Deep Dive with Jess Hunt

Intro: Welcome to the Daily Bolster. Each day, we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- Founder and CEO of Bolster, and I'm here today with Jess Hunt. Jess is a Senior Technology Operating Executive. She is an independent board member and a CEO advisor. She has a lot of experience working in some really interested talent oriented marketplaces, which we're going to talk about today. Jess, welcome to the Daily Bolster.

Jess Hunt: Thanks, Matt. Glad to be here.

Matt Blumberg: Yes, so I love doing these Friday interviews because I get to walk with someone through their career, and I feel like you learn so much when you take that journey with someone and understand not just how they got where they got and why, but what were the things that they brought from one thing to another.

Jess Hunt: I love it. I agree.

Matt Blumberg: So my research on you begins at Gerson Lehrman Group, and I don't know if there's a chapter before that that was missing from LinkedIn.

Jess Hunt: Well, it was grad school. The chapter before that was grad school. I was studying to be a human paleontologist all through my 20s.

Matt Blumberg: Okay. What is a human-

Jess Hunt: It has almost nothing to do with the rest of our conversation.

Matt Blumberg: I don't know if that's right. If you worked in labor marketplaces, what is a human paleontologist?

Jess Hunt: I was studying human evolution, specifically early hominid evolution. So when our ancestors started to walk on two legs. So I studied fossils.

Matt Blumberg: Okay, well, so now I'll ask, how did you get from that to not academia? Because there's really only one thing you do with that.

Jess Hunt: I had the good luck of overlapping in school with some of GLG's founders, and I left academia knowing I wasn't going to cut it. And I was lucky enough to get an entry- level position at what was a very interesting startup in the late 90s and early 00s in New York City. And it was an internet- based non- MarTech startup that was an early talent marketplace.

Matt Blumberg: So I'm a big fan of GLG. I have gotten to know in different ways over time G and L, but actually years after they I think had both left the business. In a lot of ways, GLG is a good comparable for the first part of the Bolster business model, the marketplace for fractional executives. So talk a little bit about your time there. I think when you left, you were either running sales or you had a very senior executive role. It sounds like you were entry level to begin with.

Jess Hunt: That's right.

Matt Blumberg: Talk a little bit about your rise there and also how that coincided with the rise of the business. The one thing I've never known about that business is was it an overnight success or was it one of those companies that took 10 years to become an overnight success?

Jess Hunt: Well, I wasn't there the first couple years. I joined and I'm sure that I wasn't one of the first 50 employees or even 75 employees. And so I imagine it as an overnight success. Certainly, we got big quickly in the first couple of years and we also became profitable rather quickly and had some really interesting inquiries to bias. We were building a new category that was an alternative to sell- side research. And so we were creating a category and we were a challenger, and that was a heck of a lot of fun and I think we were unusually successful in the beginning. We'll have to ask G and L about that.

Matt Blumberg: Right. And what made the business tick? Did it turn something that wasn't an organized marketplace into an organized marketplace? Did it create demand for something new? Was it a little bit of both?

Jess Hunt: My perception is that we had product market fit very early and the market that we were in were ready, ready buyers with relatively big budgets for what we were selling.

Matt Blumberg: That sounds like a good formula right there.

Jess Hunt: You can get that and we will also, over time, it didn't feel like it in the moment, but we ultimately benefited from the regulatory environment, which was expecting certain compliance from our customers and from our platform. And we invested heavily in being independent, not part of a bank and we invested in compliance. So I'd like to think we made a lot of good decisions in the first five to 10 years about the kind of platform we were building. And then we benefited from the internet. LinkedIn came along while we were, I don't know, six, seven years old and we were using note cards in the beginning. I think they're probably framed in the office somewhere now, but the way in which you could find people at the end of the 90s and the early 00s benefited us a heck of a lot. So we were lucky in that regard.

Matt Blumberg: Yeah, it's funny, I had never thought about the compliance element to that business and it reminds me of something that I want to ask you about. So one of my mentors, someone I worked for years ago at MoviePhone, used to say that people bought products along what he called the fear greed continuum, and that you could buy things because you were afraid to, you had to. You could buy things because they were going to make you more money or make you look better or whatnot. And the best businesses are the ones where you had both. Did you all have both?

Jess Hunt: I don't know that I've ever had such a fear greed combination in any business I've worked on since, because there was certainly an element of you were able to say, here are the hedge funds that are working with us now. Wouldn't you like to be one of them? And that was probably more effective there than any other business. And of course I've been in sales and marketing for a really long time in any business since.

Matt Blumberg: But compliance is something that will just make people make decisions about things because they feel like they have to.

Jess Hunt: Right.

Matt Blumberg: So that's interesting. So now many years later, you've worked at lots of other different places. Have you ever used GLG as a client?

Jess Hunt: I have, and I'm also an expert in the network and I occasionally do phone calls.

Matt Blumberg: Yeah. I have done one or two of those over the years. And they're always interesting because they're just kind of random.

Jess Hunt: They are random. This is the thing about labor marketplaces is that labor marketplaces, if you're a part of the supply side of a labor marketplace, your experience can be a lot wonkier than if you're on the paying side and the customer side. And I'm sure you see this at Bolster and that's true for every labor marketplace I've worked on.

Matt Blumberg: Yeah. Okay. So from GLG, the next step in your career was at Axiom Legal.

Jess Hunt: That's right.

Matt Blumberg: And Axiom Legal was actually one of the original labor marketplaces and trying to bring that to lawyers. One of the things that I always really admired about Axiom, and we were a client of Axiom's right after they got started at Return Path, we used Axiom for a couple of things.

Jess Hunt: Oh, cool.

Matt Blumberg: And I thought what was so interesting that they did was effectively was they basically productized a service. And when I think about labor marketplaces, successful, high- end labor marketplaces, they're really good at productizing a service. So I'd love to hear about your time there and does that resonate as one of the success factors?

Jess Hunt: Yes, yes. And it reminds me of something. So at GLG, it was one of those experiences where when you're at a startup, and I was there for the better part of 10 years and I got to make a lot of mistakes and wear a lot of different hats, but mostly I became a sales leader, a sales and marketing leader, and a general manager there and helped to build the enterprise business. And that's sort of all the businesses I've been working on since we've been enterprise businesses. At Axiom, I was really ready for... At that time, Axiom and GLG were about the same age, but Axiom was actually, I think maybe by then it was bigger. And so I took a job to have a bigger P& L and more people. And scale was really important to me. By then I felt like I had had some functional expertise and I wanted to put it to use. So that was great. But I learned a lot at Axiom. And one of the things that I reflect on that Axiom got right was brand. And I think that's related to your point about productization. I did lots of research before I joined Axiom and I would call customers, anyone I could find and Return Path would've been an odd customer at that point because we were mainly working for large enterprise, so we were innovators on so many things. And you called a customer, and Axiom as a service was so locatable for them, which is really interesting because it's a legal. Legal tech has changed a lot, but at that time, to have such a strong brand, was something that the founder and CEO and a founding team were really deliberate about and invested a heck of a lot in. And I think I probably, to be honest, took brand for granted until that point. And I think I probably thought my investments in brand were potentially wasted, or at least half of them are as the saying goes. And I don't take that for granted anymore.

Matt Blumberg: Yeah, no, it's a really good point. I also think there's something about being known as the first brand in something or a pioneering brand. And Axiom really was. And obviously not the first law firm or not the first collection of lawyers, but they brought that notion of lawyers on demand on a platform to the world.

Jess Hunt: Right. It was also, on the supply side, it was a really interesting alternative path for attorneys. We had hundreds and then eventually thousands of attorneys. And if you're an attorney that doesn't want to work at a big firm and wants more flexibility than in- house, especially primary caregivers in certain stages of life, Axiom is a terrific, terrific path.

Matt Blumberg: And actually that was our use case. So we had essentially our general counsel, but we didn't need a full- time general counsel, and it was a mom who was extraordinary an lawyer, caregiver, and she ended up coming in- house after many years.

Jess Hunt: I love it.

Matt Blumberg: But in- house in a more flexible way, because we still didn't need full- time, so.

Jess Hunt: Fractional labor.

Matt Blumberg: Fractional labor.

Jess Hunt: We too are believers.

Matt Blumberg: Going to be big. So let's talk about Andela. Andela, in some ways, it's similar business, but actually quite different in a lot of ways. And why don't you actually tell people first what Andela is because I think it may be less well known than the other two, and a little bit about the things you did there over time.

Jess Hunt: Sure, sure. Andela is a company that offers fantastic, fantastic software development talent to companies on an outsourced basis, but it feels insourced and today, Axiom's software talent all over the world. But Axiom's heritage is in Africa.

Matt Blumberg: Andela.

Jess Hunt: Sorry, Andela's heritage is... Sorry. There you go. Andela's heritage is in Africa. So we started in Nigeria and by the time I joined, I think we were in four countries. And so we benefited from remote work, we benefited from technology and the flexibility that software teams and certainly technology companies have to work with talent all over the world. And so we believe there was such big pools of extraordinary talent in places in the world, especially in the African countries we were operating in to offer exciting opportunities for that talent and to offer exciting talent to software companies primarily in the US but also in Europe.

Matt Blumberg: Yeah. So this is parallel to my last comment about Axiom. So Bolster is actually an Andela client. We've had a great experience with Andela. We have three engineers in Nigeria and one in Kenya and have for three years. So it's been a good experience for us. The one thing I always was a little confused about is I seem to remember when we started working with Andela, the positioning was that they were a marketplace, but I haven't experienced as a client them as a marketplace so much as just really high quality engineering staffing. Was the business one and then it became the other or is it a little of both or they're different models?

Jess Hunt: I think it is a marketplace, and you always have to be careful when you talk about marketplace business models and human talent. But just like you said before at Axiom, the offering is such that if you're an end user, if you're a customer, you either have a great team that is a part of your company or you have great individual talent that is a part of your team. And so that would be how you would experience it, ideally. The business model itself, the operating model looks like some of these other talent marketplaces we've been talking about.

Matt Blumberg: Oh, interesting. But clients aren't in and out of their... It's so different from GLG where you're getting someone for 30 minutes, right?

Jess Hunt: Totally.

Matt Blumberg: I think we've had an engineer from Mandela for three years.

Jess Hunt: That's right. But companies can scale up and scale down, do project- based work with Andela. I think yours, it sounds like your experience has been ideal. If you've got fantastic talent that you want to hang on and that wants to hang onto you, that's where we'd certainly like to go, and that's the best economics for any marketplace.

Matt Blumberg: Yeah, no, like I said, we've had a great experience with it. The one thing that's challenging with that model, like GLG, you hire someone, you talk to them once, you never expect to talk to them again. Our culture is very people oriented and we care a lot about the growth and development of people on a team, et cetera, et cetera. When someone's a contractor, it's a little bit harder to make that work. And when they're a contractor on another continent, it's even harder. So for example, once a year, we get the whole company together in person because we live in a bunch of different places and we literally can't bring them because of travel visa issues. So there's some things that end up being a little bit disconnected. But yeah, they've been tremendous parts of the team.

Jess Hunt: And I will say that, and at Andela we invested a lot to make sure that for those who could travel, for the engineers who could travel, that they were allotted one trip a year, at least one trip a year, where they would be in person for two weeks with their teams. And so-

Matt Blumberg: You were there before COVID though, right?

Jess Hunt: Yes.

Matt Blumberg: Yeah. I think a lot of things are different after than.

Jess Hunt: I agree.

Matt Blumberg: And then so the next step in your career after that is what you're doing now, which is fractional work, advisory work, board work.

Jess Hunt: That's right.

Matt Blumberg: What led you to make that jump and can you ever see going back to doing full- time executive work?

Jess Hunt: Well, first of all, like you, I'm a big believer in fractional labor and sometimes I hear when people are far enough in their careers, they talk about a portfolio. And I suppose that I'm closer to that than I am as an operator. I'm also an operating partner at a growth equity firm called Longridge with 2 billion under management focused on business tech and FinTech. That's also an important part of my portfolio. So I look at myself right now as enjoying the portfolio while it lasts, but I am definitely not finished operating. I really do encourage people, operators like me, I'm not a founder, I'm not an entrepreneur, to do board work, to do, not necessarily advising, but look for these kinds of opportunities to expand your perspective and continue learning past your functional expertise. And I've certainly found that to be true of some of the work I'm doing right now.

Matt Blumberg: So what your ideal next role is?

Jess Hunt: I think I would operate again.

Matt Blumberg: In what capacity? Do you want to be on the selling side? Do you want to be more of a COO president, CEO? Could you ever found something?

Jess Hunt: The latter. Oh man, I don't have the ideas. I really love working with teams, especially founders, and I've almost exclusively worked with only founder CEOs in my career and I love being next door to that energy shoulder to shoulder with someone who has a vision. And I really enjoy being the person that helps to carry the vision, but is all about the how and reaching the potential of the vision. And I know that about myself.

Matt Blumberg: Well, it is important to know what you like and what you don't like and what you're good at.

Jess Hunt: Totally. Totally.

Matt Blumberg: All right, so probably my last question question for you, unless it leads to another one, is when you approach your... So you are an operator, right? As you said.

Jess Hunt: Yes.

Matt Blumberg: Now you're doing advisory work and how do you approach that? So adding value on the outside is different than adding value on the inside. How did you learn how to approach it? How do you approach it? Is it more of a push model with you or a pull model? How do you make sure you're giving great advice but then actually own the outcome?

Jess Hunt: I do some advising, but I would actually say most of the work, the advising type work I do, I'd like to do through board work. So I've been on inaudible.

Matt Blumberg: Same thing on a board. You don't own the outcome.

Jess Hunt: So on board work, one of the things I've learned is I know if you can take stock and know what you can bring to the table, you find opportunities where they really need what you have to offer. I think the least good board experience I had had nothing to do with a great company and the board. It was the fact that they didn't really need or could put to work what I had to offer. So it just wasn't high value for anybody. The second thing is I really do look for learning opportunities and the quality of the investors. And if we have a shared understanding of the investment thesis, even though you have common shares and you're a independent board member is so important. And if you con sit on a board for years with really talented individuals who are parts of really great firms, I think it gives a lot of lift and it makes you a better operator, really expands your perspective. So those are the kinds of things I look for. And I am actually looking forward to doing that hopefully for the rest of my career. And I also encourage my team members to do advising and board work and come back and bring what you've learned back to us. I don't mind if you take a few hours a month to go do those things. I think it's a net positive for our operation.

Matt Blumberg: I think that's such a good point. I tell CEOs that all the time, every CEO should sit on someone else's board if they can. And it's great for any operating executive to advise another business. You get as much out of it as they do.

Jess Hunt: That's right.

Matt Blumberg: And that's a great note to close on. So Jess Hunt, thank you for talking to me today. I am glad to have gotten to know you over the last couple of years and really look forward to watching your career as it continues its next few chapters.

Jess Hunt: Thank you, Matt. It was a pleasure.