Kevin Gaither - Founder at Inside Sales Expert: Transitioning from Individual Contributor to Manager, Manager to Director, Director to Executive, and Deciding if a Career in Leadership is Right for You

Kevin Gaither  00:00

Going into a sales office that has 350 salespeople in it, you get off the elevator and you hear the roar of the sales team, before you can actually see the sales team, is sort of like wow, look what we've done.

Callan Harrington  00:17

Welcome back, everyone to this week's episode of That Worked. I'm excited by this week's guest, it's Kevin Gaither, and many of you may know him as KG. KG is the founder of Inside Sales Expert, where he helps early stage tech companies avoid mistakes in all aspects of growing their sales team. Prior to Inside Sales Expert, he spent a little over seven years at ZipRecruiter as their SVP of Sales. And there's one thing about KG, he has the experience. He's been at eight startups, three of which have successfully exited. He's built teams from 30 to 550 sales reps, and in his own words, he's made lots and lots of mistakes. And if you follow him on LinkedIn, you know he loves to go into detail on these mistakes specifically. In a fun fact, KG was actually one of my first mentors I had in sales when we first met in 2013. And the reality is he's had success at every level of sales: sales rep, sales manager, sales director, and ultimately leading a very large team as a sales executive. He gave an excellent breakdown of what it takes to be successful at every level, and what mistakes he made as he was transitioning from each one of those promotions. If you know KG, you know he brought some spicy hot takes on the episode as well. In particular, answering the question of: should you be friends with your team when you're their manager? It's a great question. I'm glad we dove into it. But with that, I'm going to jump right into it. Let's get to the show. KG, welcome to the show.

Kevin Gaither  02:21

Hey, thanks for having me. Happy to share, happy to help.

Callan Harrington  02:26

One of the reasons that I'm honestly most excited is, if anybody follows you on LinkedIn. I mean, your posts aren't necessarily just opinions, most of these, the lion's share of what I've seen that you put out there, are from real experience. So I want to dive into that. I want to start from the beginning. Where did your career start?

Kevin Gaither  02:46

Yeah, well, listen, Callan, nobody ever said to me growing up, "you should be in sales, you've got the gift of gab." No one. In fact, sales and asking for money, scared the absolute daylights out of me. I mean, I used to have a paper route and going door to door to collect money. Just in that way, I was delivering a product and they have to pay for it. Even in that way, I felt like it was uncomfortable asking, you know, for money. And I started college with a degree in aerospace engineering, of all things. Engineering, of all things. For a variety of reasons, mostly party related, I switched over to architecture, of all things. And that's what I graduated from UC Davis. But I learned that the average architect, regardless of experience makes a whopping $50,000 a year. And even when I was 23, I was like, gosh, that's a lot of money for a 23 year old, but that's not a lot of money for a 53 year old. So I probably should do something else. I got into customer service. And this was through networking. And I was sitting there one night with a guy next to me, playing cards, in this call center. And I learned that I was making ten bucks an hour, and he was making like $11.50 an hour. I'm like, how the heck are you making more than me? And he's like, well, I've just sort of been here several years. And it just sort of hit me. Wait a minute. So like, I could be here for another couple years. And I can get a raise from $10 an hour to $11.50 an hour. That's a bunch of baloney. That does not suit me well. What can I do, Callan, to control my destiny and control my income? And I thought, I could start my own business. But I didn't have the guts or an idea. Or I can get into sales. What are the businesses? And I was very intentional about that, Callan. A lot of people write these days about how they "fell into sales" and sales wasn't the thing that they wanted to do. And it was sort of like the second prom date or something like that, okay? Yeah, absolutely very intentional. Why I got into sales. There's a lot of people that write about how they "fell into sales," and how sales was sort of a back-up plan for them. I very specifically chose sales, because sales was the thing where I knew I could control my destiny, control my income, and in theory, the harder I worked, the more money that I made. And I got into sales in November of 1994. And my very first commission check was 19,000 bucks, Callan.

Callan Harrington  05:17

So, one, that's incredible. I want to break this down a little bit, because you are right. In mine was- I very much, and I've said the story multiple times. The only reason I got into sales because my best friend, I was only number he had memorized when they asked him for a referral, who else would be good at his job? And he wanted to look good. So here's the question. Now I understand totally from the, you know, like, control your own destiny and everything else. But it sounds like you had to get over a hurdle. You had to get over a fear, in order to go into sales. Is that correct?

Kevin Gaither  05:46

A thousand percent. And other people going, "what are you thinking? Sales? What if you don't hit your quota, you won't be able to make your rent!" And just a lot of negative stuff around me that was sort of encouraging me not to be in sales. And of course, yes, there was that fear. But, and I write about this a lot. I have this, like burning desire to achieve and to succeed. I'm very, very competitive, played sports all my life. And I now know what I didn't really know, then is that I have fairly thick skin. And so I can deal with a lot of adversity. I actually had to deal with being bullied a lot in elementary school, by the way, turn that into a positive. And here's the thing, Callan, when I was hired by my first sales manager, who literally gave me a shot- God bless him. I was hired with two other salespeople that had experience. Turned out they had one year of experience each, working at ADP. But that was an infinite amount more time than I had. And it really was intimidating. But I thought to myself, yeah, but what do I have that I know they don't have? I can outwork them, I'm likely smarter than them, I'm likely ten times more coachable than they are. And so I just, in order to get over the fear, I controlled the controllables: reading books, seeking out mentors, getting on teleseminars. That was the thing, you'd actually dial into a teleseminar way back in the day. And I would come in earlier, I would stay later, I would get coaching from my boss, and just if today was the day you stood on one foot and hopped and made cold calls, I'd be like, that's the thing I'm doing today. If that's what they said to do, that's what I was doing. And it proved me right. And that first year I made President's Club and they did not.

Callan Harrington  07:36

How did you do that? Like, what was kind of that turning point? Because you couldn't- were you good right out of the gate? Or was there- did something click where it was like, okay, of course, all the things that you're doing behind the scenes, but in the actual job of sales itself? What were you doing that kind of clicked that got you there?

Kevin Gaither  07:54

Yeah. Again, this is that architecture, engineer background, the systems thinking, this process thinking, that worked for me right out of the gate. And of course, with engineering, you're constantly optimizing. Okay, great, let's make it one percent better, one percent better. So what I learned was these experienced, quote unquote, "experienced" salespeople that I was hired with. They were already sort of like, I got this. And I didn't know diddly. So I'm like, well, I'm going to write out a script. And that script had dog ears, and then I'd tear it up and rewrite it again, and I would just keep tweaking the script. And I'd get objections, and I'd tweak that. I'd be writing, you know, rebuttals to my object, my objections. I remember one time, I had literally written out a list of like, twenty discovery questions that I was going to ask this prospect, and I got like ten questions through, and this was a VP of Finance at this manufacturer in Indiana. And he goes, next question. And he could just tell that I was reading these questions just to get through the interrogation, basically. And I was like, ah, let's optimize from there and make it more conversational. Since I didn't know any better, Callen, and this is like, sort of the message: since I didn't know any better, and I didn't have any bad habits ingrained. I had no sales experience. Whatever my boss told me to do, I just did. So people would say, gee, KG, how did you make President's Club in your first year? I'm like, I don't know. I just did what he told me to do. I just did what he told me to do. But I also leaned into it and became a real student of the game. I was committed to my profession. And these other dudes, they'd come in, they'd make their calls, they'd leave, you know, and I was out-working them, out-learning them, and out-being-coachable. That's a winning combination.

Callan Harrington  09:38

How much did that experience help you when it came to hiring reps later in your career?

Kevin Gaither  09:43

I don't think it did. Because I wouldn't have even thought about that at the time. I don't think it did. Because I had to make enough hiring mistakes as a leader as a sales manager myself. That was really the learning lesson. Like when I started making mistakes and had to lay people off or fire people... I mean, those are- or they quit on their own because they just weren't good fits. That's where I got most of those learning lessons, you know, from. But I can tell you that I learned a lot of sales leadership lessons. And when I reflect back on that- not hiring lessons, but like sales leadership lessons- and I'll give you an example. And I wrote about this the other day. One of the things that my sales manager didn't do very well, was that he took a heavy hand in helping me close my deals. Well, why is that a problem? Well, when he left to go do his own thing, I realized that I was sort of dangling in the wind going, well, wait a minute, like, he's always helped me get to from here to here, and I'd never crossed certain chasms before without him. And I thought, when I become a sales leader, I'm gonna let my reps fail, they have to learn how to fail. So that they can get, they can get better, if I'm always there, to catch them before they hit the ground. They don't learn anything. And there were certain areas in the sales process that I didn't, I didn't learn anything, because my boss was always there, to like, make sure that he was helping me.

Callan Harrington  11:10

I mean, it's such a good point, and it's one of those things, it's- not only is it in the end, a disservice to- I mean, it in the short term feels great if you're the rep, right, because you're getting commission, you're closing deals bigger than what you would be able to close on your own faster. But the reality is two things. One, as a manager, that's almost impossible to scale, because you're going to be stuck in the weeds at all times. Which you know, also is going to have the impact on your own career, because it's going to be hard to make that leap up, because you'll never get out of the weeds. And then two, like you said, you know, it's not putting the rep in the best position for them to grow long term. Is that what I'm hearing you say? Totally! The only reason I can bring it up is I screwed it up, that's for sure. I know exactly what you're saying on that.

Kevin Gaither  11:48

A hundred percent. And that scalability piece, the way that I like to refer to it is a little bit grim. But I say, as a sales leader, if I got hit by a bus tomorrow would the machine keep running. And in that instance, it wouldn't run as well, you know, sort of like a car running on one flat, or something like that, you know? And that's, that's sort of where it ended ended up. And it was very- and that was a huge learning lesson for me. And you're right, by the way. You know, you want to get from that management to director or VP or above, you have to think about ways to remove yourself, remove the humans from the process, so that it continues to run. As opposed to making it dependent on the humans or the or the boss. In that instance. He was a single point of failure, he became a single point of failure in and of himself. Again, a lot of learning lessons, a lot of learning lessons. Some people can't get out of their way, though. They think they're being really helpful. They think they're being really helpful, but they're not seeing the forest through the trees. And then they wonder why they're not getting promoted to director.

Callan Harrington  13:01

I think you're right. And I think the flip side of that- So there's the people that are doing the best intentions are really helpful. And then I think the other- yeah, I've also seen it on the other side where somebody wants to make themselves so important out of fear of losing their job. It almost kind of, you're building this around me, I don't want to lose my job, which ends up being a real problem.

Kevin Gaither  13:19

We're going all over the place. And I can tell you, there was a person I was hired with at one of my last jobs. And this person, run it- ran a different department, not the sales department. And I saw just that exact behavior. And I called him out on. I said, hey, why are you involved in this and this and this? And why are you staying up till 11 o'clock at night making decisions about that thing right there? And he goes, "Oh, KG, let me tell you, because it creates job security." And I said, you're an absolute buffoon. Do you understand that actually, it doesn't create job security for you even in the slightest. In fact, it makes the leaders above you look like a jerk, like a dummy. Because you can't figure out how to get out of the way, you become a single point of failure. So it's awful for you, because you can never take a vacation. But then when the company needs to grow, and it- and your department can't grow with it, because you have to be involved in every little piece of the puzzle. Because you're trying to create job security. You're out. "Yeah ,KG, KG, you don't understand, it's a different department." Literally a year and a half, he was removed.

Callan Harrington  14:34

That exact advice has came up on this podcast before, and I think it's excellent, right? If I got hit by a bus tomorrow, this thing doesn't miss a beat. That's kind of the mark of the- of a real operation that you've got going on. So, I want to talk about that transition. How did you get into your first leadership role?

Kevin Gaither  14:52

Gosh, I was just mentoring somebody about two hours ago on this exact topic. And if you look on LinkedIn like yesterday, I wrote about this very, very specifically. So, I love to help people. And I never viewed my peers on the sales floor as competitors. I never viewed them as some, you know, they're going to take, if I tell them something, they're gonna take something from me, and I can't make the top of the leaderboard. And so I was, you know, infinitely helpful with these people, with these peers of mine. And, and I'll give you an example. I was a salesperson, but I would get involved in training the new hires. So, we were- it was a small business. And I could have said, no, I'm not interested. But I'm like, no, team player, you know. I played sports all my life, team player. Coach, put me in. Great! So I would, you know, train them how to use our CRM system, or how to book a sale, or how to, you know, it was a financial service, so spread financials and things like that. And I would just take it upon myself to help these people out. And what ended up happening, Callan, is that other sales reps started seeing me as a resource. And so they were coming to me, and they were asking me questions. And there's the CEO, the founder, with his binoculars going, "wait a minute, they're going to KG a lot. And they're asking him questions. And then there's performance." And it became one of those "act as if" scenarios. And the CEO said, "hey, it seems like everybody kind of gravitates towards you anyway. Do you want to move up into sales management?" Yeah, no problem. And let's give it a shot. And a lot of people fear that, by the way, they're like, well, wait, you know, what, if I suck at this job, and all this kind of stuff. I knew that my worst case scenario was just to go back and be a quota-carrying rep and not care about anybody else's, you know, number. But again, the honest answer, the primary answer is, I was helpful. I was openly helpful with other sales reps. In addition, the manager, he was the founder of the company. He also saw that I had a very methodical way of going out selling, and it's going to date me, man, I'm fifty-two years old. We were, I was using Lotus Notes, okay. It's like the predecessor to Excel or Google Sheets. And I literally would have a funnel, from conversation, you know, calls, to dials, to conversations, to proposals sent, to conversion rates, to close, to approval rates, to commit, you know, average dollar size. One year, I had my entire year planned out to make the kind of money that I wanted to make. And it boiled down to making $177 a day, guess what I made the money that I wanted to make by the plan. And that methodical, systems thinking way, that repeatable way of like, hammering out a goal, was another thing that the boss noticed and was like, "we need you to level up, so you can teach other people to do the same thing."

Callan Harrington  17:57

I love that. I want to break down a couple of pieces on there that you mentioned. You knew you really liked helping people, so you wanted to be in a leadership position. I personally think that's super important. You know, I think a lot of people think that, "well, I'm in sales- for me to grow my career, I've got to be in leadership."  Well, now, I don't agree with that, personally. Top individual contributor, a top enterprise sales rep, you're going to make way more money than you will in sales leadership. And if you're at the top, you're gonna have more autonomy. You get to decide what you really want to do. That's the reality. So if you're an individual contributor out there, and you're like feeling you have to go to leadership, you don't. It's a great route to go. And then, that is what I heard, you know, that was the first thing. You knew that you wanted to be in, in leadership. And then the second thing you said, I think is fantastic, is that start doing the job before you have the title. Worst case is you don't get promoted to it. But you're building the skills on how to do that. So when you do take it, you're going to be ready for it. Did you find that to kind of be the case with you?

Kevin Gaither  19:01

A hundred percent. Yeah, a hundred percent. But I wasn't doing it in a manipulative type of way. I truly was trying to help people. And it was acting "as if." So the first time I got promoted to a director-level role, by the way, was, all these other managers were coming to me, and I'm happy to help them out. And the VP takes me to coffee. While we walked back from coffee, and by that time, he had offered me the, you know, the director role. Because he's like, you're already doing the job. You're already doing the job of director. So it's just a natural fit, you know, to do this. I'll give you another example. This guy that I was coaching earlier today, mentoring, he wants to get into sales leadership, and I said, how many people on the team? Nine people on the team. How many of those people are struggling right now? There's like three or four of them. I said, dude, you know where all the dead bodies are in the business. He's been there forever. You're a high performer. You've gotten promoted several times, and you're an individual contributor, but you want to get into leadership? Proactively reach out to those people, and don't be lame about this. Don't say, "hey, if I could ever be helpful, let me know." Click. And that's it on Slack. You know, like don't do it that way. Say, "hey, I can tell that you're struggling. Would you like to put thirty minutes on the calendar for the next couple of weeks with me? Because I've been there, I've done it. I've been where you're at, I've struggled as well. You know, I'd love to help you out. Would you like to put some time on the calendar?" Like some real intention and real action behind that? He's like, "oh, KG, I never even thought about that." And that's precisely what I had done, where I'd see people that are not doing so well. And I'm like, God, let me help you. And to your first point, the former point, I always tell people don't go into leadership, like for the money. It has to be a calling, it has to be a vocation, you have to want it. Because having your number depend on six, nine, twelve other people? This sucks. And dealing with the human resources crap that we have to deal with? It sucks. And having to roll a number up to the- you know, director and the VP and all this kind of- it's sucks. And having to fire people sucks. Like these- there's a lot of things... If you don't have, like if it's not a calling, a vocation for you, don't even think about doing it. Just like you said. Individual contributor, oh, I "should" move into management because I'll make more money, or that's the next step in my career. Uh uh. If you're not inclined, if you're not drawn to it, don't bother.

Callan Harrington  21:27

I love the idea that you just said. I just want to go back to that real quick about, it's one thing to say, hey, if I can be helpful reach out. You know, especially if you're looked at as one of the top reps. Nine times out of ten, they're probably not going to take you up on that, because they're like, "well, I know that Steve's really busy and that's nice. Like, he's a great guy. I don't want to bother him." But if you say specifically, "hey, if you're interested, find thirty minutes on my calendar, I've been in your shoes." That's a great idea. I've never heard that. I really like that. So, you brought up kind of the next one. Before we get into moving on to a director, say what were the biggest challenges that you had transitioning from individual contributor to a manager?

Kevin Gaither  22:09

You mean, what mistakes did I make? Oh, God.

Callan Harrington  22:12

Well, mistakes, challenges, things that you just did not expect?

Kevin Gaither  22:17

Well, first things first, going from peer to manager, I had no preparation for this whatsoever. No clue, no idea, like, how am I supposed to manage. And you get, there's like three, four different kinds of personas that you're dealing with. The people that are like, they're gonna kiss up to you. And it's like, great, whatever KG says, fantastic. There's going to be people that are going to be actively working against you and trying to test the boundaries right out of the gate, just to see what you're, you know, what you're going to do. And I wasn't prepared for that. And that was, you know, trying to figure that out. Another huge mistake that I made was, remember I told you I had a very systematic way of making my own sales with the numbers and calculating the conversion rates. Worked for me. Why won't work for everybody else? And of course, the old adage goes: manage everybody fairly, but not necessarily equally. And when I read that in some other book, I was just like, ohhh, that was my mistake. I was trying to manage everybody the way that I like to run my own playbook, and I had to realize- and I remember this guy to this day, Terence Gordon. Terence Gordon was a guy, he'd make twenty calls in a day, talk to fifteen of them, and have high conversion rates. And I'm like, why aren't you making seventy-seven calls, you know? It didn't work for him. It didn't work for him. And I didn't quite understand how to manage to different, you know, personality types to help them get to where they need to be using their own assets and things like that. And that was, that was certainly a mistake. Another huge mistake that I made. And this- thankfully this happened early on, and there was no repercussions. But like, what I say next comes out exactly the way it's supposed to sound with all the connotations that go along with it. I was the president of my fraternity in college. Okay. King of the idiots, okay? And that was my leadership experience. That was relatively formative. And so I brought this sort of bro-y, frat boy, formality- informality, informality to leading my sales team that resulted in sometimes saying things that were a little bit, you know, inappropriate. Not a little bit a lot. Inappropriate. Because I was just sort of like, Yeah, well, that's, you know, that's how I talked when I was leading my fraternity, and, you know, now I got a band of salespeople here and, and I was just too informal. And not that I had to be straight laced and wearing a tie and a suit and all this kind of stuff there. But there's a line, there's a line. These are not my friends. These, this is- these- we're part of a team, but it's as a professional organization. And I had to learn the hard way that you cannot be friends with the people that you're leading. You can be friendly. You can be professional. You can be acquaintances. But being bro-y, and like trying to be friends, just doesn't work. And God help you if you think you're friends with somebody, but then they're not hitting goal, and you have to fire them? You'll find out real quick that you are not friends, because they will sell you out as quickly as they possibly can. Again, this is experience, not opinions. And it's like "God, I thought we were friends." Don't be fooled. The list goes on. We could talk for three hours about all the frickin mistakes I made. But that's, you know, certainly- don't try and make them your friends. It's sad to say, but don't don't make them your friends. Keep it a professional and, you know, environment.

Callan Harrington  25:47

I know I made a ton of mistakes as a- that first switching over to new manager. Yeah, that's a tough transition. What I would love to go to next is, I'm not necessarily going to use titles as much as functions, right? Because once you start getting into Director VP, CRO, it- they all kind of bounce around. I mean, maybe there should be something standard. But what about that transition to managing managers? What was that like for you?

Kevin Gaither  26:10

That was the first time that I had to realize that the manager is about their individuals, their team, and they're an advocate for their for their team primarily. So it's sort of like 80%, team 20% company, and being a director and moving up, even, you know, VP CRO role, it started to index the other direction. This is about now, making decisions that are in the best interest of the business and the team almost equally, maybe a little bit more on the company side. And that results in- that results in getting comfortable, making difficult decisions that you know that the managers and the individual contributors may not necessarily like. Your garden variety examples here, Callan, would be raising quotas, and cutting leads, and territories, and all these kinds of things that are just sort of this, the garden variety bitch session that ends up happening when sales directors or VPS, you know, end up making those decisions. And it taught me how to become very intentional, data driven, thorough, methodical. When I'm going to make those decisions, I know that there's going to be blowback, I know it's the right decision. Now, how do I communicate this transparently, you know, to my team, my managers, of course, to help them? Because remember, they're like, 80% team 20% company. So how do I then take this difficult decision that I'm making? Or that's being thrust upon me by the CEO or the VP of sales, okay.. And how do I enable my managers to be able to stand and deliver in front of their individuals, there people, who are going, "this is bad, this is awful, you're crushing morale, we're leaving." Like all the normal stuff that a manager- a frontline manager, you know, has to deal with. So enabling the managers.  And feel free to double click on that when you want. But the other thing I think, is- er, I think- in my experience, became, and this again, this engineering, system thinking really started to kick into into overdrive. It's about creating systems and processes. And I always joke: founders hear the phrase, "run fast and break stuff." And it ends up being sort of this call to arms for entrepreneurs, and founders of these, you know, VC backed startups just sort of, shoot, shoot, shoot, shoot, shoot, not really aim that much. And there's there is a benefit to that, no doubt about it. But what I have observed is that running in quicksand is not nearly as good as running on a nice track, a nice cushy track, you know, and that nice cushy track is some process. Take an hour or so just to figure out process, steps, tracking. What are your metrics for success? Didn't take long, just- you don't have to labor over it for three weeks before you do something. But like a little bit of planning, do you right even at an early stage startup, six salespeople, four salespeople- still a little bit of thought in that process. And so my point is going from- you know, as a manager, you don't think about that kind of stuff. But getting to director, when you're managing managers, now it's about: oof, okay, how does this thing work? You know, at scale? Let me stop. I could just keep going on and on and on. Let me stop.

Callan Harrington  29:40

No, I think it's great! So if I play that back real quick, the two kind of really big things that were there changes in difference in that transition was, one: now you're responsible for making these decisions that are going to impact all the people below you. So, if you've got three, four managers, they each got ten people, you've got fifty people, and you're the bad guy, period. And you have to accept that, and you have to make those decisions based on what's going to be best for the business. And you have to understand that you may not be the most liked person. And then the big point that I that I had heard you mention, was when you're in a director role, and you're managing managers- And not to say that leadership and all those things aren't important. But just as important are, we need to have a repeatable process in place that everybody can come into. We can scale the company in order to do this. And we have to know our metrics. We have to be making decisions based off of data. And in earlier stages, we can get away with more run fast, break things. But as we start to kind of grow and scale, you can't do that as much. Or if you're going to do it, you better have hard data to prove that that makes sense to do. Am I hearing you correctly on those?

Kevin Gaither  31:02

Yeah, that's, that's a hundred percent correct. And let me go back to your former point about being the bad guy, and being comfortable with being the bad guy, so now you're- or gal- you're the director, you're the VP, CRO, whatever. And you have to make these difficult decisions. Let's go back to the learning lesson. As a manager, if I'm concerned about being friends with the people that I work with, that's going to be a very, very difficult transition, because then it's like, oh, it's so personal. And it's Jane, and Bobby, and Pat. They are pissed at me, and that affects me more. Whereas if I recognize that this is a business, and we're making the best possible decisions as a business, and I'm not friends with these people, I'm professional, I'm acquaintances with these people, it's easier to have those conversations. And there is a point- I've gotten to this point a couple of times in my career, not not a lot, it's sort of break glass in case of emergency. If you can maintain that healthy distance, okay, we're professional, we're friendly, but we're not friends. And you get a set of sales reps that decide that they want to be riot leaders. And they're very difficult, either publicly or privately, and they're stirring stuff up. It's much easier to have the "get on the bus or get off the bus" conversation with them. We're not doing this any longer. This is just not happening. I've made a decision. I know you don't like it. It's now for you decide to commit and disagree. But I can't tolerate you continuing to stir it up. I've made a decision. And this is it. And if you don't like it, get on the bus or get off the bus. I've only had to do that a couple of times in my career. Like I said, Callan, that's not my leadership style. It's something that- I don't threaten that. Don't be that leader, don't be the leader that's constantly threatening that. If you are friends with the people that you're working with, you can't draw those lines. It's harder to draw those lines and say, "these are the decisions that we're making in the best interest." It could be wrong, I could be wrong, and I'll admit it if I'm wrong. And so, I'm "yes, and-ing" you. And I would also go so far as to say, Callan, that the leadership that I grew up with, when I- you know, in sales was this is it, this is what we're doing, get back on the phones. Okay. And I learned very quickly that most people need more transparency. And so that became a watchword for me in my leadership, as I ascended to the higher even higher levels, which was, you know, my sales team deserves to understand the why behind this and how they fit into it at a granular level, you know, we're raising quotas. Well, why are we raising quotas? And really take it seriously, not just because. Not just because, it's why? And why are we raising it by this threshold? Or why are we cutting territories? Or whatever, and being very thoughtful and intentional and putting PowerPoint decks together to explain that to the team, so they understand. That's, that's certainly a big learning lesson on my part too, because people aren't just going to just take it and just- anymore, for sure.

Callan Harrington  34:15

I think the point about being friends is interesting, and candidly, it's one that I would say that I've struggled- WelI struggled maybe a difficult word, but I've been friends with with a lot of them. And I will say a lot of the things that you're saying are accurate. Definitely when it came to having to let people go. Even having difficult conversations. Those were harder. Like I will be a hundred percent honest, and those were more difficult. So I think you bring a great viewpoint to it. And you know, I agree with a lot of those. I may not have always done that. But I agree with it, and you are right, it makes it a lot harder. One of the things I'd love to kind of jump into is when you got to the highest level, and when I say highest level, executive leadership team, owning the department. What was that change like for you? Where essentially, in that when I look at that it's more you tell us the amount of money that you need from this business in order to hit your numbers and set up your department accordingly. What was that, like when you first started making that transition?

Kevin Gaither  35:17

It was a natural transition, actually, because, and I'll tell you some of the funny things that became hard at real scale, but like, I was already inclined- Remember I told you my individual contributor story of how I had planned out for the year how much money I wanted to make and broke it out in a spreadsheet? You know, by the daily numbers, what I needed to do. Well, that exercise works very well at at scale, when leaders are planning for the business. And it's a matter of heads and productivity, and you know, what levers I can pull in terms of conversion rates or deal sizes, and, and things like that. And so, for me, given my predispositions already, it was already a natural transition. That said, at those highest levels, some of the non sales responsibilities were became a drag, for example, TCPA. Was it TCPA? That's not- GDPR. GDPR comes out, okay, the privacy thing that came out of Europe. I'm involved in these discussions where the head of legal, our General Counsel, is asking me, "so tell me, when your sales people go to a trade show, and someone hands them a business card, what do they do with that? Can you document that from soup to nuts?" I'm just like, oh for gosh sakes! This is like- C'mon, this is, you know- Or, you know, I'm flying into Tempe, Arizona, and I get a call from the head of HR, and she goes, "well, KG, one of your sales reps pissed on the building next door to us. What are you gonna do about it?" What? So, what? Like, are you kidding me?! Like, so that- you know, at the executive level, there's, there was a bunch of other things that I that I became. I have a smile on my face, because, you know, it's it was part and parcel, and the good things outweigh the, you know, the bad things for the most part. And...but there's just stuff that you get involved in: legal stuff, risk management stuff, you know, HR stuff. I mean, shit, excuse my language. I was deposed a couple of times. Actually, I've been deposed like four times in my career, like law, you know, sitting down with a lawyer and a stenographer, who's taken notes. And, you know, hey, there was this employee issue that occurred, I'm like, I don't even know the name of this employee, but I'm the top of the heap. And so they're gonna want to depose me. That kind of stuff, you know, it just goes with the territory, and it's not fun. But I'll tell you what, there is some fun things and going into a sales office that has 350 salespeople in it, you get off the elevator, and you hear the roar of the sales team, before you can actually see the sales team is sort of like, wow, look, what we've done. Look what we've built, you know. And so being at that level, where it's like, and these people report up into me, I've built this with help from friends like this is, this is so cool. And one of the toughest challenges that I was up for was walking down the aisles and greeting people. So I get off the plane, get off the elevator, come into the building, and I go up and down the aisles, 350 salespeople, and remembering a lot of their names and being able to greet them and give them a fist bump. I'm kind of a germaphobe, so you know, give them a fist bump and say, you know, hello. You know, good, good morning, Rabbani. And, you know, good morning, Stephanie. And going down the line. That was really challenging, and I was up for the challenge. And I can tell you that that wasn't just sort of like a tactical thing. It helped to provide a connection between the SVP of sales at Zip, for example, and people doing the job, you know. So there was a lot of things that were that were different. Being in board meetings. That's interesting. That's- preparing for  board meetings and having to stand in front of people that have given you a hundred million bucks. That's, that's an interesting, interesting transition, because you just you know, first time you're going to a board meeting, you don't know what, what's going to happen there. So, well, a lot of a lot of differences. Again, if leadership is calling for you, it's all good. You know, it's for the most part, it's all good, but it's not without some heartburn. At times I- we can have a whole episode on that type of stuff, that's for sure.

Callan Harrington  39:52

So true. And then last question, if you could give advice to your younger self- your age is up to you- what would that advice be? What would that conversation look like?

Kevin Gaither  40:05

I get asked that question quite a bit. So I'm fifty-two. And somebody once asked me, what would you tell your twenty-four year old self? And I find myself so conflicted, but this is the gut answer. This is what comes out. Don't work so hard. Don't work that hard. And I know that sounds so strange, and you know, all this kind of stuff. I believe in work ethic. Don't get me wrong. But KalinCallan, I missed a ton of dinners. Like, what, what was I doing at work? What's more important than my wife and my two kids? Like, what's more important than that? You know, and- You know, we talk about making sacrifices in your personal life in favor of work success, and I did all those things. And look, Callan, I don't have to take another job for the rest of my life, if I don't want to. But I look back on that and I go, right, but I wish I hadn't missed as many dinners, you know. There was material things I didn't miss. I wouldn't miss birthday parties and, you know, family events and things like that. But like, sitting around eating mac and cheese with my kids at 6:30 at night. What was I doing? What was so important at work that I couldn't have made it home? Like, why didn't I draw the line. And so I would tell anybody, don't work so hard, you know, don't work so hard. And I would also say, the other piece of advice that I would say is quickly when you know it's not working out, and I've done this twice in my life Callan, twice. And it's some of the best stuff I've ever- best decisions I've ever made in my entire life. I started a job in San Francisco in January of 2011. And I quit on March 15, two and a half months later. I quit. Originally, I was like, quitters never win, winners never quit. I'm gonna make this work. And I was literally putting in fifteen, sixteen, seventeen hours a day trying to make this thing work at this new company that I was going to prove myself, you know. And I said to my wife, I'm going to grit my way through it. I'm going to make it make it happen. It was awful. It was awful. I was miserable. And finally, I was just like, I can't take it anymore. I'm quitting. And my career just went- accelerated. It got better, because I stopped doing something that was frickin awful. And then literally, most recently, so I left Zip Recruiter, and I went to another company, and I was at that job for two and a half months. And I slammed my laptop closed one night, it was like nine o'clock at night. And I'm like, nope, this isn't right. You know, I got high blood pressure, I can't sleep at night, I'm waking up sweating, I got some chest pains. That's not good either. And I was like, nope, sayonara sucker. And I'm out of here. And I gave them- I was the chief sales officer. I was the chief sales officer and I gave them two days notice. On a Wednesday I gave them notice, and Friday was my last day. Why? Because by that time, I was like, this ain't working. No, two weeks, three weeks, four weeks is going to make it even better. And guess what? It's about, you know, it's about my health. It's about my life. So I'd say don't work so hard, and then quit earlier than you think. I know, it sounds sort of antithetical to winners never quit and quitters never win. But when you know it's not working, stop. Go do something else. And my career has jettisoned to whole new levels each time I've done that.

Callan Harrington  43:23

I think there's no better place to stop it than right there. There's so many good things in this, man. Thanks for coming on the show today.

Kevin Gaither  43:30

My pleasure. Thanks for having me.

Callan Harrington  43:36

I hope you enjoyed KG and I's conversation. Moving into a leadership role for me was one of the best decisions I made in my career. And if you want to learn more about KG, he's very active on LinkedIn. I highly recommend given him a follow. Also, if you like this episode, you could find me on LinkedIn to let me know. And if you really want to support the show, a review on Apple podcasts or Spotify is very much appreciated. Thanks for listening, and see everybody next week.