William Leonard
Hey everyone, welcome back to the Atlanta Startup Podcast. William Leonard here, your host for today, and I’m excited to be sitting down with Peg Olson, who’s the founder of jPEG Executive Search. Peg, thank you for joining me this afternoon.
Peg Olson
It’s awesome to be here. I’m excited to chat with you.
William Leonard
Likewise. And you know, today’s conversation is going to be tailored really around early-stage startup recruiting and you are an expert at this. And so we’re going to do a deep dive today and our audience is going to have a lot of takeaways and insights. So I’m excited, but let’s take it back a step and start with your background. Who is Peg? Give us the Peg Olson story.
Peg Olson
The Peg Olson story. Well, I’ve done this for three decades, so that could be longer than you want this podcast to be. But I grew up in Maine in a small town in rural Maine. Went to college in Colorado, and moved to California. Never thought I want to be a recruiter when I grow up, but about three decades ago, I started as a recruiter. I’ve always been a generalist recruiter, but I’ve worked both in-house and for search firms but started my own organization in 2009. Because when I look back in my career, the things that I loved the most were helping founders and earlier-stage companies that were growing scale their teams. I would get bored just recruiting for accounting, finance, or sales. I love helping build a culture for a company and honestly, I guess wanting to be more, not just independent, but I wanted to be able to choose the people that I wanted to work with, the companies that I was excited about. And I wasn’t afforded that in other roles. So that’s why I’m here today. I took the big leap in 2009 in a horrible economy, but yeah, so far so good.
William Leonard
Yeah. I was going to ask about you starting in 2009 when there was probably more firing than hiring going on. What was that experience like for you?
Peg Olson
Well, I guess it was a leap of faith because everyone was telling me I was absolutely crazy for doing that then. But I’d been through economies that were pretty cyclical like that before. I graduated from college in a poor economy, moved to California, and then we had the.com to age myself boom and bust and had the opportunity to, unfortunately, see those situations previously. So maybe it was just kind of my gut instinct on I’ve survived it two other times, I can survive it a third time and it worked and I’m thankful I did it. If it weren’t for my previous experience with some of the other situations that I was trying to walk away from, I wouldn’t have had, I think, the contacts across the country and the courage to actually do that.
William Leonard
Right and let’s talk a little bit more about jPEG and the types of clients that you all look to serve today. And then we’ll definitely go deeper into your experiences and insights on early-stage recruiting.
Peg Olson
Okay, great. Well, when I started my own firm, because I’m a generalist recruiter, I really needed to kind of focus on a niche and create a niche for myself. So I fell in love with companies that have a mission. I had been exposed to healthcare, and a majority of my career had always been focused on B to B or B to B to C. A lot of fintech, a lot of technology companies that were so big in California when I lived there. But I love companies, I guess, at my age, where they have a mission to help people. So since I started my business, I have focused exclusively on health tech B to B, B to C, companies that are at various stages. So Seed Stage through post IPO sometimes, but Seed Stage, you just don’t do as much of in the space because they’re worried about burn and all of that. I have one right now I’m working on. Is that good?
William Leonard
Yeah, no, that’s great. And I want to take this conversation a bit further now. And you’ve been doing this like you said, early-stage to IPO type of companies. And I would say the majority of our founders here are early-stage, let’s say C, Series A, Series B, and some probably a bit later as well. Let’s talk a little bit more about stage-appropriate startup recruiting, and what those types of roles look like at each stage there, because it sounds like you see the entire spectrum here, and many people are fundraising right now. Some are getting capitalized, some aren’t. And oftentimes in investor conversations, VCs like myself and our team at Valor, we want to know what’s on your roadmap. What are you going to do with the capital? And oftentimes the greatest expense there is going to be building out and expanding the team. So I would love to get your insights on how you see that taking shape at the early stage.
Peg Olson
Absolutely. To your point, I think there’s a huge investment in hiring, but a huge loss if you don’t do it well. Replacing people is so expensive, not only for the time, but it can be disastrous and make or break, especially at the seed stage. I’m assuming a lot of your seed-stage founders are first-time founders.
William Leonard
Yeah, the first time. Some are founders as well.
Peg Olson
Okay. I just noticed a huge difference in Series A in working with founders that have been there, done that, and the newer founders. So let’s focus maybe on the newer founders since there’s, I think, different nuances there. I think my approach is it’s very consultative. With Seed A, you oftentimes have to coach the founders a lot on some of the processes that you need to build out in order to be successful on the back end. And what I mean by that is, for example, how do you do a job description? What should be your next fire? They need to be coached, which I’m sure you do a lot of that from your side on what is that roadmap, what does it look like? So, for example, Seed Stage, I do a lot of first sales leaders because that’s typically the first person that they’re looking to hire and oftentimes it could be engineering and product as well, but it just depends on how far along that Seed Stage company is. So it’s not only about building the job description but figuring out who is on your interview panel because that becomes really important when you’re thinking about drilling down on the skills and the fit for the company. So that’s super important is to communicate that across the organization. I see a lot of companies not do well because the left hand isn’t talking to the right hand. So I think being super transparent with what’s happening, what your charts looks like today, what it’s going to look like down the road, these are the positions we intend on filling. And then the job description is a really good tool because I think it makes the founder or the leader doing the hiring focus through what’s our why? Why are we here, what’s our mission, and how do we sell that properly to people? What is our roadmap, what’s our platform? Why would a salesperson want to go out and sell that in the market? Or why would an engineer want to work on any of your projects? Right? So depending on the role, you would kind of gear your conversation accordingly and then the what of what are you going to do to add value and the benefits that the company can offer. So you need to think through all of that because it’s an important part of trying to attract talent today. Does that answer your question? I could walk you through examples of what a Series A like, a sales leader might like, and what you might look for, as opposed to an A, B, and a C, if that would be helpful.
William Leonard
Yeah, I was going to that next. I think that would be incredibly helpful because that is oftentimes, like you said, the first hire that people are going to make at the Seed Series A Stage when they’re trying to they’ve got product market fit. The CEO has been selling for the first maybe half a million dollars of arr and now it’s time to institutionalize your sales process a bit and bring on that formal hire. So what do you see in that process?
Peg Olson
In that process, post job description, you try to figure out where in the market are these people sitting. Most of my searches are all direct, sourcing, and very targeted to the market that they’re in. And it’s not always the exact same product, but a product that’s similar in B to B, B to C, whatever the case may be, where you would have great transferable skill sets because they need to come in and hit the ground running quickly. Oftentimes budget constraints, you’re not going to go into the market unless you happen to get extremely lucky to find someone who’s had coming off a huge exit and they can work for the comp that you’re probably willing to pay at that Stage. So most of those searches I target someone who’s been promoted, you want to see that they’ve done well, met the quota, three to seven years experience maybe. Hopefully, they have managed a couple of people. If they’re a super shop, it could be one or two. Maybe they’ve built a little region within a company that has scaled and they know what a good process looks like. I think that’s really important. And oftentimes to attract that talent, maybe they’re a director, a senior director, they’re typically made a VP level person. So as opposed to if you go to A, Series B, and C, typically that’s where you find someone who’s built out the process of lead gen. They really get knee-deep in helping build out all of the technical aspects of what it takes to sell. And in both Stages, I think the founders really, need the lift. Founders are typically the first salesperson, right? So for example, the CDA I’m working with right now, he’s closed three or four deals but he is so overwhelmed that he needs someone tactical to come in and help either execute on those deals and he’s probably always going to be at the table still when those deals are being signed. But they need somebody who can give them that lift and can hit the ground running quickly and exponentially accelerate the amount of deal flow potential that’s coming through. Hopefully, that is clear. Series B, you would basically expect that person to have a little bit more experience. Again, hopefully, if you could find someone that’s been there, and done that with a successful exit would be good. But they should be able to close more business I think at that point than the CEO. So they come in, they build out the lead gen and the marketing. But they have to be scrappy because they’re probably going to be the only person doing that out of the gate. Right then it will transition to a point once some of that process is established that they would bring on another salesperson and it could be someone more junior. But the CEO doesn’t need the sales team as their direct report. They will just get too bogged down. So that person is someone who when you drill down, how have they scaled, how did they build the lead gen, how did they hold the team accountable to bringing in qualified leads? That 50 to 75 calls a day I used to make back in the day. How do you hold them accountable for that? And once you get beyond Series B, Series C, and greater, the sales leaders that I’ve looked for the kind of really more Chief Revenue Officer, they really understand the go-to-market strategy. They’ll usually have marketing and customer success and some of the other functional areas underneath them and become a true strategic partner to the CEO and to the executive leadership team. So they’re all very different.
William Leonard
Yeah. And you’ve seen the spectrum of startup life cycles, boom, and bust here over the last decade or so, starting in 2009 and then really the last couple of years, how the bull market has come to an end, and now we’ve entered the bear market. And how would you say recruiting at the early Stage has evolved since 2009?
Peg Olson
Okay. I think founders need to adapt to how things have changed, not only due to the recent market but post-pandemic. And what I mean by that is, I think we all, during the pandemic, had a window into people’s lives. Right. You would see, oh my God, William didn’t shave today, and Pegs in her stretchy pants again. And you’d see kids running around, dogs barking. And leaders today, I think, need to be as much EQ forward as IQ forward. And that’s super important. And companies that don’t screen for that, I see fail. So it’s not just about the technical skill sets. The other misnomer that some of the leaders have had as well, is the market, there have been so many layoffs. We’re going to be able to go out there and find someone cheap or someone who’s desperate to get in and whatever so that I have not found to be the case. It’s interesting, that even though there have been a lot of layoffs and things happening with tech companies across the country, candidates are getting jobs really quickly. I offered up during kind of the beginning of this whole swirl that was happening. I offered up 5 hours a week to kind of help people that had been displaced. And it was very interesting because I would have my first meeting with them and set up a call two or three weeks later. And they almost always had established a position already, which is great. But leaders, you really need to be able to sell, especially if you’re Seed or Series A. You need to be able to sell your value, prop the growth opportunity that’s there, the platform, and what your roadmap is for that. What your burn rate is. That big question I get today is, what does the runway look like that I’m getting myself into? And also they’re going to really look at the founder. If you’re Seed and going to Series A, is this founder backable? Is it someone that you’re going to be able to go into this competitive market where it’s harder to get funding and command that? So that’s what I’m seeing with a lot of the candidates I’m talking to now. I think people are still very open to doing early Stage, but they are really savvy and they’re doing their due diligence. So the founders and leaders need to be prepared on how to execute on that and also do it nimbly with good process, and good candidate experience.
William Leonard
Right. That’s excellent insight. And I want to go deeper on that point there because you talk about how leaders should be able to sell the value, prop the vision, the mission of the company to these ever increasingly savvy candidates. Now, I guess from the candidate’s perspective and from the founder’s perspective, looking to bring on talent, we can start with the founder’s perspective. What are some of the types of questions that they should be asking to understand how these candidates think? And then I’ll turn it over to the candidate side. What should they be asking? You hit on a few of them, runway burn rate. What is the vision of the company like? Can this founder actually go out and raise funding for the next successive round? Those types of things. Walk us through what those questions look like from both the founder side and the candidate side as well.
Peg Olson
Okay, well, from the founder’s side, I think past performance is indicative of future performance. So that is huge. Is really drilling down, and it comes back to the process. Right. So if you’re looking for a sales leader, what are the key things? Because it’s a little bit different with every company, right? And what you need to drill down on. But you need to figure out who’s going to be on the interview panel. Everybody needs to be on the same page. And you want to drill down on have the person assigned to the interview, each one evaluates I don’t think I’m articulating this clearly, but each person evaluates a certain specific skill set that you need. And you take that internal expert right, or an advisor, someone who really knows that for sales, you want someone who’s been there, done that. With sales accounting, you don’t want the sales leader to be the final decision-maker on your account. Right. So you need to really drill down that way and get a ton of examples from the candidate. And you’ve got to sometimes ask it three times before you get to the real meat of the answer, but really getting specific examples because that past performance is going to be super indicative. And as far as evaluating, there are tons of tools you can use to evaluate. I offer those assessments on EQ and all these different personality profiles. But I think really earlier Stage founders get if they’re not as confident about bringing on people, they’ll use that as a crutch, and it’s really just a guideline. It’s not an indicator of who you should hire. But I think there are certain qualities that you need to have today. Grit, right? Has someone been scrappy? Are they used to working with minimal resources? Are they comfortable with that? Are they comfortable with ambiguity? Because what was yesterday is not tomorrow and you have to be comfortable with that. The culture fit. I mean that’s huge and that’s a whole separate podcast. But do they fit with the team and does the team complement each other and do they bring different and unique skill sets to the table so that you can be successful? Creating a culture where it’s safe to fail and safe to agree to disagree so that you can create a better outcome is really important. And the EQ I think is again super important. Just as a leader, especially not especially across the board, it’s important to have a mix of both now.
William Leonard
That’s great insight, Peg.
Peg Olson
Did I hit all the points?
William Leonard
Yeah, you did. As we wrap up this conversation here, you’ve been doing this for, like you said, three decades now and you’ve seen some great companies form from initial relationships that you were able to connect and be that glue. And so from your perspective, I would love to hear maybe one or two of your best recruiting stories or outcomes that you can talk about today and some lessons learned in those stories as well.
Peg Olson
Yeah, I have a few and after three decades you think about I started with no computer phone, I had a landline and a phone book. Then we had the internet and the cloud and now we’ve got AI which is creating a whole different world for recruiting and a whole separate podcast but one of the first ones, and it might be too, just that it was so much fun and probably made me fall in love with this crazy world of growth Stage. It was actually a startup done by E-Trade out on the West Coast and they acquired a company that had two or three people and they were building out their entire mortgage lending business and it went from the heyday of real estate in 2000, 2001 was huge. And I was there first and only recruiting a hire and we scaled it to about 2000 people within two years. So that was a rocket ship ride that I really learned how being thrown into. I built out their entire leadership team right on down except the loan processor level and the company had great outcomes so it felt satisfying walking around the halls of the company at the time we weren’t remote and you had helped build that. So that I was proud of. And then fast forward, the most recent one was actually in healthcare technology and ironically I got referred to them because of that gig I did at ETrade many years ago. They brought me in initially as a consultant but the company is Labongo. If you’re in healthcare, you probably know they were acquired by Teladoc, but I came in when they had about 50 or 60 people and helped them scale through to the IPO. And then the acquisition of Teladoc, which was the largest $18 billion acquisition, but had the opportunity to not only work with an amazing group of people but help build out all of their teams and execute on that. And there’s nothing like helping a leader create a culture within their own department that ties in with the overall mission and values of the company. I would say those are two of my favorites. And it comes down to people when you just love the people and you love the mission. What started as a twelve-hour consulting gig worked into a 70-hour consulting gig on top of running my own practice for a couple of years. But it was a blast. Sounds like it. No, those are great stories and definitely Lavango is one of the notable names in the world of healthcare.
William Leonard
This was an amazing conversation. How can some of our audience, maybe those who are early-stage founders, get in touch with you or someone on the jPEG team?
Peg Olson
Sure, you can email me at peg@pegolson.com. That’s probably the best way to get time on the calendar. If I don’t have time, I could have you talk to one of my directors if you need to learn more. And one other point I’d like to add that sometimes leaders don’t think about, but really having your own great bio out there on LinkedIn, because anyone, when you’re trying to attract talent, the first place they’re going to go is, who is this person I’d be working with and what is their company like? So even if you’re super early Stage, having a basic company page set up, making sure all of your employees have a standard company name that will pull everyone in to show the amount of number of actual employees, you have, and making sure that your leaders are super buttoned up in kind of giving a feel through their bio of what they would be like to work with and engage with.
William Leonard
Yeah, so it sounds like a little bit of an online presence that is pretty uniform, but also enables employees at the company to showcase their individuality.
Peg Olson
Absolutely. And that’s where the EQ comes in, right? So just a little bit. So they go this person seems like they’d be interesting to meet with because it is competitive out there. And I think even at a very early stage, it doesn’t cost money to do that, but it will give you huge traction on the back end if people are all aligned on your team.
William Leonard
That is an excellent insight and piece of knowledge there and I’m sure you’re not going to charge us for that.
Peg Olson
One, but I help people a lot with that, actually.
William Leonard
I love it. Well, Peg, this was an amazing conversation and I think the insights that you shared around what to look for from Hires, specifically sales leaders at Seed Series A, Series B, and beyond is important as a lot of the founders that listen to our podcast think about scaling their teams and businesses with talent. So, Peg, really appreciate your insights today.
Peg Olson
Thanks. Well, if there were a magic formula, there would be no need for me. Right. It was awesome to be here. Thank you so much.
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