From 0-$12M ARR in 18 months with Jake Dunlap

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Episode Outline

[00:36] Jake’s background

[02:50] How Jake scaled Glassdoor from 0 to almost 1M in MRR in under 16 months

[04:00] Some of Jake’s early pitfalls and how he learned from them

[08:28] Jake’s process for evaluating whether someone is a good fit for his team

[11:02] Why Jake started his own firm

[16:17] Don’t underinvest in process or infrastructure as you grow in scale

[18:15] How Jake unwinds

[18:44] How Jake works smart and efficiently


Jake’s Inspirations

Clark Beacom


Connect with Jake

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Elias Rubel: (01:02)
Let's get on to the episode. All right. So today I am super excited to have Jake Dunlap on the call. Uh, Jake has had an incredible career. I mean, he was 10 years as the vice president of sales success and sales ops at glass store, um, led them through tremendous growth and an acquisition, um, Chartbeat, same thing, uh, VP of sales at no weight acquired by Yelp. And we met, uh, because Jake is an LP at stage two capital and now running scaled consulting. Um, so Jake, welcome to the call. Hey man, I'm looking forward to the conversation. So, you know, I just want to dive right in because you have so much amazing in the trenches experiences, um, starting really early and growing through to, you know, $1.2 billion exit at glass door. Um, where would you like to begin given, you know, should we start really early days when you were just building that team up from, you know, zero to 40 in the first 18 months?

Elias Rubel: (02:04)
Would that be a good place to start? Yeah, I mean, we can start there. I mean, I started my kind of sales leadership journey at CareerBuilder before that. Um, and you know, I think the important thing for a lot of people, it's just, I talk a lot about career advice and how to think about building and being thoughtful about your career. But, you know, th the thing is I laid the foundation to be able to put myself in a position to get a job that, you know, when I got the offer letter for Glassdoor, I, you know, I'd hesitated to tell his story, but I've told it a few times now it had someone else's name on it. And that was literally 16 years older than I was. Maybe he might've been even older than that. And, and it's because of the decisions that I made around how I was, how I was mindful from, uh, you know, how I developed as a leader, going back into the field to learn enterprise sales. And so, you know, when I put myself in that position, um, when that role became open, it was, you know, I was kind of a good candidate for that first phase. So I wasn't at Glassdoor through the acquisition, you know, I was original builder,

Jake Dunlap: (03:00)
You know, so I was the, I was a perfect person to come in because I had a repeatable sales process that I'd learned at career builder and hone there. I had proven track record as a, as a sales leader and a proven track record as an enterprise, you know, sales individual. And so I think a lot of people, you know, they, they want that VP role, but they don't have the skillset. You know, they want the title, they want the director, they want the whatever, but a lot of people got it. You got to put in the work first. And so for me, no, we scale, I scaled that team from zero to almost a million in MRR in, in under 16 months. So, and how we did it is one, I had a framework, like I already had a proven process for how to sell.

Jake Dunlap: (03:39)
Um, and you know, we, we close 24 of the fortune 100 and the first year. And it was because, you know, it's the ability to craft a value to the industry. And I think what we did a really good job of was not talking about the reviews, not talking about him. Like I would, my team was not allowed to talk about reviews. I would know if they talked about reviews, if they talked about employment branding, like that was a no, no. Instead we talked about outcomes. We talked about getting the right individuals. And I think when you're in those early stages, not too many companies early on don't focus enough on the outcomes versus what the product does. And I think we figured out very quickly how to have an effective conversation with people around outcomes, we would generate for them versus what the pro, how they viewed the product.

Jake Dunlap: (04:29)
And so that's why we were able to be so successful. So, so fast. So, I mean, surely coming from career builder, there, there were pieces of your process that fell into place and worked, and you could run the playbook and then others that maybe needed adjusting and you weren't expecting to, you know, push back on what were those? Oh yeah, no, I made lots of mistakes, man. Let's, let's not get that twisted whatsoever. I made lots of mistakes, so there's a few, and I think that these are canned. So look when you, I, it's so funny to look back at it. So I want you to imagine I'm 30 years old. Okay. I just turned 30. Maybe I was just turned 31 sitting literally right next to me is bill Gurley, sitting at the head of the board table is rich Barton. And if you guys know bill Garley was bill Gurley was VC of the year.

Jake Dunlap: (05:17)
I think last year, the year before rich Barton started Expedia Zillow glass, like I had, I didn't even know what I was doing. Did CEO TripAdvisor's ever here. I just, like, I had no clue how random this was. You know, we got battery battery sitting right next to me and this, this board meeting. And I'm just, I mean, we're crushing numbers, so that helps everything. But, you know, I didn't really, I didn't know the game that well, right. I didn't, I didn't come from the VC world. And so I think some of the mistakes I made early on is one getting mentorship, uh, getting mentorship from men and women who have been where you're going to be two to three years from now, um, to help understand kind of what, like a we're talking about now, uh, you know, pitfalls to avoid. And I think some of the pitfalls I made one were around hiring a training and onboarding, I think, look at the rate that I was expected to scale, man, that stuff's gotta be dialed in.

Jake Dunlap: (06:08)
I think we, I think we had a fairly dialed in, um, onboarding process, but the hiring and interviewing process was, you know, a little sloppy probably. And I think as you grow and as you scale, you know, that ability to have a playbook to have all of those details worked out is just so critical. You know, I probably let HR handle too much of it and should have taken more of that on myself. Um, I think that was probably one of the most critical mistakes that we made that I made whenever we were growing and scaling was, was that is not just nailing that role profile, um, faster when you did, what did that look like? And who were some of your first mentors who really made a big difference for you? Yeah, so, so what we finally did is we, we did it at the end of 2012.

Jake Dunlap: (06:57)
I can't remember 11, 12. We basically started doing assessment tests and what we saw consistently. So we did kind of a, uh, a look back on like, okay, well, well what worked and what didn't work that year. And when we looked at and we had current employees fill it out, then we had it from previous employees that didn't work out. And we started to see, um, this, it was called profiles. X T is the one that we used. And it kind of tests you, there was a consistent skill that if someone wasn't strong that they were an underperformer, unless they really over-indexing some other ones. And it was logical thinking that when you're trying to make a market, you need someone who kind of thinks like, you know, in a, outside the box yet logical format, so they can explain things. And so what we found is like, intelligence was really important, you know, like, yeah, two plus X equals five, what is X?

Jake Dunlap: (07:45)
Right. Like even basic stuff. But I mean, it did, it had geometry, it had some stuff in it, man. And, but it was a very common theme. So I'm a big fan, a proponent of a using them in the process. They're not the end all be all, but I'm a big fan now of using that in the process to try to do it. Um, and then I think that that was the big adjustment, right. Is now saying, okay, going forward, um, we need to maybe, maybe weight this characteristic more than we had in the past. And I think that, that, that was kind of the big learning and the big aha for us. Um, is that okay, we need to start to really, over-index on making sure that people fit this profile for where the product is today. Cause keep in mind, this is bad Glassdoor head like man, how many unique visitors did we have two or three, 2 million a month?

Jake Dunlap: (08:28)
I mean, it is. I mean, yeah. So I mean, we was early days, right? And so what you need from your sales reps changes rapidly as, as your name becomes more well known, you can hire different types of people. They don't have to be an educator. They don't have to be, you know, somebody who can provoke thought they can be more of an executer. And I think those are the types of lines that you look for. And now you don't have to work in a hundreds and hundreds and hundreds of startups. You know, I think that's a pattern that just emerges is that need for a specific type of sales individual early. And then how that evolves when you go from one to 10, 10 to 30, 30 to a hundred,

Elias Rubel: (09:03)
How do you now have a good process for identifying early and just as quickly as possible when folks aren't going to be that fit. Like if you step into an org and you didn't make that hiring call, how do you quickly?

Jake Dunlap: (09:18)
Yeah, I mean, for us, we, there's a great series of books by a guy Jeff smart and his father's, I can't remember his dad's name, but it's theirs. It's just kind of a, there's three books it's called topgrading power score and who, um, and we've really just institutionalized, you know, key components. And I'll just give everyone kind of the quick, quick rundown. So the first is a skills interview. So we've got, um, for each role, we've got skills and, you know, with one through five, but also red, yellow, green, right. Red means integrity. There's those are the things that like, I can't coach that. I can't coach red things. It's like, it's just who you are. The yellow are things that are, or you can coach you, but they're hard ingrained or easy things that you can coach to. So you're not just measuring a skill set by how good are proficient.

Jake Dunlap: (10:02)
It's also how important is it to this job and how easy is it to change? So we do a skills interview. The other thing is, is what's called the experience interview and we go back in time, dude. I mean, I'll go back. I don't care if you have 20 years of experience, I'm going to go back to your first job out of college. And we asked the same set of questions every time. What were you hired to do? What was the high point? You know, and what accomplishment are you most proud of? Uh, what was the low point when I talked to your boss, how are they going to rate you on a scale of one to 10? And then I make them spell, spell their boss's name, even if it's John Smith. Right? So then guess what, you know, how somebody answers that question versus like, so what do you think your boss will say about you versus when I talk to your boss, how are they going to rate you?

Jake Dunlap: (10:40)
And then you make them spell their name and then you start to see a pattern, right? And then it's, why'd you leave? So it literally, and we go through every job we ask the exact same questions. The other thing that our process does is eliminates most bias, right? You know, obviously I think every organization is trying to figure out how to make sure that their interview and process is more inclusive. We're going to be releasing kind of our whole plan for free and, you know, helping companies for free to implement this. It also eliminates all that bias for, you know, looking for this type a alpha whatever it is for sales, you know, for sales and other roles. Um, but, but that process has cleaned up a lot because it's a consistent process. It's uniform across the team, everybody on my team knows it. And so it doesn't matter, you know, and when we're implementing it for our clients, it's just a very streamlined, easy way to get uniformity and to get consistency in what success looks like in the role and what success looks like for when someone, someone hopefully, you know, hopefully predicts when they get started.

Elias Rubel: (11:35)
So here's a weird question for you. Would you pass your own test? Like if you, if someone did this to you and went back, like if you were, if you were applying for one of these roles, like, would you pass your own test? Depends on

Jake Dunlap: (11:48)
The role. Yeah, it depends on the role for sure. I would say there's elements of the test I've would pass and then others, I would not pass. And so for me, part of the reason I started my own firm, you know, was after glass door, I went to Chartbeat again, same thing, super successful. We scaled from one to 4 million in, under a year. Um, and uh, today I suck at politics dude, but I mean, keep my nose third. I was like 30, 31 and 32 30, one 30, two 33 at this time. Right dude, like, I didn't know what the, I didn't know what I was doing, man. You know, it's like, I just, I didn't, I never had that mentorships. It's funny. You asked me the question. I didn't answer it. I've never been a big mentors, dude. I'm just, I'm like, there's people I talk to and I pick their brain on, but at the same time, you know, the amount of people that are at where I want to be is just not like, or just a different breed of like what I see now, back then I pro I needed it more than I did now.

Jake Dunlap: (12:43)
I probably still need it more. I mean, I have a coach now. Right. Which, which I think is like a different relationship. Um, but, but for me, as I went through that process, I just realized like, dude, I suck at being an employee. I am not a good employee. I'm extremely good at the job. Like I put myself in the top 5% of all sales leaders, right. And sales people. I put myself in the top 1%. I don't think I'm being able to egotistical. I've got the stats to prove it. But with that being said, I put myself in the bottom 20% when it comes to like, you know, uh, okay, well, Hey, okay. Yeah, that's great. You know? Okay. Like placating conversations with small talk internally, which by the way, is a skill that I, I looked over the course of last seven years.

Jake Dunlap: (13:26)
I think I've gotten slightly better at it. And it is something that you need to get better at, you know, could I have stayed longer at glass door if I, you know, wasn't a prick to our legal guy, maybe I don't know, would they have not wanted to layer me for another year or two? Maybe. I don't know. But I just, I just realized like, look, my path was, I love solving the problem. I love sales. I love building and fixing. And why don't I just do this for myself? You know? Like, why am I killing myself for these companies just, and I'm completely disposable. It doesn't matter how good you are as a sales leader. Now, Jason Lincoln just put this out. 70% of sales leaders. Now don't even make it a year. 70% of venture backed sales leaders don't even make it a year.

Jake Dunlap: (14:14)
And I re up, dude, I realized I back in 2013, I realized, dude, I'm signing up for a loser's game lose. Now, granted liquid glass door exited. I made money, you know, like fantastic. But you know, I just realized that wasn't my path. And I feel like the VP of sales job. And I know you guys hit the marketing side. It's the same man. It's a losing proposition. You're not going to make it four years. I literally, I can count on two hands out of hundreds or thousands of sales leaders. I know that made it four years. Wow. Maybe even one, even one hand, it's the classic, like, uh, you know, if sales and marketing aren't

Elias Rubel: (14:52)
Working right then the, uh, it's like when product, you know, when the company

Jake Dunlap: (15:00)
Yeah.

Elias Rubel: (15:01)
When the company doesn't win it's to be a sales and marketing,

Jake Dunlap: (15:03)
You're fucking it all up that dude. And I heard that. So this is last year, there was an ex sales leader. Who's now in house at a VC. I'm not going to say his name. I wanted to vomit and he's on stage on a panel. And he's talking about, you know, you look, if you're, because now he's on the VC side. Right. He's like, so look, if you're a sales leader, it's, you know, look at the product, you got to figure it out. I'm like, fuck you, dude, bullshit, dude, bull shit. Like it's that attitude, man. It's like that again, like I realized it very early in my career. I'm like, wait, so wait, this is how these dudes play. That not me. I'm not signing up for that. I'm not going to be your, you know what, I'm going to go do this shit for myself.

Jake Dunlap: (15:42)
Like, I'll let you dictate my future. And I feel like too many sales leaders. And let me tell you the sad part. You might see this in marketing too. Um, the amount of sales leaders. So we have a lot of XL. I mean, all of our, all of our consultants, our exhales leaders, right? And there's a big batch of them that will come to us. They'll work on a couple of engagements. And because they built a $400,000 a year lifestyle because they made that amount of money. Once really there are $250,000 leader who made three 50 once or four. They can't get out of it, man. They got two kids in private school. They bought that extra house in Connecticut or Tahoe or whatever, and they don't want to do it, man. They don't, but they built a lifestyle they're trapped in. And I see this was so many sales leaders, man.

Jake Dunlap: (16:22)
They come, they work with us for three to six months. They have a blast. And they're like, because they're not fully working. And there's some anxiety that first year when you start something, they have to go back in house. And it's just, it's just, you know, that's my other advice when you're a VP, you know, first time director, first time VP stay hungry, you know, don't, don't build that lifestyle, you know, leave flexibility, leave yourself options. Um, you know, so you can do what you want and maybe it is to be a sales leader. That's great right. Internally or not. So,

Elias Rubel: (16:53)
So what are some of the biggest, you know, you're doing tons of engagement, what, like some of your customers are Microsoft and LinkedIn and Palentier. I mean, you've got your, the list goes on. Um, what are some of the biggest aha moments that you drive for your customers?

Jake Dunlap: (17:11)
Yeah. I mean, look, our, our client we use, I mean, we still are. Our biggest segment is, is your segment. It's the gross stuff. Right. Companies trying to go from one to 10, 10 to 20 or 20 to 50. And it's really, there's there's I think that the aha for a lot of those companies is the importance of non-revenue producing heads to support the efforts. Meaning I think so often, um, we, we under invest in enablement. We under-invested ops and we under invest in leadership training, which are infrastructure things. And because of that, what ends up happening is the, you know, it's like, it's like building a building with like, you know, shaky scaffolding, you know, and like shaky. And so bringing people early to help with you. And I mean, obviously, look, this is part of what we do. You know, we have interim operations people we're doing more sales technology implementations, you know, with outreach alone, we're doing 10, 15 a month.

Jake Dunlap: (17:59)
Um, so there's these tech op optimization and then there's content, you know, how many sales teams do you know? They're like, yeah, we've got the content we need to be successful. Uh, none, maybe a zero. And so, you know, but you don't need someone full time. You might need them two to four days a week. And so I feel like, you know, we're trying to build the same way marketing marketing has all these resources. They've got outside demand, gen agency, PR website, you know, PR. And so, you know, I think as a, as an organization that's growing and scaling don't, underinvest in process, you know, don't under invest in infrastructure, you know, because it'll just allow you to get your people up to speed, you know, 40, 50% faster, you know? So again, it's like, I think a lot of founders early on under invest in support and it's, it's a, it's a mistake.

Elias Rubel: (18:46)
All right. So now let's shift gears. You, you know, you work in a really high paced environment with clients who I'm sure

Jake Dunlap: (18:52)
They are super demanding and just like

Elias Rubel: (18:56)
Type a, what do you do to unwind and enjoy life outside of work? Well, and like this and this whole time,

Jake Dunlap: (19:03)
The COVID world, um, I've been golfing a lot more. I went, I played 18 last night, so I've been golfing a couple times a week now it's been kind of great. Um, you know, I'm in the office right now, but I've been working from home primarily. Um, and you know, I think just taking that for, for me, I'm a, I'm a calendar freak. Like I, I have in any given week, I have 50 to 60 different meetings and a lot of people are like, Oh, what, like, dude, you must be crazy or mental. It's like, it's actually not, it's actually very freeing for me. Like I work everything backward, you know, like, let's say I've got a meeting or a project or something that needs to happen in two months. Everything for that project is in my calendar before I ever get started. And what, what that allows me to do is I just show up and execute every day.

Jake Dunlap: (19:47)
Dude, I'm not thinking about what's next because already I've already prioritized for myself and I'm managing every day. I'm looking at my calendar, you know, one, two, three, four weeks in advance and making sure I'm always prioritizing the right things. And so I'm not one of those people that works, you know, 80 hour weeks, et cetera. I work like a, probably a pretty solid 50 to 60 and I'm efficient, you know? And so I can go and, you know, have, you know, a couple of glasses of rosé and hang out and smoke meat and you know, on the weekends. So I think a lot of people, a lot of people, what happens is they also reward, you know, one of our core values at scaled is work smart. When I see people working too long hours, I check them. I'm like, that's not how we roll here.

Jake Dunlap: (20:29)
That's not our culture. You don't send emails at 3:00 AM here. You don't send out emails on whatever. And because I chances are that means that there's an inefficiency in their day to day. And so let, let's go focus on working smart, not working hard, work smart and hard, right. But work smart first. And, um, a lot of people have that twisted. And so I think I, I've a very young age, I've figured out ways to be wildly successful using data and being lazy. Um, and then when I coupled it with work work hard, then that allowed me to kind of Excel pass my peers relatively quickly.

Elias Rubel: (21:01)
I, uh, I love that. I sometimes try to explain that inherently, I'm an immigrant

Jake Dunlap: (21:05)
Probably lazy person, but I'm also super driven and I work hard when I'm working. So it's it's so that I can be lazy. I work really hard when I'm working. I totally relate to that. That's it, man. And it's about, I'm always looking for the angle. Always, look, I'll tell a quick story here. So like just to illustrate my very first job out of college, right. I went to Missouri state university at the Harvard of the Ozarks, um, uh, as we like to officially, uh, you know, uh, call it, um, you know, and I wasn't a great student by any stretch I take over, I think like what five and a half years to graduate, like, but I love stats and I've always been kind of an analytical thinker. And so I went to Tampa Bay rays. That was my first job out of college.

Jake Dunlap: (21:43)
Um, got promoted really rapidly. Um, I had sales experience in college and so I hit the ground running. I've been talking to that a lot about more, like I came out of college with two years of work experience. I was working full time and going to school full time. I was doing telemarketing, waiting tables, all kinds of stuff. And so I decimated every new grad. I mean, I destroyed, I was out selling people have been in sales for, for years because I got real work experience in college, which is like the advice that I give to every, you know, kind of college person, um, and, and new grad too. But, but what I did is after the first year I did a scatterplot of all the inbound leads. I went into our shitty CRM and I pulled out the timestamps of when all these deals came, inbound that closed and our inbound machine, like it worked on a loop.

Jake Dunlap: (22:27)
And so what would happen is if you picked up the phone, it would skip that person and go to the next person. And what I saw was there was a pattern of behavior where between like 11 and 11, 22 and two 40, like four and four 20, where nobody called inbound. So you say, you know what I did, I sat there for the first two hours and just sent emails, it's up and Tampa Bay, rays, this Jake Tampa Bay, rays. This is Jake that were all my peers are making cold calls. And they're like, dude, this is messed up that you're doing this. I'm like, dude, here's the date. I literally showed these people, the Excel sheet. I go, guys, this is the data. Why are you making calls? You shouldn't do that. And then they kept making calls stupid. Like, why would you keep doing that?

Jake Dunlap: (23:06)
Now? They fixed it like three weeks later. But I literally, I've always thought that way. I'm always like, if this is the way it's being done, that's the baseline. Like, how am I going to break this thing and drive exponential results? And I feel like that's always been, my mindset is once you get the baseline, it's like, okay, where am I going to go squeeze out another five or 10%? And I'm telling you, it's like, I was talking to someone about data and salespeople. I'm like as a sales rep, man, I would be micro-tracking every activity I did not for my boss for myself, because if I can pinpoint where I need to get better, or my team needs to get better than I can go and make changes. This isn't for pipeline meetings. This is so I can analyze my own sales process. Realize, look, I, for some reason I'm stuck in stage two.

Jake Dunlap: (23:47)
Lisa's really good at the stage two of the sales process. Let me go sit down, whatever Lisa's doing, I'm gonna rip that off and go do it for me. Now. Now I'm better. And I feel like not enough people take that proactive mindset, even leaders, leaders, don't take that proactive mindset around a lot of this. Totally. All right. So Jake, when I call the Tampa Bay rays, and how do you spell your manager's name again? Uh, that would be Clark, uh, beacon, Bea. He actually lives in Austin. Now. He's actually the head of the CRO for the Austin FC, our new MLS team. Oh, no way. That's fun. Yeah. It's pretty cool. We haven't hung out yet, but we will nice comes full circle. Well, Jake, this has been a pleasure. I really enjoyed the conversation. Yeah, man. I had a good, I had a blast too.