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

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 onto 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, Enthrown, 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 Enthrown. Private businesses use Enthrown to unlock liquidity without bloating costs. With Enthrown's 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 enthrown.com slash liquidity. That's enthrown.com slash liquidity. Thanks again for joining me today. I am sitting down with Chris Hartvigson, who is the founder CEO of Dooley. Now Chris has a 20 plus year career in sales, having worked in a variety of roles, but most notably, he has worked as several senior level leadership positions, so SVP, EVP, and most recently, EVP sales. He's also worked as several sales leaders, directors, vice president, and the 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 sales looks like now in terms of sales within large SaaS organizations, 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 $0.06 figures all the way through to over $100 million. He has that entire scope of working within an organization, scaling a commercial organization, working across all these different roles. He has 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 Dooley. So thanks again for joining me, Chris, I appreciate you sitting down. I want to understand your story, your career, and then let's speak about what you're doing now. Okay, so we can go way back. Yeah, let's do it. I think that when you look at an entrepreneur, there are a couple of really important traits, and 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 career, you either get the buzz off of the 11-8 stand that you started as a kid or you don't, and then you started 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 used that to pay for a lot of my education in my fourth year. And just starting seeing this really interesting opportunity to be your own boss. 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 Mad Men 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. My passions 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 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 exactly the kind of technology I'd want to have in my own dream system for doing that kind of work. And when Comdex 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. They're like, man, you know, more about our product than we do. Why do you come work for us? I'm like, okay, I've never lived in Montreal before. So I moved to Montreal, and started working deeper into tech and started really digging into hardware when we took Matrox to a billion dollars manual record training 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 it came back, I ran a distributorship that basically sold high-end technology to medical imaging companies and all sorts of stuff. We sold that to Bell Microproducts in the early 2000s, nice legs it, and that started to get me more involved in SaaS. What I realized in my career is that 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 because I hated administrative work. I think the funny thing is, if you asked a salesperson about their job description, nobody would ever say that they had to spend a lot of time filing information. If you said that during the interview, it's like, hey, get us a great cake for you in sales. Your territory is going to be the Pacific Northwest, and you're going to sell the companies like Microsoft and Intel and all these different companies. By the way, the best part of your job filing, you're going to love it. When you're tripling your number, I was tripping my number at Vision Critical when I started there and into my career and I was a junior known with the world with them. Nobody ever stops to say, hey, you decided to be a baseball, but did you enter the competitive field in Salesforce? I started to look at that challenge and wanted to take it on with a little bit more rigor when I left Vision Critical and figure out a way, again, going back to that, well, empathy story for you and digging into the problem. I wanted 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. I guess that's just such an impactful point for somebody who's worked in sales, like the non-sales activities just kill, like absolutely kill your day, it just takes away and it's like the, and it's also, I don't even know if you ever want to go into this, but it's also a personality thing. There are intrinsic personalities that are less, if you ever run like a disc profile on anybody or anything like that, like the personalities that are less apt to want to do that kind of work and salespeople traditionally aren't. So this is a huge pain point that you're solving. So 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 start this company coming, you know, you've had some success in the past? What is the first steps you've taken to create duly? Because you've had success but you've never had success in this realm in particular in SaaS. 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 really fascinated with workflow and trying to optimize workflow primarily because I hated doing all 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 from 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 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 research goes into that to understand how big the market is, how big the problem is because if the problem is small and the market is big, it doesn't really matter. People are going to try to solve it 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 happen as a result of that problem too. 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 as not bigger than the first problem. When the most people didn't really understand and that's, you have a sales organization that or even a like organization in general that is there to support the sales person and try to help to expedite sales. We always talk about like customer acquisition costs 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 sales person was off on their own and it's like here's your bad go and sell, right? Now the organization supports, but the reality is they didn't know when to support or how to support because again the data is coming across. So 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 you'd be whiteboarding stuff and you'd be looking at the deal and like, yeah, I didn't know about that, I wish you told me about that earlier, I wish I knew about this and because you just told me about that, did you know we have this really great case that is this really helpful white paper or you should talk to Susan because she just did a deal exactly like this. That information wasn't making its way back to the sales person, which is anyone, right? An 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. Giant file, like Salesforce, giant filing cabinet, content management system, another giant filing cabinet. What did we do? We threw 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 get rid of a super big pain and update Salesforce automatically before them, turned into this brokering of information between the salesperson and the rest of the organization. So the salesperson could be smarter in moments of truth as well as having the business, having the information they needed to do their job. And how do you get tighter and tighter? It makes a lot of sense. Now, help me understand as you, I want to just understand how that, like the lessons learned at vision critical. So as you grew vision critical from, I don't know what your starting point was when you joined the company. 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 life cycle of what somebody can't experience at a company through the different stages of growth. Yep. So what do you see at all those stages? What are the nuances of growing a business from that six figure mark to a hundred million? And how does that, like the trouble that the founders see when they hire those extra people or they have those extra deals or the processes are, I'd love to know all of that. That's a lot of, a lot of different cycles in a business. For sure. And I think that at every inflection point, you're like, damn it, how are we going to grow this and double it again? And it always seems like this insurmountable job, right? You're like, oh, we've already got all the low hanging fruit. There can't possibly be more low hanging fruit. But that is not, usually not the case, it's usually never the case. And so I think that part of actually growing with a company like that is also understanding the art of the possible. We walked into a market at Vision Critical and in the very early days, they were trying to sell the business or they were trying to sell the product with market 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 company is getting rich. This is Vision Critical and the company that is maybe not seeing the advantage is the research agency. So why the heck would they ever lead with you? They're always going to say in their back pocket, they've got this thing but they're never going to lead with it. So changing the distribution model was probably the first aha moment. And that's actually how I ended up starting 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 time that this happened, and I remember the CEO coming in and basically doubting that I was doing the right thing because it was taking a while to figure it out. And I like that. I actually really like it when people doubt it because he gives you a villain and you need to have a villain and sales you need to have a villain and my villain was disbelief. And so I was like, I'm going to prove you wrong. And that's the most exciting thing 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. It was one of our first paid customers that we were actually allowed to show the logo for. And you walk in and again, Canadian company, you walk into the room and you're like, everybody, here's a contract that we decided with the National Hockey League and we're like, it was like this huge moment. But it was also like, there's a moment of relief, but it was also a moment of belief because you knew that if you get the NHL, you get all the other leads. And you knew that if you got one magazine, you would get all the magazines and you would get all the 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 saying this when I was in France once, I used to live in the UK with Vision Crypto 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 you sell, right? It's just this beautiful snowball effect. So you create momentum in a market. 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, my time at BC to where I am now, one thing that we really try 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. And, and as you grow, and as you found that, not say product market fit, but I guess best, best way to take their product to market. And market model fit. 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? Some of 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 going to 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 in sales. Now you got somebody else that has to ramp into a role. And so there's that awkward sort of, you know, the messy middle, if you will, that happened. And some people don't have patience for that. Again, it kind of goes back to the role 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 sales people 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've already, that's ship it sale. So, you know, we had to, we had to do a really good job of trying not to run in this exact 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. And that I, 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 the issues that actually 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 into business once they get has a certain. Rachel, yeah, I think you got to try to capture as much of it as possible or in the early days. So what you'll notice in terms of process and problems that 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. I mean, 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, mostly enablement tech, like sales and even 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 in 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 ocular change the rules in the game based on the research that was done in their community. I could tell you stories about how majorly baseball selected the American team America uniforms for the Olympics based on information from the research. We also 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 are some of those stories are more specific to different verticals and others. But 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 in the early days at BC or started at Dooley, it was really responsible for both sides. I still am to it, obviously to a degree, to degree, but the post sales stories become the launch pad 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 while people build their own narratives. And it's like, why would you want to reinvent the wheel every single time new people come in now. 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, 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 dooly to your employees along with the playbook. 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 at dooly when you hire people, when they come on board, you can build that passion and 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 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 and I 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 eb 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 slave dragons. And is that and 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 I think that's very I think that's that's something to to you know pie yourself on the back of it because I don't think every CEO understands that but I would also ask you somebody hiring for jobs how do you make sure that a CEO has a 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 as a as an employee as somebody who's being hired as a hiring I don't know if that's up for work but as a hiring or whatever that person is called how do you how do you gauge an organization's effectiveness to to build that culture for you. 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 days the CEO is probably not going to have much to do with the interviewing process unless they're hiring for the executives we don't 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 is bigger you do it. So cohort of people at the same time where you bring them on to when 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 in a prospective employee the questions that you want to ask are around why did you join. How you know how is you know you say you join for these reasons. How is it lived up to that yeah for you how are you how are you capturing that magic how are you capturing the lightning in the bottle yeah and you can see like you can see I remember going down to visit one of my. My partners in the states buddy 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 this almost like there was like this invisible nightclub that was happening in there where there's just this. Going through the office right and it just it stuck with me saying now we got to build like that. 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 two million and growing it 300% year over year I didn't have the name of that startup is that duly is that the startup. Is that what is 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 duly yeah okay so it was so talk to me about I guess you know we spoken about vision critical are there any other I guess fun fun stories and I say fun as a reference point but it's like you know any any trial tribulation lessons learned through growing duly and. Now growing it you know 300% year over year I don't know where your AR 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 white assertively that you you've been in that role so now you start from scratch. And you go caviar to ramen right exactly so what are what are the lessons learned building out duly 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 in 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 building you might be building for the market might get lucky but you really need to validate that stuff and make sure that whatever your building is being built for the masses or your product is in your business is 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 in a bunch of small ones that you don't just build for them. It will it will deviate your plan and it can create a lot of confusion I would say the other thing along the lines of focus is just because you place 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 begin to make sure that 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 are a number of things that we built in the product that at first blush that's like nobody's using this why do we build this stupid thing but you knew there was an end game. So you know let's even cubby 101 or which I think is chapters 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 road map 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 lean heavy on culture you spend a lot of time in your day with the people that you hire and then 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 a part of the crew whether you're at the top of that hiring structure at 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 person so so much I really 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 or able to deliver to your needs so. You know they always say like feel fast feel faster all parts of your business right feel fast when it come it's higher fast and fire faster I sure but obviously for the right reasons and same thing in a product like build quick 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 to 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 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 of mine 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 so this in a podcast not too long ago for because people ask me like how does how does what you're doing in your work impact what you're doing to 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 jail be 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 and you got to work hard at it. Now I appreciate that a lot I want to touch on one point when you're going back and forth an email one of the points that that you mentioned was just discussing some of the hardships of start up life yeah and then also you mentioned it's up to you want to go there but you sent it over for for somebody in the family based terminal illness while you were building out duly. You don't have to go into specifics so it's comfortable as you want but I want to understand. How you deal with that when it's that's a tough topic and yeah. Yeah going to it's a tricky it's a tricky one to navigate right so. 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 an 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 with what 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 of 2018 you got pretty sick in late or sometime in October. I remember October 24th 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've been each other's golf buddies all that stuff for 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 to what that means to the business and I'll talk to you what that means as an entrepreneur as you need to step away from the business I had like it wasn't a choice it wasn't even a thought on mine that I needed to step away from the business to deal with my dad's health so we did and we were very very lucky so let's see dad was operated on around November 22nd of 2018 and through 2018. In 2019 we had a number of different incidents where he was like touch and go really touch and go the surgery to get rid of a. And you know at no car Sonoma it which is like really aggressive cancer is so invasive like they rip out organs and they build new organs out of your old organs to try to put you back together it's like I'm going to take all these five pieces but was it's like taking out a structural beam in your house and somehow holding the roof up. So you know we he had to go through a pretty pretty gnarly surgery you got like a 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 Sean you know I'm a problem solver and so. So I said this I said this at an event in December I think family dad the best surgeon I found my dad like the all all things he needed to give himself a chance through like a really good. Like it's wrote like here's the Hail Mary gold call email and it worked got him into to the right surgeon and he is you know we're we're a year and a half from move from his surgery and he played this 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 you know my dad was the guy would take hey bring your car with my place I'll change your brakes at 72 right like oh okay here you go and he jacked the car up and ripped 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 in bedside in the hospital for like on different days right just coaching and talking to dad making sure that yeah what you need it. And so yeah you do you understand who your leaders are through that process in that journey and in that I think is the silver lining for the business is 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. So that's and that's something that I think a lot of entrepreneur stories or entrepreneurs don't take into consideration just like the that's an obviously an extreme example and I you know you know a lot of people aren't going to have to experience that thank God that's a very nothing to go through 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 I know glorification of becoming an entrepreneur starting your own thing you started later on in your career 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 we can't just step away from the business. In some cases you were fortunate you could and so yeah but what are some other like tough lessons for entrepreneurs that they may not hear enough things you've had to go through with duly or with over your career. Yeah look I think we live in a really delicate era right now too right we're not in the madmen years of say whatever the hell you want 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 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 I stay so I'm saying that very candidly. And there's all these different things that are happening and you're going to fuck up so much as an entrepreneur with the things you say and things you do because the thing that makes you great of a being an entrepreneur is pushing the edge and pushing the envelope and thinking radically different in many cases sometimes I mean you say things that are wrong and you do things that are maybe not. They don't land right not you but people who's here business really aware of that and so we will you're going to 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've come from a different generation then 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 of the vehicle and not going on autopilot so that you can adjust when you need to adjust trim the sales if you want to use the 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 bigger small everybody is going to 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 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 you 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. We know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we know we w w back w y l you're not gonna earn very good money in years of your start up, right? 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 we're growing a business and how the whole team is on for the ride, 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, I guess my question is as we continue to develop all these tools, all these tools are meant for, including duly 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 ever increasing. Now, you know, this is partly due to technology but also automation and other types of naming tools that 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 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 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 is the cutoff point where we can no longer increase the effectiveness or the efficacy of an individual with a tool? Yeah, I think so. Like every single product that you bring on board will report that it's going to improve your performance by testing. So theoretically, at some point in time, you're exceeding the limits of what's possible. This one makes me 10% better. This one takes shapes off 10% of my time. So if you have, you know, you buy 20 products at each shape 10% of your time off, theoretically, you're going back in time. 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 work. Future work is letting people do the job that you've told them that they were signing up for. Right? So if you look at the definition of a salesperson and you say, okay, what does a salesperson do? At its core, if you were to sum it up in five words or less, you would say a salesperson sells stuff, right? More or less. Now, that's not what a salesperson does. A salesperson forecasts. A salesperson does expense reports. A salesperson has one-on-ones with their manager. A salesperson takes notes and meetings. A 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 seller with or the worker with, are going to solve the problems of the things that you didn't tell them were in their job description. All right. That's an interesting way of thinking, but it makes a lot of sense because that's right. Yeah, that makes a lot of sense. Yeah, it's, I mean, maybe it's oversimplified, but I think that the reality is, again, I'll go back to that initial example when I signed Major League Baseball or at the NHL. Nobody came up to me and said, high 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 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, they're not going to do those things, right? Like I'm really not. 50% of the salesperson's paycheck, 50% plus, actually, if you're a good seller, is based on your performance. It's an open-ended paying role, right? You can make as much money as humanly possible within that job unless you have a cap commission plan which I think 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. You might miss your bonus, but your bonus is probably not going to cut your pay in half, it's probably incremental. That's why it's called a bonus, right? Commission is not a bonus, it is your pay. 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 daily chores and activities. So that's why like 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 of woman, the perception of a lot of people in perception of this perception of that, even though perception of work, and I don't want to compare that to 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. 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. That's a very good takeaway for anyone listening. And I think that that's why we see such high turnover rates. 25% in sales. Yeah. Some of it's unregraded, some of it's because somebody doesn't have a passion. I crushed my number at an antivirus company in one year, sort of between vision critical on my last entrepreneurial role, where I figured I wanted to get into SaaS. I hated my job, and I left, because I hated selling antivirus software. Some people would be like, so if you're a software, sign me up. This is really cool. I was like screw that, again, got it kind of aligned with passion too. So 25% people cheering year over year, unregraded, regretted, misfit. Now, just to tee it up, I want to, first of all, I just want to ask, is there anything outside of what we talked about in your journey, in your life, before duly or at duly that we didn't cover? Because if we're teed up for that, then I want to ask sort of closing questions, just lessons learned from your career. But just a floor for you to before we go. Yeah, I would say the only other thing, there is one lesson that I really try to bring into my job, which I learned is 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 kid on my baseball team a few years ago, and I had just gone through 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 any time soon. But 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 and he goes, coach, I don't learn the way you're teaching me. 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 who learn from hearing, and then people who are learning 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 a mistake. Here's the bat. All right, let's break it down into smaller bits. Let's put you in your back swing, okay? Elbow in my position, hands in my position, hands up by the ear, all that kind of stuff. Now you need to go to here. Now you need to go to here, now you need to go to here. And as soon as we did that, he, like his game changed. He was a kid who couldn't swing a baseball bat, who went on to be, there was an award that he was nominated for at the end of the year for basically the most improved player of the kid who gave his heart and soul into the game. And it 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 is in the way that everybody else learns. So you need to really sensitive to that when you're delivering training or material to other people. And when 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? That is a very good lesson. And I think that when you are looking to coach a trainer, or even build a product like that has to be something that has to be taken into consideration as well. And I don't think enough people do. It's a whole other conversation, not just on building the best possible user experience for a product, but the way to coach people is a whole other conversation that I have a lot of issues 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 person who usually defaults into like a leadership position and doesn't know. The best way to coach or trainer on board, and then you get that rocky period and 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 as good fix either. 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 and then I think most entrepreneurs do with the people who are learning that don't know it as well as you do. I see it even with the way I work with my kids. It's like, I can let you cut that onion, but this is my lesson from last night. I let you cut that onion, but I can do it way faster and way easier. So I'm just gonna do it. And my kids are like, but I wanna learn. It's like, okay, so the art of letting go 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 add it if you give them enough opportunity. And you need to make sure that you are aware of that. And I would say that's an ongoing lesson for me. The art of letting go is hard. When it's your baby, when it's your thing, when you know that there's an easy way of doing things, that's a tricky one. Very good. Okay, so to close this up, rapid fire, two questions that I like to ask. The first question is one life lesson that you would tell your younger self. One life lesson that I would tell my younger self. Oh gosh, that's an interesting one. You give a lot of stuff. So I feel guilty. Yeah, I'll give you one that is actually a quote that I really like 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 with the crowd all of 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 that 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. That's a good life lesson. I like that a lot. Second question, what's a resource? It could be a book podcast, Audible, something or it could be a person too. Something that you would recommend people go check out and that you have learned from. Oh, there's lots of those as well. What are two? What are two? Yeah. So I'll give you a couple. One book that I'm really in love with right now from a sales perspective is called The Transparency Cell. The Transparency Cell is a really, really strong read. And it actually, it really talks to you being empathetic but also helping your buyer understand your position better because buyers don't understand 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 of Todd Paponi. So Todd, there's your plug. And I just enjoyed the read of eight keys. He's a really just genuine individual. Let's see what there are other resources that I think that you should definitely tap into. But the biggest thing for me is you got to dive into understanding other, if you're not sure, 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's biography and things like that to just figure out how somebody became so well-rounded at other parts and understanding other roles within their lives. I'm a huge biography consumer. Steve Jobs, Elon Musk, all those ones, they're all fascinating. Very good. And last, where do people go to connect with you? If they want to go learn more about Dooley, LinkedIn, what's the best place? Yeah, www.dooley.ai. C-O-O-L-Y.ai is how you'll see what we're building, 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 about anything that is around what we do or around what you do. It's Chris K.R.I.S. at Dooley.ai. 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 this podcast on YouTube. If you haven't already, please subscribe and share this podcast with your friends, family, co-workers, and peers. Please leave us a rating on iTunes. It 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 contains five stars. I'm Scott Clary from the Success Story podcast, signing off. 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