Sales Hustle is now Sales Transformation
May 24, 2021

Episode #101 Leading Sales Teams with Kyle Petersen

Kyle Petersen joins Collin Mitchell in this episode of the Sales Hustle Podcast. Let’s hear from Kyle as he takes us back to his story on how he got into sales and how he absolutely love it from the moment he started. More importantly, Collin and Kyle talk about Sales and Sales Leadership in this episode.

Kyle Petersen is the VP, Head of Health Insurance Sales at Gusto. Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 100,000 businesses nationwide.

Kyle is also a member of the Revenue Collective - a private, invitation-only community of sales and marketing executives at growth-focused companies. Founded by industry veteran Sam Jacobs, Revenue Collective brings together leading operators at dynamic companies around the world to form direct and honest relationships.

Find out more and connect with Kyle Petersen on LinkedIn at

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Episode 101 - Kyle Petersen

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales change makers across various industries. The only place where you can get what you're looking for too. Uh, your sales game today's episode is brought to you by sales cast sales cast helps sales professionals transformed the relationship building process and win their dream clients.

[00:00:30] I'm your host, Colin Mitchell. All right. What is happening? Sales hustlers. Welcome to another episode. Uh, today I'm excited. I'm going to be talking with Kyle Peterson. He's the head of mid-market payroll and health insurance sales at Gusto. He's a husband, father veteran and sales leader who is passionate about people and process in that.

[00:00:53] Order my personal, his personal mission is to learn, teach and seek, to inspire others, to be more than they thought they could be. Kyle, welcome to sales. So how are you doing? I'm good calling. How are you doing? Yeah, I almost messed up the bio there. You kind of, I was going to talk in the, uh, in the first person as if it was me.

[00:01:13] I'm excited. I'm excited to chat through all things. Sales and sales leadership. Yeah. Yeah, this is going to be a fun one. Uh, I know for sure, we kind of started brainstorming on sub topics and we hit one on the head that I know that there's going to be a ton of value in and we can go pretty deep on and you're passionate about, but before we get into, uh, the topic we planned out today, just give the sales hustlers, the short version of your sales story.

[00:01:42] Okay. Sales stories. So, Colin, do you want to hear something crazy? I did tell you. I did not plan on getting into sales crazy. Right. Everyone that we ask the question to be like, Hey, how'd you get into sales? It's always, it's always like, oh, I never planned to get in there. I'm in the same boat. Just like everyone else.

[00:02:00] I fell into it. Absolutely love it. I'm surprised. I've never heard that one before. It's more than that. I, I know you want to just a tiny bit more than that. Um, so my story, I was, I was in the Navy for a while. As you spoke about earlier, calling got out, wanting to get into finance. There's a whole reason behind that long story short is I really think there's a missing link.

[00:02:27] In our society about financial literacy, it leads to a whole host of problems that impact people in society. I wanted to go tackle that problem. Absolutely loved it. But before I spent the rest of my life doing it, I had this itch like, man, is there something else out there I might like. So I scratched it and it happened to be in B2B sales, jumped off, uh, off a limb, so to speak, went out on a limb and I fell in love with it.

[00:02:51] And I like it because there is a direct correlation to what you put in and what you get out of it. And if you're someone who's willing to bet on yourself, then sales is the right place for you. Boom. I love that. You said that if you're willing to bet on yourself, uh, because so many people are not willing to bet on themselves, you know, um, I'm one of those crazy people that like the commission only sales jobs, like, you know, that's how much I'm willing to bet on myself.

[00:03:16] And it takes a level of confidence in your craft to be able to do that. Now I'm not saying go out and get a commission only sales job. And that's the only way that you're going to prove that you can bet on yourself. Uh, there's definitely other. Um, safer ways to do that. Um, but yeah. Yeah. So, so tell me, um, all right.

[00:03:36] So what we decided we want to talk about today is, you know, you're a sales leader and you said something really interesting is like, you know, when you're meeting with your team, one of your meetings out of the month is. Fully dedicated to talking through personal development stuff. So tell me a little bit more about that.

[00:03:56] Yeah. Yeah. I mean, so as, as a sales leader, right, we all hear the best practice, which I, 100% agree with that you should be meeting with your team on a weekly basis. And generally speaking, there's a pretty solid framework for what a good one-on-one looks like. And it's always focused around pipeline and call coaching and deal strategy unblocking, so to speak.

[00:04:17] But what I think I've learned over the the years is if you truly want to have an incredible team and incredible culture, it's not just about performance from a day to day. How much did you sell? You want to have a team of people who are invested in growing. You want to see them get promoted to different levels in the organism.

[00:04:36] And so we have a cadence where the third week of each month we take that one-on-one and we repurpose it specifically to the professional development plan so that we can make sure that we're focusing on a monthly basis on all the things that that is driving. That person's why. So that's, that's something that I'm pretty passionate about and something that I think, and I hope most sales leaders are passionate about as well.

[00:05:01] Mm. Uh, I don't know if all of them are sneaking suspicion, but if they're not, they should be. And, and so, and so I love that because, you know, I just know from my own personal experience, I didn't get better in sales because. You know, I got better at some of those like sales skills. It was really, you know, more of the soft skills, right?

[00:05:28] Like when I started investing more in myself personally, and, you know, meditating and eating healthy and taking care of my body and all of these other things that I started doing, then I got better. So when I invest in myself personally, then I was able to see more success professionally. And I think a lot of people don't understand, you know, that there's a link there and it needs to be integrated.

[00:05:51] Yeah. Well, and in addition to that, cause I agree with everything you said is a sales, as hard as hell. Like anyone who's been in sales for more than a month knows this is an incredibly difficult profession. There are highs, there are lows. It's high stress. If you, if you have a role like calling over here a hundred percent commission, it's even more stressful.

[00:06:10] Right. Um, but what I've, what I found at least to resonate with most sales professionals is if you. No, you're working towards something bigger and better in the future. Like that keeps you motivated. So when you have that day of just no, no, no, no, no, no, no. And then another, no, you can still go back and like, all right, what am I working towards?

[00:06:30] I'm staying incredibly focused on that trajectory. And that serves as like the one kind of constant. And what is the rollercoaster life of sales? Yeah. Yeah. I mean, yeah. When you're getting your ass handed to you and you're getting a bunch of no's and rejection and. Losing deals is everybody does. Even if you're at the top of your game, you still get more nos than yeses.

[00:06:55] I don't care who you are. Uh, and, and if you're not, then you're not, you're not getting enough at bats. So, uh, you know, w when that is part of what you do, You got to be in a good mental state, you gotta be in a good mindset. You gotta have a, a level of confidence to not let that, you know, derail you from whatever.

[00:07:14] Like you mentioned your, your, why is your reason for doing whatever you do? So what's your why? Like what drives you? Yeah, I mean, it's, so my personal mission statement is something that you talked about and that's actually one of the key categories I would say is in any professional development plan, but.

[00:07:32] My mission statement, we'll start with that first. And then I'll break it down is learn, teach, and then seek inspire others to be more than they thought they could be. And if we dissect that a little bit learn as is the first thing for me, it's, it's going back to this concept of like a growth mindset.

[00:07:49] Right. I find myself getting bored incredibly quickly. I want to be challenged. I want to be learning something new and there's a sense of humility that I think comes with that, right? Like if you're. If they're always talking, then you're not learning anything. Same thing with, you're always in your comfort zone and you haven't gone outside.

[00:08:07] You haven't pushed to those boundaries, then you're really not. You're doing yourself a disservice, I guess, is the best way to put it because there's so much out there to learn. You have to figure out what it is that is exciting to what intrigues you or peaks your interest. And then I like to dive into that.

[00:08:22] So I want to learn first and foremost. But then, you know, anyone I think in, in the leadership role, and even if you're not in leadership, there's this like human nature to want to teach, to want to help and lift other people up. So when I'm learning some of that self study, some of it's from mentors, people who are sharing their knowledge with me, I want to return that favor.

[00:08:42] So anything that I've learned, either the easy way or the hard way, let me go and share that with somebody else, someone who's seeking that information. And then lastly, just inspiring people to be more than they thought they could be. Everybody has imposter syndrome. Everybody has that doubt in the back of their head, whether it's a professional goal, maybe it's a physical goal, like running a marathon.

[00:09:04] There's always that whisper in the back of her head telling you it's not worth the risk or you can't do it. And it's helpful to have someone push you through that, to inspire you, pass that. And so those are kind of the three main like tenants, so to speak of what is my, why. Mm. Mm. I love that. And so I'm curious, because it seems like you've given it a lot of thought, right.

[00:09:28] And for people that are, you know, you coach and that are on your team, that maybe haven't really figured that out. Do you coach them through that? Do you help them like figure out what their, what you called their personal mission statement is I do so. When we, what I love to do is yeah. Dive into like, what are the six key elements of a professional development plan?

[00:09:50] I always encourage people to start at the absolute top. Um, and then you work your way down. And for me, even above a personal mission statement or your core values, so. I took an entire day on a weekend to just think through that, you can Google this, right? Just Google a list of values, come up with hundreds and thousands of all of these different values and start to soar through them and think about which ones resonate with you and pick three or five, right?

[00:10:17] These are going to be non-negotiable guides to how you show up every day. Yeah. And that's where I started. Where am I? What are my core values? And then from there, you can start to formulate your personal mission statement. And that should be clear. It should be concise. And it'll be your north star when you inevitably come across a fork in the road and you need to decide which way to go.

[00:10:37] That's when I turned to that personal mission statement to make that choice. Boom. All right. I like that. And so sales hustlers, if you haven't done that, maybe now's the time to hit pause, go Google that and write your personal mission statement. Um, and so I'm curious when, when you get new people on your team, like, is this something you, you, you dive into right away, like when is a time where you start to really, you know, make this professional development, you know, part of.

[00:11:07] You know, working with them and developing these reps rather than just the more traditional, you know, call coaching, deal structure, you know, dashboard, you know, uh, pipeline monitoring, all that sort of stuff that is necessary. Um, but you know, this piece that you're talking about here, there's a lot of leaders that aren't doing that I wouldn't even call them leaders.

[00:11:27] I like to call them managers and my good friend, Andy Paul likes to call them sales bosses, but.

[00:11:36] Um, but I'm curious, like when do you address this with a new member of your team? Um, you know, for the sales leaders that are listening, if this is maybe not something that they're doing with like, give them some tips of, of, of how to build this out and how to address this with their team. Yeah, I do at 90 days in the first 90 days, this is all about getting someone up to speed.

[00:11:57] And that typically involves learning about the company and the company culture involves learning about the customer, learning about the product, understanding the sales playbook. Like there is a lot to digest in 90 days is already a tall. So the approach I've always taken is just setting clear.

[00:12:16] Expectations of what this is going to look like your first 90 days, or we're going to be giving you the tools and the support to just be as self-sufficient as possible. We don't expect you to be fully ramped. Like let's give you what you need to be successful. But I do set the expectation that 90 days in, I want to start to build out a professional development plan.

[00:12:36] Not because 90 days in we're already talking about your next promotion, but because if you're doing this right. Then we will be working towards this methodically over the next several quarters or years. And when that opportunity presents itself, you'll be ready. And what I found is that most people are inspired by that, right?

[00:12:54] It's, it's a change of pace. First and foremost, there's going to be plenty of conversations about sales and all the things that you know, most sales podcast talk about. But to know that 90 days in you've already got a leader, who's saying I want to get focused on your, why. I want to build a path and a plan for you and help you get there.

[00:13:15] Like, that's just that little extra, like just reassurance that you're in the right place. And you've got a leader who genuinely gives a shit about what you're doing with your career. Yeah. Yeah. No, I think that, that's definitely a way to show that you actually care about the people on your team and not just the numbers on the dashboard.

[00:13:34] Right. And so, yeah. Uh, I'm, I'm curious, uh, you know, how often do you check in, right, because, I mean, I know you said it's one of your meetings per month is, is dedicated to this stuff. And sometimes the, what they want to do changes. Right. And a lot of people don't check in and they're working off old information to try to motivate people on their team.

[00:13:57] Yeah. So that's a great point. And so let's talk about like, what are the different horizons we're working on? We talked about like first you got a, such a core values, then your personal mission statement. The next thing, the third element for me is a 12 month goal. So this is relatively short term. I know we live in a world where like, everything needs to be now, now, now, but if you're really planning to make a transition in 12 months, I guess that's pretty quick.

[00:14:22] Right? So what are you actively and specifically working towards for the next 12 months? This is what you're going to build your action plan around, which is the fourth key element. Like what are three to five? Very specific actions you can commit to over the next six months making those smart goals, right.

[00:14:40] They can't just be generic, then need be very smart and you'd be specific, measurable, actual, relevant time constraint, all of those things. And then you've got a much more ambitious, kind of be had goal 36 months out. And this is the thing that is inspiring. This is the thing that like really gets you excited to have the conversation to get up and maybe put in a little extra time on the weekends.

[00:15:03] Um, so I check in that's that's the framework, but to your point, things change. And so in our, one-on-ones not just the professional development plan, but in every one-on-one we start with a help you here, you handle it. And it's just a quick check in on the person themselves. Before we get into the sales aspect of things, of what I can help them with, what they just want to share with me.

[00:15:26] I need to listen to, um, or just anything that, um, They need me to take care of, take off of their plate. And in a lot of those conversations, that's when you can tell if there's a shift in either the 12 or 36 month vision we'll table it, put it in the parking lot of the professional development plan. And then in that next, that next month, we'll, we'll talk about if there's been any change or if that was just a short term kind of, um, panic, so to speak.

[00:15:52] Hmm. And is this something that was done for you or where did you pick up these. You know, um, this framework and, and, and kind of the passion for investing in people's professional development and not just their sales. Yeah. I'm so glad you asked this because this is not something I created on my own.

[00:16:13] This is something that is a culmination of. Best practices. I saw Tia where I had a fantastic manager, um, and Daryl Watson. I learned this at ADP and I got a lot of this from my current organization, Gusto, where we invest heavily in our, in our teams. So it's a combination of all of that. The passion piece though, is something that I actually don't want to just skip over because everything I'm talking about right now is the framework that I recommend.

[00:16:41] The framework that I think makes the most sense and all of the like timelines, 90 days, third week of the month, these are all what I try to set expectations on, but what can not be true of any leader is that they want this more than the other individual. So if we get into a spot with someone specifically where they know this is our best practice, but they're not filling out the next steps, or they're not bringing this up, I'll ask, right?

[00:17:09] Like, Hey, you know, this was our professional development plan. Why haven't we touched on it? Sometimes it's just an honest miss. Sometimes you start to realize it, like maybe you do want it more than them and that's okay. But you better be honest about this. Like, if you really want to get to this ambitious 36 month goal, you talked about like, let me help empower you, but I can't do it for you.

[00:17:28] So that passion has to be mutual. And when it is like, it's, it's pretty powerful tool to have for sure. Oh, absolutely. And I think in, in some cases there. You know, 90 days on the job, you could run into some situations where very ambitious, you know, maybe the relationship's not fully nurtured and they might just kind of give you what they think you want to hear.

[00:17:52] Right. And that might not be a hundred percent true and, or, you know, another 90 days on the job and maybe things changed, you know, somebody's in an SDR role may always want to stay in STR role and that's okay. But in 90 days, you know, they might have some big goals because they think that's what you want to hear.

[00:18:13] And, and, and, and, you know, might not be comfortable enough yet to be totally honest with you. Yeah. Yeah. I agree. I mean, let's, let's pause on that example of an SDR and AAE. Wanting to stay in a, I think that's the magic of the professional development plan. Let's say, you know, we're in this meeting, we're doing a role-playing call on you.

[00:18:35] Tell me, like my goal in three years is to be a sales manager and that's what I'm going to work towards. So we start to build out our agreed to actions. And as a part of doing that, you start to get a taste of like, what are the responsibilities of a sales manager? I know when I was in a, I had no idea what my sales manager did, right.

[00:18:53] It's like, Hey, what is this person doing all day long? And then you get into the role and it's like eye opening of just how much responsibility goes with that particular role. There are individuals who were like, honestly, like now that I've kind of seen it on the other side, even to the degree that they can.

[00:19:09] That doesn't appeal to me. It's not what I thought it was and learning what you don't want to do is just as important as knowing what you do want to do is weird as that sounds. And so I think it's fantastic if someone has that realization, that what I thought I wanted to do in a year or three years from now, like it's not the case anymore.

[00:19:25] So let's pivot. Yeah. And so do you have anything in place to like kind of test if that's what they really want or not, or, you know, how do you kind of navigate whether like it's something they really want or it's something that they maybe think that you want for them? Yeah. So I never tried to guide the conversation.

[00:19:47] It's just asking a lot of open-ended questions and then to gauge whether or not they really want it. This is where it just comes back to. We'll set the plan here, the agreed to actions. And this is where you can be helpful as a leader of like, Hey, this is what I recommend. Right? Cause sometimes you don't know what you don't know.

[00:20:04] And that's where you rely on a leader who's been there and done that to share this path. But if we start to have these conversations and the timelines aren't being met, or they're not taking the steps that they agreed, they wanted to take. No first assume positive intent. I don't know. Maybe something happened in their lives.

[00:20:20] So like, I'm not just going to assume they don't care, but dig in a little bit. But if a trend starts to be established where it's like, I feel like I want this more than you, you know, Mr. Or Mrs. A E like, am I misreading the situation or can you help me understand? Y, you know, this specific thing you said, and we agreed you were going to do by the state didn't take place.

[00:20:41] And I think if you're having honest conversations, which you should be able to do, if you've built trust with your team is you'll, you'll quickly realize, like, is this just going through the motions for them? Or is this someone who's like really passionate about driving their career? And I like to focus my energy on the ones who are more wanting to drive their career and not just be a passenger.

[00:21:03] Yeah. Yeah, no, I love that. And creating that space for them, to be honest, if, if, if they, if they've changed their mind, if that's not what they want, or they want something different, um, now, but also, you know, giving them the benefit of the doubt. If like, Hey, they just got busy for God, whatever the case is, where life happens and they don't do to what they committed to and giving them opportunity to correct the course, but also, you know, come clean if, you know, Hey, maybe the runway has changed a bit.

[00:21:31] Right. Yeah. Awesome. I love this. Uh, Kyle, thanks so much for coming on and talking about this. I know it's a topic that you, you are very passionate about. Um, any final thoughts or just, you know, tell all the sales hustlers, where they can connect with you, learn more, uh, or anything else you wanna let them know the final thought I want to share.

[00:21:53] Um, Is this concept of like, life doesn't happen to us, right. It happens through us and I've heard it articulated beautifully in a sense of this old phrase, grass is greener on the other side, someone once said, and I'll never forget it. The grass isn't greener on the other side, it's greener where you water it.

[00:22:13] So if you are an individual contributor, if you are a manager, like take some control of where you're at. Seek help seek guidance, but you ultimately get to drive where you're going. And that to me is a huge, just like degree of freedom. Once you recognize that the only thing getting in your way as you, so go after it, go get it and then find cheerleaders to help guide you along and sponsor you along the way.

[00:22:41] Yeah. Yeah. I think that's a perfect high note to close this out. So thank you so much for coming on Kyle. Really appreciate it. Where can people connect with you? We'll drop a link or anything that you want to share with them in the show notes? Yeah. Find me on LinkedIn. Uh, Kyle Peterson. And, uh, yeah, send me a message.

[00:23:00] Would love to connect and share more best practices, uh, via direct message or even just one-on-one call, call sessions. So happy to help. A lot of people helped me. I want to return the favor. Appreciate that. Uh, if you enjoy today's episode, write us a review, share it with your friends and as always, we're listening for your feedback.

[00:23:19] Thank you for tuning in to this episode of sales hustle. Are you a sales professional looking to take your sales career to the next level? If the answer is yes, then I want you to go over to. Sales check us out. And if you feel that you are ready, set up a time to talk with me and my co-founder Chris, I'm your host collum Mitchell.

[00:23:43] And if you enjoyed this episode, feel free to leave us a review and share the podcast with your friends.