Kris Hartvigsen, Founder of Dooly | Why Modern Sales Is Broken


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Kris Hartvigsen is the CEO & Co-Founder of Dooly and a leader in the tech industry with over twenty years of experience. Before founding Dooly, he held senior consulting and management positions in sales for companies like Mobify and led Vision Critical as their EVP Sales from its early startup days to revenues in excess of $100 million.

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On the Success Story podcast, Scott has candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights.

He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.








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people, salesperson, business, sales, lesson, learn, company, build, product, problem, sell, early days, job, enablement, understand, entrepreneur, happening, hire, dooley, role


Kris Hartvigsen, Scott D Clary


Scott D Clary  00:06

Welcome to the success story podcast. I’m your host, Scott Clary. On this podcast I have candid interviews with execs, celebrities, politicians and other notable figures, all who have achieved success through both wins and losses. To learn more about their life, their ideas and their insights, I sit down with leaders and mentors and unpack their story to help pass those lessons on to others through both experiences and tactical strategy for business professionals, entrepreneurs, and everyone in between, without further ado, another episode of the success story podcast. Before we start today’s episode, a quick note from our sponsor, and throughout a fully comprehensive equity management platform. This is what they do business owners, are you looking to raise capital and unlock shareholder liquidity? Before hiring expensive consultants or brokers you need to know about enthroned private businesses use enthroned to unlock liquidity without bloating costs. With nth rounds equity Management Suite you’ll be able to create liquidity, engage with shareholders and control your company’s Destiny all in one secure platform. Get your free guide to liquidity go to That’s


Scott D Clary  01:17

Thanks again for joining me today I am sitting down with Kris Hartvigsen, who is the Founder CEO of Dooley. Now, Kris has a 20 plus year career in sales, having worked in a variety of roles. But most notably, he has worked as several senior senior level leadership positions. So SVP, EVP and most recently, EVP sales. He’s also worked as several sales leaders, directors vice president across other organizations. But what I wanted to speak to Chris about why I’m excited that he’s on is he has a strong opinion on what you know, the what, what sales looks like now in terms of sales within large SAS organizations, and the problems that these organizations have, as well as he has the scope of experience from working as an executive at a high level, scaling, sales, Ad Vision critical from zero volts from non $0, or from, you know, low six figures, all the way through to over 100 million. So he has that entire scope of working with an organization scaling a commercial organization working across all these different roles. So he has a very much boots on the ground view of the problems that exist within companies as they grow, and they scale. And that’s really what led him to build out dually. So you know, thanks again, for joining me, Kris, I appreciate you sitting down. I want to I want to understand your story, your career, and then let’s speak about what you’re doing now.


Kris Hartvigsen  02:54

Okay. So we go way back? Yeah, let’s do it. I think that when you look at an entrepreneur, there’s there are a couple of really important traits. And I think I think I possess some of them, I think you have to have a real big curiosity for exploring a pain or a problem and really digging into it. But it usually starts a lot younger in your in your career, you know, you either get the buzz off of the lemonade stand that you started as a kid or you don’t and and then you sort of build from there. So when I was in uni, I actually had my first quote unquote startup, where I imported sweaters from Ecuador, and brought them back in hockey bags and sold them for a mass profit and use that to pay for a lot of my education in my fourth year, and just started seeing this really interesting opportunity to be your own boss. When I when I graduated university, I was convinced I was going to be an advertising executive. I wanted to be a creative director, I wanted to live in New York, I wanted to do, basically a modern day version of madmen without all of the misogyny. And I graduated in the mid 90s. And I was super into Tech Tech was really just starting to come into its own and I got a job in tech, and I kind of just ran with it. And my passion started to build around certain aspects of technology. I was working in corporate sales for, you know, hardware sales. And back then we used to have global trade shows called Comdex where, you know, you’d have these big computer expositions around North America and around the world. I was actually in multimedia design school at the time while I was working, and learning how to be an animator learning how to do post production work, all that kind of stuff. And so I knew like exactly the kind of technology I’d want to have my own dream system for doing that kind of work. And when Congress was in Vancouver, I got the opportunity to meet These people from this company in Montreal called Matrox. And they were blown away by my knowledge of their product like, man, you know more about our product than we do. Why did you come work for us? I’m like, Okay, I’ve never lived in Montreal before. So I moved to Montreal and and start working like deeper into tech and started really digging into hardware, we took Matrox to a billion dollars in annual recurring revenue, only to have this little company called Nvidia pop out of nowhere, and really starts to take the market on, right so Nvidia became the dominant player in graphics technology, I moved back to Vancouver and started my career as an entrepreneur. That’s sort of the beginning of the runway for me. When I was in Montreal, we were like, crushing absolute crushing our number, relative to the rest of the world. I ran all of Canada at the time. And when I came back, I was I rented a distributorship that basically sold high end technology to medical imaging companies, and all sorts of stuff was sold out to build micro filmmaker products in the early 2000s. Nice legs it and that’s started to get me more involved in SAS. What I realized in my career is that I, I was really good at sales. Probably because I didn’t think like a salesperson, I thought about people, I thought about empathy, I thought about the challenges that other people would have first, rather than thinking about how I could push a product onto them. But I was also horrible, horrible at being compliant with systems that were put in place as a hated administrative work. You know, I was not. I think the funny thing is, if you ask the salesperson, you know, about, like, their job description, nobody would ever say that they had to spend a lot of time filing information, right. And if you said that during the interview, it’s like, Hey, I got a script gig for you in sales, we’re going to you’re going to your territory is going to be the Pacific Northwest. And you’re going to sell to companies like Microsoft, and Intel, and all these different companies. And by the way, the best part of your job filing, you’re going to love it. And so when you’re tripling your number I was I was tripping my number at Vision critical when, when I started there, and into my career was a journey around the world without nobody ever stops to say, hey, you decide Major League Baseball, but did you enter the competitive field in Salesforce? So I started to look at that challenge and wanted to take it on with a little bit more rigor when I left mission critical. And figure out a way, again, going back to that whole empathy story and digging into the problem, or to figure out a way that salespeople could spend their time doing the things that would actually help them earn their paycheck as opposed to the things that helped keep the business informed. I figured there was probably a better way to do both. So that was the genesis.


Scott D Clary  07:57

And and I guess that’s a such a impactful point for somebody who’s worked in sales, like the non sales activities, just kill like, absolutely kill your day. It’s just taste away. And it’s like the and it’s also, I don’t, I don’t even know if you ever want to go into this. But it’s also a personality thing. Like there are there are interesting personalities that are less, if you ever run like a DISC profile on anybody or anything like that, like the personalities are less apt to want to do that kind of work. And salespeople traditionally, aren’t is a huge pain point that you’re solving. Yep. So. So you, you understand the pain point, you’ve lived through it. And that’s usually what makes the best entrepreneur, right? It’s somebody who is actually who’s actually lived through this problem, and they didn’t want to go solve it. But how do you? How do you start? How do you start this company coming? You know, you’ve had some success in the past? What what is the first steps you’ve taken to create Dooley? Because this is not you’ve had success, but you’ve never had success in this realm, in particular, in SAS, to this,


Kris Hartvigsen  08:55

Yeah yeah. And look, I’ve been a part of failures before too. So I glanced over a couple of parts of my career where things didn’t go quite the way you expected them to. But they still went, okay. Because you learn lessons from all of those different things. I became, I became really fascinated with workflow and trying to optimize workflow, primarily because I hated doing all of the things that I felt other things could do for me. And so the start point for me was just digging in and doing the research, right, you got to figure out if the problem is you, or if the problem is universal. And there’s a massive difference for you that if you want to build a product for yourself, that’s a pretty small market. So you go through the traditional stuff, right? Like, I mean, Steve Blank talks about this stuff all the time, get out and get out, get out of the office, get out of the building and talk to customers talk to prospects, but you really do need to figure out like, is this a repeated pattern that you’re going to see elsewhere? So a lot of a lot of research goes into that to to understand, you know, how big the market is how big the problem is, because what the problem is, is small and the market is big, doesn’t really matter. People are going to try to solve And it turns out the problem is really big, because data gets really old really fast and sits in the wrong spots. And there’s all sorts of things that remnants that happened as a result of that problem, too. And, and that was the cool part for me was, as we started to dig into the problem, it was clear that there was actually a second problem, which was probably as big if not bigger than the first problem was one that most people didn’t really understand. And that’s, you have, you have a sales organization, that or even like the organization in general, that is there to support the salesperson and try to help to expedite sales, we always talk about the customer acquisition cost and like, the time to close and all of those different things, the organization is there as a support mechanism. And the old days, the good old days, the salesperson was off on their own, and just like here’s your dad go and sell right now the organization sports, but the reality is they didn’t know when to support or how to support because, again, the data is coming across. So what what was happening was, and I saw this myself, you go and talk to the salespeople, have your one on ones with them as a sales leader or sales manager. And they’d be talking about their deals and your whiteboard and stuff. You’d be looking at the deal. Oh, yeah, I didn’t know. But I didn’t know what that I Wish you’d told me about that earlier. I wish I knew about this. And because he just told me about that did you know we have this really great case study or this really helpful white paper or you should talk to Susan, because she just do the deal exactly like this, that information wasn’t making its way back to the salesperson, which is enablement, right. And activation of information. And all of these content management systems that were out there were, they were purporting that they could help the salesperson be better at their job, a giant file like salesforce dot giant filing cabinet content management system, another giant filing cabinet, what do we do, we throw them up in the cloud, and then thought people would work with them. The content management system was supposed to be activated by Salesforce or by the CRM in general. And because nobody was updating anything in the CRM, the content management system was just this place where content went to die. Right. So the traditional model wasn’t working well, again, data wasn’t moving. So the premise that we started with, which was let’s help salespeople and get rid of a super big pain, and update Salesforce automatically for them, turned into this brokering of information between the salesperson and the rest of the organization. So the salesperson can be smarter in moments of truth, as well as having the business have the information they needed to do their job. And get tighter and tighter.


Scott D Clary  12:38

It makes a lot of sense. Now help me understand as as you I want to just understand how that like the lessons learned at Activision critical. So as you grew vision critical from, I don’t know what your starting point was, when you joined the company, oh, nine, six figures at best. Okay, so that’s very low. So as you join a company at that stage, you basically were on board for almost the full lifecycle of what somebody can experience that accompany through the different stages. Yeah. So what do you see at all those stages? What are the nuances of growing a business from that six figure mark? To 100? million? And how does that the like, the trouble that that the founders see when they hire those extra people, or they have those extra deals or the processes, or I’d love to know all of that. That’s a lot of a lot of different cycles in a business?


Kris Hartvigsen  13:32

For sure. And I think that every inflection point, you’re like, dammit, how are we going to grow this and double it again, it always seems like this insurmountable job, right? Like, we’ve already got all the low hanging fruit, there can’t possibly be more low hanging fruit. But that is usually not the case. It’s usually never the case. And so I think that part of part of actually growing with a company like that is also understanding the art of the possible. We walked into a market of vision critical. And in the very early days, we were poor selling wood, they were trying to sell the the business, or they’re trying to sell the product, with smarter researchers being the salespeople and market research organizations being their distribution channel. And my very quick observation there in the early days was, Why the hell would they do that? And the CEO who came from market research background goes, What do you mean, I go, so a market research agency makes their money with consulting revenue. And what you’re saying is that by putting in the vision critical platform, you don’t need to do as many projects you don’t need to spend as much on research. So now you’re robbing Peter to pay Paul. And so the person is getting rich is vision critical. And the company that is maybe not seeing the advantage is the research agency. So why the heck would they ever leave with you? They’re always going to say in their back pocket, they’ve got this thing, but they’re never gonna leave with it. So changing the distribution model was probably the first aha moment that’s actually how I ended up starting to vision critical because I was in talking to them about what I thought was flawed in their model. And as soon as we did that, it took about six months to really figure out the narrative and the story of going direct to the buyer. And I remember the first first time that this happened, and I remember the CEO coming and basically doubting that they were doing the right thing, because it’s taking a while to figure it out. And I like that I actually really like it when people doubt it, because it gives you a villain, and you need to have a villain in sales, you need to have a villain. And my villain was disbelief. And so I was like, I’m gonna prove you wrong. And that’s the most exciting thing is to is to prove people wrong and to kind of challenge the status quo. That’s really how tech companies get started is by disrupting and challenging the status quo. So as a good Canadian, I went and said, We’re going to sign the National Hockey League. And we did, we got the NHL was one of our first paid customers that we were actually allowed to show the logo for. And you walk in, and again, Katie company, you walk into the room, and you’re like, everybody, here’s the contract that we just saw with the National Hockey League, I was like, ah, it was like this huge moment, there was also like, a moment of relief. But it was also a moment of belief. Because you knew that if you can get the NHL, you get all the other leagues. And you knew that if you got one magazine, you would get all the magazines, and you would get all retailers if you got the gap, and so on. Right. So that was like the early learning is that the art of the possible would allow you to scale it, and the art of the narrative would help you to scale it faster. So I remember seeing this in when I was in France, once I used to live in the UK with vision critical as well. And I sat down in front of the sales team that I was in charge of in France, and I said, You need to understand the more you sell, the more yourself, right, it’s just this beautiful snowball effect. So you create momentum in the market. The The other thing that was really interesting for us early on is I think we created a new energy in an old space. And for me, that’s, I think that’s a fundamental thing that you need to try to do when you walk into a space that’s fairly traditional, or has been the same way for a long time. So if you look at if I sort of draw it forward, from my time at BC to where I am now, one thing that we really tried to do is bring new energy to something that was really almost complacently aligned to enterprise Tech has to look a certain way and feel a certain way. And really challenge that.


Scott D Clary  17:42

And, and as you grow, and as you found that not so product market fit, but I guess best best way to take their product to market and a market model fit market. Yeah, that market model fit is the best, that’s a really good way of putting it as you found that you started to scale. What are some of the problems that you started to see as the company grew exponentially?


Kris Hartvigsen  18:03

So the problems were some people wanted to hold on to a certain way, and some people were were ready to let go and try something even more aggressive. And, and you know, when whenever you have a blip, like you’re and you’re always gonna have a blip, because at some point, you promote Chris out of sales, and you put him into a leadership role. Well, Chris was doing really well on sales. Now you got somebody else that has to ramp into a role. And so there’s that awkward sort of the messy middle, if you will, that happens. And some people don’t have patience for that, again, it kind of goes back to what the roll and it took six months to kind of get the wheels rolling, well, then you have to go through that cycle again with your next wave of salespeople as they come in. So you get people that want to snap back to what was working in the very, very early days, and we learned that ship had sailed. So you know, we had to, we had to do a really good job of trying not to run in a zigzag pattern, you want to try to run in straight lines as much as possible. It gets harder to do when there’s more voices and more influencers involved in the in the business to keep that alignment and that that run in the same direction mentality.


Scott D Clary  19:21

And that I that I’ve I completely understand that point. What I actually meant with that question was more along the lines of scalability issues more in terms of actually like incorporating software enablement tech, to actually help with some of the scalability issues and issues that I feel let me say this. Are there. Are there process problems at six figures that are just just sort of taken to another level or magnified at? Yeah, yeah. 50 million, and that’s what I’m saying. That’s what I was trying to get out. Like, what are those process problems and And how should you should you target them or tackle them right away? Or is it something that you only see come up in a business once they get past a certain threshold?


Kris Hartvigsen  20:10

Yeah, I think you got to try to capture as much of it as possible in the early days. So what you’ll notice in terms of process and problems, as I was sort of alluding to it, when I said, you know, you promote me into a different role, and suddenly, I’m not selling anymore. Part of the problem you’re not selling anymore is that all my tribal knowledge traveled with me, unless we had a document somewhere. So one of the biggest problems that we had, was conveying that tribal knowledge to the next generation of sellers, and making sure that everybody had this built up playbook. Now. I want you to rewind the clock a little bit when when I was at BC, I started in 2005. Most enablement, tech sales, and it wasn’t even a thing, right? Product Marketing was barely even a thing. So we were largely making it up as we as we went along. And the way that you convey knowledge to everybody was at your annual sales kickoff, once a year, you would share knowledge, which is like, it’s almost disastrous to the business to wait that long. So we, you know, I learned from that, and really held on to that lesson of the importance of immediacy and sharing information and the importance of trying to help people to shape a story into their own words, I could tell you stories about how the National Hockey League changed the rules in the game based on the research that was done in their community, I could tell you stories about how Major League Baseball selected the American team America uniforms for the Olympics based on information from the research, we can tell you that unless I told them that, right. And then they got to put it in their own words. The other thing that I learned is that when at scale, there are so many stories flying around, right? Because you got so many deals. And there’s some of those stories are more specific to different verticals and others. But the the gatekeepers for those stories were typically the post sales people, the customer success and implementation folks, they knew every ROI story, they knew every reason why a customer loved us or hated us, getting that information from them was actually really hard. Right. And as you start your own company, and you know, in the early days a VC or a dually, I was really responsible for both sides, I still have to obviously to agree to degree but the the the post sale stories become the the launchpad for your next sales. You got to get that information into people’s hands. If you don’t, you will bottleneck and you will choke out for a period of time where people build their own narratives. It’s like, why would you want to reinvent the wheel every single time new people come in?


Scott D Clary  22:57

Now I have I have a question for you as a CEO of a company now and you’ve seen, you’ve seen how a lack of tribal knowledge can hurt an organization. Now CEO, a CEO has an extra responsibility because not only does that CEO have to pass on the knowledge and the playbook that they’ve used to really build out their initial iteration of a product or whatnot, but they also have to pass on that evangelism and, and the love for the brand. Now, some may say that it’s impossible for for an employee to ever love a brand, as much of it as a CEO. But what would do you agree with that? Or do you disagree? And you can, and you, as a CEO, have now found a way to pass on your passion, your evangelism, for Dooley, to your employees along with the playbook.


Kris Hartvigsen  23:43

I think that you have to. So when I look for people to join the business, I do look for people that have natural curiosity that like to solve big problems. And frankly, people that get what we do and why it’s important. And so I think if you start with a basic building block of, I totally get what you’re doing it duly, when you hire people, when they come on board, you can build that, that passion and that that desire to win, but it is it’s a mentality as much as anything else. And people either have the mentality or they don’t, you can try to build infectiousness through culture, and through but again, that’s that’s part of good hires, too, right? You hire really good people who are really passionate and who all get aligned on a mission. And the job is half done. Now, as a leader, there are incremental things that you need to do. If you can’t sell your own product. Please don’t expect somebody else to do it. Ever. Right? Hey, guys, we’ve built this awesome thing. I’ve never been able to sell it myself. But I’d sure love for you to do it. Good luck, right? That’s, that’s not infectious. But if you can say, You know what? Last week, I went out and I took my spear with me Did some hunting and I brought in this, and this is this is the story behind it. These are the critical milestones. This is why it was great, those things are really important. It’s like passion and enthusiasm is also a momentum game. Right? So the more momentum that you have, the easier it is for people to feel passionate about it. If you are on a slow ebb, it can start to feel like a job. You don’t want it to feel like a job you want people to come to work on. Today, we are going to slay dragons.


Scott D Clary  25:34

And is that and that that culture? Obviously, you understand the importance of it? Is there is there because I appreciate that you understand the importance of it as a CEO. And it’s very, I think that’s, that’s something to do, you know, pat yourself on the back of it, because I don’t think every CEO understands that. But I would also ask you, as somebody hiring for jobs, how do you make sure that a CEO has the right mindset is framed the way you are? Because I think the way you understand how to grow business, how you understand culture, you understand how to hire people, that’s the right way to do it. But how do you how as a as a as a employee, as somebody who’s being hired to hire you, I don’t know if that’s up for work. But as a hiree, or whatever that person is called? How do you how do you gauge an organization’s effectiveness to build that culture for you?


Kris Hartvigsen  26:22

I would ask the the person that’s interviewing me a bunch of questions around that as well, tell me your journey here, right. So you may I mean, in the early days, you can be interviewed by the CEO, and the later date, CEOs, probably not gonna have much to do with the interviewing process, unless they’re hiring for the executive suite. Unfortunately, I’d love to be able to sit down and talk to every single person that that came in, and tell them why I believe in it. And usually what ends up happening now is when or when the company gets bigger you do a cohort of people at the same time where you bring them all into a room, you say, Look, this is the story. This is the journey, this is why I’m so excited to have you on board to be a participant in the journey with us or a member of the journey with us. So I think that as, as an A prospective employee, the the questions that you want to ask are around why did you join? How know how is it you know, you say you join for these reasons? How’s it lived up to that?


Scott D Clary  27:22

Yeah, for you, thank you,


Kris Hartvigsen  27:25

how are you capturing that magic? How are you capturing the lightning in the bottle? Yeah. And you can see it like you can see, I remember going down to visit one of my my partners in the States, but a year and a half, maybe two years ago. And you could feel the energy in their office. And I just I looked at my co founder and I said, Man, this is awesome. This feels good. Like, what a great place for these people to work. You can just like you can just feel the surge, like almost like there was like this invisible nightclub that was happening in there where there’s just this, this going through the office, right? And it just, it’s stuck with me saying now we got to build that.


Scott D Clary  28:10

Now, there’s there’s one point here that when I was introducing you, I said I want to talk about you scaling a startup from 2 million and growing at 3%. Year over year. I didn’t have the name of that startup is that dually is that the startup


Kris Hartvigsen  28:27

messages? That is the that’s the story from really in terms of the funding that we’ve taken on and where we are. That’s definitely dually


Scott D Clary  28:36

Yeah, okay. So so talk to me about I guess, you know, we’ve spoken about vision critical. Are there any other I guess, fun fun stories and I say fun as a as a reference point, but it’s like, you know, any any trials tribulations lessons learned through growing Dooley and, and now growing at, you know, 300% year over year, I don’t know what your ARR is. And I don’t know if you want to say it, but that’s fine. But you’re you’re obviously it’s, it’s a success. So walk me through some of the lessons learned even though you had the career and you were you know, EVP is pretty much upper echelons of 100 million is like that’s, that’s pretty much you know, where you can be in terms of sales leadership. I think you can say quite assertively that you’ve you’ve been in that role. So now, you start from scratch. And what are you learning? gaviota Rahman. Right. Yeah, exactly. So what are the lessons learned?


Kris Hartvigsen  29:29

Building out Dooley. Ah, so a couple things come to mind. First of all, you you need a lot of focus, right? You need to again, you need to run a straight lines. I alluded to it before. There is a tendency in the early days of a business to become beholden to the needs of a customer as opposed to a market. And if you become beholden to a customer, you start building for that one customer you might not be build, you might be really for the market, you might get lucky. But you really need to validate that stuff and make sure that whatever you your building is being built for the masses or your product is and your businesses are going to scale as quickly as you would hope. And so, you know, you want to make sure that even if you have loud voices in the room, because you have a big customer and a bunch of small ones, that you don’t just build for them. That will, it will deviate your plan. And it can create a lot confusion, I would say the other thing along the lines of focus is just because you placed a small bet in something and it doesn’t pan out doesn’t necessarily mean that that small bet won’t pan out down the road if you continue to bet on it. But you need if you’re going to continue to bet on something, you need to continue to research it and dig in and make sure that the the initial bet was based on a problem that you knew, and that the incremental investment was based on problems that were surrounding that. So, you know, there there are a number of things that we built in the product, that at first blush that’s like, nobody’s using this. Why did we build this stupid thing. But you knew there was an end game. So let’s Stephen Covey 101, or I think it’s chapter chapter one, which is begin with an end in mind. And so you do need to really think about that, as you’re building up anything in the product. And in the roadmap, and, again, making sure that you’re building things for the right reasons. A couple of things that I think were important to me, I, I lean heavy on culture, you spend a lot of time in your day with the people that you hire, and that you have to go to the work with every single day. And I never ever wanted to go and work at a company where I felt like I didn’t feel like I was a part of the team or part of the crew, whether you’re the top of that hiring structure or the bottom or anywhere in between, everybody has to feel aligned. But and this is the important but culture, if you focus solely on culture, you can still kill your business, you still need people that can execute. lovely, wonderful people can come through the doors of your company that you’re like, Man, I really, really like this personal so so much, I really want to keep working with them. If they’re not able to deliver, you still need to make hard decisions to to part ways. And I think that that’s a hard lesson for people to learn, there’s always a fear that you’ll never be able to hire the next person, if you release the person that isn’t necessarily performing to your your needs, or able to deliver to your needs. So, you know, they always say like, fail fast, fail faster, all parts of your business, right? Fail fast when it comes is hire fast and fire faster, I sure. But obviously for the right reasons. And same thing in a product like build quick and and scrap it quicker if it if it sucks, those are some really, really, really important lessons that you can learn in any business. And two that I really hold on to, I would say, you know, if I were to look at any other things that are really important, it’s set the pace, you have to be the pace car, right. And that means that you’re going to make some sacrifices in certain parts of your life. You know, being an entrepreneur means that you are probably spending a little bit less time with your kids probably means that you’re focused a little bit more heavily on your work and your work family. And they do become a family. And that part is you have to know if you have an appetite for it. Like I love, love, love my kids, and I love love, love my partner. And, you know, it eats at me when I don’t spend time with them. I always begin with the end in mind to recognize that, you know, there is an end game for this, which is, you know, a level of comfort for them. But more so and this is this was I said this in a podcast not too long ago for because people asked me like how does how does what you’re doing in your work impact what you’re doing your family? Everything that I do I do with the aim of helping my children to understand the art of the possible, right. You don’t have to settle for a J. OB, you can do other things. You can be other things you can invent yourself, you can invent something that’s amazing. But you got to be convicted, you got to work hard at it. Now


Scott D Clary  34:26

I appreciate that a lot. I want to touch on one point we were going back and forth and email. One of the points that that you mentioned, was just discussing some of the hardships of startup life. Yeah. And then also, you mentioned it’s up to if you want to go there but you send it over for the for somebody in the family faced terminal illness while you were building out dually young. You don’t have to go into specifics so as comfortable as you want, but I want to understand how you deal with that when it’s at the top Topic and yeah, yeah, look, it is going to


Kris Hartvigsen  35:04

be tricky. It’s a tricky one to navigate. Right. So, uh, let me rewind the clock. So we took funding to the business and sort of the first half of 2018. In the second half of 2018, my dad was diagnosed with pancreatic cancer, pancreatic cancer is is awful. It’s evil, evil disease. And I will say this, I think that there are two things that we all get to deal with in our life, one with our parents, one is dying. And the other one is death. Right, dying is way worse than death, the process the journey, and so we’d watch my grandfather go through having pancreatic cancer before so it sounds like some sort of a family thing. It’s actually ironically, it’s not. And my grandfather’s brother went through it. And my grandfather’s other brothers son went through it. So my dad started losing weight in September 2018, he got pretty sick. In late, or so sometime in October, November, October 24, was the day that we got that diagnosis that dad had pancreatic cancer, and that hits you like a lead balloon pretty hard. So my dad and I are pretty close. We, we, we’ve been each other’s golf buddies, all that stuff for a long time. So when that diagnosis came, it was like all hands on deck, we are dealing with this. And I’ll talk about what that means to the business. And I’ll talk to you what that means. As a as an entrepreneur, as you need to step away from the business I had, like, it wasn’t even a choice. It wasn’t even a thought in my mind that I needed to step away from the business to deal with my dad’s health. So we did. And we’re very, very lucky. So let’s see, Dad was operated on around November 22. of 2018. And through 2019, we had a number of different incidents where he was like touching go, really touching go the surgery to get rid of a dino adenocarcinoma. It which is like, really aggressive cancer is so invasive, like they rip out organs, and they build new organs out of your old oriens. To try to put you back together, it’s like, I’m going to take all these five pieces, but where’s it’s like taking out a structural beam in your house, and somehow holding the roof up. So, you know, we had to go through a pretty, pretty gnarly surgery, you got to get 9% chance of five year survival on cancer of this nature, this is not the one to get. So again, we were I was really, really committed to getting my dad into the right surgeon into the right hospital into the right care. And that was, frankly, where my entrepreneurial spirit shone, you know, I’m a problem solver. And so, I’ve said this, I said this at an event in December, I think I found my dad, the best surgeon, I found my dad like the all the things he needed to give himself a chance through like a really good email. Like it’s really, here’s the Hail Mary gold call email. And it worked. Got him in to the right surgeon and he is, you know, for a year and a half removed from his surgery, and he played his first round of golf about a month ago. Now, he ain’t the same guy, you know, he’s pretty beat up. He’s 40 pounds later he is, uh, you know, my dad was the guy that would take Hey, bring your car we might place on change your brakes at 72. Right? Like, oh, okay, here you go anything jack the car up and rip the brakes out and put a new brakes. He’s not that guy anymore. Now he’s the guy that teaches me how to do it while he stands back. But he’s there. And you know, that, to me was the most important part. So from a business perspective, what you’ll learn through that process is, who your real leaders are, and where your deficiencies are, because I did need to step away for considerable periods of time, both mentally and physically spent. I’m guessing that I spent between 20 and 25% of my 2019 year bedside in the hospital for like on different days. Right, just coaching and talking to dad and making sure that you get what he needed. And he still Yeah, you do you understand who your leaders are through that process and that journey. And that I think is the, the silver lining for the business is we have we might have suffered from me not being around. But we also gained an opportunity to level up in certain parts of the business where we needed to.


Scott D Clary  39:50

So that’s, and that’s something that I think a lot of entrepreneurs stories or entrepreneurs don’t take into consideration. Just like the that Obviously an extreme example, and I, you know, yeah. You know, a lot of people aren’t going to have to experience that. Thank God, that’s a very tough thing to go through. Yeah, but I still think that even for Yeah, it’s tough. But entrepreneurs don’t even think that I think there’s a lot of a lot of hype and a lot of a lot of glorification of becoming an entrepreneur, starting your own thing. You started later on in your career after you had multiple successes, and you’re still, you know, dealing with things that are difficult. So I guess you know, what, outside of that, what are some other, like sobering truths of so you mentioned time, and obviously being and having to be able to balance like real life things, you can’t just step away from the business. In some cases, you’re fortunate you could and so but what are some other like tough lessons for entrepreneurs that they may not hear enough things you’ve had to go through with Dooley are way over your career?


Kris Hartvigsen  40:57

Yeah, look, I think we live in a really delicate era right now, too, right? We’re not in the madman years of say, whatever the hell you want, and do whatever the hell you want. There are no repercussions for your actions. We’re living in a moment in like, literally a moment in time right now, where the Black Lives Matter movement is finally getting some proper recognition. We’re living in a moment where misogyny is unacceptable unless you’re the president united states. So I’m saying that very candidly. And there, there’s all these different things that are happening. And you’re gonna fuck up so much as a as an entrepreneur with the things you say and the things you do, because the thing that makes you great about being entrepreneur, is pushing the edge and pushing the envelope, and thinking radically different in many cases, sometimes I meet you say things that are wrong, and you do things that are maybe not the that don’t land, right? Not just you, but people in your business, really aware of that. And so we you will, you’re gonna make mistakes like that, I think that the biggest thing that you need to be aware of is that accountability is so, so, so important. And awareness is so so, so important. You will say things I will come from a different generation, than the majority of my employees, I’m probably 15 plus years older than most of my team, which means that I was brought up in a slightly different era where you said slightly different things. And you’ve got to be aware of that. And you got to be aware of like where the world is going. So that part is, I wouldn’t call it hard. But it certainly, it certainly requires you to be at the wheel of the vehicle and not going on autopilot. So that you can adjust when you need to adjust. Trim the sails if you want to use the ceiling analogy. So that part I think, is it is not a tough lesson, but an important one. And everybody is going to make mistakes, right? Big or small, everybody’s gonna make some mistakes. And so you also have to, you have to really work with your team on what the what the road to recovery on any mistake might be as well. So that that I think is one that I’m pretty aware of. Again, one of the other things that that I would say for any entrepreneur is fear can really hold you back. Fear of making a call to a customer that might reject you fear of trying something new fear of going in a direction that seems like it’s counter to the the argument but might be the right thing. Fear can really hold you back. Other lessons, we so we built. This is more of like a go to market lesson, we built a product that users love. And their bosses thought was a nice to have, thank God for the product, lead growth movement that’s happening right now, like zoom and Calendly, and Expensify. And all these different companies where users are becoming more and more empowered. But you know, in the very beginning because of the business, we we didn’t understand how to convert that into a message that the market consume, and really help to get that buy in. So some go to market challenges, you really have to understand like, who your actual buyer is and how adoption is going to happen. I think it took us a while to figure those market motions out. And you know, some people figure it out faster. Some people think about slower, some people don’t figure it out. So that’s that’s certainly one that I would would hold on to. And, you know, I don’t know if this is a lesson, but it’s a reality. You know, I was an EVP of sales at my previous company earning very good money. You’re not gonna have very good money in the early days of your startup, right. And so you have to be willing to make that sacrifice right like I Think about the trips that we don’t take right now. Because you know, we’re growing a business and how the whole team is on for the ride, not just not just dad, the kids are on for the ride, my wife is on for the ride, you got to think about how it impacts them as well. And really make sure that everybody has the appetite for that journey. Now,


Scott D Clary  45:22

I guess my question is, as we continue to develop all these tools, all these tools are meant for, you know, including dually. And other ones. They’re meant for enablement. So they’re meant to basically make things easier for sales reps, and each tool is making things easier, and the sales reps, responsibilities and KPIs. And what they’re accountable for is, is ever increasing. Now, you know, this is partly due to technology, but also automation and other types of enablement, tools that allow, allow sales reps to basically increase their personal effectiveness. And I guess the question is, what does the future of sales? What does the future of work? What what do all these things look like when we’re continuously giving new technologies to increase the performance of these individuals noting that they’re still they’re still only human at the end of the day? So is there a limit to how effective we can make people? Is there a limit psychologically, to how effective we can make people when when is the cutoff point where where we can no longer increase the effectiveness or the efficacy of an individual with a tool?


Kris Hartvigsen  46:36

Yeah, I think so. Like, every single product that you bring on board will purport that it’s going to improve your performance by 10. Right? So theoretically, at some point in time, you’re, you’re exceeding the limits of what’s possible. This one’s better. This one makes you 10%. Better this one tip shaves off 10% of my time. So if you have, you know, you buy 20 products that he shoots shave 10% of your time off, theoretically, you’re going back in time. Yeah, that’s obviously not the case. So I think that what you’re going to see in the future of work, and I’ll talk more about the future work is if future work is actually a really interesting thing right now, like Bloomberg talks about it all the time. And a number of other major media companies are really engaged in this whole concept of the future of work. The future of work is letting people do the job that you told them to they were signing up for. Right? So if you look at the definition of a salesperson, and you said, Okay, what does the salesperson do? At its core, if you were to sum it up? In five words or less, you would say, a salesperson sell stuff, right? More or less? Now, that’s not what a salesperson does. A salesperson forecasts. A salesperson who does expense reports, a salesperson has one on ones with their manager, a salesperson takes notes in meetings, salesperson updates the CRM, and does all of this other stuff. But you don’t talk about that. Right? So the reality is, I think that the future of work is that the definition of your job, at its simplest level, is what you’re actually going to be doing. And all of the technology that you surround the this seller with, or the worker with are going to solve the problems of the things that you didn’t tell them more in their job description.


Scott D Clary  48:19

Alright, interesting way of thinking. But it makes a lot of sense. Because that’s, yeah, that makes a lot of sense.


Kris Hartvigsen  48:26

Yeah, it’s, I mean, I maybe it’s oversimplified. But I think the reality is, again, I’ll go back to that initial example. When I signed major league baseball or in the NHL, nobody came up to me and said, Hi, five, Chris, really good job on signing those deals. Did you update the competitor field in Salesforce? Did you file your expenses for that trip? Nobody said that. Right. It’s, it’s assumed that you’re going to do those things. But as a seller, it’s assumed that because my paycheck is so predicated on my performance, I’m not going to do those things, right? Like, I’m really not 50% of the sales salespersons paycheck 50% Plus, actually, if you’re a good seller, is based on your performance. It’s an open ended pay, paying role, right? You can make as much money as humanly possible within that job, unless you have a cap commission plan, which is that you’re terrible. So if that’s the case, you’re hiring somebody that you know, is under the pump to perform no other role in the business, engineering, HR, nobody else has quotas that if they miss them, their paycheck gets cut in half. Make it you might miss your bonus but your bonus is probably not going to cut your pay in half. It’s probably incremental that’s what’s called a bonus. Right? Commission’s on a bonus, it is your paid. So when you’re thinking along the lines of that, you have to really be empathetic to the needs of that person. The future of work is the ability for us to deliver on The promises of what your job is supposed to be, and getting rid of like all the block and tackle crap that get people all tied up in their, in their daily chores and activities. So that’s why they you look at all of the revolutions that are happening around the world. It’s all about trying to improve the perception of a specific thing that’s happening, right? Perception woman, the perception of black people perception, this perception that even though perceived perception of work, and I don’t want to compare the two because they’re not even close to the same thing in the perception of your job. You never signed up for all the other crap. Yeah, so we want to get to a point where we give them an empathetic solution. And if you don’t provide them with an empathetic solution, they will find it and it might not be at your company.


Scott D Clary  50:49

That’s a that’s a very good takeaway for for anyone listening. And I think that that’s why we see such high turnover rate


Kris Hartvigsen  50:56

of 5% and sales. Yeah, some of its, you know, on regretted Some of it’s because somebody doesn’t, doesn’t have a passion. I, I, I crushed my number at an antivirus company. One year, sort of between vision critical and my last entrepreneurial role, where I figured out wanting to get into SAS, I hated my job. And I left because I hated selling antivirus software. So people would be like security software, Sign me up. This is really cool. I was like, screw that. Again, got to kind of align with passion too. So 25% People churn year over year on regretted, regretted misfit.


Scott D Clary  51:34

Now, just to tee it up, I want to, first of all, I just want to ask, is there anything outside of you know what we talked about in your journey in your life before Dooley or actually, that we didn’t cover? Because if if we’re teed up for that, then I want to ask sort of closing questions, just lessons learned from your career, but just the floor for you to before we go on. Yeah,


Kris Hartvigsen  51:54

I would say the only other thing like there is one lesson that I really tried to bring into my job which I learned as a baseball coach. And look, you sure there’s tons of stuff that we don’t know. But let’s talk about this one specifically. I remember I had this this kid on my baseball team a few years ago, and I had just gone through this this coaching program to learn how to be a better coach, I still think I’m an Okay, Coach, I don’t think I’m a great coach, I’m certainly not going to coach at the major league level anytime soon. But this, this kid was so self aware that it was like wild to experience this. I was trying to teach him how to do his swing. And I was teaching him wrong. And this kind of goes into the whole idea of enablement. Right. And he paused, he goes, Coach, I don’t learn the way you’re teaching me. I’m a, I’m a hands on learner, I need to have the bat in my hand in order to learn, you’re trying to teach me the visual learning. So there’s actually three types of learners. There’s people who are tactile people that learn from hearing, and then people who learned through seeing, and he was very much a tactile learner. And so I’m like, okay, holy crap, I didn’t even realize that I was making the mistake. Here’s the back. All right, let’s break it down into smaller bits. Let’s put you in your bathroom. Okay. elven repetition, hands, right position, hands up by the year, all that kind of stuff. Now. Now you need to go to here, I need to go to here. Now you need to go to here. And as soon as we do that, he like his game changed. He was a kid who couldn’t swing a baseball bat, who went on to be wood, there’s a an award that he was nominated for, at the end of the year for like, basically, most improved player, the kid who gave his heart and soul into the game. And that was like this moment of great pride for me. But again, I think what I learned from that is you the way that you learn isn’t the way that every else learns. So you need to be really sensitive to that when you’re delivering training or material to other people. And we think about that, again, from an empathetic perspective. We think about that inside of our product, like how and when is it appropriate to educate you?


Scott D Clary  54:15

That is that is a very good lesson. And I think that when when you are looking to coach a trainer or even build a product like that has to be something that to be taken into consideration as well. And I don’t think enough people do the whole that’s a whole other conversation not just on on building the best possible user experience for a product. But the the way to coach people is a whole other conversation that I have a lot of issues with when it comes to sales feel that not a lot of people coach sales individuals properly either. But a lot of it is again because of we touched on this at one point it was just the the person who usually defaults into the leadership position and doesn’t know you know, the best way to coach or trainer on board and then you get that rocky period in that person’s onboarding, a lot of it is because it’s usually just the best person in that role that moves into the next role. Right. And that’s not a good fix, either.


Kris Hartvigsen  55:09

There’s probably one other thing that is interesting, as an entrepreneur, and somebody who likes to be hands on and whatnot, you need to have a bit more patience than I think most entrepreneurs do with the the people who are learning that don’t know it as well as you do. You know, I see it, even with the way I work with my kids. It’s like, Ah, I can let you cut that onion. But there’s my lesson from last night, a lady that I knew, but I’m gonna get away faster and easier. So I’m just gonna do it. And my kids like, but I want to learn, like, Okay, so the Art of Letting Go is, is I think important and realizing that despite the fact that you probably are better at it out of the gate, you can let people get better than you at it if you give them enough opportunity. And you need to make sure that you are aware of that. And I would say that that’s an ongoing lesson for me, the letting go is hard. When it’s your baby, when it’s your thing, when you know that there’s an easier way of doing things. That’s that’s a tricky one.


Scott D Clary  56:09

Okay. Okay, so to close this up rapid fire two questions that I like to ask first question is one life lesson that you would tell your younger self,


Kris Hartvigsen  56:19

one life lesson that I would tell my younger self? Oh, gosh, that’s an interesting one. You gave a lot of


Scott D Clary  56:31

stuffs I feel good.


Kris Hartvigsen  56:32

I’ll give you one that is actually a quote that I really like fearless and be yourself, fearlessly Be yourself. Don’t hold back because you’re worried about how other people think about you or perceive what you’re doing. And I commend my eldest for this, where he doesn’t necessarily want to go go with the crowd all the time, and he’s very comfortable in his own skin. My wife is actually very comfortable in her own skin as well. And from time to time, I get uncomfortable in my own skin. It’s okay to be uncomfortable. But being yourself is the most authentic thing you can do and often really hard. And the sooner you can figure that out, the happier you’re going to be in your life.


Scott D Clary  57:12

That’s a good, that’s a good life lesson. I like that a lot. Um, second question, what’s a resource, it could be a book podcasts, audible something or it could be a person to something that you would recommend people go check out and that you have learned from?


Kris Hartvigsen  57:26

Oh, there’s lots of those as well.


Scott D Clary  57:29

One or 211 or two? Yeah.


Kris Hartvigsen  57:33

So I’ll give you I’ll give you a couple. One book that I’m I’m really in love with right now from a sales perspective is called the transparency sell. The transparency sale is a really, really strong read. And it actually it really talks to you being empathetic, but also helping your your buyer understand your position better because buyers don’t understand how how you sell, or what’s important to you all the time. So it just lays out a bit of a different framework. And that’s by a gentleman by the name and talk a pony. So Todd, there’s your plug. And I just enjoyed the read. He’s He’s a really just genuine individual. Let’s see what else is there other resources that I think that you should definitely tap into. But the biggest thing for me is, you know, you got to dive into understanding other if you’re an entrepreneur, you got to dive into understanding the other roles within your business. And I don’t know if there’s a brilliant resource for this, but I would be reading like Bill Gates, his biography and things like that, to just figure out how somebody became so well rounded at other parts and understanding other roles within within their lives. I’m a huge biography, consumer, Steve Jobs, Elon Musk, all those ones. They’re all fascinating.


Scott D Clary  58:51

Very good. And last, where do people go to connect with you? If they want to go learn more about Dooley? You know, LinkedIn, what’s the best place? Yeah,


Kris Hartvigsen  59:01 D O L is how you’ll see. We’re building a real empathy driven approach to make you insanely productive as a salesperson. And if you want to reach me personally, I’m more than happy to chat with anybody but anything that is around what we do around what you do. It’s Chris KR is absolutely Nadia.


Scott D Clary  59:27

That’s all for today. Thanks again for joining me on another episode of the success story podcast. You can download or stream this podcast wherever podcasts are available, including iTunes, Spotify, Google, Stitcher, I heart, radio, and many others. You can also watch his podcasts on YouTube. If you haven’t already. Please subscribe and share this podcast with your friends, family, coworkers and peers. Please leave us a rating on iTunes takes about 30 seconds as it allows other people to find our podcast and lets our amazing guests reach even more people with their message. And remember any rating is fine as long as it can Paynes five stars I’m Scott Clary from the success story podcast signing off

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