YOUR INTENTION MATTERS! The Sales Podcast
YOUR INTENTION MATTERS! The Sales Podcast
Ep. 214 - Jamie Jackson (Sales Leader Focused on building a high performing, dynamic team)
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Hey everybody, welcome to another episode of Your Intention Matters the Podcast. My name, of course, is Paul Madot. Thank you very much for being here. Today we have Jamie Jackson, sales leader, coming to us from the six in Toronto. Jamie, how are things, man?
SPEAKER_01Doing great. Excited to be here.
SPEAKER_00Good to reconnect. Been a long time.
SPEAKER_01It has been.
SPEAKER_00Yeah, how's your summer been?
SPEAKER_01So far, so good. Um, still out there doing deals and hopefully got some holidays planned for the tail end as well.
SPEAKER_00How about the World Cup? Have you been into it?
SPEAKER_01I have been. Uh I lived in England for many years, so I followed the World Cup quite closely. And England losing to Argentina was an absolute gut punch. So I think we're all still recovering.
SPEAKER_00I thought it was coming home, man.
SPEAKER_01Me too. Since 1966, look, we had a shot.
SPEAKER_00Well, as a Leafs fan, uh I'm 67, so I feel 66, right? So that's the real pain. So and it was nice to reconnect. Do me a favor if you would say hi and uh provide a quick intro if you would.
SPEAKER_01Sure, no problem. I'm Jamie Jackson, and I'm a frontline sales leader uh right now selling B2B services. And before that, of course, we met. I was in commercial real estate as a frontline sales leader. And before that, I led frontline sales teams and I was the CEO of a marketing agency uh before we grew it and sold it.
SPEAKER_00Gotcha. Married father, neither, both.
SPEAKER_01Married. Uh one daughter who's wonderful. And uh all the fun challenges which comes trying to balance out the family responsibilities with work. And as you know, in the sales business, it's not exactly nine to five. Um, there are times to do that. And that's one of the reasons why time management's so important in this job is it's not a nine to five job. And I don't think it ever has been, probably never will be.
SPEAKER_00Nine to five would be great, wouldn't it?
SPEAKER_01Would it? Wouldn't it be great?
SPEAKER_00Ha! You know, Jimmy, thanks again for being here. You know, as we were talking before I hit record, the context of the podcast is about mindset and intention and ultimately their roles and overachievement. Because from my perspective, you know, salespeople can be armed with every tool to go dominate product training and system training and skill set training. You can give them inbound leads as well, but if they're not wired up top mentally, as soon as they counter resistance, they're probably gonna crumble at the knees. And that's kind of the root of the podcast. And I'd love your thoughts on mindset in this world and overachievement as well from your chair.
SPEAKER_01Sure. Well, the the reason mindset's important is the same reason why they don't teach basketball this way. They don't say, you know, you know, if you're a basketball coach, here's every single thing that's gonna happen during the game and what you should do if that happens. Why do they not do that? Sorry, I know you had your mic off there. Why don't why don't basketball teams train that way?
SPEAKER_00Because it's not that effective. It's not gonna work. It's not gonna work. Why? Why isn't it gonna work? Yeah.
SPEAKER_01Say here's what's gonna happen in every situation.
SPEAKER_00Because it's tactics only.
SPEAKER_01Correct. It's tactics and it changes too quickly. And just like in basketball or hockey or whatnot, you're working on the basic drills, but what the mindset allows you to be able to do is put those all of those drills in context and to be able to pivot. How many times have you sat in a client meeting and it went in a completely different direction? I did it this week. I was sitting in a client and we had two specific ideas for them, really well researched. You know, I used Chat GPT and the whole thing to get rear, very specific data, really met with some people ahead of time to see what was going on. And it turns out only one of those two ideas actually had traction. And it turns out there was something else that we hadn't never talked about that was actually more valuable to them, than even more than those two ideas. So we had to pivot. And when you're in the right mindset, you have the confidence and the curiosity to be able to pivot. And that's part of mindset. The number one trait you talk about being wired right up top is curiosity. Tell me about that.
SPEAKER_00I love you, and congrats on having the foresight to make that change midstream and adjust accordingly.
SPEAKER_01Well, you have to just stop. And I mean, here's my record. Uh, I I I tend to prepare for plant meetings. Um, I like to be have very specific ideas, and we'll talk a little bit about that, but how to prepare for those. But even that, with all the time we think in ahead of time, I'd say probably 70% of the time, the client goes, Hey Jamie, really interesting. Don't care. Uh, here's what I really want to talk about. And you go in a completely different direction.
SPEAKER_00I think everybody can probably appreciate that comment listening for sure. So, Jamie, let's go back in time a little bit, if you would. I want to go back to uh to when you first got into sales, you know, with with my background. I took economics in school. I went into a bit of a finance background, and how I got into sales is I was laid off at the time, and a buddy of mine reached out and said, Hey, Xerox is hiring, you should apply for this sales job. And I I had a bit of a uh my mindset when it came to sales back then was it's kind of a dirty word. Why would I want to get into sales? I know I have no background here for this, and so I'm curious about how did you get into sales as a profession?
SPEAKER_01Yeah, um it's interesting. So I guess I was always doing sales growing up, different different jobs I'd have, different businesses I'd started. I was always doing sales, you know, selling golf clubs at a golf course and all sorts of other things, telecom, whatnot. But when it professionally, um I ended up getting into like a real full-time sales role when I got hired with this marketing agency, and they had some really interesting, uh, they had an incredible value proposition, and they had a lot of different uh salespeople. And they had a contracted sales force which had amazing sales production, but quality control issues, and they had an internal sales team, which had great quality but some production issues. And they said, we need somebody to figure this out. No one's ever figured this out, dig into it. So I did, I rolled up my sleeves, worked right alongside, learned that, and then ended up you know becoming the CEO of that company and before it was sold. But along the way, I thought it was really interesting because after I exited that, I kind of looked around. I didn't want to be in the same industry at that point. Um, and I wanted to change a career. And the only thing that I was really qualified to do was sales. So I went right into a frontline sales role again. And at the time I think it was really scary. Um, it was gosh, you know, can I still do this? Have things changed? Um, you know, am I gonna be pressuring people into doing things that they don't want to do? And I turns out that none of those things were true. Um, it turns out that um if you spend some time ahead of time, like I always do, thinking, how can I help this person? And you have a legitimate common sense-based reason of how you can help this person, things go really well. And I think that's part of the part of the mindset. People can tell right away. You know, as I talk about it a lot in in commercial real estate and commission breath. People can tell right away if you're there just to make a buck. If you're coming from a from a place, place of I can help this person, um, people get that right away. And it leads to a much more open conversation. And that's where I think mindset really comes in.
SPEAKER_00You know, Jimmy, I'm curious about something. You know, when I think about my own selling career, and I talked about how I kind of fell into it as opposed to this real forecasted plan and action plan and so on. I I when I think about my first year as a professional salesperson, I must have mentally quit half a dozen times in year one. I just I could not, I was all in, I was in early, I was out late, but I just couldn't figure it out. And I'm curious about your experience. Was it the same? Did you take to it right away? Was it harder than you thought? What was it like for you early on uh when you got into sales? Either early on before you became CEO or as a revision or as a revisit going back into an individual contributor's role.
SPEAKER_01Um, I think it was harder going back to an individual contributor role, but I had some some basics that helped. Um, that really helped. There's a couple of things. Just through being um, you know, in sports most of my life, you realize the amount of work it takes. And you know, how many times have you thought, okay, okay, so this went wrong on a call. Now I know what to do next time. And say, okay, next time that's it. It's gonna go great. And of course, you get on the call and something else goes wrong. Um that's incredibly disheartening. But you learn through sports and even music things that seem impossible in the beginning, you keep going. And it's you got to knock down a thousand of these things to actually get a real handle for how things go. And even then, you're never sure what's gonna happen. You never know what's gonna happen in a meeting. Anything could happen. Personally can hang up, they could have a heart attack. Um, anything. Um, so you'll never come to the end of it. And I think sports and music provide a good base. So was I ready to quit at those points? No. Um, I think I was, if anything, I got just discouraged with how many of those things that I needed to learn again. But I think I found my feet, again, as an individual contributor, quite quickly. Um for a couple of reasons. Um, one, I always kept really meticulous notes, not only in my client meetings, but my prospecting activity. I sent 37 emails, 27 follow-up emails, I made 13 phone calls, and I got this many meetings, and this many meetings turned into this many opportunities. And because I was able to keep track of that on a numeric basis, I was able to adjust a lot faster.
SPEAKER_00You know, Jimmy, you mentioned earlier in our conversation that uh you and I met from your commercial real estate days. And so I know you as a sales leader as opposed to a sales rep, so to speak. And so when I think about my own career, I went through the the path of sales rep, product specialist, and sales manager. And sales managing and being a sales leader, director, VP, and so on is totally different than being an individual salesperson, different skill set, different requirements, different responsibilities. It's totally different. Both are challenging, of course, but they're very different. And I was so ineffective as a sales manager because the way that I managed was here's how I did it, so here's how you should do it, which was just like a recipe for disaster. And so, but I but I had it in my head that I I have to go to I have to go to this level, I have to go from rep to manager, and I'm curious about your choice to do that. Was that yours? Or someone did someone tap you on the shoulder to say, hey, consider this, or what was your path going from sales rep, so to speak, into sales leadership?
SPEAKER_01The second time around, yeah. I got tapped per shoulder, and I thought it was an interesting opportunity because I got to influence the direction of what that was going and even even product development. So what not only you know who we're selling to and what the process looked like, but actually what we were selling, and it allowed me uh just a little bit more control over how to do that, and that to me was really interesting. Um yeah, I think it was it was hard for me to be making that transition into sales management because I thought we would be focused very clearly on to a certain extent, yeah. What worked for me. It's like your job as a rep is to book meetings with people that you don't know. That's it. All the rest of it is like everything bowls down to that thing. If you can do that thing, you've got a career in sales. If you can't, you need to find a new career.
SPEAKER_00Because that's so true.
SPEAKER_01It's just booking meetings. You're not selling anything, you're booking meetings with people that you don't know and piloting that conversation from that point forwards. There's there's there's bluntly, there's a lot of people that can do that. Um, there's a lot of different folks that can apply a lot of expertise to that. But getting to that person, getting convincing them to take a meeting and getting them to show up, that's the key. And when I found that I had so many other things that would get in the way of developing that and holding people accountable to say you're booking meetings. And the other thing I discovered too was that there's a good chunk of people that were never going to be able to do that. They were really good account managers. Clients liked them, they got it done, the accounts grew, perfect. But the skill set for hunting was completely different from the skill set from farming. And delineating those two roles was really, really key. And the the skill sets, like those are completely different jobs, suitable for completely different people, is what I learned. I think that was my biggest learning point.
SPEAKER_00You know, Jimmy, as you think about your your career over the past 20, 25 years or so, maybe more. Any time come to mind where you were challenged, you had to really kind of dig in mentally and kind of figure it out.
SPEAKER_01Lots. Lots. Um wow, so many. I think I think the the most one was when I started with the marketing agency, and they gave me this completely unstructured problem. Contracted Salesforce, great production, poor quality, internal sales force, great quality, poor production. And they just didn't figure it out. No one knows what's going on there. No one no one has any idea. And it was um, I think definitely that you know the imposter syndrome arose. And you think, oh, who might have figured this out? Um but there was an enormous amount of goodwill built with both teams just by showing up and listening. Show up and listen, it you know, is really funny. Uh the older I get, the less I think it's it's about having the right answers, particularly as a sales leader, it's not about having the right answers, it's about asking the right questions. Um a lot of the time, somebody just needs someone to listen to and to to care. That alone will put you in the top tier of sales management. Care about your people. That's it. And that helps a lot. And if you uh because I went in with a listening mentality, I think that bought me a lot of goodwill and got me through that initial period of you know, unconscious incompetence, conscious incompetence, and and back up the back up the tiers.
SPEAKER_00You know, Jamie, I'm I'm curious, I'm curious about something because I met you, if I recall correctly, kind of in the heart of COVID 2020, 2020, 2021, 2022, kind of it was in that kind of like 18 to 36 month period, and you mentioned you were in commercial real estate, if I recall correctly, you were leading the office leasing side of the coin. And at the time, the the whole work from home movement was prominent. And so, how did you manage that?
SPEAKER_01With great challenges. I mean, there was another challenging point, too. Here's somebody like me who came into commercial real estate not having been in the real estate industry their entire life. That was very unusual. Everybody comes into commercial and they stay there. And here was me coming in, and I think that was a variety of challenges because I didn't have a lot of the technical real estate skills to be able to advise these folks. Um and yeah, in the height of COVID for office leasing when everything was was tanking, um, I think there was two things that helped. That was a very no, there's no getting around it. That was a really challenging time. Yeah, there's no way around it. It was really hard. There was a couple of things that helped. One, just listening. I think listening to people's frustrations uh helped. And I think also delineating what I can do to help and what I can't. I was really honest with everybody and say, look, if you throw this transaction in front of me and want some real technical advice, I'm probably not your guy. Um, what I can do is I can say, I've been the guy on the other side of this desk for as a CEO doing the transaction, and I can tell you about what's important, what they care about, and what approaches really work. And I can help you tailor that to that person and really focus on the business development aspect of getting meetings with people that we don't know. I can help with that. Um, and I think those two things helped. But I mean, was it a wonderful happy time with everybody high-fiving each other? No, no, it wasn't.
SPEAKER_00Well, congratulations uh on figuring it out and kind of battling through a global problem. But like I said, in in your world, it hit harder and different because there's no one in the office. Like there was nobody there. If anything, it was just a so how do you have a conversation about renewing a lease for five years when it's when it's empty desks, right? So congratulations on figuring it out.
SPEAKER_01I don't know if we did. I think we I think we weighted it out and we doubled down on the basics, which is keeping in touch with your clients, solving their problems, and talking to people that you don't know and trying to help. And when they were trying to downsize, we were there to help. And then now that the you know it's going the other way, we're still there to help. And they'll remember. They will remember your clients remember, again, it's about mindset. If you have the right mindset as I'm trying to help this person, they remember they remember because you spent the time with them, which is your currency as a salesperson, when you knew you weren't going to make any money out of them. And they knew that as well. And then when it's time to actually do a transaction, they remember.
SPEAKER_00Well said. You know, Jamie, I always like to close the kind of the podcast around best practices and things that have served you well. If you think about your career, any advice been given to you or any advice you would pass forward if anybody's listening, like one best practice that comes to mind.
SPEAKER_01There's a few. I've always had um really good mentors. So it's that's it's actually uh there's a bunch of different advice. Um, I one I had a mentor when I lived overseas. His name was Jonathan, and we were about to pitch this client. And I said, Well, here's you know, what I think about this, what did I think about this? And he said, Jamie, no one cares. Here's the one question you need to answer. Why should I care? That is the only question as a salesperson you need to answer. That's it. There might be technical expertise, and in this particular instance, there was. There's a ton of technical expertise that I was never gonna have. Um But what can you? Why would this person care? Why it's the benefit to them given their specific situation? That was the single best piece of advice as a salesperson and a sales leader I think I've ever got, which is your job is to translate into who cares. You will never be an expert in everything you can't be. Don't even try. Be an expert where you need to be, but realize that your main expertise is listening to that person, understanding the situation, and mapping out some steps forward in a way that would help them. And if you have a really credible answer for who cares, everything else falls into place.
SPEAKER_00I love that. I love it. Jimmy, great to reconnect, man. Thanks for being here.
SPEAKER_01Not a problem. Anytime.
SPEAKER_00All right. Listen, everybody, thanks for being here. We're gonna wrap it up right now. Remember, as I always say, your intention matters. Why? Because that's the result we'll tend to get. We'll see you on the next episode.