Sales Management Podcast

54. Leadership Battles: From Army Ranger to Tech Entrepreneur with Kyle Morris

February 09, 2024 Cory Bray Season 1 Episode 54
54. Leadership Battles: From Army Ranger to Tech Entrepreneur with Kyle Morris
Sales Management Podcast
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Sales Management Podcast
54. Leadership Battles: From Army Ranger to Tech Entrepreneur with Kyle Morris
Feb 09, 2024 Season 1 Episode 54
Cory Bray

Kyle is the co-founder of Kicksaw, one of the top revenue operations consulting firms in the tech world. In this episode, we dig into the lessons he learned as an Army Ranger and how these can be applied in the world of business. 

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Kyle is the co-founder of Kicksaw, one of the top revenue operations consulting firms in the tech world. In this episode, we dig into the lessons he learned as an Army Ranger and how these can be applied in the world of business. 

Speaker 1:

Welcome to the sales management podcast, your source for actionable sales management strategies and tactics. I'm your host, coach, crm co founder, corey Gray. No long intros, no long ads, let's go. Today I've got Kyle Morris with me. We're going to talk about a very interesting topic, which is about leading people in the civilian world versus what it was like for him to lead folks in the military. Kyle is a former Army Ranger and also the founder, co founder of kick saw, so he's had the experience in both areas. Let's dig into it, kyle. Good to see you. Yeah, thanks for having me. So when it jumps the, what's the first thing that comes to mind? Biggest difference between leading people in the civilian world versus what it was like leading them in the military?

Speaker 2:

So first off said I didn't lead anybody in the military. I was a follower, I was joined as an enlisted person, started working my way up. I left before I managed any team. So I got exposure to really incredible leadership, but I didn't lead people in the military. The different, biggest differences I noticed between military leadership and civilian is it's not life and death, right, it's like how do you really push people to achieve a goal when, if they miss quarter or they don't hit a target? It's not life and death, where in the military a mistake could literally be the end of a platoon or a person or a squad. So it's there's. That's like the biggest differences. It's it's driven into you very early on in the military and the Rangers that, like you, can't make mistakes. Here we need to be on point. In the civilian world it's it's a little bit different. You can't drive people quite so hard.

Speaker 1:

What are some of the things they do to help instill that culture? Because I think there's probably still some really good parallels. Even though you're not physically dying, being able to tease somebody up to take something very seriously, that's a good skill for for all people.

Speaker 2:

Yeah, well, I mean it starts with in the Rangers there's a thing called the Ranger Creed, which they drill into you from day one and it tells you. It talks about how you know you're superior, you're a better selected and well trained soldier, you move faster, fight harder than any other soldier, you never leave a fallen comrade behind. This is drilled into you from day one of trying to become a Ranger and that's the culture that you step into is everybody is the way I describe it is. Life in the Rangers is like the most intense fraternity you could possibly ever meet. You know you're the one that you go into. Everybody's an alpha, everybody is the most competitive person you've ever run into and you're just thrown into the mix as an 18 year old kid, so you kind of sink or swim.

Speaker 2:

You know half of the people that make it in the Rangers are eventually weeded out. They don't stick around. The other half kind of stick around, and so that I think that culture that comes out of that really is you have to be the absolute best at everything you do all the time, because you are being watched by people constantly, kind of like in a sales room, right, and I can remember my first cold calls I made. The CEO was sitting 10 feet away and that was kind of intense for me, but the kid coming out of college may not have had that kind of pressure around them. So I think that that experience there just is really helpful. It helps. Helps you become the best you can possibly be.

Speaker 1:

I mean I need backwards a little bit. How do you become a ranger? Is that substantially different path from people that go into the army through the typical and listed program? I mean, aside from Nicholas Cage and I don't know that most of us have real clear exposure to Rangers.

Speaker 2:

Yeah. So I'll give a high level overview of what Rangers are relative to other units in special operations. So Rangers fall under joint special operations command, just like Navy SEALs and Delta Force and some other units that you may not have heard of. To become an Army Ranger, you join the Army. I enlisted as an infantryman, so I knew I want to shoot a gun versus being a medic or a comm guy or something like that. So I was an infantryman with your basic training and then after that you go through jump schools. You learn how to jump that airplane. Then after that you go through selection for the Rangers. At the time it was called rip, now it's called rasp, but that doesn't matter. It's about a month long course where they just try to make use miserable as possible to make you quit. Most of the guys end up washing out. So then you show up in a Ranger battalion.

Speaker 1:

This was in 2000. What's most when you say most wash out? What's that?

Speaker 2:

Half, may be more. It depends on the class. If it's winter or summer totally changes. It's pretty dramatic. A lot of people don't make it, but there are standards. You have to be able to run a certain speed. You have to be able to do certain amount of push ups. You got to do pull ups. You got to rock march.

Speaker 1:

How fast, how many push ups? The people's want to know.

Speaker 2:

So I mean you need to be able to do 50. It's been 20 years since I thought about 57. Maybe 60 push ups in two minutes Strict you can't like flop or anything like that. You got to do 70 sit ups, 65 maybe Someone holding your feet. You got to do six strict pull ups. You got to wreck march, I think it's like a 12 miler in like three hours or something like that. And then you got to run a five miler in 40 minutes. So not crazy, but you got to be able to run in a two miler. You got to do in like under 1430 or something like that. So not insane. You're not like world class athlete, but like you got to be able to hang to be able to do those things. That's the bare minimum just to get in. Then you have to stick around.

Speaker 1:

Got it, so you can pass that first 30 day period. You weed out half, maybe more. And then what happens next?

Speaker 2:

You show up in Ranger Battalion. So I showed up and first day they're like we're deploying in 30 days to Afghanistan. I'm 18 years old, I just got out of basic training and basically have no experience. Like we're going to Afghanistan 30 days later. I did my first mission overseas. So you're going to Afghanistan on a three month tour. You're catching bad guys every single night for 90 days straight, 100 days straight. Then you come back and you train for six months, and in that window I went to Ranger school.

Speaker 2:

A lot of folks get confused about the difference between Rangers and Ranger school. So you're getting documentaries on Discovery Channel about Ranger school, where you basically don't eat or sleep for two months. You get one to two meals a day and no more than three or four hours of sleep, typically not consecutive, and you're rucking through the mountains of Delaniga, georgia, and the swamps of Florida for weeks on end, and so that's another kind of hitch on your caller that helps you move up within the Rangers. To be a leader in the Rangers you have to have attended Ranger school, though not everybody who goes to Ranger school is in the Rangers. They're kind of disassociated, but they have the same name. So it gets confusing, got it?

Speaker 1:

So you first 30 days you're out there in the field doing, doing hard things.

Speaker 2:

Yeah, I remember my very first mission was like I turned 19 two days before that and we're in the tiny village in the middle of nowhere in Afghanistan, two in the morning, booting down a door, and we walk in and there's like it's a madrasa school for boys. There's like 100 kids and a bunch of adults and I'm like I don't even know what to do here. I flex, cut the kids, of course not like you're flowing through and there could be guys with AK 47 is just waiting for you to walk in there. You have no clue what's about to happen. So you know, we're doing that night after night after night for three months and I did four deployments like that one to Afghanistan, then three to Iraq afterwards. Subsequent.

Speaker 1:

So when you make a mistake, what type of coaching do you get?

Speaker 2:

Typically it's swift, immediate, like there's a lot of swearing. I'm not necessarily gonna swear here, but it's like immediate and swift, like correct and move on, like we don't need to dwell on it. You just need to not make that mistake immediately. Then, once you go back to base, you get smoked for hours and hours, like, for example, on that very first mission. I can remember I was running in. I was carrying a rifle and a 203 grenade launcher and I'm running running. I was carrying a sledgehammer. The sledgehammer is in like a little pouch on my back. It happened to flop out and fall on the ground. That ends up being a major problem because I lost gear.

Speaker 2:

Part of the Ranger Creed is care of equipment. You don't lose or destroy or damage your equipment. I didn't take care of equipment for me, so you better believe I probably did a couple thousand push-ups over the next few hours after I got back for that To teach you don't fucking lose your equipment, take care of all of your stuff. Like this is critical in everything that we do. So that stuff gets drilled into you and that's one of many uncomfortable situations I had.

Speaker 1:

Well, I think that's an interesting example, because a sledgehammer doesn't sound like that big of a deal Totally. How do you extrapolate that to be in a big deal? What's the culture there?

Speaker 2:

Yeah, so a sledgehammer by itself is not a big deal. The fact that I didn't take care of my equipment means I could have lost a grenade, or what if I lost one of my 203 rounds or an explosive charge or something else critical? What if I lost my medical pouch? That would have been needed if I got shot and I needed a tourniquet. What if I would have lost that? Then a guy's got to use his on me. What if he gets shot? Then he may die. So it's like they use this little example to extrapolate to this is critical all the time for everything that you do, Because you don't think that that's that important, but it's absolutely. That mindset of being on all the time is the only way you can function at that level with those type of people.

Speaker 1:

So once that's instilled in you, you know, and everybody around you knows, that that's the way that you're going to operate.

Speaker 2:

And you pass that down to the new guys that come in. Right? You don't just like, let a new guy slide because he forgot something. You go correct him right away because there's tears in the range. Right? You're a private, then you become a team leader, then a squad leader, as a private or a senior private. You need to take care of the younger privates because that will reflect on you. You're always teaching someone below you and you're always learning from someone above you all the time. You're constantly passing that information along. You're not just hoarding that information. It's very much like we all learn together, because it's you need to know how to put a tourniquet on me, because I need that in case I get shot. I need to be passing that information all the time, and so that's very much part of culture. Is that constant ongoing training, right?

Speaker 1:

So you mentioned at the top that you weren't formerly a leader I mean you weren't a general or anything but you had people coming in behind you that you were exercising this kind of feedback on.

Speaker 2:

Yeah, absolutely In the same way that people did the same thing for me. So I can remember vividly, like on my first deployment we were practicing clearing rooms and I mean it's a new thing because you got to think there's a million things going through your head. You're going into a room in the middle of the night, under night vision, there's stuff everywhere, it smells weird. There could be guys in the corner like where do you go? How do you flow through these rooms as you're going from room to room to room.

Speaker 2:

And remember this one guy he was a senior private, he'd been there, he'd been through the invasion. He was teaching me, using his flashlight, a really simple way of how to visualize clearing rooms and just clicked with me, and so that was really helpful for me. And then I used it on other people and I came up with other ways to train things like that to other folks below me. So it's like you know, I had good leaders, whether they're formal or informal, constantly teaching me things, and so I just tried to do my best to pass that on, because that's kind of the culture that we had.

Speaker 1:

Yeah, that's great. This is one of the things we've been talking a lot about with remote work. When you're in the office, things rub off on you, oh sure.

Speaker 2:

Yeah, yeah, just the prosmosis. You hear people doing it, making a mistake. You hear them do something. Well, you copy that and you mimic it. I don't know how you do that over a remote environment, and you guys, you guys live together.

Speaker 1:

Yeah, we're together 24, seven, the entire time.

Speaker 2:

Absolutely as close as we can possibly be and drilling all the time, like we'd go out to the range in between missions. We'd be out at the range practicing and training. We'd be in our hooch first thing in the morning, I guess in the evening as we woke up training and drilling for the mission that we're going to do that night. So there was no. There's a mindset and a whole lifestyle. Right, work is like you come in, you work through a period of time, you go home, yeah, so that whole immersive thing where you're just always getting better, always giving feedback.

Speaker 1:

You are, you're basically religious around the rules, absolutely yeah. Contrast that with some detailed examples of the professional world here.

Speaker 2:

Yeah, so my first job out of school is I was an SDR working at a tech company in Mountain View, california, and there are a handful of SDRs. The team started to grow and they're like Kyle, can you manage this team? I mean I've not really managed people. So I said, sure, we started to grow, at its peak at about 75 people. But so I was managing 75 SDRs, but early on I was managing just a handful and I didn't know how to hire people. I didn't know how to train people, I didn't know how to like manage them appropriately. I just knew how to do the job well and kind of show them.

Speaker 2:

And remember this gal was on the team. She was fresh out of college and she showed up late, religiously late, to every single all hands meeting. We do all hands meeting on Mondays at you know, 8, 30 in the morning. She would walk in 10 minutes late. It was a tiny room with 15 people. She'd walk in late every single time and that reflected on me as a leader because I couldn't take care of this person.

Speaker 2:

I remember sitting down with her saying look, you just have to be here on time. Every seed can't miss the all hands. And she cried she's like you're holding me to too high of a standard, and it's like that's what I realized. She, what she cried, saying that this was too much for her to be able to handle. It was too much pressure, like it was unreasonable for me to ask this of her.

Speaker 2:

And I remember just thinking OK, the mindset I had in the military is not the same mindset I have here. I have to use different tactics for this person to show her that this is critical, because I can't use life and death, because it's not life and death, but it may be my job and hers, and so you know you have to use different tactics, and so part of it is a learning experience that who's going to succeed in this role. At first I didn't know. I was brand new to this. I have no idea if these folks are going to sink or swim. So there's, there's a lot of learning I had to do, not just her.

Speaker 1:

How do you?

Speaker 2:

motivate people? How do you, how do you coach a 22 year old who's been in college, you know, living a good life, that they got to show up on time?

Speaker 1:

It's hard, it's crazy, though, because class starts on time. I just wonder if I should have locked the door and if you weren't there. You just didn't get a class that day.

Speaker 2:

Yeah, I remember I had a really hard time my very first day of college. I was taking math 111. I showed up for the eight o'clock class cause I liked to wake up early and a kid walks in 15 minutes late and that really fucked me up. That was part of my transition from military to civilian was hard because I'd been held to such high of a standard with this group of people that was completely gone and you don't ever run into those people again. So I remember really struggling with just like other people, having a challenge with the things that felt obvious to me, but they didn't have the same kind of upbringing I did or the same experience I did.

Speaker 1:

Well, I'm sure you've seen people cry when really terrible things happened, but not over the fact that they were being asked to show up on time.

Speaker 2:

Yeah, yeah, yeah, I mean it's. It's totally reasonable to cry, there's nothing wrong with that, but being asked to just do your job and the standard is not worth it.

Speaker 1:

What's the? Has the idea that the US culture is pretty litigious crossed your mind at all? Cause I imagine you can. You can't do anything you want in the army, but you can do a lot of things in the US. If you do something that could be perceived as maybe not perfect, then people can be like, oh cool, I'm going to sue you.

Speaker 2:

Yeah, you know there's. There's this perspective I'll use military as an example that it used to be hard back in the day. Now it's easy. It doesn't matter if you're the guy in Vietnam. It was harder for the guys in World War two and guys in World War two is harder for the guys. It's like always getting easier, right, and so part of that's true. It's. It's evolving. You know, you go meet an army ranger. Today they're kind of treated like professional athletes. They get like they're really well treated, where in my generation they treated us like shit. They beat our bodies down to figure out who could sink or swim. Now they're recognizing this is an asset we need to take care of. So is it better or worse? I don't know. It's different as the, the forces evolved and as the wars have evolved, that's interesting.

Speaker 1:

So they're building people up. They're saying, look, you've got the capability to be great, let's work on you physically, mentally and all those other things Totally.

Speaker 2:

Me, the guy that was in the Rangers in like the 90s. Those dudes they were like all they did is rock, march and do pushups. That's not the most critical thing to do to go fight a war. It's really good for weeding people out and making a really hard culture for people to break into because there was no war going on. Once you have a war for 20 years you recognize wow, these are, these are really valuable people. We spent a lot of money to train. We don't want to lose them or damage them, so let's take care of them. It took 20 years of war to kind of figure that out. But you know it ebbs and floods based on where you're at in that cycle of war or not. So I'm sure if we go a long time in the war people will forget the standards. We'll start to raise and raise and raise and I'll make the culture may change a little bit as that happens.

Speaker 1:

But we'll see. You've got two candidates that apply for a job. They're exactly the same, except for one had 10 years of military experience, the other one didn't. Is there a hiring decision that's easy for you, or do you need to know more?

Speaker 2:

I would like to always try to support veterans as much as I can, being one of those people. It depends if they're an officer enlisted, I joke. There's this like kind of distinction between officer and listed. Like I came up as an enlisted person, I've met in technology and tech companies People that were enlisted and served in war five of them. I know three or four of them well, like they just aren't lots of us. So I want to give those people an opportunity to move up. If you're an officer who went to West Point like you basically went to an Ivy League school you're going to get a job somewhere great for the rest of your life. I'm not worried about that. If you're a kid who came from a small longing town and worked his way up and used military to pay for college and this is your shot at tech, I might give you a little bit of a shot because you've been working hard for a long time. I love it.

Speaker 1:

Yeah, tell us a little bit about the education that you receive through the military, both while you're there and anything that happens on an ongoing basis. Now that applies to the civilian world, because it's not all just shooting, right.

Speaker 2:

Correct it's. I mean, you're learning how to function with other people. Like you've got a squad that you're a part of. There's 10, 12 guys in there. You're learning how to operate with them and like you're just thrown into the mix with a bunch of these alpha dudes and trying to hang with them, and so you know, the education is pretty informal. They don't sit down, they say here's your syllabus and for the next two years you're going to learn this and this is how it's going to work. It's like we're going to the rage today and everything that you do from preparing your year to leave, to how you shoot, to how you police up all the brass that you shot, to everything you're being watched by your team leaders to understand your ranking among the other privates, to figure out if you're going to be moving up, who gets to go to ranger school next. There's only so many slots available, so you're kind of competing all the time.

Speaker 2:

You know, I remember a story of one guy that I was I was on a search and rescue team with. He was a private who he struggled a little bit. He would walk and he would kind of drag his feet and his team leader hated it because it made him look like he was sloppy, like he was lazy. So he made a walk like he was high-stepping everywhere for two or three days. Just the fuck with the guy. He uh. They went out to arrange one time and he forgot his helmet. He left it back at the base because he's in such a hurry and he ran out. And so he made the guy wear a helmet for a whole week in the shower and the shower hall. And now, like you know, you just do those types of things and and the training you get I don't know what you call that training it's pretty disciplinary and mentality. But he never left his helmet behind, he never drugged his feet ever again. It's like those lessons are hard to teach sometimes but there's effective ways to do it. But in a civilian world you can't apply that like draconian measures to train people in these ways. In the military you can kind of get away with it because again it's life and death. You volunteered to be here. You had to get selected to be here.

Speaker 2:

They're going to keep that bar pretty high and I think once you've been in an environment like that you're always kind of seeking. I wish I could find another team like that I can imagine Michael Jordan is looking for. He wants another Scotty Pippin around him all the time and it's just hard to find those type of people. And you know, when I use that example of that gal walking in Lata, that really I struggled with that to recognize that I'm looking for a team that's high performers and this person's not a high performer and I struggled to kind of be on those type of teams. But over time you have to learn to adapt. That's one of the things that they teach you a lot in Rangers is you have to be very adaptable. You're going to be comfortable, uncomfortable, hot and cold, hungry, thirsty, tired, whatever. You have to be able to handle that and adapt to it and be able to perform at the highest level despite all that.

Speaker 1:

Yeah, what did you learn from the chain of command that's applicable in the civilian world?

Speaker 2:

So the very first day I showed up in range of battalion, my squad leader was a student. He was salty, he'd been there for a long time. He ended up going dealt force like he was big guy, just like it really intimidating. And he sits me down with another guy I was brand new with and we're just like literally scared of this guy, like it felt like he might just reach over and punch us in the face at any moment. So it's like that's what it feels like when you're around this guy and he's like I'm gonna give you three lessons to live by. He's like first, you're a fucking commando, do it right. Like own this. Second is let me oh my god, I haven't thought about these lessons in so long always look cool. It's like you're commando. Always look cool, no matter what.

Speaker 2:

If a general walks in, you can't be all disheveled and scared. You got to be like lock it up. You're again. You're commando. You need to carry that presence. Number two always know where you're at. So if that general walks in, you salute him. You say yes, sir, no sir, all that type of stuff. Number three if you don't know where you're at, at least look cool, because that's like the worst thing is to look like again, disheveled and all over the place, and I think that that gets you pretty far. If you just kind of lock it up and act composed, that kind of you can fake the phone quite a bit.

Speaker 1:

I love it. That definitely works with executives. It works with customers.

Speaker 2:

Yeah, just pretending you know what you're doing, you'll be okay. They sense weakness. Yeah, absolutely.

Speaker 1:

Yeah, yeah. And so now your company works with folks on sales operations and I think there's a lot of parallels here, just from listening to some of your stories. You've got a world where discipline, rigor, focus I mean what you just described in terms of how people are taught to think about their equipment and their day and all of things like that. If folks did that when it comes to sales operations, you might not have a big business like you did.

Speaker 2:

Yeah, yeah, fair. The thing is that most people that are put in operations don't have that background. Most people are just shoved into it. Right, you were sales rep. You're kind of okay, you kind of like Salesforce a little bit. So now you're gonna charge a Salesforce. It's not like, hey, you've had this pipeline your whole life where you've been a disciplined, organized person and you've been thinking about systems, and now we're putting you on it. It's like you just get shoved into it.

Speaker 2:

Some people sink or swim and so, luckily, a lot of people, a lot of companies, don't really think about who the right person is to do this, so they need us to kind of help them really do that the right way. You know, when I first inherited Salesforce, I'd just been an SDR manager like, and they're like, you're running Salesforce for a 250 person organization I didn't know about validation rules, I didn't know about Apex. I didn't know any of those things. I had to learn them all on the fly, which is very similar to how being an Army Ranger is like everything's on the fly. You're just learning it as you go, and so you need to make good decisions. You need to communicate up and down right the people above you and below you. So what you're doing and why get by and from everybody. Those are the types of things you also do in radio battalion communicate to the guys you're right and left, what you're about to do and why. So a lot of ply, that discipline and rigor.

Speaker 2:

But I think what's also critical is that, as an Army Ranger, you're not just like there's a building here, you go in this door, you go in that door, you do this, this, this. You have to be able to make decisions, because sometimes you walk into a room and there's 50 kids and you're a really only person walking in. You have to be able to make decisions on the fly. As an operator, you have to do the same thing. Hey, my sales team is struggling with this. The management's asking for this thing, but they actually need this. You have to be able to fight for them and make those changes too. So you have to be dynamic on your feet as well.

Speaker 1:

Yeah, I see a lot of teams get paralyzed with Salesforce or with just integrations between their their tech stacks. I remember geez, when was it? This was probably three or four months ago one of my clients were trying to get some data for him to coach their team. Yeah, they were digging into coach CRM and they said, well, I need to coach on this topic, but I don't have good data to back it up. And he said I asked SalesOps for report on this two months ago. They won't give it to me because they're busy with other stuff, so I know enough to get around and so we just made it. Yeah, yeah, what's the deal and I know this is generalization, but what's the deal with agile and quick and dirty and good enough versus trying to perfect or prioritize and backlog and all these types of things? What are teams doing when it comes to being able to do things fast and good enough versus trying to make something perfect?

Speaker 2:

Yeah, you know my mentality on this is perfect as the enemy of good. I need to get my reps something so they can execute. I can't sit and spend months and months, and months, and months, and months so that I can finally get them a report. They've kind of missed their opportunity.

Speaker 2:

There's a challenge because with companies, depending on where they are in the lifecycle, you can act differently. If they're brand new, quick and dirty is fine, like let's just move on, we got to get stuff done. If they're an established organization with thousands of sales reps, you can't just go ripping out stuff and make changes and say we'll figure it out later. You've got to really be responsive to where your customer is in that lifecycle and then dance the dance so you're not stepping on their toe. I tend to do much better with brand new, smaller companies that want that dynamism. I don't do well with companies that need that rigor and discipline and 20 people on the call. Getting buy-in like that doesn't work well for my style of work, though many of our customers are like that and we have employees that are very much like that as well. So you need you need all types, but you have to be aware of where you're at and where you're not.

Speaker 1:

Well, the companies that want 20 people to get buy-in, do they ever get there? Or is the end product so diluted down it doesn't accomplish the set of the goal that was set out to accomplish.

Speaker 2:

To say they never get there wouldn't be fair To say that they got there too slowly and too painful. Absolutely, they're taking way too long to do stuff Like I don't. I would never if I, if Kicksaw grows to that size and I have any influence to be able to control that. I don't want 20 people making a decision. I want like two. Right, I want to minimize the number of people there, so I have, you know, two people to talk to if something goes wrong. I think that that's just their culture. You know as cold as companies get bigger. My perspective, having only worked in a 400 person organization, is that everyone's trying to minimize mistakes. They just don't want any heat coming on to them all the time. They don't. The wind isn't nearly as good as the downside is if they, if they screw up.

Speaker 1:

Yeah yeah, it's like playing credit card roulette with your friends.

Speaker 2:

Yeah, there you go.

Speaker 1:

If anybody doesn't know, what credit card roulette is? Five people dinner, everybody throws a card and they pick out one, then two, then three, then four and five pays for the whole thing. Yeah and five depending on the personality type, five either says well happens to me, ever know then, or five is more curious, or ruin their week.

Speaker 2:

Yeah, yeah, yeah. Same thing goes when you work in big companies. Everyone's just trying to deflect responsibility and blame if this goes wrong.

Speaker 1:

Well, it's funny because I was listening to Brian Chesky, the Airbnb CEO, on a podcast the other day and they've got over 6,000 employees. Yeah, he's aware and approves every product decision.

Speaker 2:

Which is good and bad. I mean, you know it's interesting, his companies get big. Is the right move to like, do you need this, like Farrow, who makes all the decisions for everyone, cause like ultimately it all goes up to him and he has an opinion about those things. But I mean, is Apple as good without Steve Jobs? Is what they were with Steve Jobs? Like I'm clear, like I don't know what the right answer is he was that Farrow right.

Speaker 2:

He was absolutely that person, all going through him, everything went through him, and so I think it's generally good, for it's hard. Having worked in the military where there's thousands of leaders or millions of people in this organization and everyone wants to deflect blame and massive bureaucracy I don't like that. I don't want to work in a company that's that way. I'd rather have you know one figure had to work towards, and this is the vision that Brian Chesky, as the example, is. I think people can do better. You can do more impactful things when you are driven by one person versus avoiding responsibility.

Speaker 1:

So when you run into the room in Afghanistan, there's one person in charge. Is that fair or are you kind of there's a ground force commander.

Speaker 2:

Yeah, there's one person in charge technically, but he's not like hey, kyle, go get that room, hey, steve, go get that room. No, no, no, it's like you're making decisions on your own.

Speaker 1:

So everybody's making decisions. You're running in there, you see a door. You and the guys next to you make the decision around who's going, whatever when.

Speaker 2:

Yeah, I don't go like hey, let me call my team leader and figure out if this is the door we should go into, cause there's a guy right behind it, somebody made the decision to take the house or whatever it was, got it and then, in terms of the day to day not day to day like second to second you got.

Speaker 1:

Those are executed.

Speaker 2:

You're executing. Based on your prior training, you've cleared houses thousands and thousands of times. You generally know the guy who's closest to the door will be the first guy, second guy to go. You go in, go left or right, based on whatever you want. You respond like you've learned to read their body language to understand what they're going to do, versus them literally saying over the radio hey, let's go into the next room, because there's the way we think about it. When you're standing at a door with a breach about to go off, is there's a guy inside somewhere that's got an AK-47 or a suicide vest and I need to get to him and lock him down before he gets that. Yeah, so you can't, you can't wait, you can't slow, it's all. You go as fast as you possibly can, as safely as you can. Those two things are kind of intention sometimes, but you don't have time to sit and ask. You've got to rely on your instinct to be able to do those Well.

Speaker 1:

I think this works really well when you've got the fundamentals in place, and this is where fundamentals are critical. Where we see a breakdown all the time with coaching is that you've got a salesperson that doesn't have fundamentals, and so the manager feels like they've got to be sitting. They're holding their hand, and that's like having the commander saying okay, well, Kyle, you're going to go through this door.

Speaker 1:

Oh hey wait a second, timmy. I can't tell you what to do next, because I'm working with Kyle over here because he doesn't know how to clear a room. Yes, and so imagine one person having to independently direct each person on a team. It's a disaster, and that's what happens when you end up in these super closer cultures where the manager wants to jump on the call and talk a lot and all of these types of things, as opposed to actually developing their people, and I imagine the same thing in sales operations.

Speaker 2:

Absolutely, those fundamentals are critical. If you don't understand how data models work, if you don't understand how just APIs work, you can't build a functioning CRM generally, right, you need those basics, like you need to think about how validation rules work and how people even use CRMs before you start. You know one of the things companies would always tell us they just bought Salesforce, their brand new company, just got funding. They got like 10 employees and they're like we want to implement CPQ and it's like that's sprinting. It's got to be crawl, walk, run, not crawl to sprint. And so many companies try to get ahead of themselves because they don't know. You know, that's again why we're in business, because there's not lots of people with experience doing this type of stuff. But you can't run until you can walk, can't walk until you can crawl. So focus on crawling first and get that done so that you can start to walk.

Speaker 1:

That's very much how I try to. So if you've got that person who is the employee that folks like they're okay at sales but not going to be a sales person longterm and, hey, I'm going to be in sales operations, what resources are out there for this person that you think are good?

Speaker 2:

Okay. So one thing that's important is you have to think about how people learn. I learn by doing. I can't learn by watching a course and ingest it. I have to go. You know validation rules and Salesforce. I'll keep picking on those. I need to write that formula 500 times before it clicks for me. I'm not going to watch the thing you be like got it, I'm good to go now. Like I need to practice, I need to bump up into stuff. I think what's important is understanding how the people that are doing this learn. Some people can learn by reading, or learn by watching or their experiential in the way I am. I think you have to be responsive to how they actually learn that stuff and you can get it at Salesforce developer account.

Speaker 1:

Anybody can get one right and actually go and do things Absolutely absolutely Absolutely.

Speaker 2:

You can do that, and what was helpful for me is I had pressure. I had tasks I had to accomplish. I had a sales rep screaming at me. Before we had Slack, we had GoogleJet. They're like I can't close this opportunity. It's the 31st of the month. I need this for my quota, it's four o'clock in the afternoon and this validation rules coming me up. That pressure forced me to learn how to do these things really quickly.

Speaker 2:

Doing it on your own, I think, is you can come up with those scenarios, but I think a lot about some sort of an academy where it actually takes practical exercises and you learn how to do those Cause. I think Salesforce's certifications are great. They get you to some they're foundational, fundamentals but they don't really teach you how things actually work on the ground. Right, when you're in a seat and a rep is screaming at you and a VP sales is breathing down your neck, you need to fix something. How do you do that? You can't go look at their trailheads to teach you how to do that stuff. You need to have had that real experience and I think that's lacking in the ecosystem right now. You guys should build that. Think about it a lot. It's easier said than done, right it's it.

Speaker 1:

Well, I know I've written eight books and build a lot of courses. I feel you man it is. It is a function of hours and hours and tens of hours and hundreds of hours.

Speaker 2:

So it kicks out what we've kind of done. We started to kind of operationalize some of the things we do. We call them SOP. We call them SOPs for standard operating procedures early on. Now we call them off the shelf solutions, which a common example of companies always ask for is I need to understand opportunity velocity. We have opportunities moving through the pipeline. Where are we getting stuck? And his and Salesforce is reporting won't give you that. You have to build some custom things to do that. We built it 50 times at least. We go to customers are like I'm stuck. Well, we've done this so many times so it's actually pretty easy for us to build.

Speaker 2:

So we've got all these off the shelf solutions we think about because we're doing, you know, 70, 80 implementations of Salesforce at any given moment. We're learning so much information about how CRM work. We need to codify that and say this is how you should do X and Y and Z. But there's so many different problems to solve and where do you start? Cause we work in a bunch of different verticals and industries and customer sizes. So you got to really think about what's crawl, walk, run, look like there. So we're starting with crawling, just defining our own off the shelf solutions over time. We train on it. Sprinting would be sharing that externally, so we're thinking about it.

Speaker 1:

I love it. I love it. Well, you brought up a really good point. I was talking to some sales enablement folks this week and the comment that I made was that you've got folks coming into a business who might have done something once, twice, three times, five times in their career. Maybe they've done it zero times, but they've likely worked in companies that have a similar industry or similar size or similar. You know one product versus multi product, whatever it is. But an organization like yours and a company like mine, we've done it hundreds of times or thousands of times from all different types of companies, and so you're not taking this oh, I've done it twice, I'm going to do it again here. You're doing this. I've done it 500 times, so I'm going to do a variation of it that I'm prescribing, based on exactly what I know about your business. So I think that's why it's really interesting to talk to folks like you about hey, it's not just your three prior experiences, it's our hundreds of prior experiences.

Speaker 2:

Yeah, it's hard to replicate that. Go to the best internal sales operations person you can possibly find. They may be done this at four different CRMs and done it even well at four CRMs. We've done it across hundreds and so that is a. It's a couple of things I think about. From a company side. It's like it makes sense why they hire consultants to come help make sure that their reps are doing it right. As a person who's an internal operations person, they want access to that knowledge so they can speed up as well and so that there's a lot of potential for ongoing training there. But it's a big, I think, competitive advantage.

Speaker 2:

When we're going to sales cycles, the last thing we want to do is kind of throw their rep under the bus, their operations person under the bus. But it's a reality is that your sale, your ops person just says only done this once. They're not going to think of they can solve the problem right now, but they may paint your new corner. They may not be thinking over the long term because they haven't seen the whole cycle of where this ended up going and they may not have seen how your company matures from just two reps for CO selling into now reps to verticals, into blah, blah, blah. They just haven't seen that happen, so they can't forecast what's going to happen there. They just may make some mistakes and that really do paint you into corner and you can't make the changes later.

Speaker 1:

So we see that a bunch Right, a lot of custom codes, because they just learned how to write custom code.

Speaker 2:

Absolutely. It happens all the time when, yeah, they get a little excited because they're starting to learn how to code. They call themselves a developer. I did the same thing and then, all of a sudden, when you're hammered, everything looks like a nail and then you've got all the safe hacks you can on the wind.

Speaker 1:

Yeah, yeah, interesting. So, as somebody that's in sales ops, how do you recommend hiring an external firm while maintaining your own worth importance? I don't know how to phrase it. It's not coming to me right now.

Speaker 2:

You know what I'm talking about.

Speaker 2:

So when we talk to companies, the thing that the capitalists they should do in their head is really think about what they're looking to solve for. And when I first started Kicks Out Kenny, I was ultimately looking for a solution and I needed when I was an operations person so that really informed how we do things. And most companies oftentimes they just have pain right, salesforce sucks. My reps hate it. They couldn't build out a roadmap for the next 12 months to say these are the changes we need to actually make our reps happy. They just know they're struggling.

Speaker 2:

Most consulting firms out there will come in and say I want a clear SOW. It's six months long, we're gonna bill you this, we'll do X, y and Z. But the reality of every business is so dynamic as you start going, as the market evolves, as COVID happens and things change, you need a system that can be responsive, and most consulting firms are very much. I have resources that I can deploy. I'm gonna collect money on them, but I wanna minimize the amount of time they're doing anything so I can put them on more projects to basically make more money.

Speaker 2:

We've tried to think about this in another way, which is like how can we commit people to folks and have them really understand and guide you through. So, rather than doing these fixed bid projects, we're like we'll just keep it open-ended, we treat it month-to-month cancel anytime if you're not happy with us, and that what that does is it gives customers kind of comfort that if they're not happy they can step away, but also that as you build and you recognize that's the wrong way to go, they can make the change. Versus most consulting firms go okay, time for a change order. That's gonna take another three months and we'll re-scope this out. So that kind of flexibility I think companies really want, and most consulting firms are older companies that have been around for a long time. They do it a certain way and we're trying to do it pretty different because both Kenny and I neither of us have worked in consulting firms prior to this we're just making up how we wanna do it and we really apply our kind of SaaS mentality, having come from B2B SaaS companies, through this.

Speaker 1:

I think you can fire us whenever you wanna fire us. It's a great way to come out, yeah absolutely.

Speaker 2:

If you don't like us, you shouldn't be paying us money. I don't want to stick around. I don't want my reps to be on call with you just so unhappy all the time. Just let us go, we'll find another customer. There's plenty of wood to chop in the ecosystem right now.

Speaker 1:

Yeah, that's true, there is so much out there.

Speaker 2:

Yeah, so many companies are struggling with this stuff.

Speaker 1:

What are your thoughts on these API solutions that are coming out? It seems like there's more and more companies that are being built to connect databases together, and what's the impact gonna be on people's CRM ecosystems and just beyond that and broader?

Speaker 2:

just sales tech perspective. Are you talking like through, like a Zapier tray, things like that that just connect systems?

Speaker 1:

Yeah, and then there's a bunch more merge API. Yeah, it was on, and on and on.

Speaker 2:

There's certainly no shortage of need for those types of integrations. The where the challenge is that if you ask a developer to work in the Salesforce ecosystem, they do not wanna work on it. The APIs kind of suck. It's not that sexy relative to building some new front end database or front end web component or something like that. So there's always gonna be need for those things.

Speaker 2:

I think the challenge is that they give people too much power to make some bad decisions. You take a sales rep who doesn't understand how databases work. I can hook up this to this, like Trey makes it really easy to do. Then all of a sudden, data is flowing, seems cool, everything's right. But are you building it the right way? Where, if you have an architect that comes in and can say, actually you don't wanna do this, you're building it in a way that doesn't scale, it will allow you to make those bad decisions where a person who's gotta spin up a terminal and write in Python may recognize that this isn't something you wanna do and they may push back on it. So it's good and bad. It's good that it really decreases costs. You don't need so many devs to build integrations and maintain them. I do worry about the just the long-term impact and satisfaction people have with those. They work great if they're very straightforward, but as soon as you need something really custom or dynamic, they can start to struggle a little bit.

Speaker 1:

So it really is duct tape and WD-40?

Speaker 2:

I wouldn't call it that. Some of the things that are out of the box, like HubSpot to Salesforce straightforward, you click them, they're hooked up, everything's fine. I think those are great. It's when I need something custom in HubSpot, to come from Salesforce in a way that no one predicted. That's where it's like, that's where you get a little bit of need and effort, and this goes back to fundamentals Absolutely, absolutely right.

Speaker 1:

So what are the fundamentals of getting the databases to work together? And, like you said, you bring something else into the mix. Is that gonna break everything that you've built and do you want?

Speaker 2:

Absolutely, and as a brand new operations person, when I'd just been a BDR manager five minutes before, I didn't have a clue how to do this. But I knew they told me that this could work and if I just click these buttons and hook it up and map this, it'll be just fine. Until all of a sudden it isn't and I had no clue as to why. I had no idea how to fix it and I'm kind of stuck. So I think a lot of operations people are unfortunately given these really big responsibilities because everyone in the organization is kind of dependent on Salesforce working well, Like it's a hub for so many companies. And if you have a person who's just like winging a duct tape and bubble gum, WD-40, what is the drag on your organization? If it slows everybody down by 1%? That's 1% loss in your company. What if they could speed you up by 10%? Right, those things can be really advantageous for folks.

Speaker 1:

Yeah, all right. Last topic I wanna dig into and then we're gonna cut it out. When it comes to the ownership you say they want you to, who is they and how do you make sure that the person that's driving this from the executive level actually understands what's going on? Because they're probably not technical, they might not be an operations person. Who is that executive, and how do you make sure that they're aligned with what the business needs today and tomorrow?

Speaker 2:

Yeah, it's tough cause. I think Operations should be independent, right, you have to be able to take requests and prioritize and make good decisions and I think that kind of needs to report into the CEO, because ultimately that's who cares about the company the most. That said, if you're a VP of sales or CRO, you've got a stake in Salesforce working well. I think it's all about partnership. You've got to get buying with folks. You have to communicate early and often as to what's my pipeline. What am I building first? What are we prioritizing? Because the VP sales will show up and say I want 20 things done. It's like, okay, we have good faster chief, you can only pick two of those?

Speaker 1:

Well, the CFO. The CFO probably wants 20 things done too. Right, Absolutely.

Speaker 2:

And so a lot of what operations becomes, unfortunately, as you get bigger, is just deconflicting. Cfo is asking for CPQ, vp of sales is asking for reports and dashboards. Like which one do? I do Like they almost have to fight it out to make the decision for you, because Opsons up being the bad guy all the time. It's like this isn't done, everybody's disappointed that their thing hasn't been built yet. So it ends up being kind of it's a really hard job. What I found is a consulting firm. It's the opposite. You're the cavalry coming over the hill to save the day. They brought us in to fix these problems and you can naturally kind of force them to prioritize where, if you've been internal for a long time, you can kind of let that get away from you when the tail's wagging the dog a little bit. So I really like being on the outside relative to being inside. It's a hard job being an internal operations person Because everybody's competing for your time and you've only got so many resources to be able to accomplish these tasks.

Speaker 2:

They tend to take outside people more seriously too 100%, despite the fact this internal person has all the experience understanding your system inside out. They built it. That's what was really frustrating for me. So I've been. I was an internal operations person. We were 250. People grew to 400 or so. I went on paternity leave when my first daughter was born. I came back and they'd hired a firm to make all these. They bought CPQ. They tried to do all these things while I was gone for three months and it was just like I'm cheese. Yeah, it was hard, it's a tough job. So I definitely empathize with the operations people.

Speaker 1:

Did they not tell you while you were gone? It was just, hey, surprise, welcome back.

Speaker 2:

No, VP sales just decided they wanted to buy that stuff. Two years later they had not finished implementing CPQ after I left. So that's kind of how it goes, oh gosh yeah.

Speaker 1:

CPQ, I hear, is one of the funnest things that you can do.

Speaker 2:

It's challenging. It's their hernia surgery.

Speaker 1:

Yeah it's their hernia surgery. The operations yeah, it's a blast. I remember I had hernia surgery one time and the doctor told me he goes. Oh yeah, this is very straightforward procedure. I do it all the time and then I come back afterwards and I was very frustrated. Oh yeah, this is one of the worst things you'll ever go through in your life.

Speaker 1:

I said you told me it was just very straightforward and you do all the things I said. Yeah, that's true. I just didn't tell you the other part because I didn't want you to back out of it. Yeah, dang, oh man, it's scary though you read the stuff and you don't do it, it's bad for you. So anybody that has hernia, go get it taken care of, because we're Google the things that are gonna happen to you if you don't. Very serious, but recovery is gonna be bad PSA. Yeah well, the worst part is that I'm not gonna get graphic, but let me just tell you this the first time I tried to dunk a basketball after my hernia surgery, I fell on the ground and cried All right, yeah. So Watch out, take the rehab instruction seriously and don't tough guy it.

Speaker 2:

Yeah, right on, that's good medical advice generally.

Speaker 1:

Absolutely. Move around more, eat less and take the recovery advice from the doctor. All right, Kyle. Thanks so much, man. How do people get in touch with you? And kicks off.

Speaker 2:

LinkedIn is probably the easiest I'm on there or kylekickscom I get a bunch of emails, so I archive a bunch, but don't send me any spam.

Speaker 1:

Oh yeah, you're. How much I gotta ask you this your LinkedIn profile says don't spam me. How much spam do you get?

Speaker 2:

I rarely get okay. The reason for that is I get so many people that are not so many. I get one a day. Person's like hey, I wanna connect with you, I'm like cool. And then immediately it's like sales pitch. Sales pitch, like okay, you're basically spamming me, like that's what that is. I'm happy to connect with people and share whatever I can, but that's what it becomes. It's just that they wanna try to sell me some shit. So I don't get probably four sales emails a day and one new email spam a day, or LinkedIn spam. So it's not terrible. Keep showing your toes. Keeps me on my toes, for sure. Better than people shooting at you. Yeah, any day.

Speaker 1:

All right. Well, kyle, thank you so much for joining us. Thank you for your service and we appreciate having you on Reach out to Kixaw. I've personally worked with these guys. They're great. I'll tell you that, and if you know from listening to my show, I don't endorse people very often, so that's a special shout out for kind of like Kenny over at Kixaw. This is the sales management podcast. If you wanna check out free version of Coach CRM, go to coachcrmcom. I'm Corey Bray, subscribe to us on Apple and Spotify and we'll see you next time. Stay healthy.

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