Kevin Dorsey on Scaling Sales with Missionaries not Mercenaries

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Kevin Dorsey, better known as KD is the VP of Inside Sales at Patient Pop inc. Kevin has built numerous teams from 0-150+ reps and revenues from 0-$750M (and counting). He’s a mentor and consultant for early, mid, and late-stage SaaS companies across the globe

Kevin Dorsey | PatientPop - TRANSCRIPT

Bam. Sure enough, it looks like it's doing the thing. Um, why is my thing going so slowly? Are you getting a delay on my end at all? No, it seems fine. Pretty fine. Cool. Um, yeah, so, I mean, as far as, uh, the format for today, I usually keep these to around 20 minutes. Um, and we'll edit out this beginning where we're just kind of shooting the shit.

But, um, I usually just like to ask if there's stuff that you're interested in chatting about, you know, our, our focus, our audiences series, ABC investors, operators, founders, um, typically talking about the sprint from either. One to 10 or 10 to 20 plus, usually that we choose to focus on kind of the earlier stage or the later growth stage.

Um, so whatever you're more excited to talk about. And then the goal is to chat through specific stories from the trenches of life, you know, the patterns that you keep coming back to, um, you know, when you joined, like when you first joined patient pop, like what are some of the things that you just innately.

Do as your top priority and things like that. And the stories that go along with those, um, yeah. No man, like, um, I can speak to, to all that. So I'm down for, for whatever there. And I think also too, something that I always asked, like, you know, the, the podcasts, like what are the topics that either you've been asked for that people just haven't touched on yet, or the topics that people dance around and don't really get into, you know, like, Cause, you know, your audience, right?

Like, I don't know your audience, you know? So it's like, what are those things? And I'm down to touch on those things too. So I'll just follow your lead, man. We'll get into it. Perfect. Yeah. The episodes that do the best are the ones that really dig into specific examples of challenges or blockers that had to be overcome.

And, and then like, I think people really like the ones where somebody, where we talk about things that just were flat out like failures and then things that were really hard, but that ended up turning into successes. Um, just cause like, you know, you can hop on any podcasts. People talk about everything that went right in their career, but it's more rare for people to be open and like share some of those harder things.

Um, so I'd love to go through that kind of thing. Oh, I get it. Okay. Sweet. Okay. So we can do it. Um, perfect. Let me pull up my notes real fast and we can get going.

Hopefully the puppy stays put, so he's not wandering around my background, like chew on my feet occasionally during these and I have to keep a straight face the whole time. Excellent. That's been a nice part of this movie is I finally have my own office. Like back when we were living in a two bedroom apartment in LA man, I was like working for my seven foot corner in my bedroom.

I was like, this is not ideal. I can not continue this. Yup. No, we though, I mean, we were in a we're in like a 800 square foot, one bedroom in San Francisco before moving out here and now backyard and it's just like getting crazy. It's amazing. All right, let's get going. Uh, so today I am thrilled to have on the show, Kevin Dorsey, um, formerly the vice president of sales at snack nation.

A head of sales at service Titan, and he's a mentor at 500 startups. And now the VP of inside sales at patient pop, Kevin, welcome to the show. Hey, I'm excited to be here, man. Excited to talk, shop scaling sales, all of it, man. Let's let's dive in. Let's do this. Yeah. So I mean, let's start where you are now. I mean, you guys just raised a monster series C.

Right. It's like exciting time. So what, what is just top of mind for you as a sales leader today? A patient pop? So I think top of mind for me right now is better growth versus faster growth. Right. And so I'll take a step back too, to like fundraising. Cause it's always so funny, right? Like I posted about it and.

Everyone treats it like that's the end goal? Like yeah. Congrats, woo. Series C congrats. Like it's like, and they tend to forget what raising money actually means. People want their money back with a return. So you can, you can treat raising money as a celebration, but at truthfully as a sales leader, I look at that and go, okay, how am I going to go get those people there?

50 million to turn 250 million, right? And the only way you do that through better growth, right? Patient pop has gone through the stages of, of, you know, fast growth, growth at all costs to now. Okay. We gotta keep growing. Let's do it the right way so that we can get the return on that money. So everyone listening, like yes, phrasing money is great, but it comes with higher expectations of that.

And you've got to go meet. Yeah. I feel like, I feel like especially now in the. I don't know, I keep wanting to call it post COVID, but we're still in it, uh, in this world that we're in right now. So many companies have shifted from that mindset of growth at all costs. Let's just crank it out. It doesn't matter how sustainable it is or how much you have to spend to get it at to this mindset of like, what is the most efficient and effective way for us to actually go out and get growth in a way that scales.

It's a very fun, it's a very fun. Fine line to walk though, because I've been a part of startups where I think we waited way too long to raise money. So then you're, you know, everyone says, okay, well bootstrapping, or are they truly, this one's the other that you raise money? Are you bootstrap? But when you bootstrap.

Oftentimes it actually can squash creativity can squash ideas because it'll they'll cost money or you become very risk averse because you only got 22 K in the bank and you got to hit payroll next month. And so you become very risk averse. Whereas on the flip side, people go raise this money and they feel like they can just take risks.

Yeah. Right. And so you got to find that, that middle ground of making sure that cause you can, you can, what's the, I'm trying to think the right word here. You can have a man, I'm gonna make up a word. You'll get what I'm saying. You can have fish assize yourself to death. You can try to be so efficient. I love that.

Right. You know what I'm trying to say here? Do they make up the word that you can try to be so efficient? And so bootstrappy that you actually die because you never grew. Right? So it's a very fine balance to walk. So as you think about this transition from growth at all, costs to smart or better growth, um, what do you think is going to be the hardest part or the biggest challenge in making that shift?

Well, it's the biggest challenge in any shift it's people. Right. Like people, sales, people, marketing people, product people like people are pretty adverse to change no matter what. Right. It's actually really funny, man. Like as human beings, we crave novelty, but we resist change. Right? We don't like to change, even if we know what we're doing is wrong.

We're, we're the only species on this planet that does that. Like we will intentionally continue to do things we know are bad for us. Right. Like a bear doesn't wake up and go, you know, I'm just not going to hibernate this year. No, there's not going to do it. There's not like, no, they do what's best for them.

And that's it. And so it's shifting the mindsets on, on thoughts, right? Like when you start going after better prospects or different prospects, there's always going to be those ones that you have to say no to. There's going to be the ones that you use to close and now you can't. Right? Like it changes a lot of things.

And so. People are always the toughest part of any change, which is why you need to evangelize it. You need to start very early. You can't just drop it on people. You can't just wake up one day and be like, surprise. This is what we're going to do. Um, and that's one of the challenges, even though we went through with COVID is COVID forced our hand a little bit.

We didn't get to evangelize and pre-sell and do all those things. It was like, all right, y'all we gotta make this shift now. And so we've been kind of building the plane as we go a little bit and it's starting to. Pay off, but it was a hard shift for sure. So I know that you've talked about this, this concept of like missionaries versus mercenaries.

Can you walk me through how it is that you're really fostering that with your team and the folks that you mentor? How do you approach that? For sure. So the, I actually, I posted about this, I think it was earlier this week or last week around the Adobe missionary and mercenaries. Right. And missionaries, they spread the word because they believe they spread the word because they're are bought in.

They do it at all costs. They aren't afraid of rejection because of it because they just want to evangelize the message. Right. Whereas Aires. They, they do what they're told because they're paid, they do it just because you told them to they'll go to the highest bidder. They won't work through hard things because they'll go and try to find an easier battle to fight.

And so one of the things with my sales team that we talk about is we have like our own mission within patient pop, right? So patients pops mission, right. Is help practices thrive. And I actually think part of the reason why I post this. I think we can ask, talk about that more as a company and as a sales org of really talking about that mission and how we are helping is something we bring up a lot is customer stories, but then the internal, like our mission is to become the best sales team in America.

And we talk about that. All the time. Right? We talk about that when it comes to promotions and hiring, and we have our virtues that we follow and we shout people out for, right. Of like how we choose to behave as a company or sorry, team. I think that's really important. Like most orgs don't have their own mission.

They don't have their own vision. They don't have their own values. If you have an org at a company and their values are the company's values. They're, they're not yours. You know what I'm saying? Like company values very often or something that just goes up on a wall somewhere and gets talked about once a year at the all hands of the kickoff.

And then. That's it, you know, like we, we talk through our virtues, every team meeting, we talked through our virtues daily and Slack. Y'all want to call out this person for, you know, celebrating the process. I want to call out this person for owning their shit. I want to call out this person for preparing to win, right?

Like things like that, where you build them into the day to day communications, that's how you really can, can set things up the right way to have a missionary based team where they believe in something bigger than that themselves. I love that. I'm curious how you. I mean, that sounds amazing on a, on a team level, how do you share that or champion champion that with other orgs?

So I, I don't, you know, I guess like, that's what makes it our mission, you know, like the sales or, and this is not th this is by no means not to other org. Every org I believe should have their own mission and virtues. Right. The way a great product team behaves is probably a little bit different than how a great sales team behave.

So just probably a little bit different than a great customer success team. And so I'm not trying to evangelize our mission. So other orcs I'd like to evangelize the idea of having a mission. Right. But no, like my, our mission is our mission. Right? Our virtues, our values or our, is that what that's, what makes it awesome.

Right. So I don't, I, you know, I don't know if any other, the orders that the company know are for, for our cheese. In fact, I'm probably, um, absolutely that they don't and that's okay. Right. And it's not about keeping secrets. It's about, this is how we operate in the standards. We're holding ourselves to.

Sure love it. All right. So now let's talk about, you know, your work as a mentor or even other orgs you've worked with. What's maybe the most common thing that you see getting in the way of success. When you're getting to know a new organization, you know, maybe some of the patterns that you just see crop up time and time again, that that are holding them back.

So again, back to people first, right, is there's generally poor people development. Right. It's not clearly defined, like what makes someone it's successful? There's very little training or ongoing coaching. Right? It's a lot of like, just winging it, like and hoping things work. Right. So having really strong people development is something that tends to be missing from a lot of orgs that I work with, but going even, I guess, a step further of like, you know, working with, you know, 500 startups and some of the companies I consult with that are very early, right.

They don't even have people yet. Right. It's two dudes in a garage. The most consistent problem that I see is they don't actually understand their prospect very well. They understand their product really well. They don't understand their prospect very well. And that's one thing that I think I've been able to do pretty successfully as I, my career is a mishmash of industries.

It's not been one type of industries. I have sold fitness equipment, sold franchises and venue machines. I've sold snacks in a box I've sold softwares to home services. Now software is to the medical and healthcare industry. Right. You don't have to have a lot of industry experience because you got to be, you have to get to know the prospect better.

And a lot of founders miss that, right. They build a product, but then in the building of that product, they lose sight of that prospect and the problems that they're actually selling. I just had a conversation with a founder last week. And he's like, you know, my messages isn't sticking. I, and so I was like, all right, let's, let's go through this.

Right. So I was going through his messages going through it. And I was like, well, you're talking a lot about storage. You know, like, you know, I won't give away what his product was. We were talking a lot about storage, but really the whole reason why someone would ever use your product is for the decision making.

Capabilities. It gives you're over here talking about storage, but people care about decision making. You're not talking about that. You lose sight of what prospects actually need or want. And a lot of early founders get that to Institute. So they pitched their customers the same way they pitched their investors.

Those are two very different pitches, very different pitches. Yeah. I feel like, uh, especially product minded or technical founders, they've just been so in it with their product. I mean, we see this all the time on the marketing side of the org as well, where it's, you know, the messaging and the positioning.

They're like, what is not clicking. Like you just, nobody cares about your product. Nobody cares about their feet, your features. They care about solving their own problems. Right. And whether or not you can align with that. So, yeah. I totally totally agree. Yeah. The first thing I did at both service Titan and at patient pop is I spent a good week in customer success.

I wanted to talk to customers, right. I didn't like I'll talk to prospects, but I want to understand. What they think about. Right. So I was asking them, why did they buy, what problem were they hoping to solve? What were they doing to solve that problem before they used our tool? Right? What's their favorite part of the tool?

What were they most afraid of before I get those unspoken objections, a customer will tell you that a prospect never will not have, like, what were you afraid of before buying this product? And what's changed the most since you've bought any founder in salesperson, any one. You go and ask 50 customers those questions.

I promise you, your messaging gets better. Your success rate gets better. Your close rates go up. Everything improves. When you start to understand how the prospect talks about their problems. I need one. That's what I recommend that they go do. If their messaging isn't landing, this is probably because they don't understand how the prospects actually talk about their product.

Right? We use words like disruptive and innovative, blah, blah, blah. Really? Have you ever, ever heard a customer say this is disrupting the way I used to do business? No, they don't talk like that. Yeah. I love the, uh, You keyed in on something right there, which is actually using their words, not just understanding the sentiment, like that's obviously the first most important thing, but then using their language as well is just something people overlook so frequently.

I call it the long day at work test. Right? If you can't picture your prospect working a 12 hour day, getting home, kicking their shoes off, pouring a glass of scotch, sitting down, taking a deep breath and going, God, I wish I had a.

If what comes after that sounds ridiculous. You need to change the way you describe your product. It happened at patient pop. When, when I came to patient pop, the way we were describing our product, even to prospects was an all in one practice growth platform. Okay. Now, do you, you think a podiatrist has ever gotten done with four ankle surgeries in a day, 12 hours gets homes get off the scrubs kicks off his shoes.

She pours a glass of scotch. He goes, Oh God, I wish I had an all in one practice growth platform. Like no. Right. They don't. So if you can't picture them either saying your product that way or describing the problem that way, right. What do you think a doctor in private practice might actually sit down and say after a long day, God, I wish I had more patients or God, I wish I had better patients.

I wish I had the patients I wanted to work with. I wish I was getting more of. That's how they talk, right? Like, so all these super smart founders and tech people and marketers are, it takes sometimes a dumb sales guy like me to step in and say, guys, no one talks that way. So stop it. We gotta change what we're saying.

So what I'm curious, you know, you said you touched on a lot of different industries or selling, uh, meals in a box. Your franchise is like all across the board. Has there been, I know you've said people, so that, that seems to be the, maybe the. Most common thread, but have there been lessons that you've learned that have turned into patterns that you've now bring with you today in what you do?

Oh, absolutely. And like, so I believe pattern recognition is something that I think has actually has led to some of my success has been able to pick up on actually what's working. What's not. And asking those types of questions, right? Like I take people through kind of like the five PS of like, you know, scaling, right.

People, prospect problem, process, and product notice products at the bottom of that. But what most they will never do is establish processes, create patterns, right? You need to be able to identify what is working. And document, and then train your people and coach your people and create a process to make it repeatable.

If something isn't working, same thing, you need to untrain your people, something new and create processes to also stop the other behavior. Right. Um, I can't remember what book I read this and I think it was scaling up. I'm not sure, but it talks about, especially for startups, things break at every multiple of three.

So if it's just, you. It is what it is. The moment you have three employees, things start to break. Cause you're used to just being able to make decisions. You go from three to nine, nine to 27, every multiple of three, you need new processes in place. And what a lot of startups can get in trouble with is they never establish a process for, for hiring, for interviewing, for selling, for onboarding, just because nine of you made it work.

Doesn't mean 27 of you we'll make it work. And it sure is. How does that mean? What would it be? Seven. Yeah, the one I do my math right there. I don't know somewhere around there, like 71, one of you can make it work, but there's a lot of startups out there that have nine person processes for a hundred person team.

Right. They don't change their processes as they grow. Right. Like you got onboarding that was meant for five people. Yeah, a team of 50 now, like no step up those processes. So I think that's a very common pattern is one, a lot of startups, teams, founders, they don't document anything it's all up in their heads.

And so then yeah, when new people come in, they have to either reteach the same things. Or you get too big and you can't teach it anymore. And you wonder why things go amuck. You wonder why they get away. You wonder why your culture is changing. Cause he never taught it. You never wrote it down. So I'd say that's a big pattern.

Is you gotta to document everything. One of my biggest regrets, um, earlier in my career that I didn't start recording everything. I record every training I do now. Every single one. I have hundreds of hours now of trainings on hard drives and things like that. Cause once I've recorded it, guess what I don't have to do.

I don't have to do it again. Okay. Looking record. Right. It's like, Oh, what was the topic of this training here? Is that topic? Oh, someone's struggling with this three months later. Hey, go watch this training. Right. It's that type of stuff that you need to do. So early founders record everything. You're rolling out virtues and values record it.

You want product described a certain way where core, like document everything it'll make your life so much easier as you grow. All right. Let's talk, highs and lows. Now I'm curious what, what's the hardest. Thing you've ever had to overcome in your professional career, um, whether it was a challenge or a period of time, just something that really, really tested you that you ultimately had to push through.

And then let's talk about a contrasting high point. So I'm, I'm in it right now. If I'm being honest this year with the pandemic we sell to doctors private practice during the pandemic. We can just let that simmer for a second. Right? Like I own fortunate earlier this year had to go through layoffs and it was the first time in my career I ever had to let go of a significant portion of my team for no fault of their own.

Right. This wasn't about like, not hitting numbers. We had, we had, my org had missed our number in almost 13 months. Right. Like it wasn't about not being efficient. Wasn't about doing things the right way, but. Bottom falls out on our market and the company. Yeah. I asked to make those challenging decisions.

The hardest thing I've ever had to do, because what people don't remember, sometimes one about leaders is we are people too. That broke my heart. Like I shed tears in front of my team. Right? Like that absolutely crushed me. Right. And it also crushes the people that are still left behind. Right. And then still trying to power through and sell and hit numbers when all these things are going on.

When my team that used to be. 90% of the office is now remote and we can't go grab that coffee. We can't go take a 1:00 PM tequila shot because yeah, that happens sometimes because we can and we're adults, right? Like they miss each other. And so trying to navigate all of that has been a massive challenge, right?

Because as, as a leader, you need to guard your emotions. You need to guard your mindset because. A hundred people are depending on you to get them through it. Right. So that is absolutely a challenge to make sure that I'm taking care of my people, but also taking care of myself during this, you know? And so there's been a lot of things that we've done and rolled out to improve her.

I like we've done guided meditation together. We've done visualization practices. We did, we did new years in August. Right. We had Evelyn reset their goals. It was like, you know, anyone listening right now, how those new year's resolutions treat and you right now, anyone even remember those. Right? So we, we reset.

We're like, yo, we still have four months left of this year going into September. Like let's reset. Like let's set new goals, new resolutions now to roll into 2020. Right. Doing things like that way more intentional with like individual shout outs and all of that stuff. Making sure that recognition is not conditional, right?

Whereas always, if you do this, then you get recognized. Or if you do this, then you get this spiff. If you do this, then you get this little gift. I told my managers, we need to reverse that. It can't always be conditional. In fact, which actually works better. Hey, go hit this number and here's a hundred dollars or go hit this number.

I'll buy you lunch. Or dude, I know you're gonna get after it this week, lunch on me, Tuesday and Thursdays. Which one is actually going to drive the behavior that she want. Right? So those are things that I'm trying to encourage and to deal with as we all navigate that, because there's no formula for this, right.

I was just texting actually with a former, um, um, was a former rep of mine who then became a manager. Now he's actually the director of sales over at swag up. And I was like an exercise. So I mentor him a little bit as he's a new director at, at a young company. And I said, one of the exercises you should do at least twice a year is what would I do if.

Right. What would I do if the market fell out? What would I do if right. Like we couldn't sell those certain segment. What would I do if right. We doubled our price or you think of some of the things that could go wrong. I do that. I didn't wake up one morning and go, what would I do if we had a global pandemic?

I hadn't gone that far. You know what I'm saying? So there's no, we weren't thinking full three 60 on this man. Like, dude, I look back, I got full regrets there. So it is, it's like, there's no playbook for this and it's just being intentional. But back to what we talked about earlier is adapting. Not trying to do things the same way, cause things are not the same anymore.

Right? So that's, that's something that I look at as definitely the hardest challenge I've gone through as a leader. Cause I also know it's the hardest time for my people. Um, On the flip side of that. If I look at highs. One is it's watching the, you know, we joke about sometimes with Washington, kind of like the Dorsey mafia start to spread a little bit.

Right. I got Austin as you know, a director of sales sales over at swag up. I got to, so at chili Piper just crushing it right at Gentry over at outreach, I got Jordan Cohen. Who's now like the director still at snack nation. Like you start to watch that. That core group really start to branch out and start to have impact everywhere.

Like it just makes me so proud to watch, you know, and also to get like the text messages sometimes like, yo, Katie, it works here too. That thing, remember that thing you taught me way back way and it works here too. I'm blowing their minds with this stuff. Right. I got Megan. Now who's an SDR manager at Oracle.

Like you're just expressing that. That is a, a huge high for me of like watching them, you know, grow and go out on their own and have impact, you know, outside of working for me. Right. And then staying in touch with it. Like that's probably one of my bigger highlights is, is that type of movement. Nice.

That's amazing. Uh, you got a proud, proud sales, Papa. What does it makes me happier? What do you do? Like, do you have a guilty pleasure? What do you do to kind of treat yourself ramping around? Whiskey. Yeah, that's all I like, I like a good whiskey or a good tequila. That's my guilty pleasure. You know, like that's my, you know, end of a 12 hour day, deep breath, you know, pour, pour scotch out.

So I'll get good whiskey, a good tequila, right? Like, like a heavy drinker. I'm not throwing it by like to sip, you know, like have one and let it last, like the night. So, um, that's, that's probably my guilty pleasure, you know, like I'm not much of a. TV guy. I'm definitely not out at the clubs or anything.

Ridiculous like that. So it's like whiskey, a good tequila. I'm very Abby. So you said scotch, are you like a smokey scotch? Are you a, like a briny scotch? What's your more, more, more Briony? I don't like the heavy peach, you know, like sometimes like, you know, it's so heavy and I'm like, did I just have a cigar?

Like what happened? Right. Freud? Yeah. Like, nah, like if I, if I want, if I want to have a smoke, I'm going to have a cigar. I don't need it in my whiskey, you know? So yeah, I'm more on like, I like the, a little bit of a smoother, a little bit like of a lighter, like flavor there. Do you have a favorite bottle or one that you're into right now?

Let's see my favorite. Hmm. That's tough tequila. I definitely know. So like, um, Casa Zul Reposado by far and away. That's my favorite tequila. It is so good. Um, my daily sipper for whiskey, like, you know, it's low key, like monkey shoulder is really good. It's not super expensive. It's just a really good, easy, um, set.

Um, I do like Glen, Levitt's really good. I like their 18. Um, Glen Meraji 18 is probably my favorite Dyke that one's so, so good. So Glenmorangie 18 is my go to for sure. Nice. I have a Talisker 10, just like I keep coming back to it. It's my. My go to for a, for easy sipping. So yes, exactly like Glenn Glenn Rodriguez for special occasions, monkey shoulders for any occasion.

That's how I look at it. Well, Hey, it was so great chatting with you about all this stuff today. Thanks for sharing some of those stories and the challenges that you're focused on this year. For sure, my man, for sure. Now I would not be, I wouldn't be me if I wasn't gonna leave people with some book recommendations, you know, especially if you're looking to like, you know, for starting up in sales, like definitely out scaling up and scaling excellence are two really, really good books on how to lay the foundation.

But for anyone that's doing like this X building a sales team, you have to go grab them. All of Jocko, Vander, cous books, the SAS blueprints to keep them here again in my office, like. These bad boys here, how to get to 10 million ARR sales method, fundamental success as a science method, SAS, you know, for customer success, blueprint, sales, development, like these they're very, they're borderline academic where it's like paint by numbers of like how to build the systems and processes in place.

So anyone that's truly looking to learn how to scale the right way I had to go scoop those up. Very cool. I love book recommendations. Um, actually, you know, I have one more question for you who are some of the folks you sound like you're really big on mentorship, who are some of the folks who have been, you know, right now you're in this place where you get to be there for others, but who are some of the folks who've been there for you?

I'm Dave Brock, author of sales manager. Survival guide has been one of my closest mentors now for, um, geez. Five six years now. So he's had a big impact on my career, Collin Coggins and other close mentor of mine in Los Angeles. Scott Leese now very good friend of mine as well, started as a mentorship.

Yeah, just very, very close friends. I'd say those are some of the foundational mentors. Yeah. And also my, my grandfather, um, he, you know, he worked at Oracle in something like the earlier days was actually worked with Liz Weisman, the author of multipliers, like, and so. I actually have, um, I know this is a recording.

I actually have an old book and, or of his, that he was given when he, um, retired from Oracle and it's like a hundred, some pages. Trying to find it. I just moved here, but like a hundred pages of just like, thank you, notes and letters from employees, like thanking him for his leadership. And that's something that's always really inspired me.