Be a Partner, Not a Vendor

with Jeremy Painkin,

VP of Global Sales, Cascade

In this episode, Pete is joined by Jeremy Painkin, VP of Global Sales at Cascade. Pete and Jeremy discuss mentorship and upskilling, getting 1% better everyday, the importance of being kind, what it takes to build high performing teams, the importance of mentorship, and more.


Key topics in today’s conversation include:

  • Biggest challenge over the last few quarters (3:27)
  • Increasing efficiency, discipline and driving repeatability (7:30)
  • The one thing Jeremy has to get right for growth this year (8:48)
  • Being a partner, not just a vendor (10:25)
  • Jeremy’s journey to a VP role at Cascade (14:51)
  • What is the context for hypergrowth at Cascade? (22:04)
  • The importance of mentorship (25:46)
  • What does it take to build high-performing teams? (30:24)
  • Favorite leadership moment for Jeremy (34:02)
  • What does SaaS(ramp) mean to Jeremy? (37:05)


The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at


Pete Thornton 00:06
Welcome The SaaS Ramp Podcast everyone. I’m your host podcast Pete got an awesome win for you here today. This is a little intro on Jeremy Payne kin VP global sales at Cascade. Jeremy just spoke with him did an excellent job unpacking a couple of custom items, some things that he’s passionate about. I think you’ll agree with me that this is an excellent episode. So look for mentorship and upskilling. In this episode, listen to what he talks about around the pavilion. Membership that he’s a part of that he really enjoys and CROs school discipline and getting 1% better every day. I won’t give it away. Wait till you find out what Jeremy’s background is. And you’ll be kind of blown away by not your day to day background and definitely been helpful on helping kind of instill a discipline within himself, which seems to trickle down to his team. And then the last one being kind to create high performing teams like why is being kind just something that’s so helpful for these hard charging a type A personalities that you sometimes have in sales, like what is it about being unkind that actually leads them to do incredibly much better things and why is that helpful in a remote environment? You’re gonna love this episode today. So look forward to those things. Jeremy does a great job. And I hope you enjoy this SaaS ramp audience got a message from our sponsor today as well. services partner rampant. So rampant provides data driven enablement automation. The fit for rampant would be for sales or enablement leaders and high growth tech leveraging gong for revenue intelligence. So rampant what it does is helps you solve the whack a mole dilemma. You are familiar with whack a mole, that’s that game where you stand at constant attention with a hammer and you try to smash each mole that pops up only for another tip here even faster than before. It was more fun when I was a kid and then doing it throughout sales leadership. So in hyper growth set sales you’ll kind of recognize this like the hammer represents the constant time and attention while those moles represent the barrage of problems that arise and you just move around from one to the next. Whack whack. So instead of blind manual efforts rampant takes your gong and CRM data and then helps you effortlessly prioritize what to focus on helps you understand clearly who moves the needle who in your your group of reps and then instantly know why a players are outperforming the pack and once you know why you can automate and reinforce the how and measure impact so connect with Pete at ramp it to understand how clients and hyper growth SaaS are using gong to drive increased win rates increase deal size and or faster deal velocity. Tell them you know podcast beats. He might know him to look forward to the episode all welcome back ramp-ins to The SaaS Ramp Podcast. I’m your host podcast Pete welcoming Jeremy pink into the show today. Jeremy is the VP of global sales at Cascade. Welcome to the show, Jeremy.

Jeremy Painkin 03:10
Hey, thanks so much. Appreciate you having me.

Pete Thornton 03:13
Yeah, appreciate you coming on today. It’s been great to kind of chat with you, catch up in the interim, like leading into this thing, understand a little bit about your morning routine and stuff. We won’t get into it all here. But every sales leader always has something that’s pretty locked up and tied. I always find that super interesting.

Jeremy Painkin 03:30
Ya know, it’s been, it’s been a pleasure to get to know you as well.

Pete Thornton 03:33
So love to know, because it’s kind of like a good opener just to dive straight in. This is like this hyper growth SaaS space. What have you seen over the past six months, or maybe the biggest challenge over the past couple quarters?

Jeremy Painkin 03:46
I mean, I think the past couple of quarters. For me personally, we had a lot of things happen. I think if we look back a year ago, you know, we’ve already seen that money was free. You know, valuations were crazy. multipliers were nuts. And so you had the ability to make mistakes, even at the cost of cash, because cash was king, and you could make you know, money was readily available to everybody. I think the benefit of that changing actually right now, which is causing a lot of challenges. You have to really put in your time and you still need to go fast, you still need to be focused, you still need to be even more accountable to your bottom line revenue, cash flow, cash burn, all those different pieces that we look at as leaders and SaaS. But I think the big challenge now is how do you stand out? So how do you stand out without taking a risk that might cost you everything you got left in the bank? How do you become a leader in space? And for me, that comes down to you know, not just brand awareness or product marketing. It comes down to how are your leaders in sales? And how are your reps in sales getting to your ICP? How are your people getting there? And again, if we look back, people are buying all kinds of great platforms and great technologies when they can afford them. Now you’re looking at the tech stack getting slimmed down, and you’re looking at resources, including people getting slimmed down. So how do we do that? A challenge for us is definitely now, how do we do more with less with a high level of efficiency, repeatability in the market space? And you know, I think we’ve done a really great job of being disciplined, we’ve done a really great job of being process focused, and but agile enough to continue to move. But I think where the big challenge now is, how do you make that repeatable? How do you bring new people in and get them to that same level? But, you know, people that went through this exercise are already at? How do you work through that? I think that’s a pretty large challenge for us. How do you scale this? How do we get from that startup world to a scale up world, in a world where cash is no longer King, and you have to get it right. And so, you know, one of the ways that, that I think we’re doing that, or that I’m doing that is we want to be focused and fast, but slow enough that we’re not focused and fast running off a cliff. We’re slow enough that we can turn before that cliff. And, you know, continue down the road. I think that’s some of the things that we’re seeing. But it’s definitely a huge challenge for us right now. And for me, personally, it’s a huge challenge in this market, to be able to do all the things that we took for granted. And you know, even in 2020, and 2021 2022, we took a lot for granted. Ease of business, lack of friction, email, deliverability, you can go visit people like we took a lot of that for granted. And now, how do we overcome that in a repeatable manner? Without saying, you know, Mr. Mrs. Board Member, I need $150,000 in tech tomorrow.

Pete Thornton 07:01
Yeah, yeah. Okay. So like this economic transition is what you’re referring to? Because if I mean, for context, for anybody who’s not listening, right, when it releases, we’re talking about March 2023. Right now. And then, you know, previously previous to this bit of a, these economic headwinds, as everybody references them as, like, the cash was flown in from VCs very readily into this space. And at this point is like, how can we still go make those big splashes or stand out in a smarter way? And like, by smart, you’re kind of, you know, not betting the house, you’re kind of talking about, like, increased efficiency, increased discipline, and then trying to drive some form of repeatability is, am I getting that? Right?

Jeremy Painkin 07:44
You are I mean, and I think, you know, I’m a big sports guy. But, you know, when you talk about things like that, you will always say, Well, are you being too conservative? And so, I’m a hockey guy, you know, Wayne Gretzky said, you miss 100% of the shots you don’t take. So I’m not saying that we can’t be taking shots, we have to, sometimes for those hockey fans out there, it’s a you know, there’s metal poles around a net. And you know, sometimes you missed an advocate that you had to post or, you know, it’s a sound that every goalie and every hockey fan knows what that sound is, it was just so close, but didn’t quite make it. You know, we still need to be taking the shots and taking those risks, but they have to be calculated risks. And not just, we think as much, you know, we do think but you gotta be calculated where before, it was easy to go back and ask for money and mistakes. Were not as glaring.

Pete Thornton 08:33
Yep, yeah. Yeah. Like the sales covers all and it’s just like, hey, everything’s gonna be okay. We’ll bring in money. And the sales could be like selling your board or selling your customer, one or the other. And right now, probably going to tend towards one over the other. It feels like

Jeremy Painkin 08:49
Yeah, absolutely. I totally agree with you on that. Okay,

Pete Thornton 08:52
so, then you got a lot on your mind. And there’s been recent transitions. I mean, if you’re VP global sales at a fast growing technology firm, you’re already going to have a lot going on. But now you’re trying to hone focus Hone scope, like you said, do more with less. So if you had to narrow it down, and this is you can’t buy No, but if this is the exercise, have you had to narrow it down to that one thing that you had to get right for your org to grow this year? What would you say that was?

Jeremy Painkin 09:20
I say the one thing that we have to get right at Cascade for my organization specifically, would be how do we begin to ingrain ourselves as a partnership further in our organizations that we work with. And I’m very fortunate to have a very strong go to market team. And we partner in this manner. But we have to get it right where we can not only get into an organization, we can rapidly expand that organization, which is, you know, land and expansion is not new. But I don’t want to be a vendor. I want to be a partner. I want to be a partner in that organization. No different than a McKinsey You’re no different than an Accenture or no different than a bain. In that organization. I want to be a partner. And I think that’s something that we have to get right. And we’re starting to really get right. And we’re seeing great results for our clients. Now, how do we do it more? Right? Like, how do we do more?

Pete Thornton 10:17
Yeah, yeah. Okay. So I kind of get what you’re saying is exactly on this. And recently this has been an uptick. And even the last two weeks, and like, I end up scrolling LinkedIn all the time, it’s probably a bad habit. But I post out there a lot too. So you get sucked into the vortex afterwards. And I’ve seen a lot of this kind of talk lately, like partnership versus vendor? Can you unpack that like a little bit more? Like, what’s that mean to you?

Jeremy Painkin 10:38
Yeah, I think, you know, I’ve been in tech sales for quite some time. And I think, you know, it was always, it was great. We just got to roam the halls and do the things in the hallways, and kind of what I called going rogue or undercover, because you could just, you know, knock on the door. And, you know, what, you had a meeting or not, you could roll the dice. And it was fun. It was exciting. It was, you know, how can I talk my way past this gatekeeper? You know, how do I get it? I liked it, I thought it was a fun game for me. That has gone away, you know, it’s hard to go walk the halls, if not many people do it. Most people are at home now. So even if they’re in the office, your chance of maybe getting them in their schedule is probably pretty difficult. So you get treated more like a vendor and less like, you’re there, that relational piece is kind of missing. And I think it’s important to have that relationship and be that partner, what’s in it, what’s in it for that person, what’s in it for their company, what’s in it for that person, and then what’s in it for the person above them, or the team that they’re on, that’s a become a partner, I think that it’s so easy to go in and just say, buy my stuff. And it’s a great product, and everybody buys it, but you’re a vendor. So at the end of the day, it comes down to cutting a partner, somebody who understands them and knows them as people was kind and, you know, spent the time understanding why this mattered to their business and why this mattered to them as a person. Now you can have a conversation like, Pete can call me and say, Hey, budgets are getting tight. If you know how important this is to me and AP. And I know that we talked about this, and you know, you got a promotion on the line for this and you got a baby on the way or whatever that conversation may be. There’s a personal element to that. But I also want to be a partner in their business. Hey, Pete, I was going through some of the information I talked to Susan, down the hallway here. I know, you haven’t mentioned this yet. But you know, there’s a big initiative coming out. And I think that, you know, we can help you solve it. And this can actually help, you know, put some light on. That’s what I think in my world, like, selling out is such a weird stigma. But I think it’s about partnering with people and doing right by people. And not just saying sign here press aren’t all three copies, see in a year or see you trick UBR?

Pete Thornton 12:50
I don’t know if some people know what that means with all three copies, by the way, probably not showing my age a little bit. Yeah, well, the people I work with, I said carbon copy one time and the email because that’s what CC literally stands for. And in my education days, you write a referral that way, kids being bad kids going to the principal’s office, whatever, you’ve got to write a referral, and you have to sign all three copies. So the teacher, the parent, that principal blah, blah, blah, people, what does that mean? I’m like, Oh, no. And so yeah, so anyway, that’s a funny one. I heard you say this, that is like it was these two avenues is like the Partnership on the relationship level. And on the business outcome level, there’s something you’re wanting to repeatedly help them solve and understand. And then there’s just a deeper driving force behind you wanting to help that individual and the company. And something that is harder to do remotely, like certainly harder to do remotely, as many things are, than would have been in person. Of course, there’s pros, and there’s cons there. But I kind of heard that example you gave, and that was the app example five years ago, like the amount of change in five years in this type of sale is massive. And I

Jeremy Painkin 13:59
also think it’s good for your people, like you can’t, I think in a remote environment, especially remote first environment, which cascade is where remote person environment, many of these large tech firms are aware of remote first environment, benefits of that work wherever you want, walk to your refrigerator, you know where sweatbands to work, whatever that is for you. I think there’s great benefits to it. So more time with your kids, less time commuting, you know, more family time dinner, like there’s incredible benefits to it. But I think we also need to be careful not to lose at the leadership level, that relationship with our teammates, that relationship with the people that are on our team, the relationship with the people that are cross functional teams of ours. And when you look at everybody two dimensional every day, can you become that vendor instead of becoming that partner? Yeah. And so I think it’s a two way street, not only externally. I think it’s an internal look as well.

Pete Thornton 14:54
Yep, yep. Yep. Makes sense. There. Okay, yeah, this place that you found yourself in after all these different years, you know, VP global sales, cool place to find yourself. How did that happen for you? personally, professionally? Like, how did this happen? How did this journey take place?

Jeremy Painkin 15:14
Yeah, I probably have a pretty non-traditional journey to sales. I was fortunate to grow up around sales by my father, my grandfather owned a business, and they were in retail. And so, you know, I’ve watched it my whole life. I didn’t get into sales until after I had a, I worked in the public sector. You know, from everything from paramedic, to, you know, SWAT officers, to tactical officers to I did some things as a, what called a TFO. For some other organizations in the US. I think it benefited me on my journey, because you train so hard for perfection, knowing that when you need it, your body’s just gonna do whatever it is you need to do. It also taught me that it was almost like a You can’t kill me mindset of like, this training is really hard. And I think they’re gonna drown me, but you can’t kill what they’re like, and not the cocky way like you can’t kill me, it was confidence in myself. But it’s also competent in the leaders that I had with warming the trainer’s and the CADRE and things of that nature. But I worked in very, you know, high risk, high reward capacity, I led some specialized teams, I was a member of those teams. And then, you know, as I had a family and things like that began to happen, it was time to transition out of that space. And spend more time with, you know, I’ve got two kids and spend more time with them in the family. And so I started transitioning out into the tech space. And I started, essentially, like everybody else started as an old, weathered BDR, not fresh out of college. But that’s where I was. And I began to work my way through BDR, to leading BDR hours to leading BDR STRS, to now being an ad to now leading eight years to now being a VP to leading managers lead, AES, and so on and so forth. And for me, the journey was more about building a team than it was about being a leader. I love being a leader, because I love the people aspect of it. I like growing and developing people. But I took a very uncanny route to get there. So, you know, I think part of it is, you know, the team building aspect and the team environment is something that’s very cool to me. But again, I probably have been in interviews before where I’ve had people say, hang on and go back. Can we talk about this other page that you don’t talk a lot about, but I know it’s a long time ago, but it just seems strange that we’re having this conversation but I did have a pretty a pretty I don’t want to say checkered I had a pretty zigzag for to get to where I am today.

Pete Thornton 18:10
Yeah, there’s kindred spirits. And then even in being in the public sector. Mine was not as cool as education. This is not as cool. Oh, sorry, if you can use SWAT in a sentence. And it’s not like oh, I’ve tried to swat a fly and missed, then it’s like, way better. But then into the BDR space and be your leader and onwards upwards like the same kind of thing. So definitely understand that. And the famous line, it was like when I’m in a pod standing next to this kid fresh out of college, good friend of mine. And then he goes, he’s like, Hey, man, you’re not using your phone correctly. Oh, say iPhone, you know, like you have apps on it. And I’m just like, cuz I had a Nokia brick before that for many years. And then I was like, Hey, man, you don’t know who Ronald Reagan is. And so like, Let’s trade information. I can just go young and I was already so old moving into that space. So there’s definitely pros and cons about it. There’s this book called range range. It is a really incredible book for career changers like that. Okay, dig that in. Have you heard of that one?

Jeremy Painkin 19:07
I have. I’ve heard of it. And I’ve read excerpts of it. I’ve actually never read the whole book. But the experts I’ve read

Pete Thornton 19:13
are fantastic. Okay. And that’s the gist of it. It’s just like, it’s like, oh, this is you don’t have to necessarily specialize for this to happen. And so I don’t want to spend a million years there. But like SWAT, federal agents like these have interesting backgrounds. What is one pro of that you mentioned? Like just that overall confidence of like, Hey, listen, you’ve been through some really hard things and you came out and you are living You can’t kill me like this. And by the way, that’s that is that a David Goggins book now does he actually have that?

Jeremy Painkin 19:39
Oh, yeah, David Goggins. And if you heed that is a book that he wrote. Yeah, he’s a great guy. I recommend reading his book. It’s fantastic.

Pete Thornton 19:47
Yeah. Individuals are fantastic for athletics, or business in my opinion, both of them. But yeah, one thing that you think is actually gives you a leg up like you lost, you know, 10 years of your journey that you could have been otherwise As you know, back at Microsoft or Google in the early days or something like that, that you didn’t do, nor did I, but is there any one thing that you’d recommend it for? Yeah,

Jeremy Painkin 20:09
I think that, you know, there’s a difference. I learned what the difference between motivation and discipline is. And so like, motivation is kind of an up and down, like, I go to the gym, I don’t go to the gym, I go to the gym, I don’t go to the gym, I go to the gym, I don’t go to the gym. But then you look in the mirror and you’re like, I’m not getting results fast enough. were disciplined to me and looked more like a bell curve. And so it’s, I go to the gym, I go to the gym, I go to the gym, I go to the gym, and every day, you’re getting 1% better. Yes, it’s a long, you know, sucky journey, sometimes, all the time. But you know, you’re getting better every day. And that’s something that I still carry with me from those years before is, I want to get better 1% Every day, everybody that I worked with in that field wants to be the best, you’re not going to be one person, that field that says, You know what? I’m pretty cool with second because they won’t be on the team. They’re just you want everybody that’s a number one player. And there’s, you know, I’m a pretty strong type A personality, so are the rest of them. You also have to learn to work with people that may have stronger personalities than you, or a different view than you do, but with the same strong way of bringing it across. But I think learning the difference between discipline and motivation was huge for me. And then every day just wanted to get up even when it was wet and cold, or it was just tired. I’d had enough. It was all you know, I don’t want to go back today. And just getting up and doing it again. That’s something I still carry with them, a big mindset guy. And I think a growth mindset is something that every seller should have, every leader should have, versus a fixed mindset. There’s some great books out there. But I think that having a growth mindset and having that discipline to continue to get 1% Better, is something that I definitely still carry with me in my career.

Pete Thornton 22:05
Very cool. Yeah, I can. I like all of those points and won’t recap them, just like them. What about the company, your company cascade? So this is obviously done very well. A recent fundraiser and everything as well. What’s the context for hyper growth? Why is it growing so quickly? What’s going on there?

Jeremy Painkin 22:24
Yeah, I mean, cascade takes strategy out of PowerPoint, and excels and takes them out of the boardrooms and puts them into real life actionable plans that can be, you know, aligned and transparent throughout the organization. And one of the things that we see now is, you know, strategies, digital strategies ever moving. When we go back to the boardroom years before, I mean, I’ve done it, you get night, you spend 45 days getting a bunch of people to put together PowerPoints and excel sheets and bring them to you to present. And by the time I present that information, it’s stale. And if the board says, I want to double click over here, everybody scrambles, it’s just what used to happen. Now, in a digital setting, I would rather know 30 days into my quarter, if my metrics are good or bad, my measures make sense, and that they’re aligned back to the objective I’m trying to hit versus waiting for day 91. And going, Pete, I’m really sorry, we missed. So cascade brings all that to life, from literally from the top of the top sea level, all the way down your executioners, we have alignment, transparency, visibility, we don’t care what framework you use, there’s lots of frameworks, there’s, you know, OKRs, there’s balanced scorecard. There’s, we can go on and on. Oh, GSM. You know, there’s, we allow you to use what you natively are using now and your system. And we allow you to tie all your people together. People who are more engaged employees know what they know what they’re rolling up to. Communication is key and heavy. No one feels like they’re in the dark. And ultimately, you’re delivering things ahead of schedule with a great business outcome.

Pete Thornton 24:02
It Was fantastic. That’s really interesting, because it all kind of trickles back from there for a large majority of the go to market team on what they’re trying to achieve. And then there’s a debrief and things that come the other side. And that is quite a process like everything has this like t minus to the next board meeting if you’re in that space, especially in leadership in that space or enablement in that space. What just to get an even clearer sense, who do you mostly speak to like, who would you partner with? What would the ideal customer profile look like? That spans a large gamut, actually?

Jeremy Painkin 24:35
Yeah, it’s a pretty large gamut. I mean, a customer profile for us, is pretty industry agnostic. We do see a lot in transportation and logistics and manufacturing and pharmaceuticals, but we also see education, we also see state, local, federal, and national governments. We see a lot of those as well. But ultimately, it’s going to be your chief strategy. reserves, it’s going to be your directors of strategy or VPs of strategy. Sometimes that were seen as law more frequently, it’s your CFO, it’s your CEO, because they’re having the issue of delivering back down to the people back down even one level, like from CEOs to SVP, there’s a disconnect of what’s who’s responsible for what? And cross functionally, how do these touch, we’re no longer working in silos. Those days are, hopefully, very far behind us. You know, we’ll see what happens. But that’s probably our ICP. As it is today, but every day we get a different conversation with a different company. And the use cases are unlimited.

Pete Thornton 25:44
Yeah, interesting. Okay. That’s very cool. This is a cool overall use case or like a broad outcome y’all are driving. You mentioned a little bit about discipline versus motivation. You had something you mentioned to me earlier, around mentorship as well. I knew you were a pavilion member. And some of the things that they say or do or the founder, they resonate with your mind expanding on that a little bit?

Jeremy Painkin 26:10
Yeah, I think that one of the biggest investments that I’ve made in my career was joining the pavilion, and I tell this story a lot. People have talked to me about revenue collected and pavilion for years. And I was always like, not for me, I don’t have time. And unfortunately, it’s a gym analogy. You know, it’s not gonna get any stronger driving past that. I have access to 10,000 Plus members. And so there’s lots of conversations that happen back and an informal mentorship perspective. And we’re learning from each other. Hey, Pete, I know that you’re working on your demand generation and can talk to me about demand gen. Hey, Jeremy XL knees for potholes right out of the gate. Versus Jeremy gonna do the same thing. And now Pete and Jeremy are talking about the same four bottles, and they both fell in. But then Pete might call me and say, hey, you know, I get ready to do some outbound. And Jamie, I know you’re really good at out bounding. And we got our demand gen. Machine finally up and running. I think we got this cool deal working. Thanks for that conversation. What was your next step? And so that cross collaboration and sharing and informal mentorship, I do have a number of formal mentors as well through pavilion. And you know, something else I learned from Sam Jacobs, whose president is that kindness matters. Like, you know, he’s got a best selling book out, I recommend you go check it out. But, you know, being kind is going to be, you know, the nice guys don’t finish last and sandwich like that. You know, and I think what I’ve learned is the empathetic piece, and I think what I’ve learned is, these are people, how are we just going to be good to our people? And how are we going to be just good out in the world, and then get good in return? Those are some of the things that I’ve learned just from that. But the upskilling as well, I mean, I took their CROs school, and got truly one of the best investments I made in myself in my career. And was it all? You know, it was learning from those people again, those best practices, what’s not working, what’s unit economics? What’s this? What’s that? In an environment where they’re not like, I mean, you were a teacher, so you’re not like wearing the dunce cap, right, you’re stupid. It’s like, Hey, what’s your point of view might be different. Let’s talk about that. Great program, and I highly recommend it. And I think it’s important, as it was, in my previous career, to always be getting 1% better, you can’t sit stagnant, somebody will be better than you. You have to constantly upskill yourself. And that means investing in yourself. And I think sometimes, whether that’s reading a book, or that’s taking a class or that’s listening to a podcast, like this one, or whatever that may be for you. But I think the best in the business are constantly trying to up-skill themselves and are constantly looking to learn from those that went before them, those that are behind them. And are working to take the information to make not just themselves better, those around them better.

Pete Thornton 29:14
Yeah, that’s a very good point. That book by Sam Jacobs. Do you happen to recall the name? Yep, I got it right here. You had reference CRO slash themes on your profile, and a few as well and so I thought I was like, okay, CRO is cool. Very cool as I use great to get a high recommendation on that one. First Person has mentioned it on the show, but I see a lot of places. And it just seems like you know, an excellent subject. And if you could,

Jeremy Painkin 29:42
kind folks finish the first great, great book. I will send you a copy to post this as well. And then you can say you have

Pete Thornton 29:52
awesome thanks, man. Yeah, that’s great. Great. I really liked that. You also have this other piece of Your background, because you have, this is something I’ve noticed a lot of and maybe I’m stringing a couple of things together a lot of cases there’s quite a weave to the sales leadership role. But there’s something it was in either sales or leadership leading up to it. It’s not like the first of both. Oftentimes, that’s a family member, like you mentioned, your dad and grandfather being business owners, or an athletic experience, you know, dependent, you know, regardless of the sport like you were in doing something, and a high performance basis, anything that you would recommend for building high performance teams? Or is there something that we talked about already, that’s just, hey, don’t forget doing this as you’re working with a ton of players might be being redundant. But I’m just curious here.

Jeremy Painkin 30:46
Yeah, I think that when you’re building a high performing team, which is something that I’ve been fortunate to do multiple times in my career, I think that building a high performing team is taking a lot of different people with different skill sets and different way of thinking, and putting them together and filling the gaps for the person sitting next to them. Maybe somebody is better at using hard skills, better at writing emails, but you’re better at making a phone call. When I was in the office, I would put those people next to each other. It’s an immediate learning from each other. I think the other thing in high performance especially in sales is this may be taboo, people are gonna go all sales cares about his money. I strongly disagree with you. Yes, sales are very financially driven. That’s why you get into sales. It’s also why it’s so difficult. Because you’re chasing your own potential. But what I’ve learned over time is and from running teams, and truly strong type A No, no, there were the highway run through a brick wall Free type people is, why are they doing it? And if you get deeper into that conversation, and you start to learn your people, when I get on a one on one, my one on one is Hey, Pete, how are you? And if it takes 45 minutes for us to talk about what’s going on with you. We’re going to take 45 minutes, we’re gonna talk about what’s going on with you. Because now I know why you’re doing what you’re doing. Now I know why what’s happening. Now I know what your drivers are, hey, I’m about to have a baby. I’m stressed out. I’m having a hard time, you know, all this stuff is super expensive. So I could go and say, Hey, let’s go map back your territory, how we can make it so you get all things for your nursery? That tells you I don’t, I heard you. But I don’t make it about me. It isn’t about me. versus saying, Hey, man, I’ve got two kids, my Oh, let’s talk through this. Let me tell you some experiences that I heard in conversations with people. And then everybody needs to be heard and feel like they’re a part of it. But now you’re a part of a team. Like it isn’t always going to be, hey, how many feet I’m looking at the I’m looking at the pipeline, you only put in one deal last week, somebody wants to hear in that situation. And I think that as you develop a high performing team, knowing what’s good for your people, I have somebody on my team right now who’s trying to buy a house. We talk about it all the time. They send me houses, I look at him, I know, it’s super exciting. So the money is driving there, but it’s not the money. It’s the means to do what they want to do, which is to buy the house. And I think we do. And I’ve been that leader where I don’t enact the one to do what your why is and everybody’s why and your team is different. And then I think we need to fill those gaps with people that are different from each other. I don’t do the other thing, let’s hire all type A personalities that are just going to make 1000 phone calls a day. And they end up killing each other. Versus let’s put different personalities and different backgrounds and different everything together. And then make a holistic team which is stronger together versus one individual.

Pete Thornton 33:53
Yeah, yeah, that’s a great point. And you did mention kind of like in another subject area that it was all about building teams for you like that was just something that you kind of leaned in towards, you know less about leadership and more about building teams, and those kinds of things. You know, they seem to cycle on each other. Do you have a favorite? It couldn’t be a favorite building moment or leadership moment or anything that just comes out and strikes. She was like, you know, a memorable piece of your leadership experience.

Jeremy Painkin 34:21
I think I was on my own either. Second, I think it was my second leadership role. And I was finally building teams of decent size. And I remember looking across the team, probably right after Christmas, you know, closing out the year, looking across the team, and in my mind, I think I was like I want everybody to be a club. I want everybody to be like on every leaderboard there is like if there’s a metric I want our team to be on. But then again what I thought was, you know what, those three guys had a club. He had a baby. She just bought a house. Her child was sick. And she was able to get through the illness of her child based on what she was able to do here. Hey, you know what? You know, they got married. When you start to look at that, again, they all achieved what they came for, that is their club, they’ve achieved their club. But I was so caught up. And I very much like people that know me will listen to this and will laugh. I mean, if you’re like, hey, I can throw rock farther than you have, like, Let’s go peed outside now rock the show. You pick it? Let’s throw it. You know, I am that guy. I’ve actually raised people in a parking garage in a business suit.

Pete Thornton 35:36
So I’m not saying that on an episode of The Office, by the way. Yeah, I’m that guy.

Jeremy Painkin 35:41
But I think the leadership moment for me was knowing that I understand people, and I helped them achieve their goal, which whether it was my goal or not, it was their goal. And it reminds me of a quote from Brene Brown, which is, you know, one day you’ll tell your story of how you overcame, what you went through, and it’ll be somebody else’s Survival Guide. So now, these people are all leaders, they can tell the story of I remember I was in it was, you know, 2018. And this was what was happening in my life. And this overcame it. And this is how I got better at my job. And now I’m the VP or now I’m not or now I’m at home, whatever it is you’re doing. I think that’s probably the most influential moment I’ve had in my leadership career to date. Okay, and I’ve done some cool stuff. But I think it’s cool to see other people win.

Pete Thornton 36:32
Yeah, that’s great. That great, great, great story connects well, with all the things you said as well, leading up to this, and I have heard that before, because we’ve had some really good leaders on this podcast. That’s excellent. So that question generates that type of response some of the time. I have another one for you. And I’m super curious about the context for anybody. SaaS frame podcast is the name of this podcast. And so I named it that based on a certain experience I had within the sales enablement realm. And I won’t even tell you why because it ruins this but like so I like to ask the guests on the show, like what does SaaS rent mean to you? And I often get wildly different answers. So then for you, Jeremy, final question, what does SaaS ramp mean to you this nonsensical question, but still, what does that mean to you?

Jeremy Painkin 37:20
Yeah, this is the hardest one you’ve asked me today. It’s because I think ramp I think like, you know, rep, ramp or leader ramp, and then I start thinking immediately, like, what do I need to ramp them? You know, in our business, you know, we use going to listen to calls and we get 1% Better we use, you know, we use sales off for a video, I was like, how do we get 1% better our sequences, and we use all these different platforms. So ramp to me is like, how can we ramp faster and more efficiently? Using the tools that we have? Right or wrong answer, that’s my final answer, Alex. Okay,

Pete Thornton 37:58
that one actually, that one dovetails a little bit with my sales enablement side. Yep, totally get it, totally get it. As far as that goes. We’re getting some new hires, we’re getting some leader ramps, and, and using some tools to do so as well. It’s great, man. It’s great. I really appreciate it. I know the audience, we get a ton of value out of this one. And I hope your team does listen, and then does want to have a rock throwing contest with you in the street and races in the parking garage after this.

Jeremy Painkin 38:26
I signed myself up . I’ll be the first one out there. I’m gonna stretch but I’m ready to go whenever.

Pete Thornton 38:32
It’s brilliant. Jeremy, thank you so much for coming on. Really appreciate you. Thanks to cascade for letting us have a few minutes of your time and looking forward to getting any guest participation and feedback from this one.

Jeremy Painkin 38:44
Awesome. Thanks again for you. I really appreciate it. It’s been fun.