Jake Dunlap, Founder & CEO, Skaled

Scaling Up Services - 012 - Jake Dunlap

Jake Dunlap, Founder & CEO, Skaled

Jake is the CEO and Founder of Skaled, a consultancy focused on helping global 2000 companies and start-ups grow by optimizing their sales process, people, and technology with customized, repeatable and sustainable strategies.

Prior to Skaled, Jake headed Sales & Customer Success for Chartbeat. Within the first nine months of his tenure, he grew annual bookings by more than 300 percent year-over-year and nearly doubled monthly recurring revenue.

Before that, Jake was the VP of Sales at Glassdoor, where he expanded the department from one to 40 employees and grew employer-direct revenue from $0 to nearly $1 million in monthly recurring revenue.

Since launching Skaled in 2013, Jake has been a sought-after industry thought leader, quoted by Forbes, Inc., and Huffington Post.


Download Skaled's latest ebook - "Sales and Marketing: Bridging the Account-Based Gap"


[00:00:01] You're listening to scaling up services where we speak with entrepreneurs authors business experts and thought leaders to give you the knowledge and insights you need to scale your service based business faster and easier. And now here is your host Business Coach Bruce Eckfeldt.

[00:00:20] Welcome everyone. This is scaling up services. I'm Bruce Excela on your host today we're here with Jake Dunlap. Jake is CEO of scaled which is a consultancy that helps companies grow by optimizing sales processes people technologies. And we're going to talk a lot about that. Welcome to the show jay. Thanks for being here.

[00:00:38] Awesome. Thanks Bruce. I appreciate it. I'm looking forward to it.

[00:00:40] Yes. So why don't we start it was like the kind of start these episodes by hearing kind of your story like how you know how did you start scaling what were you doing before scale. Give us a sense of how you got to where you are today and what were some of the challenges and experiences that you went through to get there.

[00:00:56] Yeah I think I've got to do a fairly different or unique entrepreneurial experience. You know I I grew up in the Midwest you know between being born in the age of seven I live you know in feedlot and on a farm. So you know I think move to Kansas City what when I was 7 had a really unique opportunity. And you can grow up in more of an urban city environment and then went to college in Missouri and then moved to Florida to actually work in professional sport. So you know I had like a I think a pretty unique entrepreneur experience you know really hard working parents working at the job 9 to 5 getting the pension is what's most important. And so I think you know growing up that thing that I learned the most was just the importance of hard work and that you know with a ton of hard work that you could do you know that you could be successful. And you know they ended up being you know successful and for me sales in particular you know in college they held a few different jobs they did some how I did a bunch of telemarketing waited tables and didn't plan on sales being the career you know really at least in college because there is no I mean now there are now there are sales majors but you know for me I wanted to work in sports right. I knew it. I love baseball football and so I was super super fortunate my you know my five and a half years in college I was able to get an interview with the Major League Baseball team the Tampa Bay Rays.

[00:02:19] They flew me out during the finals. We ended up getting a job with them move to Tampa. You know candidly and I was like my first experience of working with anybody outside of the Midwest and it was super well it had a lot of us from the south and I know you always think the Midwest and the south are the same. They're really not. So that was a really amazing experience. Then move to Phoenix with a different sports team. And you know what I realized when I was in Phoenix is that I love sport. I love sales. The two together weren't my jam and got it had an opportunity to win CareerBuilder was really going through their kind of big list passing monster. They opened a big office in Phoenix and I was just lucky enough to kind of get into the ground floor and it was really you know 2006 was my first exposure to kind of like this technology. And I was like oh yeah like this is this is my thing. Like I like this and then moved out to San Francisco with CareerBuilder and had a very very successful team in Phoenix the number one team out of twenty five and five teams had to get enterprise sales experience. I realized really early in my career that in sales if you can't walk the walk if people don't know that you can close Intel I can't you know at 29 I can't ask a 45 year old grown ass man to you know go out and try to close Intelsat realize how to get that field experience during that time.

[00:03:35] CareerBuilder also paid for my MBA which is also really critical helped me to get kind of a larger purview of what things look like outside of sales because when you're in the sales world you are so focused on revenue revenue grow Groberg grow grow top line went to San Francisco you know really right place right time was that crippled for four years. Glassdoor reached out. We are trying to scale up our sales team for the first time. You've been in this space you've led teams you understand how business works. What do you think. And I said yeah let's do it. So I was sales higher number one for sales leader First Vice President Sales at Glassdoor obviously a couple of weeks ago was a very good day. With the exit. But that really kind of got me. I didn't even really know what the startup world was but what I realized after my Glassdoor experience that I moved out to New York to take over the head of sales at a company here called heartbeat. But what I realized from those experiences is you know one you know I was an entrepreneur. I didn't realize that meaning like as I look through all my experiences in sport the teams are always small I was a founding member. When I went to CareerBuilder the team was small it was a founding member Glassdoor founding member heartbeat first they had always been this person and then when I started to realize about myself it's like I'm just not a very good employee.

[00:04:49] I'm good at that job.

[00:04:52] I've got you know I have sharp elbows and I think that that was kind of a theme throughout my career when I was an employee is that I was successful always increasing numbers excite etc. but working in a certain environment even if was a small business environment I wasn't where I was strongest. And so for me realize like look the only option I had is to be a CEO. It it's so clear in talking over the last five years there's been plenty of you to want to go and Southlake and rate of staying but where I'm at today now is I've kind of started to make that transition from a failed brain to see you know brain. And so you know really it's given me a really unique perspective on entrepreneurship and on being a CEO. It's always a good skill to have. But it also you also tend to overemphasize revenue growth over everything. And I think it's just been for me as a CEO just the last couple of years where I've started to really understand and I think appreciate other parts of the business I've had to you know again I think my path to this point was never pre-determined again. My parents were entrepreneurs they were just hardworking people but you know kind of fast forward to today. It was like I was kind of always on this path and you know you know now you know we're from a revenue standpoint we've already after 2017 number we should hit our 2018 goal by July. So you know we've had I think part of that is just me becoming a better Ficano an operator you know and moving from just being you know a sales base consultancy to being more growth focused organization. So that's you know how I got to this current point in time a couple of interesting things there.

[00:06:23] First I think the.

[00:06:24] So I'm I'm from Minnesota I think there's this whole kind of Midwest work ethic that I think is really important. I think that kind of working hard certainly for an early stage company and I'm sure a lot of listeners here that are kind of in the early early throes of a business you know getting it off the ground building it just putting in the time and putting in the effort sometimes is the best thing to do. You know it's not always clear exactly what the outcome is going to be or what the next step is. But just keep moving forward as is often a thing that we focus on and an early stage.

[00:06:53] I'm curious about the sports piece.

[00:06:55] Is there anything that you learned about sports either you know technically tactically or from a culture point of view that you feel sort of fed in to the sales growth culture that you have now.

[00:07:07] Yeah well I mean sport is interesting right because anytime you say you worked in professional sport people are oh wow gosh that's so cool. Like wow. You work in a sport which is what they know that too right.

[00:07:16] They know that they zation level.

[00:07:24] You know look it's funny I didn't know any better. I mean I didn't even really know what role did in sports. You know I remembered my interview I'll never forget that. You know they're like Jake what do you want to do. I said I want the general manager. And like I said I know I wasn't qualified at all I didn't understand even what that meant I just knew that that was like the pinnacle of the pyramid. Yeah you know I'll pay what I've seen more than I've actually had a call was it Friday with the head of sales at the New York Red Bulls here in town and we we talked to even met met with the sports leaders. You know as a part of scale. Now I think you know sports is an entertainment business. Sports is not secondary but it's certainly not the value proposition. So I think that my experience in sports gave me was a really strong foundation and is how to take something that appears like a platform or something that's really really tactical and instead really speak to the business value that a company would derive. I worked for the Tampa Bay Rays between 2003 and 2005. The worst team in baseball worked for the Phoenix Coyotes in 2004 2005 2005 2006. One of the worst things in hockey. Whenever you have the variables you have to learn really quickly what's the value that I can deliver and the value is awesome experience client retention and so not talking hockey is just merely a vehicle that can help you to grow your business and get help you to retain your customers. And so I think working in that environment early on helped me from a stales career standpoint to really quickly understand how to get to the value as opposed to explaining the utility of what something was because nobody was buying that. And I remember a day game in Tampa versus Minnesota.

[00:08:59] I mean like 2500 people nobody is buying the product on the field they're buying the experience.

[00:09:04] And I think that experience in sports really helped me to hone that and I took that with me you know into your sales and fast career as well too.

[00:09:13] Yeah yeah I think it's about saying that the whole idea of understanding why what is the value that that people are getting out of the product or service rather than what is the actual tangible thing that you're doing an support that.

[00:09:26] I mean that's like Samii and people have been talking that for a long time and I think a lot of people don't get it. You know I think I think a lot of people and founders and CEOs to my God like it's the same thing right. It's like I'm going to talk to you about the utility of what it is versus the impact that this is going to have on your business.

[00:09:42] Well I think and I think it's because a lot of entrepreneurs are very problem solvers. They're puzzle solvers like they want to find a solution and they get very enamored with the solution. The thing that they've created as an object worsts and getting out of that hey look I need to think beyond this thing and think about OK what am I customers what are their problems home solving or what is a value they're going to get. And beyond just a utilitarian value about it what is the emotional value that they're going to get out of this out of my product or service.

[00:10:11] Good points. So tell me a little bit more about scale what you've been doing the last couple of years where you focused. What what kind of companies are you working with. Just give us a sense of the type of work you're doing now.

[00:10:20] Yeah it's I mean again it's evolved you know and I think you know you talked about this a little bit Bruce. You kind of started in the early days I think a big mistake that I made as an entrepreneur as I didn't I didn't do a good enough job I used to think like mission vision and that stuff was kind of important. And I think what I really realized over the last two years it is the most important thing that without a clear vision a clear mission. It's really easy especially as a professional services company to get sucked into a lot of things. So you kind of fast forward to where we are today and I'd really say over the last two years I think we're getting really really good at this of really knowing who we are right of moving away from the sales training world right. I think it's really easy to loop in growth consulting with you know a one day training moving away from that. Why don't we move away from that like we want to show impact. Right. The work that we want to do with our clients we want it to last. We want people to see results. And if you look at the facts about the impact of a sales training it's like 85 percent of its forgotten in the first 45 days. There's a lot of stats that just showed that's not how we actually learn as these like really intense like eight hour sessions. Like instead there is like a reinforcement period.

[00:11:23] So I think what's happened is we've really started to focus and I think the other you know if you look at where we're at today and the types of companies are working with is the bleed between what is marketing and what is sales is becoming super apparent and over the next five years it's going to be almost indistinguishable meaning what it means to be in the marketing and nurturing and driving intent is going to be a lot of the things that we traditionally associate with sales meaning marketings role and like this role of intent is going to be driven by machines. Other platforms etc.. So what it means to be in the role of sales is just evolving at a unprecedented pace and I think five years from now is what it means to be in sales that is going to be dramatically different and and so the types of companies that we're working with you know look we have clients that are series a you know organizations that are kind of going through that first phase of operationalization and they're looking for someone who gets it someone who understands the intersection of how you scale a team smart how do you scale a team with scale technologies. You know we've implemented hundreds of sales technologies which I think completely separate us from other small firms up to really big public and private companies so you know LinkedIn talked about this publicly on LinkedIn a couple of weeks ago.

[00:12:35] It's great you know linked in the current customer of ours. We have a handful of other clients like that that again are trying to bring new ideas to the table. And so I think you know our our customer base you know more typically is like that company that is going through a different challenge around operationalization. So it's either that tower stage or it's much later on where a part of the machine needs to be tweaked and you're looking good not for training at it for more bodies that you're really looking for a partner that brings strong operational and tactical knowledge plus you know call it strategic you know go to market vision and I think that's really what separates us in this market is you know our consultants are all ex sales leaders right. This isn't about you know people from a more traditional background be tried it just didn't work. And I think really it's more about the problems that a company is looking to solve. And I think because we've worked with over 250 300 plus you know kind of growth technology from like that theories to theories F level. Now we have a really unique perspective to bring to corporates as well. But you know look again like our client base right now is probably 30 to 40 percent that like series 8 a series C another 30 to 40 percent maybe 200 to 500 employees and then you know only 10 or 15 percent is that that large corporate.

[00:13:48] So let's talk a little bit more about that marketing sales relationship. So I think that's something that I see coming up again and again and you know as companies sort of think more strategically and start doing some planning and start even figuring out organizational structure that they struggle with and I think part of it is that if as you mentioned as you look at maybe a traditional or Storck view of sales or marketing they're quite separate you know marketing is being much more about demand generation and sales being much more about closing deals.

[00:14:18] Talk to me a little bit about where what that was and then what you've seen changing over time and maybe what are the forces that you see playing into that.

[00:14:27] Well the big force is over the last two and a half maybe three years for the first time platforms are being built for salespeople that aren't CRM and maybe some version of reporting if you look at VentureBeat Bowery capitol that they'll put out this kind of sales technology landscape. You know it looks identical to what marketing technology went through starting back in 2008. And so the reason that this is happening is again sales has always been great. It's like grinding. And not only that. And we you know again like there's a difference between hard work and smart work. I think what I've done throughout my career you know I had a hard work ethic but I'm also clever you know not to digress too much but I will tell this story about again the importance of smart work. When I was that half of my very first job after the first year ticket sales I went and analyzed every single inbound sale I had because the way the phone system work is there's like 12 of us is it worked on a loop and it was a round robin. So if someone else picked up the phone it would skip them and go to the next person. So what I did is they mapped out every inbound sale that came in. You know 100 100 have been done. Tell and what I saw were these like really weird gaps where nobody called it. And so that's when I made all my cold calls.

[00:15:31] So I would literally sit there and do absolutely nothing.

[00:15:35] And then what I would do I would cross the cold calls and then like I would just sit there. Tampa Bay Rays Tampa Bay Rays. And I would like everyone else to keep making calls I'm like why are you making call the day. Nobody like it again this goes back to it like always trying to work smart. Along with working hard.

[00:15:49] So you're actually mad that you are mapping that kind of demands. You're looking at the Damanhur and saying hey look I said I should optimize I should optimize myself to be responsive during high inbound call periods and during these low periods that's when I can do my own call.

[00:16:04] Exactly. Fascinating. I mean I think that there are opportunities to beat.

[00:16:11] I think that the key thing that you know that the point there is just more about being resourceful. Like I've always been extremely resourceful. I don't get it's cost me as being an employee you like. I really don't understand where lines are or where barriers are. Like I'm always like well why. That doesn't make sense. I'm just going to do the other thing and that will allow me to crush it and go you know do better sense going back to your question like why not again that's kind of like sales technology right kind of like tantalise like I was like 2005 version of predictive analytics right. Like Google's like Geto excel skills. But what's happening is we had all these fail technology. I mean like gasified to have these tools like sales often other tools like it would have been amazing. But let me tell you some of the work that we're doing and I'll tell you why is. I know that this is true. You have a marquee automation tool that's responsible for doing all these things interacting with customers. We kind of typically look at marking automation as like an email tool that's like nurturing people top of funnel with content. It's not really true anymore like people are using it in the middle funnel to make sure you hit people with the right content using that with current customers. Now you couple that with that failed engagement platform which allows me to start to personalize things which allows me to then say OK Susan has done X Y Z or this is my perfect ICP.

[00:17:18] I'm going to you know kind of a personalized outreach. When you marry those two when you marry the ability to do more and more intense based work across email across phone with the ability to quickly utilize sales force to trigger personalized events. Once people have reached a level of intent there is no doubt that is going to be the future that future is going to be. We are following up more and more on intent and that Gritz factor is more about it in kind of more and more migrating to working smart. I think you're smarter and smarter and smarter salespeople. I think you're going to see the stigma go away of like you know lax bros as like a sales persona. I think you're going to see more and more like project management smart sales pipes to get this kind of workflow management. So I think what this means for a lot of companies and CEOs. And by the way for CRM and enterprise stealthier in particular if you're not paying attention what's happening in cell technology is that a massive deficit is going to continue to throw bodies at it while your peers are being more efficient and more effective. So I think what you're seeing is just bleed between what marketing is responsible for and what sales is responsible for.

[00:18:22] And I would argue that sales is becoming more and more responsible for intent follow up and marketing job is to drive to certain levels of content at different parts. Right now marketing should how current customers use the product more efficiently whether it's marketing or product marketing we can debate that later. You know I think that there's just such a bleed now where it's all going to bleed into you know candidly more and more marketing than sales. I think sales. It's shrunk in this process but I think too many companies and why this is really applicable to this audience. Bruce is that too many companies focused on outbound first. Like if I can just throw spears that I can just go out and find people. Not that I don't think all companies should be doing outbound. It is. It is critical but they also should be building their content their social. Getting both mid funnel and top of funnel social to get people more active. You know talking about it and then hitting those people with the right content. So again I think that's going to continue to prevail HubSpot kind of had that foresight you know maybe 7 8 9 years ago but this whole concept of inbound marketing and I think the rest of the world is just now starting that focus.

[00:19:26] So I was a founder CEO entrepreneur early stage say some ten million dollar services company.

[00:19:35] Where do you see or would you guess are the things they're probably not doing super well right now.

[00:19:42] And what are some other things you suggest they start looking out in terms of really looking at scaling that business. I mean typically the challenges that I see are that the sales process the sales work is done by some senior person some kind of partner level thing like what what are some of the things that you would suggest they start looking at to create a system a process that's that's going to be able to take them to that 100 million dollar level.

[00:20:05] You've got to be on the grind. I think the problem is I see so many found especially early like you know professional services. Early stage tech companies are looking to outsource sales as soon as possible for somebody else. And I'll tell you the people that that man the people that win are the sales leaders and C and partners that we see that go and do that grind. They're like yeah of course I need to build out the process first or I need to have a partner with me at that level. Sales is not yet for whatever reason. You would never hire I use this analogy all the time. You would never hire a computer programmer right and say oh yeah you know how to write code cool like we use C++ like. Go at it. But yes that's how we hire stealth people. We don't give them a playbook we don't give them the way that we operate the way that we do business it's asinine. I think that's why so many entrepreneurs bail's they want to outsource they both like the same way that you can't really outsource product development if you like you as the founder has to be added to all the story about the battery barrier to me is a perfect example. It's one of the founders guy named Brett. Brett was trying to figure out this last year right better he just sold 100 million dollars to Dacca. Right. Brett realized outbound wasn't working for whatever reason. You know what he did. He stopped being CEO. He started being an SVR for a month and started winning and crushing and literally less than a year later copy sold for 100 million.

[00:21:22] He destroyed outbound they did an amazing job. Why. He realized that for his business. I think the most important thing that he could be doing and this isn't the case every founder. It could be that you need a partner who is going to be able to do this. But he did it. He's like No no no this is going to fail. No no no no no no. I'm not going to let this thing like I know it can work. I'm going to do it. And so I think too many CEOs don't either don't have a partner who they can who will actually go grind it out with them or are too scared to go and fail and grind it out and figure it out and it's there is no shortcut. Someone has to build a playbook for your sales organization in items that a tenant needs to be you. As the CEO or somebody like you write or someone who's like who's into your business and I think that's that especially when we talk too much. See early series. I think that's that's probably the most one of the biggest yellow flags red flags for us. Like I you know like don't outsource sales don't outsource. Building your complete sales program to us. Because we're going to be filling it out as well to you. You need to get on the grind. We'll help you to operationalize it and then so you can scale and grow but you need to go figure out the basics and get those first like 10 15 customers.

[00:22:35] Yeah I think it's interesting I always kind of have this model that I use with CEOs who are kind of in that growth process where we say you know we start product focus you're focused on developing a product a service at solving some kind of problem. And then and then the problem is you need to focus on that customer acquisition what is that what is that process.

[00:22:52] What is this system what is that channel how do you make that not only scalable how do you make that you know financially viable. Howard how much does it cost you a traffic customer how much money are you going to make off them and you have to make that work. And then you shift to being corporate or culturally focused right.

[00:23:06] So it's build the product build the channel build the culture as kind of this this phase that I see companies go through and I think you're hitting it on the head which is those CEOs who can't successfully make that transition from being very product focused to being customer acquisition and sales channel focused. They're just going to hit a plateau they're never going to get above a certain height.

[00:23:24] Yeah and I would say like I think you had to build the culture while you're doing both. Meaning like I think I would say culture needs to be a part of those first two phases of your company's culture will evolve as you move from these different phases. And I think it's either you know how to do it or you partner with the right person who does like it totally you know if you can't spit out a sentence then like yeah then you need a partner for your business and you need to also understand the drive they bring to the business. You know what I mean like if you can't go out and make those first few sales then or do that then you need to realize that you need a partner you know and that's totally fine. And I think you know look this is not a new concept Steve Blank wrote about this in the book. It's a textbook. It's long beach obviously picked it up like these concepts or you don't know how long how it works.

[00:24:09] It's almost like it's almost 20. Yeah it's a game. It's the same process. Just go do it for a reason.

[00:24:16] Millions like entrepreneurs doing it. That's the other thing I think I've made my career just absorbing best practices to other people doing it. I know who I am I'm authentic to myself. But I have zero pride about doing what other people have done. That's the other thing CEOs and entrepreneurs especially first time CEOs brief. I see this all the time the first time CEOs had this chip on their shoulder I have to do it all myself. Oh it does. If you look at the disproportionate amount of our clients are either you know a little bit later on in their career or second time entrepreneurs because they realize there's no reward there's no prize for doing it all yourself. Grinding it out for two extra years to get to the same place at another company got you in six months because they just asked for help. You know like I said I think a lot of first time CEOs in particular. There's so much ego and so much pride that they can't get over themselves to just say like whereas I like that my entire life I'm like I'm just going to do what other people have already done that beard twist on it and just do that like you know most things have already been done before there's not a lot of original thought yet left with 8 9 billion people on the planet.

[00:25:21] So I think that that would probably be other than we haven't talked about is just get out of your own way and seek help. I don't care if you work with us I don't care who you are. Like you need to get people who are experts and not even from my own business right. That's taken me a long time that I kept hiring Mark marking the perfect sample cap hiring one or two people in marketing and they were like these weird jacks of all trades that never again hire specialists. GREENE You're amazing content. You're doing content you're amazing at social. You're doing social and maybe it means I only need them 20 hours a week three hours a week you know. So I think that concept of knowing what I'm not good at and knowing what the business hiring specialist worth jack of all trades is also really really critical you know as you grow.

[00:26:00] So that would probably be I think that's the one that we talk about that's where you think you want to become the dumbest person in the room right.

[00:26:06] You want to make sure that you are hiring people that are really smart and really expert in these areas and focus on the coordination and the long term planning and the strategy behind things. Yeah like I said there's there's no there's no prize for we're trying to do it yourself as just whoever can get to the final outcomes.

[00:26:22] You.

[00:26:22] When you think that that's the prize you like how how can you get there as fast as humanly possible and I think yeah there's just it's all ego and I see it.

[00:26:30] There's a whole nother episode we can do on that. But I think you're already too thin the dating factor and it kills you it cripples your ability to grow.

[00:26:39] You know when you're focused on just trying to do it all yourself and again then you just kind of look up and you realize like why have I been doing this. There's no like you know self-inflicted punishment.

[00:26:49] Exactly. This has been great great conversations and great points. I think there's probably a lot more we could talk about we can schedule another episode to get into some of those. In the meantime if people want to get a hold of you learn more about scale. Learn more about the work you've done what's the best place to get a hold of you and wait to find out more about the business.

[00:27:07] Yeah absolutely. I think you know look if you want to keep up on the day to day you know linked in as best you know I'm posting everyday posting about the work that we're doing with our clients or clients or posting about the work that we're doing. So I think if you want to get a really good sense for who we are as a company obviously the Web site scaled with AK K.A. led dot com but I think if you check out what I'm doing on LinkedIn what we're doing on LinkedIn I think you get a really good sense for the type of organization that we are the type of projects that we work on. Twitter is another one. Jake Dunlap is probably the second best way. And then look you know DME on LinkedIn that's the number one way. Like I'm living on LinkedIn and working with people you know have at any given time 15 20 plus direct message conversations just with people have hit me up like Jake. This is a challenge we're going through. I'm always down to help you and provide insights that I can. So I'd say linked in the Web site Twitter but linked in probably first.

[00:28:01] I think I'll make sure for listeners that all those links are on the show now so they can vote they at all. Because it's a pleasure. Thank you so much for the time.

[00:28:09] Awesome. Thanks Breece I appreciate it. Have

[00:28:13] You been listening to scaling up services with Business Coach Bruce Eckfeldt to find a full is the podcast episodes. Download the tools and worksheets and access other great content. Visit our Web site at scalingupservices.com and do free to sign up for the free newsletter scalingupservices.com/newsletter.