You Can Teach a Dog New Tricks with Chris Leon

Jordan talks with Chris Leon about being fired from Outreach in his 40s and becoming the first employee of Greaser Consulting in today's RevOps Therapy Episode.
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Show notes

It’s a cliché. But for some reason, it seems that many people in SaaS believe it.

Chris Leon, now Senior Sales Execution Consultant at Greaser Consulting and “old dog,” has proven time and again that he can learn new tricks.

That’s why RevOps Therapist and founder and CEO of Greaser Consulting, Jordan Greaser, called Chris and recruited him to be the first employee here.

Chris shares his experiences, starting with being fired by Jordan at Outreach, in his 40s, to learning and sharing as much as he can with all of his clients, even into his 50s, and he has a lesson to teach anyone who thinks they “can’t,” no matter your age.

Jordan  00:00

Hello everyone, this is Jordan, the owner and CEO of Greaser Consulting. On today’s episode, we have one of our own consultants, Chris Leon, hopping on to talk about late-stage career moves, ageism in SaaS, and the process of ultimately getting to the place where, hey, he’s found his niche. It’s a really interesting episode because we talked about some uncomfortable things. We talked about how being one of the older folks in the room, sometimes you’re looked at a little differently; do you really belong? He goes through some of those thoughts, emotions, what he’s done to counter that. And ultimately, what got him to this place where he’s literally one of the best consultants on our crew, hands-down, in all the work he does, the feedback he gets from clients. So I’d encourage you to lean into this session. Enjoy listening to Chris talk a little bit about his life, his thoughts, and how if, maybe you’re one of the folks in the audience today, that’s one of the old dogs, so to speak, how you can stay relevant and continue to make a difference, but ultimately, know your value. And that’s the big message of this session is the value is in there; you just might not know it. So hang tight. And let’s go.

Intro Jingle

Say you want some clarity in sales and marketing and SEP? Well, we have just the remedy: our podcast, RevOps Therapy. Yeah.

Jordan  01:32

Hi everyone and welcome to the show. We’ve got Chris Leon with us today. Chris, why don’t you go ahead and introduce yourself? 

Chris  01:39

Hey, welcome, everybody. I’m Chris Leon. I work with Greaser Consulting. I have my own company called RevOps Now, and I’ve worked with a lot of teams out there. So I’m happy to be here.

Jordan  01:51

Yeah, so Chris and I have a, I would say, a long and checkered history at this point. It’s one of Chris’s favorite stories. I never know if I should be embarrassed, or if I should just be like, yeah, it happened. I really don’t know. So Chris, why don’t you go ahead and let everybody how… know how we know each other?

Chris  02:12

Well, Jordan and I started with this little company out of Fremont area of Seattle. You probably heard of it: Outreach. And we started back in, what, 2015 or so? Jordan rose to the ranks of SDR leader very quickly, much to my chagrin, since I was the first SDR, but that’s a whole nother story, but no, he was, he was definitely the right, right man for the job. And anyways, another person came along: Alex, right? And then I, we formed a couple teams and Monstars! Anyways, long story short, worked together for, what, a couple of years it seemed like, and, what, the second, second year in, a little bit over the second year, Jordan had a great opportunity to let me go and fire me. And the funny thing is, is that the day he had to fire me, it was like a production and, and even though I just had the but… but… Anyways, long story short.

Jordan  03:30

We’re gonna, we’re gonna say it, Chris. Here’s the deal. I moved out to Seattle to start the team. Chris Leon was like the super high producer on the team. I was legitimately pumped. “Chris is on my team. Finally.” He had just won like SDR of the Year, Top Production, all this stuff. And I, listen, every company has politics; we hate to admit it. But I think what happened, and Chris, you can correct me if I’m wrong, Chris was promised a position, not by me but by somebody else, and a couple of things happened, and he didn’t get the position. And next thing you know, Chris wasn’t too happy to make cold calls.

Chris  04:11

Yeah, I think that was part of it. I guess that the other, the other part of it was just, it felt like the… it could, you know, felt like I wasn’t, it was moving away from where I wanted to be. Long story short, he had to, he had to let me go, and the funny thing is, I think I was consoling him through the whole conversation. “It’s gonna be okay, man. It’s okay. I’ve started a career. I’ve… This is something I want to do. I don’t think I’ll be lack for work.” So yeah, it was, it was a good break. And we’ve stayed friends even after so. Yeah, that’s all good.

Jordan  04:45

Yeah, I do have to say, just for everybody, listen, Chris was very gracious. I remember going into that thinking “oh my gosh, I’m gonna fire SDR of the Year.” Sitting across from the table from you know, a seasoned vet that has produced great work over time, and I was going to have a hard conversation. And, boy, I’ll tell you… not that… it’s always about the person being let go: How’s it go for them? But even in that scenario, somehow he thought about me, and was like, “Hey, listen, it’s okay; I get it,” which I think in a lot of ways, was why, quite literally, when I was starting Greaser Consulting, and I was thinking, “Who could I connect with to do this work that knows it, but knows it from a different angle?” And Chris was the first person that I ever hired at Greaser Consulting. So it’s kind of a strange story. “What, wait a minute, like you let them go. And then he wanted to work with you again. And you actually had the nerve to reach out to see if you’d want to work with you?” Like, I get that question all the time. Chris loves to talk about it in any team meeting he can. But, but anyway, that actually leads us though, into the, into the topic of discussion. And listen, this is a little uncomfortable. Chris, I don’t, I don’t know if you’re willing to do this. We did talk about it ahead of time. And you said, “Okay.” Chris, at that point in time, how old were you when you stepped out of Outreach?

Chris  06:17

I was in my late 40s when I left, when I left Outreach, which for SaaS, you know, that is you know, that’s, you know, I should have been like a, you know, a leader of some kind, right, at that age. But I had changed careers a couple of times when I, when I got brought over by Mark Kosoglow to work in the enterprise with Pleasant Rich, and I had been the salesman for 20 years selling everything from cars, houses, you name it. And so for me selling was no big deal. I had never sold SaaS though. And so that started, restarted my career with Outreach, with SaaS. But yeah, when I jumped off of Outreach, I was in my late 40s.

Jordan  07:02

Yeah, and so the reason I bring that up is, you know, 50s today, right? And I’m just gonna come out and say, there is a little bit of ageism in SaaS, and you can tell me if this is true or false, but a guy that’s rolling off the SDR team, bumping up against that 50 number, it’s almost a little bit like, “what are you going to do?” Because there’s, there’s a little bit of this connotation of “Oh, old dog can’t learn new tricks. What are you doing in an SDR position at that age?” You know, not considering the fact that, listen, 20, 30 whatever years in sells. It’s just “hey, this guy’s close to 50. And the last thing on his resume was SDR.” So you willing to talk about that a little bit? Well, what was going through your mind, what you were thinking about?

Chris  07:49

Yeah, you know, I was in good company. I think there was quite a few of us that were a little bit older on that team. Outreach did a good job of bringing in seasoned salespeople to start off as SDRs, which kind of is… goes against the grain of what most have … Yeah, you know what I mean? But, but I think I think they were looking for a different personality, rather personality of somebody taking ownership, someone not just making meetings, right? Someone who’s going to take it from meetings all the way to SALs, and be careful and want it to go even further. And that’s what we were and so for me, I was just a salesperson; I wouldn’t… you call me whatever you want, I’m gonna get a meeting, I’m going to make sure the meeting happened, I’m going to make sure that it gets to a SAL. And so it was a different mentality for our team. And honestly, it kind of set the pace for what I did after that, and how I instruct and help other teams think about the SDR role.

Jordan  08:50

So when you rolled off, though, talk me through that. Yeah, was there, was there a fear? Was there, was there like, no, you were like, “I got this”?

Chris  09:01

I had a job by Sunday. So you let me go Friday; I had a job by Sunday. That’s that. I mean, I was, I was ready to go. I mean, with that, with, with us, a person who had made the kind of money I made the year before and the knowledge of what a sales enablement platform can do. I had my first job by Sunday; I had them buying Outreach. I made sure that it was lined up and ready to go Monday morning. I mean, that’s, in my mentality, that’s, that’s what had to happen. And let’s go.

Jordan  09:33

So talk me through from that point to you found your way into consulting because I think that’s really the, the, the joy of this story and a lot of ways right as we were just talking about kind of late stage to be at the SDR and yet you’ve sort of found this niche all of a sudden that that just really works for you.

Chris  09:57

Well, I have a couple of people in my life that really sat me down and kind of told me my worth, because you’re absolutely right. There’s a bit of ageism in SaaS. People look at you. And they say, “Well, you know, you can’t be this, can’t be that. You need to be something else.” And I had rolled into an AE position full-cycle AE, soup to nuts. And I was, I was doing fine. But the team decided to not have salespeople anymore. So my job kind of evaporated. And somebody asked me for help on Outreach, and I knew it well. And so I, I helped them. The team was GTMStrat and Colleen Dempsey, a shoutout to her and Stephen Flink. They… Colleen sat me down one night and said, “We need to talk about your resume.” And I said, “Okay.” We talked about the resume; she said, “you know, you have worth,” and she explained to me all the work that I have, and how I can help sales teams. And I was blown away. I just was like, “Okay, I’ve been thinking about this all wrong” up until that point. And like, I don’t, I don’t know, up until that point, I was just hustling for work. But after that, I was like, “I’ve got stuff that people want.” And from that point forward, I’ve been helping sales teams, I probably helped 40, 50 now. I can’t even… I stopped counting honestly. It’s so much fun, you know, especially when there’s a use case that’s different, that’s unusual. Maybe the team has never done it before, never done outbound, never done inbound, for them to see how they can do it with a platform of any kind to help them. I’ve always had technology with my sales, even back when I started in the car business. I always had a website; I always had my own personal electronics to keep track of my, my customers. And so technology sales or technology with sales, I should say, is something that’s been part of my DNA forever.

Jordan  11:56

Let’s hit on that though. Colleen, you said, sat you down, and was like, “Hey, listen, you know, you’ve got worth.” What, what was it as they talked with you that was the things of “hey, you’re thinking about it like this? But actually, it’s like that.” Like, what were those items? If you could think about like, Chris, pre-colleague conversation, and then Chris after-colleague…

Chris  12:21

Yeah, I was trying to get a role; I was trying to get a job. I was trying to get, you know, work, right? But she’s like, “you understand that you know a motion; you know how to do something that a lot of people don’t understand. They don’t know how to go outbound. They don’t know how to set up their sales teams. They don’t know how to set up even a sequence. Right? They don’t understand the technology behind it. They don’t understand how it connects to other products like Salesforce. You do. You have tons of work; you’ve been in a very high-charge team. Outreach is very hard. It was a very highly charged team. One sliver of that would be a huge benefit to a team, any team.” And so that was, like, mind-blowing, right? Plus 20 years of experience in sales, having worked, having stood in front of a building, selling a car, right? Selling a junker with the door that fell off and still selling right? I mean, things like that.

Jordan  13:18

You were one of those guys, huh? You were selling lemons?

Chris  13:21

No, I was selling lemons to people who wanted lemons, right? But, but you know, I mean, everything from the house… sales I did, to, you know, the stuff I did with school specialty selling to schools. It just gave me an opportunity to really, to really kind of start to build what I am now, which is helping sellers sell and helping them look at it a different way. So many, so many things come up. And I’m like, well we tried this or we tried that and like, oh, didn’t think of that, right? So it’s awesome.

Jordan  13:56

You walk out of the Colleen conversation; all of a sudden you feel a little invigorated, like “oh my gosh, I have, I have worth. Okay, yeah, I have worth; I have value. You know, the old dog can learn new tricks” so to speak or has a lot more to give. What’s like, what’s your next step? Like how did you go about getting clients? How did you suddenly gain confidence? At what point in that journey, so to speak, did you go from Colleen said it to I think that might be true to, oh my gosh, I know this is true.

Chris  14:27

Yeah. You know, it, she started… she had her own clients, they, that team had their own clients, and so they started me slow, right? To give me control over, say, the Outreach implementation in a… on a team or help… having me do the data work for a team or something like that. It was always… it was small, but it was, it was, it was paying my bills, right? I mean, that’s, that, that was the best part. And then, and then it went from that to me getting some of my own work; referrals would come in from other places. I would do a job here and there, or I would work with the team. And then I would impart some of my knowledge with them. And soon it was many teams, right, using me for five to 10 hours a week and filling up my day, really. And then of course, you came along. And, and then it was like, I slowly went from what I was doing with them to mostly working with you. And that, that… Yeah, yeah, no, she was very happy for me, they all were, you know, I, you, you take it off with, with what you were doing with the teams that we were working with. And then, and then my world changed in that I needed to know more. And so even at 52, or whatever, I had to go back and learn. And I had to get certifications. And I had to learn more and keep learning… always be learning, right? Because, frankly, that’s the only edge I have against those young, young people coming in, right is that they come in without the experience, but they may have those certifications. So I’ve got to keep always be learning.

Jordan  16:19

Chris, has that gotten harder?

Chris  16:22

You know, as I joke, my wife and I say that every time I learned something new, something else gets lost. You know, but I think the important thing is that I just continually learn, keep, keep learning. And no matter what it is, sometimes I, I take on more, you know, that I can choose as far as learning, but I always try to make sure I’m on top of all my clients, helping them make sure they’re getting what they need.

Jordan  16:54

Yeah, I think you’ve said that to me a couple times. Hey, one thing in, one thing out. See you later. Kind of, kind of clearing the junk. I don’t need that one anymore.

Chris  17:07

I don’t need that one anymore. Yeah, you know, it’s hard. It’s hard. When you’re, when you’re a little bit older, you’ve got older kids, you’re, you know, you’ve got all these priorities. But, but honestly, I enjoy what I do. I, you know, we talk about this, but I’ve been remote for gosh, since, since I started with Outreach. So 2015, I’ve been remote. And I love it. I just love working remote. But I will say it’s kind of my blanket because of my age, right? I think people get a preconceived notion. They see me and they go, “Oh, he’s an old guy, like, What’s he doing here? You know, helping, helping me,” you know, or what have you. And I think it’s my blanket. But you know what? There are other times where people are blown away by my age; they look at me, and they don’t think I’m that age or what have you. So it’s, it’s kinda kind of cool.

Jordan  18:03

Let’s just touch on that, though. A little bit deeper. What do you think? Well, let me, let me think about how to frame this question. It’s certainly true that when you walk into most SaaS companies out there, most- I can’t say it’s everyone. But most of the folks that are the… I always laugh about this. This is going to be for people that are just in the nitty gritty with Outreach. So this is gonna go over a lot of people’s heads. But in the profile settings, when you’re setting up governance, you know how you could set it up? That’s like, either the owner or the manager or you’re the subordinate. Yeah, right. So I’m saying that this I always laugh at the word subordinate whenever I get into that system. So yeah, the subordinates tend to be the younger right out of college, you know, what I’m saying is the SDRs, the entry-level positions, whatever, they’re coming right out of college, typically a young crew. Your mid-level managers, and this is a big generalization, okay, sort of frontline managers are anywhere between the age of like 25 to 32, or something. Your directors start being somewhere like 30s with VPs are somewhere in their 40s. And I’m not saying it has to be this way. I’m just saying you look at the prototypical SaaS company. This is the general age range, general, general, whatever. But you’re saying, you’re over here saying listen, Outreach’s SDR team, like they’re a bunch of us in our 40s to get that thing kickstarted. Matter of fact, a bunch of blue-collar folks, you want to talk about, you know, really shift of the way things work. What do you, what do you think, like that? I would say the older generation that’s in those individual contributor roles in SaaS companies, like what did… what can they really bring in your experience because you’ve been there, that these young guys and gals so to speak, like they’re just not there yet? It’s not like we’re saying we need to get rid of them. But we’re saying it can help round out the team by having this, this sort of older crew on your team. 

Chris  20:11

Yeah. So, so just look, this isn’t a, you know, anti-generational thing. I’m not going to be anti-millennial here anti-Z, you know, it, look, the thing is, every generation has their awesome parts, right, and their generation as her kind of not awesome parts. And what I can say is that I’m Generation X. And for, for us, we, our generation didn’t get promoted too fast, because there was a lot of people in the baby boom generation that worked late, late into their 70s, you know, and so a lot of us didn’t promote. We just kind of worked, right? We’re just, and so a lot of us are just hard-working people; we just, look, put, we put our nose to the grindstone sometimes to a fault, like, working late in the night working on things when, you know, just kind of push, push, push. And so we didn’t have that what that work-life balance that you’d hear a lot about, you know, I’m learning it even at this age. I’m still learning how to try to keep a balance. But yeah, I mean, that would, that would be the biggest thing. If you’re hiring somebody that knows how to just put their nose to the grindstone, figure stuff out, work harder than anybody else in the room to figure it out if they have to. And that’s, that’s the benefit of being a little older, I think.

Jordan  21:35

It’s just… it’s funny. You talk about Gen Z, millennials, Gen X. I won’t out the individual, but we had somebody at our office, who’s in Gen Z, show up to one of the meetings, and she was all excited to show off, she said, her emotional support blanket. It was, it was a friendly conversation. I said, I said, “Yeah,” I said, “Hey, listen, like let me help you understand how the different generations hear that phrase. Okay? Yeah, Gen X is like, I might need an emotional support blanket, but I’d be embarrassed to say it, and I’m not bringing it to the office. Okay. Gen Z is like, I have one. Look at this. And I said the millennials are like, ‘Oh my gosh, like, I think I need one of those. But I would never admit it, but maybe I will. But I like, I’m kind of jealous that you’re so open with it.’ Like those Gen X folks are looking… like, I’m not gonna admit that.” Yeah. Just to say…

Chris  22:30

Yeah, what are we? Yeah, what we do? Do we comment on it? Do we not comment on it? I don’t want to be, I don’t want to be offensive. Do I just stand back and smile? I don’t know what to say. Like, yeah, exactly. And there’s nothing wrong with it. Yeah, but yeah.

Jordan  22:43

But that’s what I was saying is like, hey, there’s nothing wrong with this at all. But they’re… each generation almost has this like connotation with each thing, or they hear things through different lenses; they position a little differently. And I said, “Hey, bring your blanket, you know, all day long, it’s all good. These are how the different generations would think about that, at least gut check, right?” And again, this is a huge generalization. I’m sure somebody here is gonna ping me after this and say, “I’m from Gen X. And that’s not true, you know.” But the point is, each generation has these things that they kind of lean into a little bit differently than others. So I think that’s a fantastic call out. So Chris, here, we’re, we’re starting to get toward the end. But I want to make sure we hit a couple more of these good questions. What advice do you have for anybody else out there that’s listening, that maybe they feel like they’re the old dog in SaaS? Like, personally, professionally, whatever, what do they need to hear right now?

Chris  23:40

You know, I know right now, things are kind of slow out there. People are, you know, getting laid off, etc. But if you’re in a situation where you can learn something, there are so many different platforms and technologies that you can get on right now and for free learn. And believe it or not, there are people ready to hire those people; there are so many people out there be like, “oh, you know how to do that?” You know how to do that?” Salesforce, the SEP platforms that are out there, there’s there’s like coding Apex, you know, all these different things that you can learn a lot of it for free. And if you’re in a situation where you could take the time, even if it takes you a little longer, learn it, and you’ll be surprised how quickly you can get a, get a position somewhere. There, there’s a need for it, even, even in your 50s. Believe it or not.

Jordan  24:35

Are you willing to share a low point, Chris, where you, you thought for a second, man, maybe I can’t do this and what you did to overcome that?

Chris  24:44

Yeah, you know, there were, especially when I was, when I left Outreach and went into an AE position. I… look it was a motion that I knew well. I worked, worked in government before. Worked… selling the government agencies. And, and when that company just decided one day to get rid of the sales team and go to Marketing after I had, you know, got gotten them over to a huge conference and they, they closed a bunch of deals, I thought I was done. I thought I might just leave this whole SaaS thing behind, you know, and luckily, there were a few people that just needed a little help, you know, not a lot, you know, five hours, 10 hours, whatever. And I got, I helped them out; I got a little money in my pocket. And that was, that was the… when I kind of got introduced to that team over to GTMStrat, and I would say, now GetPropulsion. And I felt like, you know, at that point, it was the lowest that I thought was leave, I thought, I don’t even know if I survived sales in general, like, I can just go work somewhere, you know, but that was a low point. And I guess the second low point is, when I was with Outreach, and things were just slow to start. But the one good thing we had was Outreach; we had Outreach to sell Outreach. And that kept us going because it kept us sending out messages; they kept us on track with the workflow that worked. And even though they were kind of building that on our backs, we were definitely in the right place. And, and luckily, that kept building and building. So…

Jordan  26:31

All right, last question. Any high points you want to share, like, “Man, when this happened, this was the highlight.”

Chris  26:37

Gosh, you know, I think I think the high point for me has been working with with, you know, Greaser Consulting. Honestly, I mean, I’m not saying that to kind of, you know, because you’re here, but, but honestly, I mean, I went… my income increased, my, the teams I worked with quality-wise increased. I think I’m in the best position I’ve ever been, and I’m looking forward to the next 10 years.

Jordan  27:07

There’s, there’s our next promotional clip and whenever we, we start hiring again. That blurb right there, Chris, like why should you work at Greaser Consulting? But hey, man, listen, I appreciate you coming on and for everybody listening. Here’s the truth. We tell people this all the time; Chris is our, if he isn’t a top performer, he’s right there in terms of top performer. I mean, arguably number one in terms of the quality of work he puts out, the way clients respond. Exactly right. That’s what you should say; my, my point in saying this is it’s a mistake. It’s definitely a mistake to look at some of the old dogs and say, “Ah, their time in the sun is done.” So I think the message of this session is, man, there’s, there’s a lot of life yet to live right Chris, there’s a lot of good work to do. And genuinely, I just want to say this to you and not the audience. I’ve appreciated your work over the years, the professionalism you bring, the honest feedback along the way. And how you can laugh at the fact that I fired you before. 

Chris  28:19

Oh, yeah, well, you know, business decision, obviously, and I don’t know if it was a good one, but you know, it is what it is/

Jordan  28:25

Oh, gee.

Chris  28:28

But you know what, I will say this, it… and to your credit, by letting me go, it really ignited me, and, and that’s what everybody… if you, you’ve been let go and you’re, you’re a little older, ignite it. Use it to ignite your career. There we go.

Jordan  28:45

We’ll just leave it at that. Thanks, everybody, for listening, Chris. Thanks for coming on. And we’ll see you next time. Thank you.


Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.

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