Operating & Growing as a Startup’s Early Talent Hire

Overview

1. Early Days: Early-stage recruiters establish credibility by delivering on promises, following up consistently, and demonstrating results through successful first hires.
2. Growing Pains: Scaling startups require intentional culture building through written norms and strategic placement of culture carriers across teams.
3. Career Growth: How to navigate a long-term career at a startup or make your next move strategically.

Transcript

Note: transcript is auto-generated, there may be typos.

[00:00:00] Reggie Williams: Thank you guys for staying around for the panel. I know it's been a, a long day, but, um, it's been great. I think, uh, so far, hearing the really deep conversations about recruiting, I think sometimes you come to these and you hear, uh. You should try reporting. He's like, I tried that. Thank you. Um, but for this, uh, today we've really got deep into specifics around what are you thinking about reporting on how do you be a real strategic business lead, uh, business partner.

Reggie Williams: Uh, so we hope to continue some of those deep, uh, discussions in this panel. Um, so the panel focus is on early stage, you know, being the first recruiter or being the first talent hire. And how do you navigate both scaling your team, scaling yourself. Um, as well as how do you leverage that experience for your career growth?

Reggie Williams: And I have an amazing panel here, uh, who I'll introduce and then we'll jump right into questions. So first I want to introduce Leah. Hello,

[00:01:00] Reggie Williams: the Amazing Leah. Um, Leah has over nearly a decade of experience now, um, at Help Scout now VP of People. I think you've had a long kind of trajectory there, so, um, I'll be amazing to hear about as well.

Reggie Williams: Um, but, um, she's really passionate about scaling teams with empathy, intention and just the right amount of process. Which is great. Uh, and you can find her living in Philly with her wife and daughter, uh, and both of which have strong opinions strongly held. That's true. That's awesome. Thank you Leah. And now Anisha.

Reggie Williams: Um, Thomas Anisha is the head of people at Inscribe, um, where she focuses on building a people first culture that helps a team thrive and grow. She's passionate about creating high performing teams. Uh, inclusive environments and p and uh, where people feel supported and empowered. Um, outside of work, you can find her chasing her toddler in Golden Doodle.

Anisha Thomas: Yeah.

Reggie Williams: And

[00:02:00] Reggie Williams: Heather. Thank you coming. Heather par. Heather started her career at Outward Bound in exper, uh, experiential outdoor education before transitioning into research at Children's Hospital in Philadelphia. Um, after moving to San Francisco, you found your way into startups, um, which is amazing, both at Samsara and then Modern Treasury.

Reggie Williams: And now you are VP of People, uh, at Modern Treasury where you, where she oversees recruiting, hr, workplace, uh, operations, and it so. Pretty much everything. Um, so Heather loves Maine, the beach lobster. Yep. Boats and spending time with her friends, family, and her dog, Bonnie. So I think one thing we've learned is get a dog.

Reggie Williams: That's probably the first thing you should do as the first talent, uh, uh, hire. But, um, but no, we're gonna get into the panel now and, and start the questions. I joke that I would go off script and ask, um, 100 men or one gorilla. To the whole panel, but I think there was consensus that the gorilla would

[00:03:00] Reggie Williams: destroy a hundred men.

Reggie Williams: I think that that was the consensus. So we're gonna jump right into other questions. Um, and the first one being, when you're first starting off as a recruiter in the seat at early stage startup, I. You know, there's a hundred opinions about what you should start doing. Everyone has opinions about recruiting and what you should do first.

Reggie Williams: So my first question is to Leah, can you kind of discuss, um, at Help Scout maybe, how did you figure out how do you build trust with that, uh, founding team? And then also how to prioritize, what to do first.

Leah Knobler: Ah, yes. So when you actually, when we met previously to discuss this, and I knew this question, I reached out to our first VP of engineering at that time now, almost nine years ago, and I asked him, I was like, Hey, how did I build trust with you?

Leah Knobler: Do you remember? And he was a good sport. And he was like, oh, yeah, I'll tell you. And I was like, thank you. It's, it's hard to remember these things. Um,

Reggie Williams: long time.

Leah Knobler: Yeah. But he was, you know, I really appreciated that he was like, you know

[00:04:00] Leah Knobler: what, you were new to this. And I had never recruited before, but, um, I was very, you know, willing to learn and, and get curious.

Leah Knobler: And he's like, you know, you said what? You did what you said you would do, and you followed up and you didn't drop the ball. And, and that really meant a lot to me. And then it built trust and help Scouts been remote since we started in 2011, so this was. You know, trying to build trust. Yeah. In a remote environment even more.

Leah Knobler: I think you really have to do what you say you're gonna do. Um, and then from there it was just trying to figure out, okay, what do we do next? All right. We have to start hiring people. And the tools back then, you know, all nine years ago sounds. Like a long time ago, but basically we were like, all right, let's maybe create a spreadsheet and I'll throw LinkedIn profiles in there and you leave comments and tell me what you think and we'll go back and forth.

Leah Knobler: And he was like, okay, I can do that. And so it was a lot of like meeting hiring managers then, like where they were at. Um, and then you just have to, you know.

[00:05:00] Leah Knobler: Build your own proof, right? So once you start aligning on the profiles and then starting to bring in good candidates, he was like, oh, you're pretty good at this.

Leah Knobler: I really love the people I'm talking to. It starts to build your own credibility. Yeah. And it just kind of snowballs from there. And so, you know. It was nice to have that trip down memory lane with him. That's awesome.

Reggie Williams: Do you remember there if there was a moment where you knew you had their trust?

Leah Knobler: Um, yeah.

Leah Knobler: I think like once I, like the first person I, you know, sourced and got into the process, I. And then we sent her an offer letter and she signed and everyone was pumped. They were like, oh, nice job, Leah, so you

Reggie Williams: got it? I was like, you can do this. Yeah, I did

Leah Knobler: that. Let's, let's do that again. That was fun. Do that again.

Leah Knobler: Awesome. And then, yeah. You know when, when you actually are making that impact, people are like, oh yeah, I wanna work with her. Let give her my roles.

Reggie Williams: Awesome. Did the results kind of lead to that? Awesome. Um, now jumping to Heather. Yeah. Um, and what of your take on that question, both at Samsara and then modern Treasury, were there differences in how you built

[00:06:00] Reggie Williams: out or, or kind of started out within those two companies?

Heather Brouwer: Yeah, definitely. So, um, Samsara when I joined it was about a hundred people. So it already had a lot of the process in place and a pretty strong recruiting team already. Um, so we really focused on hiring people who were able to scale quickly. A lot of the recruiters that we brought in actually had agency experience.

Heather Brouwer: They had never been in house. It was a pretty intense environment. I think a couple people here might have been on the recruiting team at Samsara at the time. So it was, it was an exciting time to be there, um, and to build trust. It was really all about moving fast and getting results quickly. So if that was something you're able to do, um, you had trust from the hiring managers pretty immediately.

Heather Brouwer: At Modern Treasury, it was a little different. It was 20 people. Um, I was the first head of talent, but really just the first recruiter ever at that company. Um, and our CTO was still recruiting. So the trust that I built with him, it was really when I made my first hire within the first two weeks.

[00:07:00] Heather Brouwer: And I also, um, had to pick out our applicant tracking system and I got that implemented within.

Heather Brouwer: Three weeks, which shout out to Ashby for that. Um, I remember that conversation with Benji. I was like, well, I'll give you guys a try. There's nothing better on the market, so you can't be that bad. So anyway, it was a, it was an interesting experience to build trust Yeah. For both companies.

Reggie Williams: That's awesome.

Reggie Williams: So a little bit of results and a little bit of like, yeah, all right. Let's get some systems in place. Yeah. You just gotta

Heather Brouwer: make things happen fast. Yeah.

Reggie Williams: That's awesome.

Heather Brouwer: Yeah.

Reggie Williams: Um, and now bringing, uh, Anisha into the conversation. Can you talk through, you've been now part of teams that have gone up and down in terms of, uh, uh, team size, and I'm sure everyone has experienced that of, um, you know, just wild turns in headcount.

Reggie Williams: Um, but can you discuss how you think about your team and how you build out knowing that that might happen or having experienced that?

Anisha Thomas: Yeah, definitely. Uh, so at Inscribe I've seen the ups and downs. I was the first, um, talent hire I employee 18, which I'm really

[00:08:00] Anisha Thomas: proud of, uh, because they brought on people really early to build the foundations, but I was purely an operator at that time.

Anisha Thomas: And then I started to grow the team. I focused more on the strategic side of things while my team handled the day-to-day operations. But then during the tough times, and going back to being a team of one. I'm doing strategy and being hands-on, and that is challenging, but also super rewarding. I actually get to connect the dots.

Anisha Thomas: I actually get to make the strategic decisions, but I also get to implement it. And so I recommend, um, for any leader to always be hands-on in some shape or form, regardless of the size and stage your company is at.

Reggie Williams: Yeah. Because that would've been made harder if you hadn't like, stayed sharp on the like recruiting side if you had to kind of go back down and not have the experience, I guess, as, as a being hands on.

Reggie Williams: Exactly. That's awesome. Um, one of the rob, round robin question I'll ask is if you had to go back your first recruiter in seat,

[00:09:00] Reggie Williams: your first year, you get one hire on the team, what role would you hire and anyone can answer. For your team, for the internal talent team? Um,

Heather Brouwer: yeah, I, I know for sure it would be an RC slash sourcer, so a hybrid, um, someone who can build top of funnel and keep the pipeline going, um, and make sure that there's a really clean process.

Heather Brouwer: I think that also sets you up for success and that hopefully you can promote them internally and you have a recruiter. It's great.

Reggie Williams: That's a good answer. You cheated on the hybrid, but I'll give, I'll, I'll give you that. I'll give you that. There was new,

Anisha Thomas: you know,

Reggie Williams: anyone else?

Anisha Thomas: I'd probably go with rack ops, uh, assuming I'm the full on recruiter and I've got, you know, some solutions in place and tech stack in place to help me with that and hiring managers to depend on, but one, because it's not my strong suit, uh, but it's hard to scale and do anything if you have messy data.

Anisha Thomas: Yeah,

Reggie Williams: I like that answer that you mentioned, just knowing your own skillset, because a

[00:10:00] Reggie Williams: lot of times you, there's not a. I don't think there's a right answer to that question, especially if you, um, you know, you, you might have weaknesses in a certain area, whether that be, uh, you know, branding or, uh, other pieces that you need to supplement or the tech side or the data side, who knows?

Reggie Williams: Um, so being able to know your own, like being real about your own strength and weaknesses and doing that analysis, I think is so important, uh, first and we often skip that into thinking about the company and not like, okay, what would actually help myself? Um, but Leah, same question. I,

Leah Knobler: I, another recruiter just more, more bandwidth.

Reggie Williams: Yeah. So like a full cycle recruiter? Yeah. Yeah. That's a, that's not that either. I was gonna say, um, recruiting coordinator, I think, um, you know, something about that experience of people that come on and, uh, just, um, the, the scheduling that happens. I also know my weak points and so, yeah. Well the same, like having someone that can, uh, make sure things are smooth and running.

Reggie Williams: Um, and then I, the other one I thought about was just, um, employer

[00:11:00] Reggie Williams: branding. And I think as AI replaces a lot of the more like administrative stuff, that there's gonna be a more important piece of what we do, which is getting out there and communicating around brand and who we are. Um, and you're even seeing that with more personal employer, like recruiter is becoming their own brand.

Reggie Williams: Um, and I think that will be important as we move forward in the next few years because I don't know if, um, AI can necessarily replace that right now. Um, okay. Moving on to, oh, this is a good one. Navigating your own career growth within this, right? Because you're making a pretty big risk in joining our early stage company.

Reggie Williams: It can go right, it can go wrong, um, but you're gonna get an experience, that's for sure, one way or another. So the question is really like, success in the role is really determined by. Picking the right company at the right time. So how, when you were looking for that, and maybe we go to Anisha first, what were the ingredients you looked for when you were thinking about what company to

[00:12:00] Anisha Thomas: join?

Anisha Thomas: Yeah, so I was at, um, Intercom prior to Inscribe, and I was actually really happy there and I wasn't looking. And it wasn't until Ronan, our CEO and Co-founder of Inscribe reached out to me about this head of People role. And I was debating, I was like, should I explore this opportunity or not? And it was my dad who actually recommended to do a SWOT analysis to compare and contrast the opportunities.

Anisha Thomas: Such a dad thing. I know. Yeah. And I actually recommended it. It really helps. Um, and that's how I came to my decision. So after I reflected on the strengths, weaknesses, opportunities, and threats of both the roles and companies. I landed on, yeah, I should move to Inscribe. Um, one because I get to be a part of the leadership team and close to the business, which is something I didn't have at Intercom.

Anisha Thomas: Uh, and I also love working with Irish founders. Uh, I got that at Intercom, but I get to work more directly with them at Inscribe. Um, there's just a natural kind of low ego, relationship

[00:13:00] Anisha Thomas: focused culture, and you can actually already see that. Um, and see that shine through in our day-to-day, um, way of working and our values.

Anisha Thomas: That's

Reggie Williams: awesome. I like how you had like your Irish founder as like one of your criteria for your future jobs. Okay. You're gonna try to I love that kind. Keep it going. Yeah. Um, that's awesome. Um, uh, going to Heather, um, maybe you can share your experience, uh, with Samsara Modern Treasury, um, and, and how you made that choice between Yeah, those, those companies.

Heather Brouwer: Yeah, so there was actually a caveat there. I did go somewhere in between Samsara and Modern Treasury, and I learned a lot from that experience. I actually think it was really valuable for me to go to a company that. Wasn't a great fit. I think you can learn a lot in the, the things that you don't want in a company.

Heather Brouwer: Um, and so don't be afraid to make a move because you're gonna learn from it and you're gonna end up somewhere that really values you and where you really enjoy the founders and, and the leadership style. So with that said, um, yeah, Samsara was high

[00:14:00] Heather Brouwer: growth. I learned a lot. I scaled quite a bit there, and I really wanted to go somewhere and build.

Heather Brouwer: Um, when I met Dmitri, the CEO, I knew that his values really aligned with my, with my own. And where my strengths were is really what they needed at the time. So I knew that I could bring, um, really quick results. So that's why I joined. That's awesome.

Reggie Williams: Uh, I don't, I don't think I prepped you for this question, but I'm gonna ask it anyway, but was there a, was there a question or set of questions you asked during the process where you, you knew, like, or that you found the most helpful?

Reggie Williams: I guess?

Heather Brouwer: Um, for me it was really figuring out what the next couple of months looked like for them. Like truly like. Get into the details, like the day to day. Who's doing the recruiting right now? Oh, your CTO. Okay. Uh, do you have an a TS? No. All right. That's something I'm gonna be doing. Mm-hmm. Really think through practically what it's gonna look like for you on your day to day.

Heather Brouwer: I was scheduling my first day on the job. I was calling people, I was looking at spreadsheets where they were tracking candidates.

[00:15:00] Heather Brouwer: I mean, you're gonna go back to getting in the weeds and rolling up your sleeves, and you have to be okay with that. Um, you really can't have an ego when you go into a role as.

Heather Brouwer: Head of talent, but you're really doing everything first recruiter. Um, it's just really time to hustle, so Yeah. Ask, ask the detailed questions. Yeah. It matters a lot.

Reggie Williams: Yeah. I think sometimes near the, in the process, you're just, so you're trying to sell yourself. Right, right. Yeah. And so you're trying to get the role, but mm-hmm.

Reggie Williams: There's a time where you have to say, okay, like, let me qualify this opportunity for myself. And that means like asking like tough questions and kind of being the, the thorn a little bit sometimes when you're like asking about details. Totally. And there were some

Heather Brouwer: red flags on the first, you know, my transitional company that I ignored and I learned a lot from that too.

Heather Brouwer: So,

Reggie Williams: yeah,

Heather Brouwer: definitely keep that in mind.

Reggie Williams: All right, so, uh, go up to Heather afterwards and ask her about those. Uh, I won't, those red flags won't, won't name the company, but we'll see. Yeah. Um, Leah maybe. So you've had experience now within a company and kind of

[00:16:00] Reggie Williams: growing from, uh, you know, I think office manager into VP of People.

Reggie Williams: So that story alone, that could be a whole session. That should probably be the next in Ask P two. Um, but can you just talk through, I know when we, uh, were talking, you mentioned choosing the company mm-hmm. And not the role. Um, so can you just kind of talk through that and

Leah Knobler: Absolutely. Um, I was. At the time, almost 10 years ago, working in higher ed and feeling quite disillusioned.

Leah Knobler: Um, it's, you know, if anyone has experience in other industries like education, it's, it's just a different world. And at the time it was just a lot of bureaucracy. Um, I remember what really set me over the edge was there was a committee on committees. And I was just like, what are we doing here? Mm-hmm.

Leah Knobler: Where, what am I doing here that isn't right? And so I really, it led me to sort of work backwards and I started just trying to Google company culture and wanting to understand who else was doing this differently.

[00:17:00] Leah Knobler: And I can't remember exactly the blog post, but Help Scout has a. Really robust company blog.

Leah Knobler: And I stumbled upon it reading about how they were thinking about company culture already at like 20 people and they were fully remote. And again, this was 2015. And it just sort of blew my mind. And I was like, that I wanna work there. Hmm. And so then it began my, my campaign to convince them that I was the person they wanted to hire.

Leah Knobler: True story. I actually applied for a customer support job first. Promptly disqualified. And that's for the best. For the best. And then, you know, a couple months later, um, like a people ops generalist slash office manager came up and I was like, yes, I can convince them to do that. And we did have a small Boston office at the time, so I know, you know, we were, we are, and still, you know, fully remote and, and I think, you know, I think you were saying this too, it's like.

Leah Knobler: You know, you have to remove your ego. Like at the time in education, you know, I had like two master's degrees, blah, blah, blah. And you know, to be like, okay, I'm kind of starting over, but like, I wanna work

[00:18:00] Leah Knobler: here and, and let's do this. And, and so it all worked out. They took a chance on me and. Now they're stuck with me for at least another couple years.

Leah Knobler: I think it's, it's been a wild ride.

Reggie Williams: That's awesome. Um, how did you, in that process, you mentioned going up for a role and then being not, not a fit. Like how did you navigate staying in play, uh, during that time? You know, and not just like dismissing it completely?

Leah Knobler: You know, it's a good question. Um. I just was like, you know, I really, I really want this.

Leah Knobler: I'm, I I was pretty determined. Yeah. And, you know, I just stayed close and, you know, I subscribed to the blog. I, you know, kept up to date and then I was like, oh, now this is, they're hiring for this. Yeah. This is the one. And it, it was more transferrable. My skills coming from education and being a teacher to, you know, people and culture.

Leah Knobler: There's a ton of overlap. And I think some of the best, you know, recruiters too come from non-traditional backgrounds. Absolutely. And, you know. I was

[00:19:00] Leah Knobler: able to trick them.

Reggie Williams: Well, I'm sure they glad you tricked them because now you're a VP of people. So, um, that's, that's really, um, I think a, a great point around just like, sometimes the, the, you know, stick with it attitude can actually be a good signal for, for them on your, you know, excitement around the company.

Reggie Williams: Um, I've definitely taken bets on people that were just, they were just more, uh, more excited about the opportunity, so That's awesome. Um. Now moving a little bit to, you know, as the company scales, you're, you're starting to grow. Culture is starting to become a thing. At the beginning I think culture is like this amorphous thing, but then it starts to be the real kind of area where you want to, um, I.

Reggie Williams: Where companies want to get better at. And oftentimes you as the head of talent or the the talent person is, you're kind of the culture carrier in a way, and you're shaping the culture with each hire. So you're kind of defacto, uh, involved in this

[00:20:00] Reggie Williams: process. But, um, maybe Heather, if you can talk through.

Reggie Williams: Your experience building out culture across offices. I know you've done that even internationally and having to navigate that, which is probably a whole a, a big thing as well. But anything that you implemented early on that still sticks around and, and any general advice on like culture as you build and grow.

Heather Brouwer: Yeah. Um, Samsara did scale quite a bit when I was there. We opened a couple offices and I think one of the tricky parts was how do you keep the culture consistent across different departments and offices, right? So we had a London office. We had an Atlanta office. I think now they might have like 20 different offices at this point.

Heather Brouwer: Um, and what we would do is we would send leadership there. When we opened up the London office and the Atlanta office, so for me it was more spending time in the office as we scaled up the team. Um, I hired some of the first recruiters in the Atlanta office and made sure that. A lot of the values in the culture of, um, Samsara were, you know, people are seeing it and living it and, and

[00:21:00] Heather Brouwer: getting a feel for how you operate.

Heather Brouwer: And I think that's really important. I think, um, you know, at Modern Treasury we're a little bit smaller. We don't have a bunch of offices. We're just SF New York and remote. Um, but one of the things that I'm thinking about now is as we have more people going into the office, um, I feel like during COVI, we didn't really prioritize leaders.

Heather Brouwer: In office, we sort of were like, oh, great, you're in Indianapolis, well you're in like Indiana or whatever, like, we'll hire you. And now it's, it's really nice to be able to say to our head of cs, Hey, can you pop into the New York office and check in? Mm-hmm. So I think as you start to, um, think about culture.

Heather Brouwer: Who do you want in those offices as culture carriers and making sure that you, um, think about that as you, you know, strategically plan.

Reggie Williams: Yeah, so kind of like injecting some mm-hmm. Existing culture in there. It's hard to do, it's hard to

Heather Brouwer: keep consistent culture across offices and yeah, I don't know if there's any one magic, uh, trick for that, but that's what we've, we've tried to do.

Heather Brouwer: That's awesome.

Reggie Williams: Yeah. Um, Anisha, same question. Building up culture to early stages,

[00:22:00] Anisha Thomas: would you change anything, do anything different from your experience or.

Anisha Thomas: Yeah, intentional in person. Uh, time is really important, um, as you were saying, Heather, but one thing I do different and earlier on is write everything down.

Anisha Thomas: Um, things move so quickly, especially also being remote. Um, usually norms, right? You pick it up, um, just by being in person with each other or maybe through zoom here and there, but codifying norms and writing that down is, is really important. Um. I remember that because, uh, I remember I showed up to a presentation and all my slides were different, and I realized my CEO had changed all the slides because he cares about presentation quality.

Anisha Thomas: And clearly I didn't live up to those standards. Uh, but it was happening to other people on the team too. So I was like, okay, this. This is something, yeah, we need to, uh, write this down and, um, make this part of like our hiring process and it actually

[00:23:00] Anisha Thomas: became part of our values as well and something that we, um, carry throughout our way of working.

Reggie Williams: Gotcha. So like, um, in terms of like. Uh, writing slides and being able to create them. And that became part of your, uh, I guess, assessment of people as it came on. 'cause it was so valuable to the leadership team. Yeah. That's awesome. Um, Leah, any, any big culture mistakes? This is where you get, you have to get juicy here, right?

Reggie Williams: We need, we need the good stuff. So mistakes. Any big culture mistakes? No. It's been

Leah Knobler: perfect for 10 years. No mishires.

Reggie Williams: Oh, really?

Leah Knobler: Um, yes. Uh, let's see. So it was around, you know, 20 21, 20 22 boom times. We just raised series B. We also happened to have a few leadership openings and we thought, you know, we're gonna really scale, we're gonna get big.

Leah Knobler: And the whole mantra became, we wanna hire people who have seen the movie before. And I was just like, oh my God. And our, our CEO kept saying it. It was in like the job descriptions. And I was like, if I have a dollar for every time someone says,

[00:24:00] Leah Knobler: seen the movie before. I could buy a lot of movies. Um, but we were like, okay, let's go do this.

Leah Knobler: And, you know, interviewed a lot of folks at bigger companies, later stages who had seemed successful there. And we were like, yes, that's what we want. And so we hired three folks like this, and spoiler alert, they all lasted about a year and a half. Um. And it was just a huge lesson for us, I think internally that, you know, you can't just copy paste what worked somewhere else, might not work for you.

Leah Knobler: Really figure out what, like, makes your company unique. And in our case, I think we were like, oh, I think maybe we're a little weird. Um, and we need to, you know, really understand that and then hire for that. And it also really led to, for us writing down something we call the practitioner rule where anyone in in management or leadership.

Leah Knobler: Has to still be very much an operator and, and know what great looks like and really be able to hold that bar of excellence and also then know how to hire other great

[00:25:00] Leah Knobler: people. Um, and so it's, that's really transformed I think, since how we've operated and, and we've had like a very consistent, stable leadership team since.

Leah Knobler: And we also looked inward and also promoted from within. And that's also part of how I got to where I was too. 'cause they were like, oh. Yeah. She hasn't done this before, but who cares. Yeah. So I know about movies now,

Reggie Williams: uh, but maybe getting people who know, uh, who, who may fit your movie that you're trying to create versus the movie that they've seen before.

Reggie Williams: Exactly. So that's awesome. It's cool that you mentioned that like. That practice of hiring internally, essentially, like your journey was, I guess a result of the culture. Do you think that came from the founders and how they, you know, their philosophy or was that like a collective thing that shaped as the company grew?

Leah Knobler: Which part? The, like just

Reggie Williams: in terms of promoting from within. Yes. That was

Leah Knobler: a, that definitely came from the founders. As a result of the

[00:26:00] Leah Knobler: lessons learned when we looked else outward and it didn't work out. Gotcha. So that became about, yeah.

Reggie Williams: Yeah,

Leah Knobler: because we had like a lot of like mid-level and director folks who had been here at a long time and we're like, oh, maybe there's something there.

Leah Knobler: Let's continue to elevate and let's see what happens. And that was really successful.

Reggie Williams: Gotcha. Do you guys invest in like a lot of learning and development then? Is that

Leah Knobler: Yes. Every single person on the leadership team has an executive coach

Reggie Williams: really and it,

Leah Knobler: but it's been great and I think someone earlier talked about it, but.

Leah Knobler: If you have money or budget for l and d to get a coach, whew.

Reggie Williams: Worth it

Leah Knobler: very much.

Reggie Williams: That's awesome. Any other culture things or culture interviews that any of your companies do specifically, or is it kind of integrated into the interview process? I.

Heather Brouwer: Um, let's see. We are pretty strategic about how we interview.

Heather Brouwer: We really try to eliminate bias. I think one of the things that we did for a really long time was our CEO would interview everybody. I'm sure you probably have had this

[00:27:00] Heather Brouwer: happen to you. Um, it was great for a while. I think it definitely helps. Scale the culture, and then at some point it doesn't work anymore.

Heather Brouwer: So we're just really focused on building a strong interview process and making sure that we are also looking at the little details too. How do they treat people through the process? How do they interact with everybody? Um, that's really important. How are they, how prepared are they? Uh, things like that matter.

Heather Brouwer: And so it's, it's all of those little cues that you can pick up on that I think really help in terms of the culture.

Reggie Williams: Yeah, I think, uh, just making sure to like, inform the team around like, Hey, if you notice. Things like that. Like put that in there. Yeah. Like that's important. And that's

Heather Brouwer: where the debriefs come in, right?

Heather Brouwer: Yeah. Yeah. Like that's so helpful. Um, you know, for RC has a experience that's not positive that matters. Yeah. And so we wanna hear about that. So all of that adds up.

Reggie Williams: Yeah. So important I think. Yeah. For signals other than the official interviews, like the recruiter, you know, uh, scheduling the interviews and things like that, or, um, even their response and how they kind of respond

[00:28:00] Reggie Williams: afterwards.

Reggie Williams: Um, there's, um. I remember during one of my processes, I got, uh, we started to give feedback to candidates mid, uh, between interviews. And actually a lot of the signal is like not. Like the exact feedback that we gave, but like how did they respond to that? Yeah, that would be interesting. Um, like did they take that and like become defensive about it and like, you know, get drop out?

Reggie Williams: Did they follow through and um, learn the next time and kind of brought that, uh, became a straight, you know, did they, you know, show that skill set in the next interview? Like that was a good signal too. So that's a great idea. Yeah. Awesome. Um, talking about headcount and just that being the challenge, I think.

Reggie Williams: You know, for a lot of teams it's sta lean, right? Increased impact. That means expectations are higher for each individual. But just thinking about headcount planning today has to be so hard given also the advancement in ai, not only how our teams use ai, but how our functions changing their jobs based

[00:29:00] Reggie Williams: on the, the innovations in technology.

Reggie Williams: So like, would will engineering look the same in a year from now that it does today? Probably not, right? So. How do you go about and maybe lay a first, just thinking about having these conversations with each individual function, given this rapid change in ai.

Leah Knobler: Yeah, I mean it's, I don't know about all of you, but it's very weird to be riding like a current wave of some revolutionary technology and you know, we don't, there's no playbook to just copy paste.

Leah Knobler: So I think the conversations we're having is just how do we. You know, roll out AI internally and how do we do it strategically and what are each team doing? And so right now it feels very much like just a little too wild west. So we're, we're trying to reign that in and, you know, our last people team meeting, we just was really spent like, I wanna know how are all of you using ai?

Leah Knobler: And let's take, write it down and. Then I'm gonna go back and share with our leadership team. Then I want

[00:30:00] Leah Knobler: every other team to do it, and then we should all keep it in our, you know, shared knowledge base internally. So everyone knows like, okay, how, how's engineering using ai? How's the product team using ai?

Leah Knobler: Let's start with that and, and just understand it instead of these sort of like siloed kind of one off moments. But, and I think the other thing too is now it's like, all right, if someone, you know, moves on and it's not an automatic backfill, it's like, okay, well maybe can. We get by using AI or a person with AI doing something differently than we had before and.

Leah Knobler: Yeah. So that one's, that one's unfolding as we speak. Yeah,

Reggie Williams: these are like brand new conversations we're having about headcount, right? Like, it's usually, alright, backfills another person. Now you're like, well, does this, is this a person? Um, and you know, then how do you onboard new tools and technology where people might feel threatened by it?

Reggie Williams: Um, that's a whole, whole whole big thing there. Um. Maybe Heather, same question for you.

Heather Brouwer: Yeah, I mean, a lot of similar points to Leah. Um, you know, I

[00:31:00] Heather Brouwer: think if we were to add another member of the, to the recruiting team, I'd first have to go and look and say, how do we, do we really need this? Or can we use AI to, um, do a lot of the work?

Heather Brouwer: I, I mean, Ashby's already built in so much AI and it really has. Saved a bunch of time with scheduling. Yeah. Um, sourcing all of that. So I do, I do think that that optimization's really important. I think you get to a point where you do need to make another hire no matter what. And um, so that's where that headcount conversation is changing.

Heather Brouwer: Yeah. Also on other departments we have, I. A pretty big engineering team. But now, you know, in the management meetings, a backfills, not a guarantee. We're looking around saying, okay, we have all of these AI tools that ENG is leveraging. Let's get them ramped on that and give it a couple weeks and see if we need to, to do another, you know, backfill.

Heather Brouwer: So it's changing and that we just have to be really flexible.

Reggie Williams: Yeah. And kind of, um, I would say like even be proactive about thinking about it. Yeah. Because we know our leaders are thinking

[00:32:00] Reggie Williams: about it. Yeah. They're like, what? What can we replace with this? Are, are there areas at least that we can become, um, more efficient or empowered?

Reggie Williams: And so I think taking it into your own hands to be curious about it is, I mean, I think has been mentioned time and time again today of just experimentation, you know, using things and, um, but just coming out with the POV. Even before the business asks, I think is really important. 'cause then you can kind of drive the conversation versus being on your back foot.

Reggie Williams: Like, oh yeah, I guess we can, we should be using this. Um, yeah. So, um, that's a great point there. Um, Anisha, your, your company creates AI agents, so I'm assuming that's, this is just all top of mind for you, but keep Totally,

Anisha Thomas: yeah, definitely. Um. I, yeah, we just don't want there to be a disconnect between what we're selling and building and how we operate internally.

Anisha Thomas: It's super important for us to be AI enabled. Uh, and so of course I'm like looking at my own tech stack and AI solutions,

[00:33:00] Anisha Thomas: but also being brought into conversations with other, um, org leaders, uh, right for. Increasing productivity and development cycles with our engineering team and same with Go to Market and ai, SDR and implementing that.

Anisha Thomas: And I think it's also really knowing what are the use cases where AI actually will be valuable, um, because it's not always amazing. Um, and really knowing when we actually do need to go out and hire. Uh, so that's why I'm being brought into these conversations. Right. It does impact headcount. Yeah. At the end of the day.

Reggie Williams: Yeah. And you know, I think the argument is does it replace people? I mean, the reality is teams will be leaner, um, most likely. And, and that means like people will have to leverage this. My, my, my vision and what I think is that I. Every recruiter, whether you're a smaller company or a larger company, you'll essentially be a, a mini recruiting practice.

Reggie Williams: You might have sourcing bots that go out for you and do things or screen candidates for you. Right? And so just being,

[00:34:00] Reggie Williams: uh, ena like allowing us to enable, uh, people I think would supercharge the team. Um, but we're one last round robin question. We're in 2030. So where I'm transferring us and zooming us forward to 2030, what parts of the process are still human?

Reggie Williams: Hmm.

Leah Knobler: I mean, I mean, I think all of the like candidate interactions still will be human. I don't know about all of you, but I don't wanna be hired by an A bot or an agent. I would like to still communicate with the human and get excited about people that I'll be working with. And so. You know, we'll fast, we'll rewind 10 years out and say, we're gonna, we're gonna record this and play it back.

Leah Knobler: I mean, to

Reggie Williams: record.

Leah Knobler: And I'll be like, oh, what was I talking about?

Anisha Thomas: I like human connection. Awesome. Yeah. Plus one, the relationship building side of things. I, I really do wanna talk to candidates about culture. Team dynamics, really see, is this gonna be a fit or not? And so AI is great for, yeah, the sourcing and other aspects, but,

[00:35:00] Anisha Thomas: um.

Anisha Thomas: I like talking to humans. Yeah.

Heather Brouwer: I, I mean, plus two, um, I think a lot of the senior recruiting roles, so like executive directors, those higher level roles for sure are still gonna be very high touch. Um, I think that maybe you know more, um, evergreen res that you have open all the time, those are probably gonna be more automated, at least the initial stages of that.

Heather Brouwer: And I don't think that's a bad thing. I think. Some of that recruiter phone screen can be really monotonous if you have to do like 10 phone screens a day and say the same thing. La la la la. Um, I think we've all been there. So I'm actually excited to see that change. Um, yeah, I was, I was actually, um, talking to someone the other day.

Heather Brouwer: He was like, oh, what do you do? And I'm like, I'm a recruiter. He is like, oh yeah. I's coming for you. And I'm like, oh geez. You know? And I, I really don't think that's true. I think we're all just gonna adapt and change. Um. But I think it's gonna be interesting. One thing I would really like to see is I would like to not have to use LinkedIn recruiter by

[00:36:00] Heather Brouwer: 2030.

Heather Brouwer: I know it's like maybe a hot take, but I'm standing by. I think we, we've spent so much money on LinkedIn recruiter. Um, I think, uh, maybe over $75,000 a year right now. And it's just wild. So I'm really hopeful that all these AI tools are gonna figure out a way to, uh, change the game. Awesome. Maybe make a move a little faster.

Reggie Williams: All right. We'll see. Shots. Shots taken. Shots fired. All right. Thank you guys. I think that's good. You have panel? Yeah. Salsa. Thank you guys for this panel. I think it's great to. Get insights into it. What I've heard is early focus on results, build part, real partnerships with the f, with the founding team.

Reggie Williams: Um, and then as you navigate your career, I think it's just about, you know, how do you scale your team, scale yourself, leverage these tools. So hopefully you all got some Gs out of this and um, yeah. Thank you. Thank you to panelists.

Heather Brouwer: Awesome. Thanks Reggie Regie. Thanks everyone.

Key Takeaways

• Do what you say you'll do - Consistency and follow-through build trust with founders and hiring managers in early-stage environments
• Results speak louder than experience - Making successful hires establishes more credibility than theoretical knowledge
• Know your weaknesses and hire accordingly - Understanding skill gaps in operations, branding, or sourcing helps you build your TA team
• Document everything in remote environments - Written norms and processes maintain culture consistency as teams scale across locations
• Stay hands-on regardless of seniority - Leaders maintaining operational involvement better navigate team fluctuations and economic uncertainties
• Experiment with AI before being asked - Proactive AI adoption positions talent teams as strategic partners in organizational efficiency