Jonathan Stull on Building a $3.5B Marketplace at Handshake

Michael Koenig: Hello and welcome to Between Two COOs, where phenomenal Chief Operating Officers come to share their knowledge, advice, and crazy stories. I'm your host, Michael Koenig, and I'm excited to welcome our guest, Jonathan Stold, the Chief Operating Officer of Handshake, a company that's on a mission to ensure that all students have equal access to job opportunities. Regardless of where they go to school, who they know, or what they major in. Jonathan joined the team in 2015 and has helped lead the company through a period of tremendous growth, from growing their higher education partnerships from 60 to 1,400, to bringing in 600,000 employer partners, which includes 100% of the Fortune 500, and increasing student and alumni on the platform from 100,000 to 10 million. Just this month, Handshake announced that they raised an additional $200 million in funding on top of the $230 million they had already raised, and they crossed the to the $3.5 billion valuation mark. And they aren't just raising from any old venture capital funds. The investors include some of the best, including True Ventures, Coatue, Kleiner Perkins, Lightspeed, GGV, and the Chan

Jonathan Stull: Thank you. This is great. I'm really excited to be here. Uh, super fun and, uh, really fun to dive into this conversation about an eternal topic I get asked every time about. What is a COO and what do they do? You know, so I think it's great to dive into it. Demystify it.

Michael Koenig: Yeah, exactly. So get started. Tell us a bit more about your path. What do you do? How'd you end up at Handshake as COO?

Jonathan Stull: Yeah, well, you know, I think it's a good, it's a long winding road. I'll keep it short and we can dive into it in more detail. But I think hopefully what it exemplifies is that there's no, there's no direct path for many to being a COO. And we'll talk about this later more, but I think the high level is that, you know, COO, every company is quite different. And a lot of it depends, I think, the exact role you have on obviously your own background and past and experience and strengths, but also what the company needs. And then, you know, what the CEO is good at and what they need and how that partnership works. And that's a key part of it is that partnership with the CEO. But my background is very broad. I'm very much a generalist, I'd say. And I can, you know, high level, and we'll get this, one of the things that attracted me to Handshake is my job getting a college job out of college was a little rough. I had a job lined up senior year of college, was feeling good about myself, moved to Washington, D.C., that job fell through. I ended up waiting tables full-time for about 9 months, and then I got a job working on Capitol Hill responding to letters to congressmen, making about $20,000 a year and augmenting that on the weekends at the same place I've been working as a waiter, which was great. I love waiting tables. I recommend it to everybody as experience. It wasn't what I was expecting to do after college, what I, I wanted to do long-term, my career. And through a series of sort of happy accidents, um, and, and luck, and, and frankly, you know, a lot of hard work, but also luck and timing and a bunch of things got connected and worked. First at the 9/11 Commission, uh, where I was doing speechwriting and comms and, and op-eds for a really brief but incredibly, um, uh, really important time, um, sort of investigating actually what happened 9/11 and, and reporting on that as part of our of our book to the government and the broader public. And that led to, again, through a series of accidents, to working in London for Citigroup doing emerging markets banking. Then I worked in China for 2 years. Also, I first moved to a private equity firm called Actis that was investing in emerging markets in India, Africa, Southeast Asia, China. Then moved to Beijing with that company as well and was investing in China and also working with our Chinese portfolio companies and others expanding around the world. I met my wife in London. We moved to China together, which was a great experience. We then wanted to move back to the US and sort of build a family and be closer and went to business school for a year. Got an internship there doing product management where they gave me the international portfolio because I'd lived internationally. You know, they're like, "Wait, you've been out of the country before, maybe once. You know, you should drive international strategy." But then that led to like moving to international, doing some of their business products to then more and more work as the company grew. It's called Lookout. It was a, it was a great, um, Andreessen and Accel-backed, um, mobile security startup. And I moved from being an intern to being the senior director of consumer product in 3 years. And then joined a company called Flipboard, um, which did, uh, is amazing, beautiful, um, almost like magazine-style, uh, journalism and social content product, which, um, really started the iPad and then, and then grew beyond that. That was an amazing experience doing BD and corp dev with Samsung and a bunch of other partners. And then the handshake And so honestly, all that experience for me before that, and I can speak to the Handshake experience, of course, as well, but was a pretty broad-based business background. And where at Handshake, I've done literally everything except for engineering over time. I've been our first product manager and built up a product team. I was our CFO until May when we hired Brian Kreiner, who's fantastic, joining from Convoy. I've led legal until our new, our chief legal officer, which we can speak to in a couple minutes. I've been our CMO at different times. So honestly, all those different experiences have combined to be helpful at Handshake. And the through line to all of my time at Handshake has been working very closely with Garrett, our CEO, on what's the vision, what's the strategy, how do we get there in the next 3 years, 1 year, quarter? And then often through my time has been actually doing those things as well, but more increasingly the last couple of years has been more around obviously building the team and the operations in place to to bring that to life. So, uh, a long and winding path that I did not know at the beginning would end up as a COO, but, but, uh, all those, all those different experiences have been really amazing experience and fodder for my work here.

Michael Koenig: Yeah, it truly is amazing. And it's one of the things that is common amongst an uncommon group of folks, and that is we all have very strange backgrounds and, and ways of ending up here. I mean, yours from waiting tables to being on the 9/11 Commission to being at Flipboard. I remember when Flipboard first came out, it blew me away. It's really quite a remarkable journey that you've had. Now, one of the things that I'm super keen to hear about is, or rather, are all the different experiences you've had at Handshake, right? As CMO, as CFO, as legal. I mean, you know the company perhaps more intimately than, I don't want to say Garrett, but maybe most people. How has that played into your ability to be an incredible COO there?

Jonathan Stull: Well, uh, whether it's incredible or not, I think it certainly helped in different ways. And I think that to your other point, that this— the COO— what's interesting is my background is, if there is a traditional COO background, it's often through like sales and go-to-market, who then, uh, you know, they partner with a very product or engineering-led CEO, and they sort of balance those two things out. So like, if there's a path that's That's one. That's the more traditional path. Mine is actually sort of broad-based. I had almost— the only thing I didn't have a lot of experience was with sales before Handshake, actually. It was a lot of product and business and strategy and finance. At Handshake, that experience, I mean, as you mentioned before, I think I wouldn't have been able to do the role at Handshake without having worked in a couple startups before. I joined Lookout when there was 30 people. I joined Flipboard and there was more, probably 100, but still had a very scrappy, you know, very product-led startup feel. And so when I first— and being a product manager, I was able to come in and there was, you know, 10 people to bring, uh, experience at working at, I think, world-class product organizations with world-class mentors to say, hey, first thing is— there are two things. We raised our Series A, and I did that with Garrett because I've done a lot of fundraising and finance and knew that, and storytelling around it, frankly. And then, um, and then I set up the product to work and Both of those were just direct experiences where I'd literally been a product manager. I'd seen, you know, a great VP of product and great VPs of design build product teams and was able to institute that, that, that aspect. But along the way, things come up like, hey, average Series A, then we want to announce it to the world. Well, I've literally done comms and speechwriting, and, you know, I know I have a lot of experience through journalism and other things in the past backgrounds too. And So I'm leading that work. Uh, and then, um, the legal stuff, for example, came around, frankly, just not a lawyer, but it's probably been around a lot of lawyers, you know. I've seen one on TV and you can sort of play it, but some of that becomes, um, you, you take certain experiences like being in finance. I can raise our, our Series A. Like being a product manager, I'm going to step in. But there's so many things that come up in a startup, particularly where, uh, as you get— we're now 500 people, and so, you know, we've got specialists for almost everything. Not, not everything, but there's still gaps that happen. But When you're, when you're 10 people, when you're 30 people, when you're 50 people, you don't have roles for everything of these things. And you— a startup moves forward because of momentum, because individuals push it forward. And a lot of my role was just like filling gaps, pushing it forward, finding the right people, and also knowing enough to find an external person, to find a contractor, find the right person, assess them, hire them, and put them on the right path. So, you know, those are two examples. Literally, I just came in and we raised the Series A. That was the first problem. It was still a product org. And then beyond that, it's been sort of knowing enough around these different disciplines to find and ask questions. And then my other benefit is like, I know more about Handshake than anyone else external, and most people internally except probably for Garrett and maybe Ben, our other co-founder. And I know sort of enough about these disciplines to be dangerous and to ask the right questions. Like, I've been our head of legal for all that time. Mostly just, I ask, I find other lawyers externally, we set up the operations for them. They bring the hard questions to me where I like push them on what, what the legal issues are. And then I have to make a business call on it. So I'm not doing the lawyering, but I'm having to make the business call on how we balance those two dynamics. And so what my position has largely been like, to your point, I know Handshake better than almost anybody. I know the details, I know the data, I know the history, and I know enough about these other disciplines to be, um, ask questions, and then hopefully to find the right, the right people. And I think that's, that's always the challenge in startup is like, you can't do it all yourself. So you can do some of it yourself, and then you have to find the right people and be willing to ask them hard questions and hold them accountable.

Michael Koenig: Yeah, knowing enough to be dangerous and do exactly what you just said, be able to sniff the BS when you hear it. And so having that varied degree of background— and it's so funny you talk about lawyers on TV. I mean, I think most COOs at this point, when you get to a certain point in your career, we could all play lawyers on TV, right? We wouldn't even need a script for Law Order. So let's talk about that growth that you just mentioned. I mean, you've seen tremendous growth from 10 people in a garage to nearly 550 now. Like, taking a look back at the trajectory of the company, what did you all get right? It's not every company that can experience the kind of success you all have? Like, how did it happen? It wasn't by accident.

Jonathan Stull: Yeah, it's a really good question. And I think some of it, you know, we've been blessed with some amazing investors and backers and teammates and others. So, you know, you have to have the right, honestly, funds to do it. But, uh, what we got right— and we got many things wrong along the way, let's be really clear— and that's, that's— you can't grow a startup without allowing yourself, frankly, to take some risks and to do some experiments, get many things wrong. But I do think we got a couple of big things right, and most of that has been around, you know, the strategy and the business model, and then I'll talk to that. And then separately, the second thing I think we got right is the way we talked about this with all of our customers and all of our segments. So, you know, we're a pretty complex business. We're a three-sided marketplace. We sell first to universities who buy, and now a broader range of higher education partners, community colleges, boot camps, non-traditional education, who use Handshake. It's a system of record for how all of their students navigate from education employment. Through that, they invite all their students and all the employers to use the product. And so that's a starting point for both a partnership and a distribution strategy. And so now we have, you mentioned, 1,400 higher education partners, 650,000 employers, 10 million active students, 20 million students overall on platform. Um, and the dynamics of that was like we were really intentional about about that vision around that, and we were intentional on certain principles around those things. So for example, we were always going to be students first. That's easy to say, but what that meant is that, um, and, and we were going to build a network that was not white-labeled, it was Handshake branded, and it was going to make sure by doing so they made it easier for every single employer to post a job to every single student. So we wanted to democratize access. We talked a lot to our early partners around our mission and our principles. We want to democratize access Information. We want to democratize social capital. We want to democratize credentials. And by doing so, we're never going to white label the product. We're never going to do these things. And that allowed us, like, we were really clear on the long-term principles and mission and vision. And then we really worked closely with them on the tactics. So, hey, like, given that vision, we want to launch reviews. We want to have everyone be able to review internships. Now, reviews, we have more reviews for internships and first-time jobs than Glassdoor does today. But that was— seems obvious in retrospect. At the time though, so many concerns about all the ways reviews could go wrong. What if my board of trustees chairman's company gets negatively reviewed and then they threaten to fire me? What do we do? What if there's a Title IX violation? What do we do? And we had to work through those, but with eyes on the prize where I'm like, we're going to work these out with you. We're going to listen to you, but all in service of this vision and mission that we all agree on. Do we agree on these things? If we agree on these principles, then let's work towards those together. And we literally would do all-day sessions with 30 career centers in Philadelphia. Then we did one in Miami. Then we did one in San Francisco. So we would really be focused on like the vision and the mission, but then work and then be really clear and non-compromising around that vision, but compromising on the details and working closely with our customers to bring them to life. Another example, we— when we built our monetization for— we didn't know originally how we're going to build an employer monetization pool, but we knew we were going to. We told our universities We will never charge for access to a school. We will never charge for a job posting ever. We want the most liquid marketplace possible. We will probably, we envision charging for premium SaaS tools that do branding, sourcing, analytics. Now, that's end of what we built and we've actually built the details. We didn't know what the product would look like or exactly how it would work, but we knew what we would, and we were very open to being really clear. Some people don't want to be boxed in. You want to have optionality all the time, which I get. But when you're dealing with a lot of different constituencies, sometimes you have to create guardrails for yourself other people will believe in. And we created specific guardrails. We will never charge for jobs, and we have it still, and we never do that. We could, we could have monetized early but have killed, killed the network in the first place, and it would have gone against those missions. So by doing so, and then what we've done over that time, all this, all those, that history of that and of creating vision and commitments, living up to those commitments, listening to your customers, delivering, means we've built a tremendous amount of trust in the marketplace. Place. It's not like they'll— people just accept whatever we do. But literally we've had examples where other people have said, look, I was concerned about this, but I talked to the customers and they said they were concerned sometimes 3 or 4 years ago, but then you lived up to your commitments and did what you said you're going to do, and now they have tremendous trust in you. And so I have trust in you because of that. And so I think the major things we got right were like committing to a certain vision around that, being really clear with our stakeholders around what our commitments were and what we would not do, and then frankly living up to that. And that over time pays a lot of dividends. And you got to trust that, like, that's how relationships work. You got to live up to commitments, do what you do every single day, and then it comes back to you in spades.

Michael Koenig: That makes a lot of sense. And very successful CEO that I know once told me that you hire and fire by your mission and vision and your values, and you'll pass on a million-dollar deal from your values. Right, if it deviates from that in any capacity. And I know that you all are such a value-driven company. You're talking about, you know, that, that compromising on the details of how you accomplish anything, but you have rigidly stuck to that vision and the mission. I think that's one of probably one of the things that, that makes you all so strong. Now I want to get back to the three-sided marketplace that you just walked us through. Right. The brief overview makes it seem very, very simple. Two-sided marketplaces are really hard. It's the chicken and the egg, right? What comes first? You don't want the— what's it called? Isolation syndrome, where you look around the room and there's no one here. So why am I here? Yeah, but you guys also had the three-sided, which is essentially, you know, chicken, the egg, and then like fried chicken, right? So can you tell us a little bit about that development? How do you even tackle something like that when you're early days and And obviously you pick up momentum along the way, but yeah, how did you all break into that?

Jonathan Stull: Well, I think that's, that's, that's why startups can be helpful is because it probably, it sounded insane for most people. So most of the other companies in our space that we've been competing with a long time did not try to sell to higher education, or there were two different gaps. Either people selling to higher education as a white-labeled SaaS solution who didn't try to build relationships with students or employers. Or you had people who built relationships with students and employers and did not want anything to do with higher education because they believed it was a long sales cycle, hard to build, and that they could not build this vision. So it took, frankly, some like naive, uh, you know, uh, college students— Garrett, Ben, and Scott— to believe that was worth taking on. And partly because they just kept coming back to— and they talked to students and employers, they all still interacted through the university. And when they looked at the university systems they were using They were very bad, and they got some really good advice and thoughtful mentors earlier. A guy named Andy Chan, who's now at Wake Forest— he previously was at Stanford, he's the head of their career center and reports to the president— and other mentors in others' line were like, hey, but you should think about this, not, you know, how do you build a bigger, a bigger network around this? And they thought about that and were doing it, and were like, didn't have any obligations and didn't have any— like, it wasn't risky to them because they were college students. And this is exactly why, you know, startups can be founded, is if you It's the classic innovator's dilemma. The bigger companies were never going to— LinkedIn was never going to go try to do this. Others weren't going to try to do this, but they were frankly naive about doing it. And then they were smart when they were sophisticated in how to do it, and they worked their butts off and did things like driving all night over and sleeping in the back of McDonald's to pitch one customer. So part of it is just that, right? It's like the reason they existed as an opportunity because it was crazy. But for us, once you did get the universities on board, and that's the main thing that we were able to do, once you got them on board, then that did solve the chicken or the egg problem because the real, like, the marketplace dynamic is often between the student and the employer, right? And so, but we had a third party who helped us seed that. So, when we go to a school and we got a school involved, when we got, you know, earliest, you know, you had Penn or Stanford or UC Berkeley or, you know, Eastern Michigan was one of our first schools. Eastern Michigan. Every employer who goes to Eastern Michigan suddenly is on Handshake. They had to. Every student was invited to do so. And so campus by campus, you brought them up, and then the network effect started to spread really pretty quickly because you now have employers who had 20% of their schools run Handshake because they had one login and one password, and they had 80% were on 80 different systems. Now next year they have 50%. So we suddenly in our third or fourth year started having things where employers were telling schools, Hey, I'm not going to go to your school unless you use Handshake because frankly, like, I literally have one login for 80% of my schools and 25 logins and I have to post a job 25 different times for 25 different schools. So, that started really happening on the network effects kicked in and started to accelerate our growth in the university side. And we would see schools would say, look, I have 3,000% literally more job postings in the first, you know, couple years because they were going from having only the people who are around their campus having more. Once we, you know, and I can't, they were amazing work that happened something before me, go from 5 schools to 60 schools, going from 60 to 150, 150 to 450 is when it really just, that took off, 450 to 700. And it was because they thought they wanted a white-labeled solution, but the white-labeled solution meant that frankly, they were not giving access to their students, all the opportunities. And once we got past that, then that really was the chicken or the egg was solved. Through our university partners. And so, you can get it. It's sort of a B2B2C model, but it's like really complex, and it still means you have another stakeholder, and it's really— we spend a lot of time, and because they are great partners and really valuable to the network, and they're also amazing thought partners, and they've been living this issue about how to help their students get jobs for decades. So, they're not just a distribution partner. They're like an embedded partner in how we build our work, but from just a pure business model perspective, It was like a thing that started the chicken or the egg problem. So if you can find that, amazing. If you can't, you know, it's still quite— and there's still a lot of blocking and tackling that goes into it.

Michael Koenig: So one of the things that you mentioned outside of like the platform risk that you described, well, why doesn't LinkedIn just build this and the competitor threat there? Or what if so-and-so blocks us from doing XY

Jonathan Stull: Yeah, you know, I think it's a great question. And I think largely there was a— it's a timing wave of things, right? So in the late '90s, early 2000s, maybe early 2000s, Career centers were digitized first, but they were— and there's a, there's a company. First it was like, I think there's a company called CareerTrack and they were bought by Monster and they became MonsterTrack or something. And, but then through another longer story, there's another company came up called Simplicity, which was a government contractor originally, who then started partnering with schools and they built out Simplicity's career service center product, which became almost the de facto standard and was like had our— the market share we have before we had it. But they were a white-labeled backend system. So every single one of those schools, even if they all use Simplicity, you as an employer had to have a separate login and password of each one of those. And that was attractive to the schools because they could have their own brand on the, on the system, and they could customize them for all the different unique things of the school. That sounds very attractive because you want to have a unique community and culture at your school. The, the challenge though is that it meant for an employer, it made an incredibly fragmented system, and that meant their students lost out. So, they gained in customization, they lost out. And what had happened is that frankly, Simplicity had sort of been the big dog and was running a very different business model too. Their model was strictly to make money for universities, and so they charged a lot higher, and they were trying to be a profitable business, which every business eventually wants to be, but they were a smaller business that was running the profits, and so wasn't investing heavily., and they were trying to expand in other areas. And so just from a competitive dynamic landscape, we got very lucky that like there was sort of a fat and happy incumbent, and who was not innovating at all. And Garrett and team were very smart and able to, to, to really attack this directly by focusing his vision of the future, a student's first vision of the future that was all about democratizing access and building that narrative around it. And then they would, just as we did with other parts of our product I mentioned later, originally to even build a system They held these symposiums around the country where they'd bring together the top career services directors and others, and it was like all-day design sessions, like imagine the future, what does career services of the future look like? And then use that to help build the product and build the roadmap, and also frankly, to build a lot of engagement and alignment with their customers on the vision. And those customers were evangelists. And so that, that, that was a timing issue that they then exploited and were thoughtful about. And the technology also was like, also other dynamics which are not unique to Handshake was like, Suddenly, like, APIs were easy to build on. There was tons of other, uh, you know, open source stuff. You could build in AWS, like all the things that also fed into the huge explosion of startups in general. But in our particular space, innovator's dilemma, fat and happy incumbent, no one else in there, and an ability to— and then a really thoughtful and sophisticated ability to, to really take advantage of that.

Michael Koenig: And you touched on how close to the customer you all were. There's certainly something to be said for getting it right, not just in the timing, but also in the time you take to build and get to market. So being so close to customers kind of shortcuts a lot of that experimentation that you would otherwise have, have the pitfalls around.

Jonathan Stull: Yeah. And this is, again, I mean, partly, you know, I, and I, I only came in really after this, is that they were doing this when they were in college and they were— have the time, ability, and energy, and they, in their desire to do it. Where they would go and they were talking to people all the time and they're basically working for free for 2 years before they had the first customers. And then they had 5 customers to be able to sort of work closely with. Um, and so it looks afterwards like this tremendous growth trajectory, and it was, but it was built off of the depths of research understanding they had built over many years and deep understanding of it that they were able to layer on. And then that is infused into our DNA as a company, to be very customer responsive, listen to people a lot while also having that vision, right? And so those, as I mentioned, those two things go hand in hand together. We didn't just like, we're not like a dev shop that whatever you ask for, you put in the product, but you have to be very close to your customers to understand what they want so you can see whether they match the vision or not.

Michael Koenig: So true. And when you're early on, you mentioned this previously, everyone is really a generalist. Even, even engineers are generalists. You're a backend engineer, you're frontend engineer. Oh, you need to be mobile. Oh, I'm a sysadmin now. So The move though, as companies grow, gain momentum, get customers, raise funding, have that type of success, you need to move from that generalist and bring in those specialists. Can you maybe speak to that moment in time for Handshake and what was it like culturally? Were there choppy waters perhaps?

Jonathan Stull: Yeah, look, and I'd say it still feels like it's going on even though we're at 500 now. It's always interesting, like 500, the rules that now like you're spending doing 2 different things in marketing, maybe 3 years from now there'll be 3 different roles. And so I would say there wasn't a moment in time. It's always felt like that. And there's always conversations. Also, if you're going through this now as a team, just like give yourself some grace, understanding like it's hard for everybody. There's no like perfect process to do. So in retrospect, it seems obvious these roles exist, but in the meantime, it's hard both for the individuals going through it and as a company because you're, you still want to be smart and scrappy and you like the way it operates and So, 100%, it's a painful and challenging process to go through. And I think we, you know, we didn't go through it on every function at the same time. You sort of see it like, what's breaking? What's the problem here? Hey, we need more depth here. And you have to go in those one-on-one conversations and evolve it every time. So, I wish there was a magic point in time and you say everything flips. A lot of it is, and I sort of believe this, I think someone else, maybe Reid Hoffman or someone said it years ago, I'll say he did it whether it was like the Mark Twain quote, whether he actually said it or not, but was that, you know, startups are a series of like burning fires. And the question is sort of like, are they just like small little embers or are they raging forest fires? And so like you could look across and say every role needs to be broken up in specialists immediately. A, you don't have the funding to do it. You don't have the funding to hire 500 people immediately. And B, things are going well, they're going well. And if they're not, or if you see things breaking, you have to decide when they're breaking and how badly and when you need that specialist. And some of it's obvious and some people come to their own conclusions, say like, I need, we need help. There's other nulls. And other times you as a manager or leader have to figure that out. It's happened to all of us. I mean, my role evolves all the time. Every 6 months, if not beyond. Garrett's role as a CEO evolves all the time. You know, we've got to figure out like, What are we doing? What do we want to give up? What becomes, we need a specialist for. Sometimes we've been thoughtful to do it upfront and sometimes we've waited too long. Like I wish we had a head of legal probably a year ago now and we'll have them now soon, but that probably was well past its time. And so, you know, I think some cases you get it right and you have a lot of foresight and in other cases you don't. But that it does involve, I'd say that there's no substitute as a company in one-on-ones, literally every one-on-one with your team. It's like, How are things going? How are things evolving? Starting not every one-on-one, but every few one-on-ones talking about what's this world look like in 6 months or a year from now. You want to start setting expectations. And we do that a lot also. We've tried to do it. We've done it well at all hands and other bigger forums is to talk in general around this evolution, bringing it outside people who've been through one or two stages beyond you so people can hear from other people themselves. Sending around great articles is the classic Molly Graham giving away your Legos article that's referenced all the time. So what I would say is you need to have a conversation about it all the time as a company. It's one of the biggest conversations we have at an executive team level is evolving our team. You need to be open to having a conversation one-on-one with your team members and open to people having it with you as an individual, as a COO or CEO or anybody else. So that's the only key I'd say is like beyond that, there's no rhyme, perfect rhyme or reason for it. Other than that, you got to analyze what's breaking and all that, and you have to be constantly talking about that topic. So that's not a surprise to people who eventually get leveled or get their roles taken away, and that you're, you're planning, like, 6 months ahead. Maybe when you're early, it's like a month ahead, but like 6 months, a year ahead as you get older, right?

Michael Koenig: And what you talked about with fires, they never all go out. There's always a fire.

Jonathan Stull: It's really just—

Michael Koenig: yeah, exactly. But, and it's prioritizing those fires though. It's trying to determine, all right, which one is going to build down or burn down the house today versus all right, maybe that one can, can simmer for a little.

Jonathan Stull: Yeah. And the good thing is you get bigger, only is that there's still fires, but there's fewer that feel like they'll burn the entire house down. Sometimes they still do, and you're like looking at those. When you're early, it's hard because they almost all feel like they're going to burn the whole house down, and, um, and they probably will. And that's why you have— that's why it's so challenging, is things seem so precarious because they are. As you get bigger, obviously you have a little more resiliency built into the system.

Michael Koenig: Right, right. And so One of the things that, that you mentioned, um, around the, the fundraise, let's, let's talk about that.

Jonathan Stull: Yeah, sure.

Michael Koenig: $200 million fresh funding, right? 1,400 universities using products, 600,000 employers, 10 million active users. And on the student side, you know, what's next? What, what are the growth avenues? And quite frankly, how do you deploy fresh $200 million?

Jonathan Stull: Yeah, great question. I mean, at the highest level, like, from the funding, you know, that is to build, and I feel very good. We actually, you know, closed the round in the fall. We just announced it in, in January. Um, and, uh, when we raised the money, we weren't in need of the money, but, uh, you know, we, uh, do have big plans for the future and wanted to be able to accelerate our investments in the company so that we could plan for where we wanted to be in the long term. And being like the number one place that anybody starts, restarts, or jumpstarts their career. That's a big vision that goes beyond graduate and college. It means as the world of work is evolving, as the world of education is evolving, people are retraining, reskilling, relearning all the time. How do they navigate back from that relearning back into the— to, to employment? How do they change whole trajectories? Other platforms, either good job boards like Indeed— it's an amazing job board— and LinkedIn, I'd say, is fantastic. I use it every day, but it's really great for mid-career professionals. And it is largely a reflection of your past, not your future. You know, it, it reflects who you already know, the connections you already have, and the skills you already have. Handshake's all about building relationships and building the skills you need, whether you have zero of that and you're 18, or whether you already have that and you're in marketing, in finance, in New York, and you want to move to LA and get in entertainment, or you want to do something different. That is basically restarting relationships and skills. And so we see that happening more and more, and the data bears us out. People are moving jobs and industries more often than before, and that, you know, is something that you need in your second job, your third job, or when you're 35 or 40 and you're retraining. And so as we partner now with Courseras of the world, um, and others beyond, like, that's the vision we want to go after. And we think that's, you know, certainly a need in the US. We're in the UK now, and we started to expand there. It's, it's important. We've seen there— we want to be a, a, a massive global transformational company. And so to do that, you know, we're, we're, we're raising our investment. We're— we've grown to 500 people today. We'll probably get to close to 800 next year. You know, we're about to cross $100 million in ARR shortly and been doubling our revenue year on year. So there's some just level investment like hiring salespeople, got to get a lot of them, hiring engineers in many different ways to build out. When I talk about building relationships, it's like we have a one-on-one, we have career fairs, we have events, but we want to build in the future career communities in ways that, you know, when you have a question about what's my— I'm having my one-on-one with my boss, my first ever one-on-one. I'm talking about negotiating my comp, my salary. I'm thinking about moving to entertainment. Those are things that aren't just like go to a job board and look for a job. It's like you want to have conversations, you want to ask questions, you want to talk to people. And we see those things happening all over in a wide range of forms, and we want to build those ways to have those experiences on Handshake. So doing that requires expanding more, it requires investment. And then the last thing is just we want to be more nimble. Like we are now in a position where we might want to acquire a company or two. We might want to— we've never done that before. We might want to be able to take advantage of situations that happen. And when you look at what's going on in the market, you know, and that'll— by the time this is released, maybe the market's up again a lot, but market's been down a lot in January and valuations change. For us as a growing business, when money's offered on the table and you have an opportunity to do that at a very low dilution with a very attractive valuation, for us, we think it's worthwhile so that we have, I think, the war chest to invest and to continue investing even as the world changes a little bit.

Michael Koenig: Yeah, my brother has always said to me, if someone offers you money, take it because it might not be there tomorrow. So, yep, you just laid out a pretty expansive plan for world domination. I joke, global expansion.

Jonathan Stull: Yeah.

Michael Koenig: How are you all thinking about that? How are you choosing your company, the, the countries that you're moving towards next? I mean, what advice would you have for other companies that are starting to think about that as well?

Jonathan Stull: Yeah, yeah. You know what, and I'm gonna— it's— I think, I think global expansion is actually the starting point. At least can be, can be simpler than people imagine it is. And my first job in tech was that I mentioned Lookout, and I was hired to like think about global expansion. And actually, I think I read this blog post by this guy named John O'Farrell who was at a16z, and he was like, um, sort of broke this down, but it was very similar. It was like I basically built a spreadsheet with some like core characteristics of different markets. There's some pretty obvious around things like Language is one, right? Easier to do that. Market size for your products, competitors, etc. And you put the major countries on there, and largely they are the ones you already know about, you know, that you're thinking about. Bigger Western European countries, there's the— there's Japan and China, India clearly, and others. There's obviously— depends, you know, Brazil and other major markets. Certainly while there are, there are macro markets that have multiple countries that operate, you know, one like Africa, others that have some more regional dynamics. But still, like, when you go in Africa, you're going to South Africa first, or you're going to Kenya. Like, you really do need to think about countries have different— country level is still the easiest way to think about it, given all the legal repercussions of that. But for us, in, in, in, in our case, in, um, Handshake, UK was an obvious first choice, both from a language and also from the model they use. For us, we still, um, work primarily with the universities as a starting point. In the UK, they still have a very vibrant university-led early talent ecosystem. Other markets like France doesn't— do not have career centers at their colleges. So given the language and the different model, that made it less attractive. We also see more companies recruiting who have European and U.S. relationships. And so we were literally getting pulled in by the market. That's the best way to do it, is when you see demand. Honestly, it's like when customers are telling you, I want your products. Now, whether you ever thought about that, if you have a lot of people in Brazil who say, I want your products, you should probably think about Brazil, you know, more than other countries. But it's like, because it's a big market and people want it. But we saw that UK is a big enough market, it's an entry point into Europe. There's a lot of overlap in the model otherwise. Beyond that, I have seen the only other wrinkle I'd say is sometimes people want to start very small. I see a lot of people doing like product launches. They might launch a new app version of their app in like New

Michael Koenig: And now all that global business experience that you have, you're actually drawing on here.

Jonathan Stull: So one of my main experiences— oh, it's the only other thing— having worked in China for 2 years and beyond is it's an amazing country, obviously a huge economy growing. But like, I— my main recommendation to Handshake and beyond has been like, I wouldn't go into China, and I'd wait a lot longer. If you do it, you have to be at a much different stage of your development. It's an incredibly hard market to operate in, getting even harder the last 10 years for Western tech companies. That's probably not controversial now, but 5 years ago now, I think there is a greater degree of wanting to rush in there. And my advice, uh, has always been probably that that's— it's, it's not right now. The complications are, are outweigh the returns you can get.

Michael Koenig: Oh yeah, there's a graveyard of companies. Yeah. And Chinese, uh, offices and initiatives there. Google, Uber. Listen, if Google and Uber can't figure it out, like, yeah, slow your roll.

Jonathan Stull: They made a lot of money on their investment there, to be fair. They did really well there. But, but mostly that, that's been rare. That's That's the only other thing I've seen is like making investments in Chinese companies might be a better play than trying to start your own. Um, so, um, but, but anyway, um, yeah, international's been interesting.

Michael Koenig: So let's talk about the operating system of the company. It's gone through a lot of iterations and evolutions so far. It sounds like over, over time it's really been tied to headcount growth and then customer growth. Now you've got two things. That headcount growth is continuing on, but you now have to change the operating system to, uh, to accommodate that global expansion. What does that look like?

Jonathan Stull: Yeah, yeah, it's a good question. We're actually going through some of that, um, right now, and we think about the global— and I'd say, you know, global still, international is still not like the, the primary focus of our growth, but it definitely is an area we're doing now. So I don't want to— like, we haven't— it's not been the primary driver of our, like, things changes to our OS, but certainly has and will continue to do. The biggest driver has just been the The— I mean, well, two things. One, COVID and the change in working environment has obviously changed for Handshake and most everyone else. We used to have almost everyone in San Francisco in an office every day, and we had just opened another office. We actually hadn't actually filled the office yet in New York. We started to open a sales office in New York, and we had a small office in Denver, an engineering team. So we actually were starting to move out to more distributed team, but still an office-based, um, and then obviously COVID changed that. So the major driver for us has been COVID more than anything else. And the other one had been, frankly, moved from like when you have multiple floors and just like bigger offices, you just have more people, you have to get more serious about that. So the biggest milestones I think have been as we moved away from just being like— there's a time it was, you know, Garrett, or Garrett and I, or I, or, you know, Ben would make the decisions. And then as you build a bigger team and you want to and have great other leaders, you want to empower those leaders, and you don't have the time yourself, even if you wanted to, you need to figure out how to structure that. And that's a collection of like, it particularly goes beyond meetings, starts going like the documents, the cadence, the work. We use OKRs as our core goal setting exercise. There can be very different pros and cons to any of those. I hear a lot of people complaining about OKRs and somewhat reasonably, I still think it's like the best of a bad selection of options in front of you. But it does help whatever you use and making sure you have clarity on what the vision, the goals, and the specific metrics you're tracking is important. So we continue to use those and they're very clarifying for that. Going global, I think, has been— and the other dynamic, I'd say, less operating system than organizational structure, is that we've sort of have had different times. We still have a largely functional org structure, but clearly, like, how you— we've also have these business units aligned to our customer groups, like Speaking and marketing and selling to our higher education customers is quite different than selling to our employer customers. And so we've had different go-to-market teams there. We've had consistent engineering teams across all, consistent product teams, consistent design teams, but marketing and sales have been split. Now we're hiring a CMO to bring them all together. So in the future, maybe, you know, you could have business units. We're thinking about that. We've had, uh, UK as its own team and structure, and, and, uh, with one singular leader, and now we're moving towards actually having them more aligned to functions, and so they can be closer to their peers. Because we were seeing that there wasn't a lot of— enough communication as we wanted to. It was like getting siloed versus being embedded in every function. But you still needed a UK overlay to make sure that, like, the team is aligned. So in my mind, as you— as almost every tech company, as you get to a level of structure, you're always going to have some level of a matrix structure. You have to just understand there who, who's the— who's the direct line versus the dotted line. Like it matters, but it doesn't matter the same way. You still need to figure out and have the communication go both ways, and you have to operate in that matrix structure regardless of how you, you've, you want to do it.

Michael Koenig: So John Doerr is one of your, uh, investor investors. Um, he's never going to listen to this, but OKRs, the best of bad choices.

Jonathan Stull: He might take issue there.

Michael Koenig: So let's talk about the other big change that came with this funding. Yeah, you brought on a new board member. You announced that Dr. Michael Lomax, the president and CEO of the United Negro College Fund, UNCF, joined the board. Can you tell us about that decision?

Jonathan Stull: Yeah, fantastic, and, and super excited. He's been fantastic so far. He joined his first board meeting in December. He's been incredible both in board meetings and beyond. And I think it's a natural— two things are a natural transition. When you start out, most of your board is going to be investors, and then as you grow, you definitely for multiple reasons, you need to add independent board members. A, it's legally required eventually when you get to be an IPO, uh, but, but B, the earlier you can do it with the right people who bring unique, relevant, but different and unique contributions, it changes the dynamics of the board from being just about, you know, investors who, even if they're thinking about the fiduciary duty of the company, have their own individual interests and often a more narrow set of experiences collectively, right? They're many of them have a similar path and, and background versus bringing in different people. So we first brought in our first independent board member, was a woman named Margo Georgiades, who joined, uh, almost a year and a half ago now, who was the president of Google America, CEO of Mattel, CEO of ancestry.com, a very experienced business leader who brought— and instantly her first board meeting was like a different level of question that was actually higher level but more, you know, made you think more, right? Like, honestly, it was like less diving into the details and more like, are these the right goals? Are these the right goals for now? How are things evolving? And it sounds so simple, but they were very, uh, they, they push you to think a different way. That was not that no one's ever asked that on the board, but they just brought a different level of that, and it was more, um, felt more longer term and higher level. Dr. Lomax, we then, um, started actually searching for him, uh, that the new board member, about a year ago as well. Uh, it took about a year, really focused on helping bring me someone who had a deeper grasp from higher education, um, and, and wasn't sort of a long-time academic necessarily, but someone who really had embedded in higher education and was also committed to our mission and vision of transforming that, that, that path. Um, and when we got introduced to Dr. Lomax, um, I think knew pretty quickly that he was probably the idea. We talked to a lot of people, and I think as you're building that board, you have to be committed to— it's not going to be a month search process, probably. You want to bring in— and we were, we were lucky enough that we're now also scalable enough that we can attract a super high-caliber candidate. I mean, UNCF is the number one way, has funded the most scholarships for Black and Latinx students to get through college. It is the primary scholarship function for HBCUs and beyond. He knows, you know, he's been in higher education, was also a businessman before that, was an academic. He's, you know, worked with presidents of the United States, presidents of colleges, CEOs of companies, sits on a number of boards. So his contribution already, and also, by the way, he's like funny. Personable, like really like warm and, and, and helpful, and also gives you a kick in the ass when you need it. And like, that's a great combination. Like, you feel like he's got your back, but also already you can hold him accountable. Um, and so for us, he, he brings just a unique depth that I'd encourage anybody to be thinking about how they can build out the independent board of directors, bringing that both that customer lens, a little bit of your understanding of your space, and also bring, you know, more diversity and representation to your board. And so We've been really able and lucky enough to do that on multiple fronts, um, and already seeing the dividends from, from his joining our board today.

Michael Koenig: That's very interesting. And there's also so much movement around just DE&I initiatives in general.

Jonathan Stull: Yeah.

Michael Koenig: How do we see that playing out in Handshake, in the platform? Because there's certainly an opportunity there to help kind of level the playing field even more.

Jonathan Stull: Yeah, it's great. I'll talk maybe 3 levels of this, um, in our product, in our team, and then actually in our, in our, in our capital structure. We actually added 2 really cool new investors at this time. I think that sort of show our commitment to that as well. But in the product, I mean, it's really embedded in our mission. We want to democratize access to opportunity and help every single person find their way. And, and clearly we see the biggest obstacles often around that are, uh, either socioeconomic status, you know, geography sometimes, but clearly gender, race, and ethnicity are some fabrics that sometimes coexist in how you sort of unpick the systemic inequities there are hard. But like, those are often where we see, you know, you see it by earnings, like lifelong earnings, and also right out of college, you see unemployment rates that Black and Latinx individuals particularly have higher unemployment and lower earnings when they get out of college. And so, you know, what can we be doing to help, um, change that. So actually what's been interesting about our timing is what you mentioned in our rise, is that the, the ability to have this global network that you can search off of— every student in the United States is on there— has been one of the main drivers for employers, one of the main value propositions they're using Hancher to find. They want to find the most talented, highest quality, you know, technical talent is a huge driver, and build more diverse teams. So every CEO, as a CEO-level priority, to build the more diverse representative team over time particularly Fortune 500, huge, putting massive amounts of investment. And unfortunately, in many of these fields, you can't today do that at the mid-career level. And so they're looking to do that at early career level and build that pipeline as soon as possible. And so they're turning to Handshake to help them build that out. So the core value prop is you want to find, say, a, you know, a female computer science major who knows Python, who wants to work in Miami, uh, because you have a— that's where a team is. You can go and use Handshake to find a pool of talent who has those characteristics, build messages, reach out to them, invite them to events, and then ultimately, hopefully, like, build a relationship. And so they'll apply to your company. And so those are key drivers in the product and platform. And we work a lot, not only in terms of enabling that, but like, we do a lot of our own user research on different groups and understanding the language they use and how you would engage with them. And so really move beyond that, um, to drive that. So that's a core reason people use the product. Core value prop for our employers, and it's core attracting to our team. And I think the next thing has been how we built our team around that. You know, we're— we certainly were started out by, uh, 3 white guys from Michigan. I was one of the first hires in there. I'm a white male from California beyond, so we weren't the most diverse team up front. And I think, uh, have had to try to invest deeply in that. And there's been fits and starts, I think. Very proud today around the, the, the, the, the breadth and diversity of our team more broadly. And leadership team today. But that's, that's, you know, an issue that even we as a company that sells services to employers have had to do a lot of soul-searching on, put a lot of accountability on. Do like anything else, have OKRs around it, make sure you hold people accountable for that. You know, our engineering team has made great strides because of that. Um, and then the last thing we've tried to do is on our capital stack, we brought in, um, uh, Base10's Advancement Initiative, which is an amazing fund, the $250 million growth fund. It's Black-led and Black-owned, and a significant amount of the capital comes from HBCU endowments who are undercapitalized. They then waive carry and waive their fees, uh, half their, half their carry, the fees on the money from HBCUs so that they can increase their economic opportunity. And so through that, it's funding literally thousands of scholarships. The Handshake Scholarship is being funded by, uh, Handshake's own investment. So as Handshake becomes more economically successful and our valuation increases that funds scholarships to HBCU students and funds the endowments of HBCU colleges, which is really an amazing model. And they're, they're fantastic partners. And, you know, I think we're looking at more investors in the future who build models like that, whether it's for HBCUs or more broadly just for different college— more, more sort of populations— is how you can, you know, really ensure that as you do good, the rest of society and your customer base are doing good as well.

Michael Koenig: Y'all are really putting your money where your mouth is. Literally, I'm not sure. Yeah, yeah, yeah. But you do seem to be in one of the best positions to help continue to level the playing field and bring about that change. All right, Jonathan, now for the last and my favorite question. We've all had those moments where you stop and think and you just go, "Welp, never thought I'd see that." Is there one that comes to mind that you can share with us?

Jonathan Stull: Yeah, I mean, I think particularly early on there's even more. I mean, there's been fun ones. Maybe the two ones that come to mind is When we were first building Handshake, there's an annual event in the college space called NACE, which is the National Association of Colleges and Employers, and it's really the body that brings together career service centers and employers. And we were, you know, maybe a team of 20 or so, and it's the main way we would go and sell and put a booth out. And we— it was held in Chicago, like 2016, and we stayed in the dorms of DePaul, and Garrett Arcillo and I shared a room.. And we were, I was back to sleeping on these, you know, green, we called them, we called them the green machines. They were these green waterproof mattresses so that I think mostly for college students, if they drank too much the night before, they would not imperil all of the furniture. So I was in a single green machine, like, but like FaceTiming my wife and kids from this room. And you know, it was sort of what you'd think, you know, sometimes it gets lionized and it was, in retrospect, pretty fun. And, you know, really was like the scrappy early-stage startup, save money wherever we can, you know, have the experiences like our students. But at the time, it was like, what just happened? I went from— I was Flipboard, I was flying to Korea, and I'd be working with Samsung, and, you know, we'd find business class, staying in hotels, work with these major partners. Then I'm staying on this waterproof mattress in a dorm. So that was a little— it was a good reminder. It was really, in retrospect, quite funny. At the time, I was like, Do I make the right choice here? But yeah, but yeah, bunk beds. I get top bunk. Luckily no bunk beds, but it was pretty close. So that was fun. You know, it wasn't like— there's been a lot of other crazy stuff, some which I can't talk about in public on podcasts around dynamics. But, but, but it's been an amazing journey, right? And I just want, you know, I hope others can have a similar, similar ride once in their lifetime.

Michael Koenig: Yeah, it's great to stop, take a look back. There's so much absurdity that comes with being early stage, being early on into those companies, and one of the things that makes it so fun. Well, Jonathan, this has been awesome. Where can people go to stay up to date with you and keep up with Handshake?

Jonathan Stull: Yeah, Handshake, joinhandshake.com. So we still got the URL, but joinhandshake.com. On Twitter, also @joinhandshake. I'm @JonStull, J-O-N-S-T-U-L-L, on Twitter as well or LinkedIn. And yeah, looking forward to more and looking forward to follow more of your podcast, Mike. It's been fun.