All Episodes Primary Ventures VP Talent Jamie Sterrett

Primary Ventures VP Talent Jamie Sterrett

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Primary Ventures VP Talent Jamie Sterrett

Recruiting Trailblazer Jamie: Early-Stage Insights

Jamie joins us to offer some insight into what it takes to be an early-stage recruiter, how talent professionals can level up the entire function of a business, and when companies should consider bringing on a full-time in-house talent resource.

Episode Transcript

Jamie Sterrett 0:00
When you work at an earlier stage company, it’s almost impossible to separate the hires that need to happen from business schools.

Rob Stevenson 0:13
Welcome to talk talent to me, a podcast featuring the most elite talent leaders on the frontlines of modern recruitment.

Jamie Sterrett 0:19
We actually want to understand the themes of someone’s life, we want to understand how they make decisions, where they’re willing to take risks and what it looks like when they fail.

Rob Stevenson 0:29
no holds barred completely off the cuff interviews with directors of recruitment to VPs of global talent, CHROs, and everyone in between.

Speaker 1 0:38
Once I went through the classes and the trainings and got the certifications through diversity inclusion, I still felt like something was missing.

Speaker 2 0:46
Talent Acquisition. It’s a fantastic career, you are trusted by the organization. You get to work with the C suite and the security at the front desk and everybody in between. And everybody knows you.

Rob Stevenson 0:59
I’m your host, Rob Stevenson. And you’re about to hear the best in the biz. talk talent to me. Oh, yeah. Welcome back to the podcast. All of you. Beautiful, wonderful, talented recruiting darlings out there in podcast land. It’s me, Rob, back here with another installment of your favorite recruiting show. Why am I so singsong you hear at the top? I don’t know. I’m just trying to have a little little fun inject a little bit of levity and whimsy into your day here. But let’s get down to business, shall we? And meet today’s guest. She is the VP of talent over at primary ventures, Jamie Sterrett. Welcome to the podcast. How are you today?

Jamie Sterrett 1:35
Hello, I’m doing well. I’m excited to be here. I kind of feel like I should also sing my intro, but I’m gonna save from that. No one would appreciate it. If I did.

Rob Stevenson 1:46
Oh, well, maybe only me. And sometimes that’s enough on this show? Well, I’m glad you’re here singing or not singing. And we have lots to get into you have a really interesting role. I have gotten to meet with a handful of folks who are on the venture capital side over the years of doing the show. And I think it’s a really interesting way to go about forging a career in this space. So we’ll get to all that. But first, let’s get to know you, Jamie, would you mind sharing a little bit about your background, how you forge your way in this space and how you wound up at primary?

Jamie Sterrett 2:19
Absolutely. So my career really has been rooted in working at tech startups in New York City, leading recruiting functions in house. So I spent eight years of my career at a great company called Seat Geek where I was the first recruiter and built and grew the recruiting team from really nothing, and got to see the company and the team grow in size and stage over the years, which was super rewarding. Then I moved on to a company called orchard and the residential real estate tech space. And our mandate, there was a scale from 300 to over 1018 months. So it was just truly like hair on fire rapid growth, but so much fun to be a part of. And then ultimately, that led me to primary which is completely different. Now I’m on the VC side of things. But what we do at primary is we work really closely with our investments which we make at the seed stage level, to really help them and enable them to be able to grow from seed stage to series A and beyond. And so in my role as VP of talent, that means that I’m working really closely with founders, early stage hiring managers, and helping them think about not only what roles they might need to hire for but how they need to go about hiring for those roles. And then in a lot of cases, doing the hands-on work to help them make those hires to

Rob Stevenson 3:34
so I should think most people have some experience with seek if you like going to sporting events or concerts. And it’s interesting to hear you are so early days there as the first recruiter so were you doing everything like were you like plugging in the ATS? Were you like deciding company values? I imagine that role was was a lot different than merely recruiter.

Jamie Sterrett 3:54
Yeah. And you know, my path to the role was very nontraditional. So I was actually already working at CPQ and was working in an ad sales capacity. So I did have a brief stint as a recruiter before joining CPQ. But I joined CPQ. And I thought had sales like yeah, I can do sales. I’ve done recruiting really transferable skill sets. Let me try this. So I did do ad sales for a year when we were, you know, series A Series B, then when we raised our Series B, we realized, oh my goodness, we have to hire people. And the goal is at that point in time, we needed to hire 35 People in the next year. And there were probably about 35 of us at the time. And we all thought that was crazy to try to double inside any year. And so at that point in time was when we realized, Oh, we actually need like a director of talent to start to build out more of a recruiting function. You know, we’ve had some like part time recruiting support over the years leading up to that but never like a true formal in house recruiting function. And so that’s when I made the pivot. Luckily, some of the groundwork had already been done. Our founders had already done a lot of research around wanting a structured hiring process. Astrid implemented greenhouse as their applicant tracking system. So I got to come in and kind of see these projects through, and then really scaled the team from there. But it was really nice to already have that foundational buy in from leadership about how we wanted to approach recruiting at Seat Geek.

Rob Stevenson 5:15
So you’d had a little bit of recruiting experience, then you decide maybe ad sales is where I want to be, then back to recruiting. And after that you had the bug, you’re like, you know what, I’m a recruiter. Now. This is who I am. How did you decide this was where you wanted to forge the career?

Jamie Sterrett 5:30
You know how so many recruiters talk about how they fell into recruiting? Like I intentionally sought out recruiting when I graduated from college, which is very rare, like, like,

Rob Stevenson 5:38
I’ve literally never heard that before.

Jamie Sterrett 5:42
No, no one is like that. But for whatever reason, I was like, Yes, like this feels right to me. But after doing it for a year, I was like, do I really want to do this, I should try other things, which is why I tried ad sales. So ultimately, I say that I did have my falling into recruiting story that everyone has to have when they get into recruiting. But for me, I think I got to experience recruiting from a different side, when I was doing it for an early stage company, the impact of the work that you’re doing feels a lot different. My first recruiting job was for a really large company, where I felt a little bit more like a cog in a machine. Whereas it Sikhi guy was helping really think about what is the future of this company going to look like and a year in two years in three years, and I could look back and say, Wow, look at all these people that have joined the team and look at all the amazing things they’re doing for the business. And I felt like I got to be a small little piece of that.

Rob Stevenson 6:33
Yeah, I think that is often what keeps people in the space is seeing their hires, contribute at a high level, or maybe even just be fulfilled in their careers. That is, I think, what makes this career so noble, is that you are connecting these people to a position where they can, you know, one provide for themselves and their families, you know, but also people want to work, people want to achieve mastery and wield it. Right. So it was was that a key part of it for you seeing that people really, because of your work Shine?

Jamie Sterrett 7:04
Yeah, I think it was both seen that people felt really happy to get these jobs and be in these roles. And I also think it was on the business side getting to see the impact that was actually happening for the business and the growth there. When you scope a role appropriately, and you bring in the right person for it, you can really level up an entire function in a business, especially when it’s early stage. And so I think part of it was really seeing how my work tied to like overall business goals to

Rob Stevenson 7:31
Yeah, that last piece, tying into business goals is really important. Because there’s like the feel good hurry of seeing a higher you may succeed. And who doesn’t love that everyone has to justify their role with with this, you know, bottom line contribution in the company. And that is also I think, how you really elevate yourself. So what was that process for you connecting the work you were doing to high level business function?

Jamie Sterrett 7:55
I’ll start by saying when you work at an earlier stage company, it’s almost impossible to separate the hires that need to happen from business goals, because every hire you make can ultimately be really critical to achieving a business outcome. Right? You know, I think about my role today, and some of the seed stage companies were supporting, and they need to hire their like first three founding engineers, right? Every single one of those hires is so critical to them actually being able to deliver on the product that we’ve invested in and that customers are hopefully going to be signing up for, right. And so it’s so easy to make that connection between hires that needs to be made and business goals. And for me, I think seeing that firsthand in my time at Seat Geek made me understand that. So then, when I was operating that, you know, slightly larger scale at a place like orchard where we grew to 1000, I could still really see how making hires was ultimately impacting our business outcomes.

Rob Stevenson 8:54
Yeah, it’s a good point. And it’s just simple math do at that stage, right? If you have eight employees, your next hire is 1/9 of the company. It’s so critical, so perhaps easier at a smaller organization to connect that dot, but then you also towards the end of your time at Seat Geek and an orchard larger companies, does it get more nuanced, more difficult to connect those dots?

Jamie Sterrett 9:14
I think it can at times. And I think that’s also when you get to a point where you’ve got probably a much larger recruiting team. And if you’re a recruiter on that team, it can sometimes be harder to feel like what’s the specific impact I’m having if my job is to hire everyone in this specific function. And that doesn’t feel like a business priority right now. Right? And so I always viewed one of my jobs as the leader of the recruiting function was to really showcase and make that connection for folks on the team of like, Hey, here’s how your work is ultimately contributing to business goals and making sure people really felt that they understood the connection, even if it wasn’t necessarily articulated in the quarterly company-wide OKRs that we had that quarter.

Rob Stevenson 9:57
Yeah, that’s so important because that makes people feel like their work matters. Yeah. And then also, as they advocate for themselves, they need to understand how they’re impacting things. Like when they ask for a raise or a promotion, or when they’re just justifying their right to have a job there, you have to be able to speak that business language. It’s so important. And I worry that it’s such a crucial skill that most people never bothered to hone, or it happens by accident, if they’re lucky to have a boss like you who spells it out a little bit. But I guess for people who maybe don’t have that luxury, how should you go about really honing in on how your work impacts the business?

Jamie Sterrett 10:35
Yeah, I mean, the very first place I would start is what sort of quarterly annual goals are written down today, go through those goals and say, how is my work? laddering up to this, maybe the connection isn’t like a direct one to one connection, where it’s very clear that you know, we need to hire six engineers. But what is it about the product that’s captured in these annual goals or quarterly goals? And then how can you make sure that you’re understanding how your work ladders into that? And if you’re ever unclear about how your work ladders into that, like, ask the stakeholders, right? If you’re making engineering hires, talk to the CTO about where these people are going to fit in, and specifically, like, what products they’re going to be helping build, and what wouldn’t be able to happen if we didn’t make these hires? That can often be where you see the connection is like, what is the risk? If we don’t make these hires?

Rob Stevenson 11:28
Yes, you have to do that little bit of investigative journalists in your own company, right? Like, oh, I place these three engineers, hey, engineering manager does hire that I made this person I sourced? Did they contribute to this thing? That was a quarterly goal, this thing that was a product you were trying to ship whatever it was? And if yes, like, there it is, there’s the line. But you have to figure this out. And it’s tough, because it’s a little separate from your day to day work. But it’s so important to be doing this, because no one else is going to you have to advocate for yourself and be like, in the appropriate context, explaining to people loudly, the impact of your work, right?

Jamie Sterrett 12:06
Yeah, and I’m also the type of person who I like, personally really need to feel the impact of my work. Like that’s something that’s really just central to who I am. And I can’t be happy in my role if I feel like I’m not having an impact and not closely tied to impact. And so for me, it was always kind of like second nature to make sure I understood, like, what actually mattered about what I was doing. And if it’s not second nature for you, like that’s okay, but you should hone in practice those skills, because ultimately, as you grow in your career, like you will need to be able to tie your work back to the impact that you’re having.

Rob Stevenson 12:38
Yeah, yeah, it’s super important. And I feel like that’s the difference between getting a meets expectations, yearly review and a 1% Raise and getting promoted. I can’t be Yeah. So you had this experience at Seat Geek, gross, like basically like a mid level company, then at Orchard, you grow from 300, like 1000 people in a year and a half. And you have worked as an internal recruiter at this point. But now you have this opportunity to go to primary and the role at primary a little bit different, because because it’s for venture capital than your previous one. So I’d love to know, first, how did the opportunity arise? And then I would love to know how you evaluated it.

Jamie Sterrett 13:20
Yeah. So I will say I first heard about the opportunity, like through my network. So I had met a woman who’s now my boss at primary, originally through like an HR leader, networking dinner when I was working at Seat Geek. And she was a chief people officer we’d met and we just kind of, you know, stayed loosely in touch. But we both had that like operating in house startup experience, right, that connected us. So I saw on her LinkedIn that she posted that she was hiring. And then actually, some folks I know who I had worked with at Orchard, also let me know that she was hiring because they knew her too. And so I was kind of getting this from multiple angles, like, hey, this rule seems really interesting for you, like people were telling me that the rule seemed interesting for me. And I was like, okay, like, maybe I should really consider this. The interesting thing was I hadn’t been intentionally seeking out a role in VC, I had kind of thought I’d stay in house. That’s what I’ve done. That’s what I like to do. And I didn’t particularly feel like burnt out by in house work. Sometimes you hear about people making a switch outside of in house work, because they’re just like, burnt out and they can’t do it again, like, I wasn’t there. But when this roll kept being surfaced to me, I was like, Okay, I should really look into this. And as I had more conversations, I realized that the role at primary really is pretty different than like a typical talent role at a VC. I think what I’ve learned in my short time in VC, is that every VC operates very differently. And having a talent role in a VC firm can mean something wildly different depending on where you go. So as I learned more about the opportunity, specifically at primary at re really appealed to me because it’d be working with early stage companies, which kind of harkens back to my early days at seek, which was exciting to me, it meant that I was going to be working in interfacing with a lot of founders. Right. So rather than just working with one executive team at an in house company, I was pretty intrigued by Wow, what would it be like to work with 80 Plus executives, all at different companies. And then on top of all that, like there was still a recruiting team to be managed at primary. And I think one of the things I love is helping mentor and coach and guide recruiters in their career. And so the fact that there was already an existing embedded recruiting team at primary that helps our portfolio companies that was really appealing to me to

Rob Stevenson 15:42
so when you interface with these founders, you are coming in the early stage? Are you advising them on like how to make their first recruiting hire? Or are you kind of serving as that first recruiting hire? What is your function when you start getting into these portfolio companies?

Jamie Sterrett 15:55
Yeah, it’s a little bit of a mix. So I would say my role at a high level is to help our portfolio companies with anything they need related to recruiting and talent, right? So sometimes, that might just mean that I am a good phone, a friend for a founder, when they’ve got a random hiring question. Or they’re like, Hey, I think I need to hire this role. Let me go check this with you. Or is this a role that typically exists? Like how should I scope this, right, so sometimes, I’m just like that, like quick 30 minute phone call video call to gut check things or provide some advice or guidance. In other situations, when there’s a portfolio company that needs to go through a bit of a hiring sprint, but it doesn’t make sense for them to yet hire an in house recruiter, our embedded recruiters will come in and be that recruiting leader or that first recruiter for them. So this happens often with like our seed stage companies in our series A companies where, okay, maybe you just raised around the funding, and you need to make five to 10 hires will come in and will really lead that process for you, obviously, we’ll need your partnership and your buy in. But we will do the nuts and bolts of the sourcing and the screening and setting up an applicant tracking system and building the recruiting foundations for you. We’ll make those hires for you. And then when we step away, you’ll have this really great recruiting infrastructure that you can use over and over again. And the benefit for us is that we then know our portfolio companies are using best practices for hiring or using structured interviewing practices. They’ve got the right tooling and systems in place. So when they do need to make hires in the future, we have more confidence that they’re going to approach it in a way that’s going to help drive better outcomes.

Rob Stevenson 17:31
I’m really pleased to hear that that is sort of from primary’s point of view, what is so meaningful is that oh, now we know all these companies, we’ve invested in our hiring in a thoughtful, professional way, basically, right? It’s not just happening by accident. And that is great to hear, because I love it when folks prioritize talent in hiring, because it’s such a common priority. But it’s always like number three or four, which I think is wrong, because any other priorities stems from having the people to do the job, right. And so it sounds like it’s much more highly prioritized at primary, could you share what those conversations are? Like, I’m sure that the fact that they were bought in is what made you want to sign up with primary, but I want to know what it sounds like when someone is really invested in talent in a meaningful way, so that other people can, you know, listen out for that kind of thing.

Jamie Sterrett 18:22
I’ll share it from both the primary perspective and then also from the perspective of some of the portfolio companies I’ve had the opportunity to work with. I’ll say like, on the primary side, when I was interviewing and making the decision to join the thread and theme of the work that’s done on primaries impact team overall has been really critical to success for our portfolio companies was like very loud and clear. So the way primary is organized, we have a really large what we call impact team. And the impact team is full of operators who are not investors. But we partner closely with a portfolio companies after we’ve invested in them to help them go from seed to series A and beyond. And so that impact team is not just talent related. There’s a big chunk of it dedicated to talent. But there’s also a big chunk dedicated to like building out amazing community networks for both talent and customers and advisors. There’s an amazing segment of the team dedicated to go to market and how to build out the right go to market strategies with our early stage companies. There’s also a finance function. And we also have a CEO and residents who helps on the more like leadership side of things with our CEOs and founders. So we have this really built out impact function, right. And that’s a priority to the business. That’s a priority to primary and they make it very clear and articulate that it’s a priority, not only to new hires that are joining. But when we’re investing in portfolio companies, we’re really clear about, Hey, these are the resources you’re going to have access to if you are a primary portfolio company On the other side working with founders, you know, I think that the really early stage founders who we like have just invested in, when they hear that we’re going to be able to help them think about talent. Usually, you can see their eyes light up when they know that they could use the help, right? And they say, Oh, great, someone’s going to help us think about recruiting because it’s probably the number one worry a lot of these companies have, like they know, as soon as they raise funding, they’re going to need to make hires. And some of them don’t know where to start. And so knowing that they’re going to have someone help them think about where to start, and they’re not going to have to figure that this out on their own. I think that is, is really appealing to a lot of our earliest stage founders.

Rob Stevenson 20:42
I like that you said their eyes light up, there’s a fine line between eyes lighting up and being a deer in the headlights. Because a lot of them maybe have not had experience doing the recruiting. And yet here they are this position where they’ve raised money, and now like, Okay, we have to hire, now I have to learn this function I’ve never learned, right. I’m a technical co founder, I’ve never hired that many people before. And now I have to go out and do it, and they get the resources from you. So I call that out because it feels like a really great opportunity for any recruiter to reach out to these people and be like, Hey, I know you desperately need help. Let me do this for you. Without them needing to go out and first find a recruiter, would you advise that as like a career search, like for a company who may not have the resources of a primary or like they get the team to paratroop in and set things up? They all still need that, right, it feels like an opportunity for folks who are looking for a job.

Jamie Sterrett 21:35
Yeah, I will say I think there’s kind of a threshold in which founders and leaders recognize that, like a full time in house resources probably going to become valuable for them. And even with the portfolio companies that we support, will let them know like, hey, it’s time for you to make an in house recruiter hire, we can help you until you get there. But it’s time for you to make that hire. And then we’ll help them make that hire. Usually, that threshold is when we know that there’s going to be a consistent volume of needs open. Or if we see that there’s like line of sight into meeting 15 Plus hires in a year. And it feels consistent, we’ll say, Okay, it’s really time for you to think about making this hire. And that can happen at different stages for different companies based on where they’re at and what their needs are. But so as a recruiter who’s on the market, it’s absolutely a great place to try to dive in, because while we’re seeing a ton of layoffs continue to happen in larger tech companies, early stage companies who are hiring, still need to do that, right. And that hasn’t changed. The harder part, of course, is there’s gonna be one job at each of these companies. And these companies are hard to find, they don’t have an employer brand, they don’t have much presence. So the harder thing is really finding them and getting in front of them. And I think there’s a few different strategies you can use to do that. One, talk to VCs, who invest in early stage companies, they’ll typically know if their companies are looking for recruiting talent. The second thing you can do is really closely track fundraisers, right? Because fundraising is often so correlated with the need to hire, that if you’re tracking fundraisers through different types of newsletters, you can just you know, use your recruiting skills and do some cold outreach and reach out to founders and leaders and say, Hey, I saw you just raise your Series A, I realize you might need to hire, I’d love to chat with you about the potential of me helping you make great hires, right, and see where it goes. I mean, I don’t think it would hurt to employ that strategy by any means. And you might not hear back from everyone. And they might say no, but I do think it’s an interesting strategy to try out. The caveat with all of this is that you have to be ready for early stage work. Early Stage recruiting is not for everyone. When you are the first recruiter somewhere you are wearing all of the hats, right? So you have to be able to recruit for technical hires, for non technical hires, for senior hires, for junior hires. And in addition to that, you also really have to think about what’s the process that’s going to be used? How is it going to be scalable? How are we tracking things? How are we starting to create some like reporting and data infrastructure, right, and making the right decisions there early on is going to set you up for success longer term, but it’s so a lot of work. You’re wearing every hat, right? You’re the recruiter, you’re the sorcerer, you’re the coordinator, and you’re also the TA lead, and you’re also recruiting ops, and you’re also like a hiring partner to all of the executives. So you have to really be able to balance a lot of different hats. We have to be excited about all of that work. And if you’re not, I would say, early stage might not be for you. And that’s totally okay, too.

Rob Stevenson 24:42
It’s not for the faint of heart, but I will counter that no job that you end up being really good at is for the faint of heart. It’s all going to be a significant challenge. But this strategy you’ve outlined, I don’t know why it wouldn’t work because like you say the fundraising is correlated with hiring you know, they have money, you know that the fundraise is a mandate to grow, people are going to help you grow and build all the products that you’re supposed to make. And so even if it’s like going on VentureBeat, who raised money, you’re right, there are all these layoffs happening, but checks are still being written, investments are still being made, companies are still being I have building these new exciting products are expected to grow. There’s an opportunity, and maybe you could come along at this moment where this founder realizes they have to grow, and they have to hire people, and they have no idea how maybe it’s on a part time basis, you know, maybe it’s not like hey, creating vento full time role. For me, it’s like, let me give you 20 hours a week to build pipeline and screen for these three key roles you have, and let’s see how we get and they’ll be thrilled they can afford to pay you, you know, charge them 100 bucks an hour or charge 150 bucks an hour to do that for them. And it’s still a good deal because they know it’s temporary, you know, it’s a contract work. Maybe you get a full time job. Maybe it’s just a side hustle. Maybe you replace your income. I don’t know, if I’d been laid off as a recruiter, I would absolutely give this a shot. I feel like it would totally work.

Jamie Sterrett 25:58
Yeah. And I think you know, we’re seeing more and more recruiters be more flexible about contract work and part time work, and eager to prove themselves if they need to, to get a full time job.

Rob Stevenson 26:10
Yeah, yeah, they have to be. Well, Jamie, here we are creeping up on optimal podcast length here. This has been really great chatting with you. And this is normally the part of the episode where I ask the guest to give some last minute parting words of wisdom, but I don’t know if we’re gonna beat that. That approach for getting a job as a first recruiter. But I mean, maybe that’s not that’s not for everyone, not not everyone’s in a position to go out and get that job. So maybe I’ll just ask you to share for people who are forging career in the space, what advice would you give them so that they can really make the most of their skill set and bring it to market in a meaningful way?

Jamie Sterrett 26:42
Yeah, I think advice that I love to give recruiters is to be really intentional and thoughtful about the type of company you want to work for. And by that I mean, like this stage, the size, the type of recruiting you want to do. Is it technical? Is it non technical rate? By stage in size? I mean, are you going to go really early stage and be responsible for kind of 20 different roles rolled up in one? Or do you really want to become a deep expert and really specialize, then maybe you should go later stage right? So I encourage people to really think about that thing. When I have conversations with recruiters and they tell me I’m super open any stage, any size, any industry, that’s actually not really that helpful. Having a really specific point of view, makes you stand out more as a candidate. And it’s okay that not every single job is going to be right for you. It actually shows that you’ve got a little bit more self awareness about both what you want and what you think you’d be good at. And so I think it makes people stand out as a better candidate when they’re able to really articulate that. So I would say, have an opinion about the type of place you want to work. That’s a good thing. Not a bad thing.

Rob Stevenson 27:47
That’s tremendous advice. Jamie, you are a early stage in house recruiter, you are a small to medium business recruiter, you are a VP of talent at primary. And now you’re a fantastic podcast guests. You can add that to your repertoire, because it’s been really great to add that. Finally, like gold star in your resume. Yeah, this has been really, really great. Thank you, Jamie, for doing this and being here. I really, really enjoyed chatting with you today.

Jamie Sterrett 28:12
Yeah, thanks for having me. Rob. It’s been a lot of fun.

Rob Stevenson 28:17
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