How did Robby ascend to leadership so quickly at Zenefits?

Alex Kracov: So you worked at Zenefits during all the crazy growth. And so from my understanding, you joined Zenefits as an SDR. Then two years later, you're running a team of about 200 SDRs. I'd love to start today's conversation with this growth story. And maybe a good place to start is like, how are you so successful as an SDR in the early days of Zenefits? Then how did you sort of transition into management so quickly?

Robby Allen: Yeah, it's a fun story to think back on. I think just a different time and tech altogether. I don't know if we'll see another story like this one again. Certainly, at least not anytime soon because I think there were lessons that were learned along the way. But I guess, to tell the story, it was my second SDR gig. The first one, out of college. Then I worked for a company that folded up the shop. I was performing well out. I found out, hey, we're not going to be doing this thing anymore. I'm like, okay. So I took a good gig at Zenefits as an SDR. I had been doing SDR and kind of like SMB, AE sales for about a year and a half, so I knew what I was doing. And so a bit of a step back to take two steps forward.

I think that there's a lot of advice in Silicon Valley that shared about how to pick a company. A lot of it, to summarize some of the things that I've learned over the years, it's like more about the name on the front of the jersey and the growth of the company and the scale that you can experience during your time there and the opportunity to grow. Zenefits had all those characteristics. To be honest, I didn't even know that at the time. I got lucky in that way. I got to work with people that believed in me and work in an environment where I could really show up, do something I knew how to do, and perform at a high level.

I remember probably like seven or eight months in when I stood out as one of the higher performers on the team, we were making a decision to expand outside of just the SF Bay area as we raised a couple rounds of funding. It was sort of like time to grow. I got asked the question if I wanted to go open up an office in Scottsdale, Arizona - which I understand, Alex, you've got some experience whether we can touch on that one later. I remember talking to Parker, our CEO, Parker Conrad. He used the analogies, like, "Robby, maybe once or twice in your career, a giant tsunami surf wave will come crashing towards you. You're the one holding the surfboard. You get to decide. Are you going to jump on or not?" I am like, by the end of the conversation, I had already bought a plane ticket to Scottsdale. I was so fired up. I was ready to run through a wall. So that was one of those, I don't know, Silicon Valley indoctrination moments for me. So I moved out there. And over the course, like you said, of two years, we hired 250 SDRs and built a management layer of 25 managers and a couple of directors. I think, candidly, there were aspects of that model that worked really well up to a point. Then at a certain point, we were cutting the size of the pie smaller for a larger group of people.

I think that there were a lot of lessons along the way that I'm happy to talk about. But looking back on it, it's almost crazy to say those numbers out loud and think about how many interviews, and how many onboarding sessions we were conducting to bring that many people together, to conduct this mission as a team in such a short, compressed period of time. It really felt like getting a startup MBA in a really compressed timeline.

Alex Kracov: Parker is just such an inspirational leader and the way he can just talk and fire people up. I've heard so many stories about Zenefits. The few times I've been lucky enough to speak with him, it's just like, wow. It's like, okay, I aspire to be like him as a CEO. That leadership ability and the ability to inspire people, it's just like, it's so amazing. I love that, that tsunami story. That sounds like very much Parker analogy.

Outbound sales at Zenefits

What did outbound look like at the time? I know Matt Epstein was sending a lot of emails out from the marketing side of things. But was he managing SDRs, too? And were you doing a lot of personalized outreach? How were you able to be so successful at outbound?

Robby Allen: At the time that I joined, we were actually all in an entirely inbound shop. Matt is like a mad scientist of demand gen and marketing broadly. As a CMO, he's got a lot of skills. But at the time, at Zenefits, his core focus was really demand generation, running campaigns. He was incredibly effective at it. I've actually never seen anybody in my career since then as effective as Matt. And he's done it again now at Rippling.

I think, at the time, Zenefits was really inbound-driven in the early days. At first, it was kind of like YC referrals. Then it was like the next cut of that network, and then so on and so forth. It was around the time that we raised our series B that it became clear that moving from lower SMB mid-market up to upper-mid market in enterprise was just an initiative that we wanted to take on as a business, as we thought about total addressable market and customer lifetime value and all that. That was where the outbound efforts started. The same message of like free HR software wasn't really resonating with companies of a certain size, and it had to be more of a value message. So that's where the outbound play came in. And it worked. Pretty much straight away, we were landing that message and converting a high number of opportunities per rep. And we're able to scale that I think pretty effectively, all the way to 100 SDRs over the course of a couple years. We started to see diminishing returns around 150 or so. It's kind of on that journey to 250. So, yeah, it was the biggest outbound team I've ever experienced in my career. And quite a sight to behold just behind the scenes of all the operations that have to take place to support and feed that many mouths in terms of the scale that we were reaching.

How did Zenefits hire 250 sales reps at once?

Alex Kracov: I'd love to kind of go behind the scenes of how you were able to just hire that many humans. I think it was under two years. You hired like 250 sales reps, 25 managers. Were you just in interviews all day? Did you do training classes? What did that kind of program look like?

Robby Allen: Yeah, I mean all the above. I think it was very intentional I moved out there. The mission was to sort of grow a very large inside sales team in a very compressed timeline. So I went there eyes wide open. It was one of those things where I'd never done that before, so it was hard to know exactly how it was going to go and what to expect. But if you do the math on what does it take to hire 250 people, well, you got to do at least a couple 1,000 interviews, if you think about maybe a 20%, 30% conversion rate of candidates and the phone screens and all that that go above it.

We had, at the height of it, there were like dedicated days of the week. At one point in time, all day Tuesday and Thursday, where from 8 AM until 5 PM were just consecutive in-person interviews. We had a recruiting team that was orchestrating quite a bit of outbound recruiting efforts. We were on campus, at universities in Arizona, recruiting people. We were moving people into the state for fairly entry-level positions. I mean, it was a fully-orchestrated, almost go-to-market motion on the recruiting side in and of itself.

Then as we got folks onboarded, it was really sort of like a college introduction type of approach where we actually had, I remember in the office like a big stadium-seating lecture hall format. There were like maybe 100 seats. And so there'd be people in there. We stood up in the enablement program pretty quickly that really focused on those first couple of weeks. I think the goal was to get people onto the phone as quickly as possible. You worked at Yelp. We actually model a lot of what we did on the Yelp program. I understand that you went through that program yourself.

Alex Kracov: Yeah, it sounds very similar. I mean, I think I showed up at Yelp with 35 other people, and I didn't even know what sales actually was. Then you get put into this training program. Then day two, you're on the phones, and you're just getting thrown into the fire. Then I think by the time I left Yelp a year later, only seven or six of the people were still in the training class. It was such a churn and burn sort of program, but you learn a lot very quickly. It was, I don't know, quite the experience. It gave me some street credit later on when I was at Lattice. I was like, I could talk to SDRS. I used to do those, too.

Dealing with Zenefits' hypergrowth at a personal level

I'm curious, how did you deal with all this growth on a personal level? Because it must have been pretty crazy for you to figure out. Okay, how do I manage these many humans? How do I just very quickly go from a manager to a leader? What was like that for you personally?

Robby Allen: It was hard. I think it stretched me. I was 25 years old in the middle of all this. I was very young. Very early in my career. And so I think there was a part of me that was almost projecting a sense of control and a sense of seniority that I didn't necessarily have. I think at times maybe it wasn't - looking back on it, maybe it wasn't entirely genuine in the sense that I was maybe less vulnerable than I probably could have been as it related to the relationships I had with other managers and leaders. But myself and a VP of sales out there were essentially the heads of that office. And so I think it was one of those things where it was extreme in every way, and I got the chance to get a front row seat to see what that felt like. There were more lessons than I could possibly even count. But it shaped me.

I think what it did was, when I went and did my next play after that at Flexport and a couple of other things since then, it didn't seem as extreme I guess the next time around. There are some value in that. I think it also taught me about just some of the things, some of the way we approached it in terms of the velocity, the speed, the aggressiveness. I also learned about what are the warning signals that those aren't necessarily working or going off course or whatever. And so I think tons of lessons and takeaways.

Honestly, though, Alex, I look back on it and feel very fortunate that I was put in a position and had the trust from folks like Parker, Sam, and Matt Epstein and others, that they believed in me to do that. And we did do that. I think the outcome wasn't necessarily the outcome that we were sort of initially driving towards. But I'm grateful for the lessons and the experience. And I think probably, more than anything, the relationships that I built along the way. Many of those people who I hired and got a chance to work with are VPs, executives, founders that are doing really interesting things in the space today.

How Robby ended up at Zenefits

Alex Kracov: It's amazing how many talented people came out of Zenefits. I mean, so many of the great people who joined Lattice were ex-Zenefits, and all across Silicon Valley. And so I assume that's sort of how you ended up at AgentSync today where you're the chief revenue officer, where Niji I think sort of built Zenefits'- I mean, sorry. built AgentSync out of his experience at Zenefits. Can you talk a little bit about how you ended up at AgentSync?

Robby Allen: Yeah, the origin stories are, I think, quite cool as far as like the opportunity, spotting a problem internally at the company that one works out. For Niji's case, Zenefits. Then sort of finding a market opportunity on the back of that. One of the challenges at Zenefits I ran into was, as we were scaling really rapidly, ultimately, we were brokering insurance policies to small businesses. Selling insurance to anybody is a highly regulated practice, where you have to be appropriately credentialed and licensed to sell, whatever. In our case, property and casualty insurance. Sorry. Health insurance.

The challenge is, it takes a long time to get somebody licensed. And so, Zenefits, as we work culturally, we're always trying to optimize for speed and scale and get people ramped as fast as possible. And through all of that and a series of different things, it got fined, which actually fined by state insurance regulators millions of dollars. What I found out since then is that's actually the very regular practice that happens to insurance companies all the time. It just isn't as publicized as a high growth venture-backed Silicon Valley company that became a poster child for that reckless behavior.

Anyways, Niji was the one who, at the time, was running RevOps. Away from this problem but got put in charge, got blessed with being put in charge to fixing it. And so he got this, basically the pool of resources, to essentially evaluate existing tools in the market or go build one ourselves. He decided to build it ourselves because most of the technology in the insurance space is pretty just outdated and didn't really serve our needs. So he built basically an ISVapp on the Salesforce platform that validated that any sales rep working in opportunity was licensed in the appropriate state to sell that opportunity. I think what Niji learned, just through a series of conversations with state regulators and a series of conversations with other vendors in the space, was that no one was really doing this in a way that solved the problem for a huge industry insurance in the US.

After getting Zenefits out of that storm, he negotiated the IP of this product he built and just started working on it nights and weekends. Interestingly, his wife and partner, Jen, is a top 1% Salesforce engineer in the entire world, like world class. So they started hacking away at this thing and actually ended up bringing it to market back in 2018. It took a couple years, but they brought on 10 customers, somewhere to the tune of a million in revenue. That was when I got the call actually from the COO, who I had a pretty close personal relationship with, and obviously knew Niji and knew Jen by proxy of Niji.

It was at the beginning of COVID, I remember. I was doing some consulting work at the time. I was living in the Marina in San Francisco. Then COVID hit. It was like before the market started ripping in COVID, and it was like, oh, my God. This is awesome. It was a little bit of just the moment of like, what is going to happen here? My wife was pregnant. The whole consulting thing that I was doing which had been great to me came into question. I got a call from somebody who I had a very close personal relationship with saying, "Hey, we've scaled this thing to a million in ARR. We need a VP of sales. We just closed our seed round. Do you want to move to Denver and do this with us?" We got on a flight. We got out and visited them. It was personal, right? It was like the Zenefits' story came to an end for me. To me, somewhat on account of this problem not being a solved problem in the space. And between that, between the fact that there was already enterprise traction so early on and I was getting a chance to work with people that I knew and trusted on day one - we didn't have to do the whole, I don't know, getting to know each other thing. We could get into the work right away - all of that added up to me and my wife making the jump and moving out. A couple of months, we're having our first kid to Denver. It's been an awesome ride. We've been doing it for four years now.

Alex Kracov: That's an amazing story. Another great example of how you just got to get on a rocket ship whenever one sort of comes to you, no matter what the seat is. It's an amazing thing in a startup world where these opportunities arise out of nowhere, especially moments of desperation like COVID, which was definitely a weird time back then.

Evolving past founder-led sales

I'm curious, what did you do at the beginning? Because there must have been this transition from founder-led sales. I assume Niji or someone else was doing this. It's called 100k deals, if there's 10 to a million. And so what did that look like? How did you sort of transition the business from founder-led sales to more of a proper sales model? It's something I'm dealing with now at Dock, so I'm really curious what you guys are able to do.

Robby Allen: Super important question. I mean, sales was Niji's baby. He had a personal relationship with every customer. And frankly, there are fewer things more powerful in the early days than the CEO and founder of the company selling directly to customers. There's just a level of connection and attachment to the problem that customers want to buy from, I think. There's a lot of magic in that. So I had to show him I could sell. Day one, I remember I was on sales calls. In my first couple of weeks, I'm putting points on the board with another AE who started with me around the same time. It was like pretty much my singular priority for the first month, I would say. As soon as that happened, it was like, alright. I earned his trust by showing him I could do what he did. Then showing him I could do it better, not in the sense of being a better salesperson or something but instead doing it in a more systematic and scalable way. Then it was sort of like, okay, we need to go build a team.

I think, looking back on it, Alex, there's a lot of stuff I've gotten wrong. Here at AgentSync and just throughout the course of my career, it's a series of lessons and things that you try to just do better the next time on. But one thing we got right here was, the first five AEs we hired were really, really good. They're all still here. They're all still here, and they're all still top performers on the team. I think, especially in the space we're in which is more of like a specific vertical and longer sales cycles in enterprise, that continuity of that talent base has really carried us from a revenue growth perspective over the years.

Those were a couple things that come to mind, I guess, early on in terms of that handoff from founder-led sales to being a VP of sales. Niji has admitted to me more than once that it was the hardest thing for him to let go. And so there was a level of I really had to bring him along for the journey in a lot of ways and show him the roadmap of what we were going to be doing to build and scale revenue. And also, make sure that he still had a role in it. That we still were setting up closing calls where he could come in and just slam dunk the alley-oop. You know what I mean? Not to say he wasn't participating in a really productive way, but set him up to be a big contributor still. I think it was sort of a confluence of all those things, but it was still hard to make that handoff. I'd be curious what your experience has been like at Dock.

Alex Kracov: Very similar. I mean, it's like my baby. I have every relationship with the customer in trying to get the deal done and sell. But I am terrible at the stuff around the sale where it's like aligning to value and the timeline. I'm terrible at negotiating. I will give every discount in the world, right? All of the stuff that traditional sales is good at, I am bad at. I think I am really good at sharing the vision and obviously demoing the product because I'm building the product. And so it's been honestly life-changing since Joey has started working here as a head of sales, where he is such a good complement to me in holding the customer and the buyer to task and say, hey, what's your timeline to get something done? Let's align to that. It's led to so much more predictability in our sales process. Then I can come in, as you said, and do the alley-oop and be the senior relationship person or even be like the product manager solutions engineer, which is a role that sort of fits my personality and I think what I'm good at.

Robby Allen: That's awesome to hear. I think you have to, almost in a way, screen for a match in your selling styles. When you think about it as a founder hiring your first head of sales, is it somebody who I'm going to be able to sell with, who I can trust to hand this off to and then trust them to build a team that represents that motion that they're building? That's one of those things you can screen for that's not necessarily obvious on day one. But if you feel it, you see it, and you understand that that is what must be true, I don't know. That can set you apart and help you grow a lot faster.

Alex Kracov: Totally. Then the thing you said too about sort of being a player coach when you started and actually closing deals yourself, I mean, that's the same thing with Joey. He's still in that realm. He's like, dude, you got to come in and actually close revenue too. You can't just go hire a bunch of people right away. You got to come in close revenue yourself. Then we'll get there. You will hire the team, but we got to prove out the model and refine the pitch before we go crazy on hiring and spend too much money.

Robby Allen: Yeah, there's a trap for a VP of sales of doing it for too long. I think it depends on the business. If you're always going to be a shop that's a handful of reps selling higher ticket items, for example, you might want your VP of sales spending 50% of their time in and running deals. For me, it had to aggressively hit that and then continue but scale out of it in terms of focusing on recruiting for us to start building the team. So that is one of those things where it's a bit of an art, I think, to get in, prove you can do it. Then just as quickly, get out and hire others that can.

How AgentSync's ICP and sales pitch has evolved

Alex Kracov: I'm curious how the product and pitch and ICP has sort of evolved. Because you've been at AgentSync for a few years now, and I'm sure things have evolved since the first couple of early days. How have you sort of thought about that puzzle over time? Can you take us on that journey a little bit?

Robby Allen: Totally. It is constantly evolving. I would say the past 12 months for our business have taught us that we're going through a huge transformation in terms of moving up market to true Fortune 500 enterprise customers. Those customers look really different than the ones who we were selling the Zenefits' story to in the early days. We don't open each call. In the beginning, it was: have you heard of Zenefits? Then I'd get into it. And let me tell you a story about my experience with compliance in the insurance industry. That's not how you open with all state. It's not how you open with State Farm.

And so we've gone through a pretty big evolution. I think the thing that it's really opened my eyes too is, it's not just product. It's not just sales. It's an organizational evolution when you're actually going through, whether it's up market or into a new market, or you're just at the evolution of your ICP in terms of who you're recruiting and your alignment with your people team, in terms of your post sales motion. And do we have the kind of group that can really bring value to this new cohort of customers? For us, one of the huge ones, Alex, like a muscle we had to build was a true implementation and services practice to really help large-scale customers implement fairly complex software into legacy mainframe technology. That was something that, in the early days, that wasn't contemplated in the first year of us being here. You had to go get the first one and then learn. Okay. This is what it requires to get that first one. It's a series of milestones you're hitting, and you eventually get better at surrounding yourself in the business with people that have been where you're going and can actually forecast and tell you, "This is the capability we're going to need as a company to get to this new ICP." So it's constantly evolving.

I kind of looked at it as one of these things. It's like one of the most fun parts of the job. It's like working to refine your company around who is the company with the highest probability to buy from us, and then who's the customer with the highest probability to be successful with us? Because those two things aren't always the same. And using that as a way to align the organization around what we're doing and why we're doing it. I see that as a big part of my role as the CRO. It's like being in the field taking feedback and bringing that back to the business and articulating a position around like, this is who we think our ICP is. This is the data to support it. So not perfect at it. Not even great at it. But getting better at it just because it's something we've had to do quite a bit of.

Alex Kracov: Yeah, I agree. It's the funnest part of company building. I think product-market fit is a little bit of a misnomer, because you can have product-market fit in certain segments. But then, you're constantly trying to evolve and break into new segments that you may be having in one area but then you're evolving and pushing in another. And so, yeah, it's a super interesting dynamic, especially in the early days of pulling these companies.

Robby Allen: It's super well said. I think product-market fit, I think there's a lot of clickbaity types of ways of framing this type of thing. But it's fleeting in the sense that I think there's a tendency to overestimate the TAM of the initial product-market fit that you might have as a company, where that actually might be more narrow than you anticipate. You can have an assumption that this broader TAM that we could conceivably serve will serve in the same way in terms of our go-to-market motion and on down the line. But you learn actually that perhaps there were some unique characteristics of those initial customers that made it a really great fit. Then you have to make another evolution to take more of that TAM. And so, yeah, it's a constant body of work that I don't think ever really stops.

Enterprise sales at AgentSync

Alex Kracov: Yeah, I very much agree. I'd love to talk more about enterprise sales. Because as you've mentioned, AgentSync is doing super big deals and trying to push into the Fortune 500. Can you talk a little bit about how you have made enterprise sales work at AgentSync? What's the secret to a good enterprise sales cycle?

Robby Allen: I think it's a confluence of things. I think in the context of our business and insurance, one of the key discoveries that we made early on was that our product handles complexity really well, in the sense of we basically help insurance companies manage their distribution channels. Those are basically a series of relationships with insurance agents that are in the field selling their products. Our product is built on Salesforce. We deploy our product on Salesforce, at least one of our products. And it's built very well for the enterprise in terms of handling complex hierarchies and relationships and those sorts of things.

And so what we actually identified is, as we moved up market and the pain became more and more sharp, we actually found that there was a big value correlation with our product up market that was less correlated down market. In the sense that, people were already spending more up market to solve this problem and were willing to actually spend even more than they already were spending to solve it in a more uniform platform way versus a bunch of point solutions stitch together, if that makes sense. Whereas downmarket, it was often something where it was like, we'll take our chances, and we're not really spending on this right now. So we identified that early on. Then it was all about, alright, so this opportunity exists. Can we build the capability to go capture that opportunity? That was a slog, man. And it still is. That's like, that's okay. Let's knock down SOC 2. Let's get a pre-sales engineering team stood up so that we can really move from feature selling to value selling. Let's really build a sales process that's dialed in with MEDDPICC. We think of it as value selling and what are those pillars of value we drive.

So our solution isn't, we're not selling to executives in the sense that executives don't log in and use our product. It's typically two or three departments below them or levels below them. But we still need to get executive alignment. So how do we attach our value to executive priorities? So it's like an organizational rally. That, hey, this makes sense. We want to move up market. Fortunately, we have co-founders here at AgentSync that I think are ready to jump on that opportunity and move up market and are incredibly gifted at showing up market. And so all those things together.

I think probably the most important of all that I should have mentioned first, Alex - I know I'm jumping around a bit here, because we're doing this as we speak. I've spent most of my day-to-day working on this exact question. It's, how do you move up market and build an enterprise sales team? But most important of all is the people. Do we have the right team? Do we have the right mix of individuals who can show up on site with customers and sell value and bring customers in? And so we placed a bet pretty early on where our cycle times take sometimes more than a year to close. And so we made a pretty intentional bet early on that took some time to pay off, and we're now seeing repeatable success in the enterprise. But there was a moment where we jumped. You kind of jump off the high dive and you're just like, oh goodness. I'm floating. There was a bit of that for a couple quarters of like we're grinding out mid-stage opportunities. Are these going to close? Are we going to get these in? We had no basis for, yes, we would historically. But the things that we believe to be true were happening and eventually paid off.

We're learning every day. I think the thing I would say to anybody who's thinking about it is, it's an investment. It's a big investment that you have to make over a pretty long period of time to do it well and do it repeatedly. The problem is, if you have asset investment and you win business, you'll get stuck in an environment. You could get stuck in an environment with a really expensive customer problem. Where you've got a needy customer that has a set of expectations you don't have the capability to meet, and it can create a huge drain on your organization. And so I would just say, for anybody who's thinking about going up market, make sure that as an organization, you're aligned around what that means. Not just for sales but as an entire company.

Alex Kracov: I love that. It is such a company-wide investment, from the sales team, to the implementation team, to the product team. And as you said, the worst thing you could do is close a million-dollar contract or whatever it is, then that churns later because they didn't like the product or they didn't do the implementation. Yeah, enterprise gets so scary. Because it's so lumpy, the revenue. And so you're just looking at the forecasts. You're just hoping that a few of these deal, one or two deals, is like make sure breaks your year, your quarter, or whatever it is.

Robby Allen: You described the last thought I have before I go to bed pretty much every night of the week.

Hiring enterprise sales reps vs. commercial AEs

Alex Kracov: I'm curious, how does the hiring profile change as you hire enterprise sellers? I know you've done a lot of that. You mentioned you hired five really successful ones. I would be really curious, what you're looking for an enterprise sales rep versus maybe your standard commercial AE?

Robby Allen: I think we've been fortunate in that we hired mid-market and enterprise. They had enterprise titles but really were performing more mid-market deals in the early days. So let's say, those first five AEs we hired were really more mid-market focused in the sense of the customers they were selling to. Those five we've really coached and developed, they've just been amazing to partner with and grow up with the organization, and they're now more like demonstrated true enterprise sellers. That wasn't a skill set that they entered at AgentSync with. That was something between the coaching enablement programs. Just the shots on goal and the quarters under the belt over time developed. None of those folks were really from industry for the most part, in the sense that they weren't selling a solution like this to the market.

Since then, we've gone and we've hired in folks that have done what we kind of do here. In some cases, 15, 20, 30 years in our industry, that have the cell phone numbers of a bunch of CIOs in our industry and the proverbial Rolodex. I think what we've learned is that both can work. In industry and out of industry, lots of seniority or grows internally. I think you just have to be intentional about the moment that you're in as a company. Where early on, we didn't have the capabilities to support or handle the season strategic rep. We wanted scrappy, go-getter, can build pipeline themselves types of AES who can change with our emerging strategy on a dime and develop with the organization. And now that we've sort of built a more standardized playbook in the enterprise, we want to bring some people in who can take that to the next level with those resources already in place. So I think that those have been things that have worked for us.

Why AgentSync's sales team works in-person

To be honest, I think the other thing, Alex - it's been a little bit of a secret sauce - is that we've been in-person in terms of in-office. Really, since the beginning through COVID, I remember we were masked up in the office five days a week. There was a moment there when I moved out to Denver and picked my whole life up and my pregnant wife and everything, we were moved in, there was a huge breakout sort of epidemic moment in Denver. We couldn't go to the office for a week. I was like, did I just move to Denver to work remote for this company? This doesn't feel the right thing. But we ended up back in the office. I think that for the first three years, our entire sales team was based here in Denver. And we were in the office every day. I think that that kept us nimble. I think that that's not every team. But for us, I don't think that we would have had the success that we've been able to have early on had we not had that in-person dynamic with the team.

Alex Kracov: Why do you think the in-person dynamic matters so much, especially, I guess, for the sales function?

Robby Allen: I think a couple things. I think learning by osmosis, especially early on. If you're brand new to an organization, you're trying to learn the culture. Ultimately, as an AE, you're kind of a project manager in a lot of ways. Especially in the enterprise, you're orchestrating resources internally to create the types of outcomes that the customer needs to feel comfortable committing. Said differently, you need to know how to get shit done inside of a business.

In my experience here at AgentSync and also throughout my career has been that personal relationships with people are sort of the foundation of trust. Trust is the foundation of getting shit done. I found that, for not just salespeople but sort of our organization at large, relationships are built I think in-person in a lot of ways. That's not a universal truth, and it's not to say that everybody has to operate their business that way. But for us, we feel like that's been a real accelerator for us. And so all of those sellers have relationships with our CEO and our CTO. They had in-person interactions with them every day. And so they could pick up a cell phone and call them if there was a specific need for a customer. It's not to say you can't accomplish that remotely. But for us, it just happened faster and more organically. And so we made that choice. Now today, we have field sales reps that are remote that we see on more of a quarterly cadence. But we've been pretty intentional about building our entire go-to-market team here in Denver. Our entire executive team is here, and 90% of our leadership team is here. So yeah, it's worked for us.

Alex Kracov: Yeah, it's super interesting. Because Dock is pretty - I guess we are very much a remote company, kind of not by choice at the beginning. One of the co-founders is in France; the other one was traveling. He was in Poland. He's actually back in SF. He's sitting in the other room right now, which has actually been really nice to have him here. But it's been super interesting building a very distributed remote company. We get access to incredible talent like Eric, the producer, who's quietly listening on this call. Shout out, Eric. But it's hard. It can be hard to get on a Zoom. It can feel really transactional, all your cultures in Slack. And so, yeah, it'll be really interesting. I think we're pretty committed and deep in the remote world. But it'll be interesting to see how we scale that, especially as we grow out the sales team. I don't know. We're still figuring it out ourselves. But yeah, it's one of those interesting puzzles of company building that you got to deal with these days.

Working with an executive coach

Alex Kracov: I know you started - I believe I think I heard this on another podcast. You started working with an executive coach at some point in your time at AgentSync. Can you talk a little bit about that journey and why you started working with the coach, and how you've been able to scale yourself within the organization?

Robby Allen: Yeah, happy to. I think I started to feel for a moment like there was more that the organization needed from me than I necessarily felt at a moment in time at AgentSync that I had the capability to deliver. I think the other thing is, it's a lonely role. I report to the CEO. We talked mostly about the business, not about my personal development. That's not a knock on AgentSync or Niji anything. Niji has been an amazing leader and manager and everything for me. But it's more like, of course, we're talking about the business and problems that we have to solve.

And so the executive coach was a big unlock for me, because it gave me this outlet to just be really vulnerable and really transparent about the problems I needed to solve and, frankly, a lot of feelings that I was having that I didn't really have an outlet for otherwise. I didn't go to therapy. I have friends and family and things in my life where I could express some of those things. But I kept a lot of that. I carried a lot of that. I think that the executive coach was a big unlock because he gave me this forum to sort of name and define the things that I was feeling and needed to get done and then visualize a path to becoming that future. We met every week for a couple, for now two years. It's just created this compounding effect, where my ability to get things done has just amped up to another level. Where we just boil it down to like what is the most important thing that needs to be done in any week or given period of time, and then it holds me accountable to making that happen. I think it's also sort of helped me do a little bit of self-discovery to learn about myself.

I think for anybody who is on the fence or thinking about doing that, I'd certainly encourage having somebody in your world. It doesn't have to be an executive coach. It could be a mentor relationship. It could be therapy, in some cases. It could be any any number of different things. But for me, it's been a really huge unlock and something I feel really grateful for and fortunate to have experienced.

Alex Kracov: Yeah, I actually did the same thing at Lattice. I think we got to a certain point at Lattice where, kind of as you said, I was the best marketer at Lattice. I still needed to learn. I was young in my career and all this stuff. I eventually started working with FranÁois who's a CMO coach, and it was so incredibly helpful. Because I needed someone to push me and get me to think about marketing better, and also teach me how I need to interact with other executives, and the board, and all these things that I had no experience doing before. It was just like a huge unlock and professionalizing myself in moving I think of it from a manager to a true leader within the company. So yeah, I'm a big fan of executive coaches.

What's the difference between being a VP of Sales and a CRO?

Alex Kracov: You moved from a VP of sales to a CRO. And now you're the CRO at some point in your time at AgentSync. What's the difference? Is it just the title changing or promotion? Do you think your roles and responsibilities really shifted as you move from VP of sales to CRO? How do you think about that transition?

Robby Allen: Totally different roles would be the punch line. I think at first, when my title changed, I would say that I was actually still behaving like a VP of sales for quite a while. Where my orientation of the team, that was my first team, was the sales team. I was rotated towards problem solving on behalf of the sales team, unblocking things on behalf of the sales team, creating outcomes on behalf of the sales team. The work that I've done that I continue to do is making the executive team, the leadership team, your first team. I think that was the big mindset shifts that I've had to go through as a CRO. The roles expanded. I oversee customer success and revenue operations and channel partnerships and some other teams that weren't sort of originally a part of the scope of my role.

But it's really, for me, the biggest difference has been making that executive team the first team. I think there's a lot written about this. But it's really a demonstrated behavior of partnering cross functionally with the other leaders in the business, to build a plan and hold the team accountable for that plan and communicate and do all that as your number one priority. I think that it always felt a little scary letting the hand off the wheel, so to speak, of driving sales. But I'm fortunate that we have an amazing VP of sales, Ryan Ward, who's done an awesome job basically taking it to the next level. I'm still working on how to do that. But that's been the big difference in the roles for me.

Working with Jason Lemkin at SaaStr

Alex Kracov: I'd love to end today's conversation, switching gears a little bit, and talking about working at SaaStr. Because I think you worked at SaaStr before AgentSync. I'm a huge fan of SaaStr. I mean, it has such a positive impact on my career. I think we all have listened to the godfather of SaaS, Jason Lemkin' blog posts and stuff. I've learned so much from him. What was it like working for Jason, and what did you learn from Jason?

Robby Allen: Yeah, I mean, I think you said it right. Like godfather of SaaS. I learned a ton working from Jason, and I am so grateful for the time that I spent there. Candidly, I booked the role before I worked at SaaStr. It was a relatively short stint as a head of sales at an early-stage startup that just didn't work out. My confidence was a little rattled from that. I came on board at SaaStr in sort of like a consulting capacity really, as like an AE selling. I got my mojo back in a big way there. Really, that was the step I needed to make before taking this jump at AgentSync. And I'll be forever grateful for the opportunity. I think I learned a ton of stuff from Jason. He's an incredibly gifted salesperson, but you would sort of never know without actually observing it. Because it isn't his background per se.

I think the other thing I really learned about SaaStr is just the power of brand. It's a small team. People are often surprised to hear there's a dozen people that work at SaaStr. Because the brand and the voice that SaaStr puts into the market is, you can hear it. I think there was just so much investment made in the brand and the consistency of the value created for the community over a decade plus that just has this amazing flywheel network effect. And so the events really were the driver of the business from a revenue perspective. But it was just amazing to me how you could pick up the phone, and somebody would know, oh, SaaStr. Yeah, no doubt. Let's talk. Customers, like you guys at Lattice, when you're the VP of marketing there, that was sort of our target buyer. Right?

It was funny. I've worked at a bunch of startups, but no startup that I've ever worked at has had a better brand or a more recognized brand than SaaStr. That's something that Jason has been in the background working on for a long, long time. It makes it easier to be successful in that kind of an environment. So I think that was one of the big lessons. But yeah, just super, super grateful for the time I spent there.

Alex Kracov: Yeah, he's amazing. I think it's cool to hear that he's just as good at sales as he is in marketing. Because all the marketing stuff you just see and the volume and the quality of the content that he puts out is just so spot on. There are so many blog posts, or just tweets, or whatever that I feel like speak to your inner soul of something you're dealing with as part of building a SaaS company. You're like, how did you just read my mind, Jason? So it's really cool to hear that it lives up to that behind the scenes.

Robby Allen: Definitely some deep cuts from Jason. He has walked the mile in these shoes as far as being a founder and being in the trenches, and has gone out of his way to share a lot of those stories. So, yeah, they're doing awesome work over there at SaaStr. I think it has also opened my eyes. I think that there's just a need for more communities like that across industries. It's very SaaS-focused, of course. But now working more in the insurance industry, there's a notable absence of that kind of a community even though the demand for it exists. So I'm pretty bullish on micro communities and the events that drive those communities and everything like that. SaaStr being like a great poster child for it.

Alex Kracov: Well, thank you so much for the conversation today, Robby. If people want to follow up, ask questions, or maybe buy insurance software, where can they find you?

Robby Allen: Yeah, if you need licensed insurance agents, go to agentsync.io. Drop us a note, and we'd be glad to help you out. On a personal level, I'm on LinkedIn and Twitter, just Robby Allen. I'm on both of those platforms. I try to poke my head up at times and share things but I would love to connect. Yeah, Alex, I just want to say thanks to you, too. I love what you guys are doing at Dock. I have admired from a distance the journey you guys have been on. I'm also a fan of the podcast. So I was flattered when you reached out and almost a little bit surprised and glad to have done this with you. So thank you.

Alex Kracov: Awesome. Thanks, Robby.