you said, like, yes, you need courage, but you also need to know everything. But you know that you cannot know everything, that's how you learn. So you basically need this courage to step in without knowing everything, without knowing all the details about the business and kind of learning it on the way. And I'm curious about like your like your learning story. How did you like being in different startups, doing different business, in mem I don't know, maybe different industries, how did you learn?
Jen (08:35.308)
Yeah, I mean many, many different industries. I actually haven't done a lot of repeat industries. So it's kind of learning a whole new kind of business market and also just like the different business units too, right? I actually learn really well by talking to people and just understanding kind of their day to day. I'm I'm a bit of a talker and I I feel like not everybody gets things done in meetings, but almost everything I get done is through some kind of meeting.
And and so I am I'm one of those people that just will ask a lot of questions when I'm sitting down with somebody like tell me about your day to day, like what's what's working, what's not, like how do you work with this team over here? What would make that relationship better? Like all of those questions are are kind of putting all those puzzle pieces together. And then the other side, which I've done at multiple companies that like it makes sense is actually using the product too.
know being kind of on that user experience side and seeing it firsthand that can be really helpful as well. again it depends on the product the company is building. many I mean many SaaS companies that I've worked at as well have like sandbox accounts that anybody could have, right? So like you could go in and you know look at that that way. I actually find that looking at our help docs and seeing kind of all the demos have gotten me to kind of understanding exactly kind of the intricacies of the product here at Roofr.
But at other companies where it was actually more of a a direct to consumer kind of product, I was actually using the apps, right? I was using kind of what the the company was building. And so seeing it firsthand, you know, submitting support tickets if like something was buggy, right? Like I did those things. So I I think it really just depends on the product you are supporting, but also yeah, the company too.
Daria Rudnik (10:28.053)
Yeah, if you wanna learn you learn like by either learning about the product and talking to people, go know that it's okay to ask questions, people. Go and ask questions.
Jen (10:35.712)
Yeah. Yeah. Well, and if anything, actually people, at least what I have found is people will open up to you and they will tell you things and and kind of be excited that you're asking them questions too. So I love I love that journey and really, yeah, getting to understand a person's day to day and also kind of learning their passions along the way too.
I learned a lot about like people's like side hustles that they have outside of work. And I was like, that's so cool. How did you get into that? Like, what does this look like? So it's almost like me having a podcast with every employee at our company too, right? Like you you get to know all the all the things about their lives too. Yeah.
Daria Rudnik (11:01.845)
Mm-hmm.
Daria Rudnik (11:15.253)
Cool. Well I know one of the important parts of Roofr Company is developing leaders. Like what's your approach to leadership development?
Jen (11:28.184)
So I go back to the basics, you know, how do you give feedback? How do you want like how do you run a one-on-one? Like you have to really have that foundation set before you can you know, grow, you know, grow from there. so again, I hate to say like going back to that meeting well, but like we have an HRBP program that I've built out at Roofr where each manager has their own coach. The HRBP is their coach, so they are helping them to
How do you set up effective one-on-ones? They're also coaching them through, hey, I need to give this kind of pretty harsh feedback to this employee. Like how would you, how would you go about that? And so there might be some role play that goes on as well. but it's really just being kind of that advisor, that kind of coach that really helps managers to get like to that next, really to that next level.
Daria Rudnik (12:11.061)
Mm-hmm.
Daria Rudnik (12:23.987)
that approach because when I being coach, I do believe in in power coaching. But I also see the challenge. And like to to to those who listen to this episode, how do you build trust? So that it's very hard to trust someone who's inside the organization. So you first need to build trust with HR. They need to trust HR in general and then they need to trust this person to talk about their challenges. How do you do that?
Jen (12:51.989)
I feel like I'm an open book. I'm I'm pretty, I'm pretty vulnerable and transparent with managers. so I think that helps them to open up to me. I also genuinely, again, like I will ask follow-up questions. It's not just like a question answer, okay, we're moving on kind of thing. I like dig in more because I really genuinely want to understand and help them to solve problems.
And I I think they feel that on the other end. the other side is there's a delicate balance between kind of saying no or saying yes, but. And because there's a lot of things where like in HR, you're like, no, can't do that. No, can't do that, no, can't do that. And as a manager, if you're getting all of those things and like no is no is a sentence, right? But like it also just stops you.
immediately. And so if you can actually like have that be this isn't like this isn't right, but what about this or this? Like options that that is helpful to building trust. And again, like you want to be seen as you and this manager are tackling the problem. It's not the manager is tackling it alone either. So if you can have that be a I'm in this with you together, that also helps build up the trust too. I also have a horrible poker face.
Daria Rudnik (14:16.841)
Yeah.
Jen (14:18.827)
So anybody that sees me in a meeting, like I'm very emotive and I'm like, really? like like ever you you know you you you get you get what you see with me on that too. So I think that helps too. People know I'm like, okay, Jen, like cool, cool, cool.
Daria Rudnik (14:32.821)
So what I hear is like coaching approach by asking questions, asking follow up questions is how you build trust with people who you want to coach. But I also love what you're saying. Like when you say no, it's like they come to you and ask you for something and you're on the other side of the road and kind of you're not with them. But you're kind of trying to find the options together, that's one true partnership starts. That's that is so true. And that trust helps helps you build trust.
We talked a little bit about how COVID has changed HR and people function. What about AI? How do you see AI is changing HR?
Jen (15:15.213)
I was actually talking with a an AI enablement consultant this week because we I don't know what I don't know about AI. There's still many things that we're we're working on. we are fortunate that we have gotten, you know, access to Claude to everybody in the company. However, there's still a gap in it's more like self-guided training than like let's book, you know, trainings for every person to go through X, Y, and Z, or like let's have
a coach sit down with every single person and be like, how do you want to build this cool thing in Claude? Tell me about your workflow. so I think it's been a little challenging, but the AI enablement consultant and I were talking about how AI can be seen as a little bit of a hot potato at the moment. whereas, you know, it is very technical on a lot of instances, but also unlocked non-technical people to be able to do more technical things.
Daria Rudnik (15:59.126)
Mm-hmm.
Jen (16:11.745)
There's a lot of change management that comes with that because you're pretty much upending a person's workflow, like the way that they did their job before. So, and that's tough, right? That can be very challenging. that can be very jarring. there can be potentially attrition because of it as well. So I think that is where kind of HR can flex as a superpower is let me help understand how this is going to
evolve and affect a person's day to day. And let me own the kind of change management side, let me own the communication side, that strategy side, and then partner really closely with like a technical kind of counterpart to see like how do you actually build these things? Like what is what is realistic, what isn't realistic on that into. One of the things that we're bumping into right now because the curiosity and the excitement with AI is is there, right? Like
Daria Rudnik (17:02.665)
Yeah.
Jen (17:10.635)
We've put our money where our mouth is, like we're investing, we're we're having people be very encouraged to use AI. But at the same time, you could have two different departments building something that is exactly the same. If you don't have some kind of oversight, right? And it and of course it's gonna kind of happen because you're like, well, I wanna go build this cool thing over here, and I wanna build this cool thing over here. And this is not a new concept. I mean.
like at the at the granular even like team level, you might have, you know, two people on a team that are like, I want to go. And I'll take the HR side as an example is like, hey, I want to like talk about this survey data over here. Go build this thing over here. And then they don't know that another person on their same team is building you know, survey data for X, Y, and Z, right? And so again, building like two people building the same thing in the same department, they're just not talking to each other.
So I think there's also kind of an opportunity for HR to help with like the overall kind of communication and like, did you know that like this person's building this over here? And you should actually ask them about you know, what they're doing over here so that you're not doubling up on work. Again, you're still being very productive, but you're not doing duplicative work.
Daria Rudnik (18:27.219)
Yeah. And I love what you're saying, but AI actually anyone can be a builder with AI. Anyone can build something with AI that will help them with their work, that will help their clients. And it is important to understand what other people are building. And you do that by communication. And who's doing communication in in a in a company is HR is doing communications. And the other thing is, like you said again, it's changing how my work is changing when I use AI.
So what am I doing, what am I not doing, what I'm doing like differently when I use AI? And there's a lot of frustrations and fears. And who's the best function to address those and help them people reshape, redesign their work processes? It's HR. So HR leaders need to be at the front of this AI transformation in the organization.
Jen (19:18.507)
Yeah. And it really has been not to like not to harp on this like hot potato analogy, but it really has been one of those things where it's like you have to be fully in it. You can't just be like, well, let me do like one little thing here and then like set it and see what happens. Right. Like you have to continue to quarterback it the whole time. because again, like if not, people are just gonna go off and it it's gonna be the wild west again.
Right. I almost not again to go back to COVID, but like I almost like equate this to like when COVID first hit and a lot of companies were going like fully remote or remote first, they had like a head like this job title called head of remote. Do you remember that?
Daria Rudnik (20:03.733)
No, I never heard actually. I know remote first, but had of remote no.
Jen (20:06.429)
my gosh. Yeah. Yeah. So as a person that was dedicated to like getting the the company set up to being a remote company because there's a lot of different things that happen that happen in office that either don't happen remotely or like challenges that you have when you're not physically seeing somebody in a space. And so I remember seeing this job description popping up all over the place and people like having this role.
And it was always fascinating to me because sometimes it sat within HR and then other times it sat with like operations or maybe almost like was a chief of staff kind of role too. It really, it really was a make it like make it whatever you want it role. And I see a very similar thing here with AI enablement, where again, like you're seeing this role pop up now. And a lot of places are are hiring like a dedicated person to be like, okay, they're gonna own the strategy.
Daria Rudnik (20:40.582)
Okay.
Jen (21:05.399)
But you don't see those head of remote roles anymore because it's already been like sucked back into HR. It always it always comes back, right? So my prediction is kind of that AI enablement side of this is really gonna get kind of consumed into kind of the HR, maybe under learning and development, maybe manager coaching, maybe more ops, but like it's it's it's eventually gonna fall there anyway. So why are we hesitating to take the reins now?
Daria Rudnik (21:09.407)
Mm.
Jen (21:35.521)
Like why are we waiting for it to eventually fall on our laps? So yeah, that's soapbox off.
Daria Rudnik (21:40.637)
Well I'll get this bash I I'll return this question to you. Like why do you think HR is not seen as some as a function that can actually have that?
Jen (21:51.148)
I think there is hesitation because HR is not always as technical. You know, like there's there's still this stereotype where this kind of soft and fluffy kind of department where like we're just thinking about like employee happiness and engagement and like we just want to give more perks or more benefits or pizza parties, which I again just like, I can't roll my eyes hard enough, right? On that end.
But like that is that has been kind of the persona of HR. Even when I first got into kind of of my first startup, that was kind of the persona that I was given. Right. And there's of course like those offhanded comments of like, don't say that, HR's in the room. So like we're compliance police too. Which again, like I I laugh at that at this point, because I'm like, like that's funny. Cause I I I I'm not that person. So I'm like, I can like make that rule off my back at this point. Like, I don't care.
But it is like that persona that we've been fighting for years and years. And so we're not seen as like a technical partner or like, that's gonna go over HR's head, right? And so that's why I think, and and HR, like HR people are also very hesitant because they're like, well, I'm not technical enough for this. And it's like, you don't have to be technical to handle AI. You just have to have the right partnerships and understand kind of the mechanisms with it.
Because no one's asking you to go into Claude Cowork and build something right now. Like you can have a tech ops person help you with that. But if you're saying, hey, this department's building this pricing calculator, and then you have a meeting on like the HRBP side and you learn another department's building a pricing calculator, if you're not putting two and two together, you're not doing your job. So yeah.
Daria Rudnik (23:38.301)
Yeah, I agree. I mean it's about understanding the work processes and making sure like it's str strategy and making sure everyone knows what they're doing and how they work is how they're performing, basically. It's about performance and productivity. Well, that's so interesting. Yeah. Yeah, go ahead.
Jen (23:51.254)
Yeah. And it's really getting that visibility. it's yeah, it's just getting that kind of visibility up as well of like what are the cool things that people are doing with AI as well. Because again, like if you also don't see it, and I mean I check like the token usage. It's not we don't have a leaderboard or anything, but I'm checking it and I'm like, why is that person's spend so high? Like let me dig in a little bit and see. And I learned, they built this really cool thing that it's gonna have a very strong business impact.
Daria Rudnik (24:00.808)
Yeah.
Jen (24:21.717)
Why are we not publicly showing that off to the company, number one, so they can see it, but also get excited and also again cut down on, I was gonna build that, but this person already built it. Right? Like why hide it?
Daria Rudnik (24:36.467)
And this kind of showing what other people are building, like in our previous episodes to our listeners, we have a few episodes about AI and how HR is actually leading with the work day with some startup companies. And they say that showing other people's work is what actually inspires other people to try, go and try it also. And they try it. And this social learning people learn from each other with AI a lot.
Jen (24:59.381)
Yes. And that I think that's actually one of the questions I typically ask. I'm like, what prompt started this all? And like, what was the iterative process? Like walk me through that. Cause it's really about kind of the decision making and how your brain works that I I want to understand. Cause again, like that's going to inspire me personally, but also potentially teach others.
Daria Rudnik (25:20.901)
Yeah. Cool. Well Jen, it was an incredible conversation. I learned so much. Thank you so much for sharing. I have one final question for you. If you could have a magic wand that could solve one professional challenge that people leaders have, what would it be? What would it fix?
Jen (25:26.409)
Yes.
Jen (25:39.977)
So I'm biased here as well. I was I was thinking about this because you you gave me a teaser of like, hey, I'm gonna ask you the magic wand question. And I mentioned that my magic wand answer probably changes not maybe on a daily basis, but like a monthly basis, based on kind of what what either priorities are or or how things are shifting. I come back to the basics on this one because
the manager side of this, if I had a magic wand and could basically duplicate some of my amazing managers, like just how they are in the wild, right? If I could just like yeah, make carbon copies of them, I probably would love to do that. I was in a conversation with a leader yesterday and they were showing me something that they shared with their team because we were saying, hey, like people are
Daria Rudnik (26:18.505)
Mm.
Daria Rudnik (26:27.585)
Yeah.
Jen (26:37.291)
People are kind of questioning kind of this one thing over here. Would you like, do you have any insight into that? And they're like, my gosh, yes, I do. Here's this visual that I created to like really get people to understand the story and kind of see the balancing ball. And I was like, I want to copy you. Like, I want to copy like what you're doing, but also like just you as a human. So I think my magic wand would probably be like, if I could
Yeah, like wave of magic wand I wanna copy you, I wanna copy you, I wanna copy you. That's probably what I would do. Yeah. Right.
Daria Rudnik (27:09.061)
Nice. That'd be interesting. Yeah. Surround ourselves with people will laugh and and they can fun working together. Yeah, yeah, it's cool. Well, Jen, thanks so much. It was an incredible conversation. how people can find you, how people can reach out?
Jen (27:19.755)
Yes. Yeah.
Jen (27:25.121)
Yeah, you see.
Jen (27:29.579)
Yes, so I am pretty active on LinkedIn. So I love for people to just connect with me on LinkedIn, follow the content, engage with the content as well. I am always up for a kind of conversation and kind of somebody else kind of interjecting a different perspective because again, that's how I learn too and how I I will grow and evolve as a human. so I would say, yeah, connect with me on LinkedIn.
Daria Rudnik (27:52.689)
Okay, and we have the link to Jen's profile in the notes to this episode. And if you thanks for staying with us till the end. If you like this episode, please give us five stars on Apple Podcasts and Spotify. Subscribe to our YouTube channel and stay tuned for the next episodes. Bye.
Welcome to Built by People Leaders. I'm your host, Daria Rudnik, and this show is for HR and L&D leaders, those shaping real impact from within and building AI ready organizations. Each episode, I sit down with people leaders to talk about how they build strong cultures and shape organizations around them. It's about HR being seen as a true business partner by leaders and by HR themselves. So let's dive in. Because today I have a very special guest.
Jen Paxton, she's the SVP of People and Talent at Roofr and she reports to and partners closely with the CEO to scale a high-growing SaaS company. A three-time startup to acquisition people partner, Jen helps executive teams build high-performing organizations through leadership development, organizational design, talent strategy, and performance management. She believes the best people leaders don't just support the business, they shape its trajectory. That is so true.
Welcome, Jen.
Jen (00:59.47)
Thank you so much for having me. I'm really excited to have a conversation today. Yeah.
Daria Rudnik (01:05.078)
well we had our previous conversation. I mean, I really like I have so many questions for you, but I'll start with the first one. How do strategic people partners are different from traditional HR?
Jen (01:18.54)
Yeah, well, I mean, I think the very first thing that would set a people partner that is more strategic up is really knowing kind of the inner working of the business. there's so many different complexities within each department. And so if you can understand how one department works with other departments and kind of that flow, that's actually only going to benefit you in the long run.
a lot of traditional kind of HR departments are very siloed. They only do their work and they don't remember how much their work can impact every other department and vice versa, how every other department's work can actually impact their department. So really having that kind of understanding that it is a two-way street, I think that really sets all the leaders up for being more strategic.
Daria Rudnik (02:11.977)
Well, I I do agree, but it sounds kind of unfair. Like marketing does marketing, finance does finance, HR knows everything. Is it fair?
Jen (02:19.828)
Yeah. So I don't think life is fair on that one. But I also think they, you know, our our role is so very unique that it does cross-cut all departments. Whereas you can't really say that about maybe like a marketing department or like a sales department. Like they don't really cut across every single one. They they're not, they're not having kind of those
Coaching conversations with managers because they are you know, building the top of the funnel for our company. Now, I'm not saying that a marketing leader shouldn't know the whole business as well. I think it's potentially even a little easier for them to know whole business because they're a part of how the business works on the kind of customer lifecycle, sales lifecycle, go to market lifecycle, if you will. but it is a little bit more challenging, I think, for the HR side to to get into that as well.
Daria Rudnik (03:15.401)
Yeah. That's true. That's true. Well, well tell us about yourself and your journey and path into HR leadership.
Jen (03:24.588)
Yeah, so I have been in startups for more than a decade at this point. I have loved seeing a startup, you know, scale. So from very, you know, very small to you know getting that first you know, 50 million in ARR as well. and honestly, there's so many fun challenges and problems that come my way that I don't think I would trade it at this point.
Daria Rudnik (03:54.517)
Yeah.
Jen (03:54.599)
like I I know that sounds I mean it it's definitely like chaos and sometimes you feel like you know you are in this like it's gonna be like this huge like circus where there's all these different like things going on at one time and you just kind of have to make sense of them. but I really I really love making yeah making sense of the chaos. and my role cross-cuts you know, all of talent acquisition and HR.
So I have kind of both teams reporting into me and that's been the case at a few of my startups I've been at. And I really love owning that full employee life cycle and journey.
Daria Rudnik (04:32.967)
Mm-hmm. Well, you are in startups, like building startups, helping startups grow into scale ups. And and these are the companies that actually I mean shape our future. And I'm curious, are there is there anything you see changing and how HR role and people leaders role is evolving now?
Jen (04:54.75)
I think this really started more when when COVID hit. And I haven't said I haven't said this actually in a podcast in many, many years, like since COVID, honestly. But I think that the reliance and like the the leaning on HR really kind of came to a head during COVID because there were so many kind of change management and
things that just touched employees' lives, that that was the perfect opportunity for HR to say, like to step up and say, I can be more strategic. I can think long term. I'm not just here to be a note take or an admin or like a benefits person. Like I can think about how you know, what we're doing on a daily basis affects employees, which affects productivity, which affects, you know, the bottom line of the company. So I think that
that was probably the pivotal moment for HR to to kind of step into the limelight, if you will, and and really, yeah, kind of flex those strategic muscles.
Daria Rudnik (05:55.989)
Mm.
Daria Rudnik (05:59.754)
Yeah. I well I agree. I remember like before COVID it was always like a okay, invite me. I I wanna be in this party. I wanna I wanna be in this meeting. I wanna join this conversation. What are you talking about? Let me join in. When COVID hit, it's just hey, we need a jar here now.
Jen (06:15.118)
please. Yeah. And yeah. And I think the conversations really you know, has switched. at least I'm I'm experiencing personally, where it's not me asking to come to these meetings. It's hey Jen, I really would like you to be in this meeting. Can you be there? and it's having kind of those advocates on the leadership side as well that have already started seeing kind of the value and the impact you're bringing. And so they're already inviting.
Daria Rudnik (06:17.597)
Yeah, exactly. Like help is
Jen (06:43.232)
inviting me into those conversations versus me like kind of clawing at the door. Right. And so I love that kind of, yeah, that pivot that's happened. At least again, for me personally, it's happened, which is nice.
Daria Rudnik (06:48.168)
Yeah.
Daria Rudnik (06:52.935)
Yeah. Yeah. Well, I mean, like I I I've seen that in many organizations. It just whether HR really can bring some value, whether they're ready for this kind of conversations and when they are ready, well, they are part of the conversation. When they're not, I mean they're just moving back to admin compliance stuff as they were before. That's true.
Jen (07:14.646)
Yeah. I think there also needs to be a bit of bravery as well in this because we're stepping out of our comfort zone a bit. and again, like getting into that limelight, I mean, there's a spotlight on you. And if things go well, it's great. But if things go wrong, obviously, you know, it it gets it it gets even more tenuous to continue on, right? So I think that's also a very big challenge that we have
Personally, as HR leaders, because you either are gonna step up to that challenge and and make it work, or you're gonna kind of go back into your shell and say, Nope, not for me. Thanks. I'll just stay over here in my little bubble. So and and it it really it it depends on the leader too. And I won't say like either one is bad. I will just say kind of what my path was, right?
Daria Rudnik (08:07.475)
And like you said, like, yes, you need courage, but you also need to know everything. But you know that you cannot know everything, that's how you learn. So you basically need this courage to step in without knowing everything, without knowing all the details about the business and kind of learning it on the way. And I'm curious about like your like your learning story. How did you like being in different startups, doing different business, in mem I don't know, maybe different industries, how did you learn?
Jen (08:35.308)
Yeah, I mean many, many different industries. I actually haven't done a lot of repeat industries. So it's kind of learning a whole new kind of business market and also just like the different business units too, right? I actually learn really well by talking to people and just understanding kind of their day to day. I'm I'm a bit of a talker and I I feel like not everybody gets things done in meetings, but almost everything I get done is through some kind of meeting.
And and so I am I'm one of those people that just will ask a lot of questions when I'm sitting down with somebody like tell me about your day to day, like what's what's working, what's not, like how do you work with this team over here? What would make that relationship better? Like all of those questions are are kind of putting all those puzzle pieces together. And then the other side, which I've done at multiple companies that like it makes sense is actually using the product too.
know being kind of on that user experience side and seeing it firsthand that can be really helpful as well. again it depends on the product the company is building. many I mean many SaaS companies that I've worked at as well have like sandbox accounts that anybody could have, right? So like you could go in and you know look at that that way. I actually find that looking at our help docs and seeing kind of all the demos have gotten me to kind of understanding exactly kind of the intricacies of the product here at Roofr.
But at other companies where it was actually more of a a direct to consumer kind of product, I was actually using the apps, right? I was using kind of what the the company was building. And so seeing it firsthand, you know, submitting support tickets if like something was buggy, right? Like I did those things. So I I think it really just depends on the product you are supporting, but also yeah, the company too.
Daria Rudnik (10:28.053)
Yeah, if you wanna learn you learn like by either learning about the product and talking to people, go know that it's okay to ask questions, people. Go and ask questions.
Jen (10:35.712)
Yeah. Yeah. Well, and if anything, actually people, at least what I have found is people will open up to you and they will tell you things and and kind of be excited that you're asking them questions too. So I love I love that journey and really, yeah, getting to understand a person's day to day and also kind of learning their passions along the way too.
I learned a lot about like people's like side hustles that they have outside of work. And I was like, that's so cool. How did you get into that? Like, what does this look like? So it's almost like me having a podcast with every employee at our company too, right? Like you you get to know all the all the things about their lives too. Yeah.
Daria Rudnik (11:01.845)
Mm-hmm.
Daria Rudnik (11:15.253)
Cool. Well I know one of the important parts of Roofr Company is developing leaders. Like what's your approach to leadership development?
Jen (11:28.184)
So I go back to the basics, you know, how do you give feedback? How do you want like how do you run a one-on-one? Like you have to really have that foundation set before you can you know, grow, you know, grow from there. so again, I hate to say like going back to that meeting well, but like we have an HRBP program that I've built out at Roofr where each manager has their own coach. The HRBP is their coach, so they are helping them to
How do you set up effective one-on-ones? They're also coaching them through, hey, I need to give this kind of pretty harsh feedback to this employee. Like how would you, how would you go about that? And so there might be some role play that goes on as well. but it's really just being kind of that advisor, that kind of coach that really helps managers to get like to that next, really to that next level.
Daria Rudnik (12:11.061)
Mm-hmm.
Daria Rudnik (12:23.987)
that approach because when I being coach, I do believe in in power coaching. But I also see the challenge. And like to to to those who listen to this episode, how do you build trust? So that it's very hard to trust someone who's inside the organization. So you first need to build trust with HR. They need to trust HR in general and then they need to trust this person to talk about their challenges. How do you do that?
Jen (12:51.989)
I feel like I'm an open book. I'm I'm pretty, I'm pretty vulnerable and transparent with managers. so I think that helps them to open up to me. I also genuinely, again, like I will ask follow-up questions. It's not just like a question answer, okay, we're moving on kind of thing. I like dig in more because I really genuinely want to understand and help them to solve problems.
And I I think they feel that on the other end. the other side is there's a delicate balance between kind of saying no or saying yes, but. And because there's a lot of things where like in HR, you're like, no, can't do that. No, can't do that, no, can't do that. And as a manager, if you're getting all of those things and like no is no is a sentence, right? But like it also just stops you.
immediately. And so if you can actually like have that be this isn't like this isn't right, but what about this or this? Like options that that is helpful to building trust. And again, like you want to be seen as you and this manager are tackling the problem. It's not the manager is tackling it alone either. So if you can have that be a I'm in this with you together, that also helps build up the trust too. I also have a horrible poker face.
Daria Rudnik (14:16.841)
Yeah.
Jen (14:18.827)
So anybody that sees me in a meeting, like I'm very emotive and I'm like, really? like like ever you you know you you you get you get what you see with me on that too. So I think that helps too. People know I'm like, okay, Jen, like cool, cool, cool.
Daria Rudnik (14:32.821)
So what I hear is like coaching approach by asking questions, asking follow up questions is how you build trust with people who you want to coach. But I also love what you're saying. Like when you say no, it's like they come to you and ask you for something and you're on the other side of the road and kind of you're not with them. But you're kind of trying to find the options together, that's one true partnership starts. That's that is so true. And that trust helps helps you build trust.
We talked a little bit about how COVID has changed HR and people function. What about AI? How do you see AI is changing HR?
Jen (15:15.213)
I was actually talking with a an AI enablement consultant this week because we I don't know what I don't know about AI. There's still many things that we're we're working on. we are fortunate that we have gotten, you know, access to Claude to everybody in the company. However, there's still a gap in it's more like self-guided training than like let's book, you know, trainings for every person to go through X, Y, and Z, or like let's have
a coach sit down with every single person and be like, how do you want to build this cool thing in Claude? Tell me about your workflow. so I think it's been a little challenging, but the AI enablement consultant and I were talking about how AI can be seen as a little bit of a hot potato at the moment. whereas, you know, it is very technical on a lot of instances, but also unlocked non-technical people to be able to do more technical things.
Daria Rudnik (15:59.126)
Mm-hmm.
Jen (16:11.745)
There's a lot of change management that comes with that because you're pretty much upending a person's workflow, like the way that they did their job before. So, and that's tough, right? That can be very challenging. that can be very jarring. there can be potentially attrition because of it as well. So I think that is where kind of HR can flex as a superpower is let me help understand how this is going to
evolve and affect a person's day to day. And let me own the kind of change management side, let me own the communication side, that strategy side, and then partner really closely with like a technical kind of counterpart to see like how do you actually build these things? Like what is what is realistic, what isn't realistic on that into. One of the things that we're bumping into right now because the curiosity and the excitement with AI is is there, right? Like
Daria Rudnik (17:02.665)
Yeah.
Jen (17:10.635)
We've put our money where our mouth is, like we're investing, we're we're having people be very encouraged to use AI. But at the same time, you could have two different departments building something that is exactly the same. If you don't have some kind of oversight, right? And it and of course it's gonna kind of happen because you're like, well, I wanna go build this cool thing over here, and I wanna build this cool thing over here. And this is not a new concept. I mean.
like at the at the granular even like team level, you might have, you know, two people on a team that are like, I want to go. And I'll take the HR side as an example is like, hey, I want to like talk about this survey data over here. Go build this thing over here. And then they don't know that another person on their same team is building you know, survey data for X, Y, and Z, right? And so again, building like two people building the same thing in the same department, they're just not talking to each other.
So I think there's also kind of an opportunity for HR to help with like the overall kind of communication and like, did you know that like this person's building this over here? And you should actually ask them about you know, what they're doing over here so that you're not doubling up on work. Again, you're still being very productive, but you're not doing duplicative work.
Daria Rudnik (18:27.219)
Yeah. And I love what you're saying, but AI actually anyone can be a builder with AI. Anyone can build something with AI that will help them with their work, that will help their clients. And it is important to understand what other people are building. And you do that by communication. And who's doing communication in in a in a company is HR is doing communications. And the other thing is, like you said again, it's changing how my work is changing when I use AI.
So what am I doing, what am I not doing, what I'm doing like differently when I use AI? And there's a lot of frustrations and fears. And who's the best function to address those and help them people reshape, redesign their work processes? It's HR. So HR leaders need to be at the front of this AI transformation in the organization.
Jen (19:18.507)
Yeah. And it really has been not to like not to harp on this like hot potato analogy, but it really has been one of those things where it's like you have to be fully in it. You can't just be like, well, let me do like one little thing here and then like set it and see what happens. Right. Like you have to continue to quarterback it the whole time. because again, like if not, people are just gonna go off and it it's gonna be the wild west again.
Right. I almost not again to go back to COVID, but like I almost like equate this to like when COVID first hit and a lot of companies were going like fully remote or remote first, they had like a head like this job title called head of remote. Do you remember that?
Daria Rudnik (20:03.733)
No, I never heard actually. I know remote first, but had of remote no.
Jen (20:06.429)
my gosh. Yeah. Yeah. So as a person that was dedicated to like getting the the company set up to being a remote company because there's a lot of different things that happen that happen in office that either don't happen remotely or like challenges that you have when you're not physically seeing somebody in a space. And so I remember seeing this job description popping up all over the place and people like having this role.
And it was always fascinating to me because sometimes it sat within HR and then other times it sat with like operations or maybe almost like was a chief of staff kind of role too. It really, it really was a make it like make it whatever you want it role. And I see a very similar thing here with AI enablement, where again, like you're seeing this role pop up now. And a lot of places are are hiring like a dedicated person to be like, okay, they're gonna own the strategy.
Daria Rudnik (20:40.582)
Okay.
Jen (21:05.399)
But you don't see those head of remote roles anymore because it's already been like sucked back into HR. It always it always comes back, right? So my prediction is kind of that AI enablement side of this is really gonna get kind of consumed into kind of the HR, maybe under learning and development, maybe manager coaching, maybe more ops, but like it's it's it's eventually gonna fall there anyway. So why are we hesitating to take the reins now?
Daria Rudnik (21:09.407)
Mm.
Jen (21:35.521)
Like why are we waiting for it to eventually fall on our laps? So yeah, that's soapbox off.
Daria Rudnik (21:40.637)
Well I'll get this bash I I'll return this question to you. Like why do you think HR is not seen as some as a function that can actually have that?
Jen (21:51.148)
I think there is hesitation because HR is not always as technical. You know, like there's there's still this stereotype where this kind of soft and fluffy kind of department where like we're just thinking about like employee happiness and engagement and like we just want to give more perks or more benefits or pizza parties, which I again just like, I can't roll my eyes hard enough, right? On that end.
But like that is that has been kind of the persona of HR. Even when I first got into kind of of my first startup, that was kind of the persona that I was given. Right. And there's of course like those offhanded comments of like, don't say that, HR's in the room. So like we're compliance police too. Which again, like I I laugh at that at this point, because I'm like, like that's funny. Cause I I I I'm not that person. So I'm like, I can like make that rule off my back at this point. Like, I don't care.
But it is like that persona that we've been fighting for years and years. And so we're not seen as like a technical partner or like, that's gonna go over HR's head, right? And so that's why I think, and and HR, like HR people are also very hesitant because they're like, well, I'm not technical enough for this. And it's like, you don't have to be technical to handle AI. You just have to have the right partnerships and understand kind of the mechanisms with it.
Because no one's asking you to go into Claude Cowork and build something right now. Like you can have a tech ops person help you with that. But if you're saying, hey, this department's building this pricing calculator, and then you have a meeting on like the HRBP side and you learn another department's building a pricing calculator, if you're not putting two and two together, you're not doing your job. So yeah.
Daria Rudnik (23:38.301)
Yeah, I agree. I mean it's about understanding the work processes and making sure like it's str strategy and making sure everyone knows what they're doing and how they work is how they're performing, basically. It's about performance and productivity. Well, that's so interesting. Yeah. Yeah, go ahead.
Jen (23:51.254)
Yeah. And it's really getting that visibility. it's yeah, it's just getting that kind of visibility up as well of like what are the cool things that people are doing with AI as well. Because again, like if you also don't see it, and I mean I check like the token usage. It's not we don't have a leaderboard or anything, but I'm checking it and I'm like, why is that person's spend so high? Like let me dig in a little bit and see. And I learned, they built this really cool thing that it's gonna have a very strong business impact.
Daria Rudnik (24:00.808)
Yeah.
Jen (24:21.717)
Why are we not publicly showing that off to the company, number one, so they can see it, but also get excited and also again cut down on, I was gonna build that, but this person already built it. Right? Like why hide it?
Daria Rudnik (24:36.467)
And this kind of showing what other people are building, like in our previous episodes to our listeners, we have a few episodes about AI and how HR is actually leading with the work day with some startup companies. And they say that showing other people's work is what actually inspires other people to try, go and try it also. And they try it. And this social learning people learn from each other with AI a lot.
Jen (24:59.381)
Yes. And that I think that's actually one of the questions I typically ask. I'm like, what prompt started this all? And like, what was the iterative process? Like walk me through that. Cause it's really about kind of the decision making and how your brain works that I I want to understand. Cause again, like that's going to inspire me personally, but also potentially teach others.
Daria Rudnik (25:20.901)
Yeah. Cool. Well Jen, it was an incredible conversation. I learned so much. Thank you so much for sharing. I have one final question for you. If you could have a magic wand that could solve one professional challenge that people leaders have, what would it be? What would it fix?
Jen (25:26.409)
Yes.
Jen (25:39.977)
So I'm biased here as well. I was I was thinking about this because you you gave me a teaser of like, hey, I'm gonna ask you the magic wand question. And I mentioned that my magic wand answer probably changes not maybe on a daily basis, but like a monthly basis, based on kind of what what either priorities are or or how things are shifting. I come back to the basics on this one because
the manager side of this, if I had a magic wand and could basically duplicate some of my amazing managers, like just how they are in the wild, right? If I could just like yeah, make carbon copies of them, I probably would love to do that. I was in a conversation with a leader yesterday and they were showing me something that they shared with their team because we were saying, hey, like people are
Daria Rudnik (26:18.505)
Mm.
Daria Rudnik (26:27.585)
Yeah.
Jen (26:37.291)
People are kind of questioning kind of this one thing over here. Would you like, do you have any insight into that? And they're like, my gosh, yes, I do. Here's this visual that I created to like really get people to understand the story and kind of see the balancing ball. And I was like, I want to copy you. Like, I want to copy like what you're doing, but also like just you as a human. So I think my magic wand would probably be like, if I could
Yeah, like wave of magic wand I wanna copy you, I wanna copy you, I wanna copy you. That's probably what I would do. Yeah. Right.
Daria Rudnik (27:09.061)
Nice. That'd be interesting. Yeah. Surround ourselves with people will laugh and and they can fun working together. Yeah, yeah, it's cool. Well, Jen, thanks so much. It was an incredible conversation. how people can find you, how people can reach out?
Jen (27:19.755)
Yes. Yeah.
Jen (27:25.121)
Yeah, you see.
Jen (27:29.579)
Yes, so I am pretty active on LinkedIn. So I love for people to just connect with me on LinkedIn, follow the content, engage with the content as well. I am always up for a kind of conversation and kind of somebody else kind of interjecting a different perspective because again, that's how I learn too and how I I will grow and evolve as a human. so I would say, yeah, connect with me on LinkedIn.
Daria Rudnik (27:52.689)
Okay, and we have the link to Jen's profile in the notes to this episode. And if you thanks for staying with us till the end. If you like this episode, please give us five stars on Apple Podcasts and Spotify. Subscribe to our YouTube channel and stay tuned for the next episodes. Bye.