E47: How Losing a $1M Deal Led to Achieving 29 President Clubs with Stephen Cottrell

There was an opportunity. I was in Sydney with a large airline and it was a 7-figure opportunity. And at the time I'd been told by the project manager that I'd been selected and I could expect an order. So I was really excited and I think I told my manager and a few colleagues and was, you know, sent the paperwork over and the paperwork and the signature never came. And what I found out is that, you know, IBM had gone in, swooped in and with a team of 40 and, you know, we're talking to lines of business I didn't even know existed. Right. So it was a lesson, a hard lesson to learn, but it was, I was never in that deal. I was single-threaded, as they say, I only had one contact and I was taught a big lesson and they completely outflanked me, had me, had the 3 levels above where I was in the deal. So they got the order signed, got the deal done, and that was an aha moment for me personally.

Welcome to the High Performance Sales Leader Podcast. And today my guest is Stephen Cottrell, and I'm so excited to have this episode because I literally do not know anyone else who has had more President's Club, which he's done 29 out of 35 years. And I remember my first year in sales, if you could get to club, you were already walking on the cloud. So Stephen's worked with some amazing companies. He's worked with IBM. He's worked with Sumo Logic. He's worked with Atlassian. And he's had some really solid stints, 4, 5, 6 years in each. And within each, he's just made club after club. He's sold in 48 countries. He's done over $1 billion USD in transactions. And, you know, he says that his job is getting punched in the face. So Stephen, thank you so much for joining me for this conversation.

Yeah, thanks for having me. Exciting.

Fantastic. Now, you know, you, you and I were talking about Seinfeld, but before that you had told me about getting inducted into the Hall of Fame for tennis. So just tell me a little bit more about, uh, the, you know, how did that come about?

Oh, just in my hometown when I was in high school. My high school has a Hall of Fame. So it was a nice surprise last year to get inducted into that. Brought my daughter and my wife over. That was a lot of fun. Got to see a lot of old friends and people that I hadn't seen in many, many years. So that was a really, really nice surprise.

Fantastic. One thing I see consistently is this connection between achievement in sport and achievement in sales. So what sport were you in this Hall of Fame? Just tell me a little bit more about that.

Yes, I was a tennis player growing up. And I think the, what attracts me about sport is you get in a lot of close situations. It's a lot of tension, a lot of stressful situations that you have to work your way out of. It's like a chess match and kind of think, think through it and really lean on yourself. When you're on the tennis court, you're only by yourself. There's no one that can help you. There's no team. I really did enjoy being on a university team. My senior year, we won our conference championship and went out in style. So that was really fun. I loved being part of a team and that team atmosphere really encourages you to, you have to really stretch yourself. I took a leadership role. I was captain of the team. So that had a lot of life lessons that you can carry on into the business world. I think that was invaluable.

And I'm not surprised. And that's the reason why even when we go and look for sales talent, if I've seen that they've achieved something with sport, Already the probability is stacked that we are already ahead in terms of a potentially good hire. So anyway, back to your story and let's start with Boston because you talked me up, you told me about noodles, rats, Boston. So that's stuck in my head. But 29, before the 29 clubs, start us there. Sure.

Sure.

How did that come about?

Yeah.

Yeah.

No, I can say, I would say that first off, sales is the hardest job in the world. If you think about it, you're trying to get people to give you their money. And that's not easy to do. No one wants to give away their money. And in a lot of cases, their company's money. And a lot of people that I talk to, they think of it as their money is the company's money. So it's extremely difficult to do. That's probably one of the reasons why I love it first off. So for me personally, It started about 6 years old. I was selling lemonade in front of my house as a lot of kids do at a young age. And this car went by and I think they felt sorry for me because it was a hot day and I was sitting there and I sold them my first glass of lemonade and we had a circle. They had to drive up and go around. And I think what I learned very quickly was I could double my money. So I would cross the street to the neighbor's house and then set up again and they'd come, have to come by me again and feel guilty seeing me again. So, so I was able to double my money. I think I probably made probably $10 instead of $5. Right. So, so that taught me at a very early age, you know, how to, how to maximize sales potential and revenue. But in all due respect, what, what then happened was I had older brothers. So I built a lot of resiliency and toughness in me because we were playing a lot of sport growing up. So we fought every day and I was the youngest. So I pretty much copped it every day. So I was not very successful in the fights and I always tried to keep up and that helped me do well with my own peers because I was playing against my brothers all the time. And so that kind of built some resiliency and toughness and competitiveness in me, I think. Carried that on to college where I played Division I tennis. So that was a lot of fun and taught me a lot of life lessons that I could transfer into the business world. And then when I got to Boston, the whole noodles thing was I was living in an apartment in the North End in Boston. It's the Italian district in the back of a cafe. It was a little studio apartment with a, we actually had a tiny, tiny little bedroom. And I was thinking I was paying about $20,000 in rent per year. And I remember my wages were $22,000. So you can see that that did not leave much discretionary income for me to, to, to entertain or to, to have fun with. So I quickly learned that, you know, I was quite successful. I, they would give free meals during the week if you, if you attended and worked over hours. Oh my gosh. And I was, I was at every one, not because I wanted to work the overtime, but because I wanted the free dinner because I didn't have much, much money, discretionary income. So, so I was living in very expensive Boston at the time. And I remember being woken up by this loud noise. I was, I would eat noodles and spaghetti pretty much every night because it was cheap and I could, I could afford it. So that's where the noodles come from, the 2-minute noodles. I became an expert in boiling water and that was the extent of my cooking. And I would cook, eat spaghetti. So pretty much spaghetti or noodles was, was, was on the menu every night. But I, anyways, I heard a loud bang, a loud noise. And I got up one evening, turned on the light and there was 2 giant rats sitting there staring at me. And as in my kitchen, like, you know, what do you want? Right. So they took off and thank goodness, cause they were pretty, pretty large. And, and that was my aha moment that, you know, this wasn't going to work out. So I eventually, when my lease was up, moved out and moved to the To more of a suburb where it wasn't as expensive and got into IT sales where I remember my first, Tom Kelson was my first manager. He worked for, he works with Google now. And he taught me a lot and I really respected him. He really, I had the sales in me, but he really showed me the way of how to be successful at sales and working for a startup for him. And it was, I remember him telling me, you got an opportunity to double your money. And I was, At that point, I was so broke, I would've— I leaped at it and money kind of made the decision for me there because I had none. So, but that was probably the start of my noodles and rats.

Now you talked about an aha moment because I think a lot of people, aha moments and pivotal moments change the course sometimes, and often it actually is from a negative experience. Not always, but What were some of the significant moments that have brought you along the way that you're up, you have come?

Right. Right. Well, like a lot of new reps in the space, I took some lumps early on and it's, I guess that's the only way to learn a lot of times is by people can tell you things, but until you experience it yourself, right? That's the best way to find it. And I really was unsuccessful at a deal. In Sydney, I had moved over to Sydney with a company called PTC, Parametric Technology Corporation. They developed the, the Medic. I was one of the first people to go through Medic, but I was working with them. And there was an opportunity. I was in Sydney with large airline and it was a 7-figure opportunity. And at the time I'd been told by the project manager that I had been selected and I could expect an order. So I was. Really excited. And I think I told my manager and a few colleagues and was, you know, sent the paperwork over and the paperwork and the signature never came. And what I found out is that, you know, IBM had gone in, swooped in and with a team of 40 and, you know, we're talking to lines of business I didn't even know existed. Right. So it was a, a lesson, a hard lesson to learn, but it was, I was never in that deal. I was single-threaded. As they say, I only had one contact and I was taught a big lesson. They completely outflanked me, had me 3 levels above where I was in the deal. So they got the order signed, got the deal done. And that was an aha moment for me personally. I thought to myself, I need to come up with, rather than relying on randomness or luck, I need to come up with a methodology. And that's when MEDIC was born. I was the first one to go through the MEDIC training at PTC, and it was incredible for me. It was a real eye-opener. It helped with the probability of getting a deal. So that was a big moment for me.

And that's really interesting that you say that because, you know, the probability of getting a deal, I would say, is actually a superpower because I know so many people who have literally You know, depended on one deal to happen and then they got, get found out 2 or 3 quarters later, they get fired. They've done a year and a half here, a year and a half there. And, you know, it almost seems too good to be true when you say outta 29 outta 36 years you've made sub, and some of the ones that you didn't were actually because either the company didn't have it or they were, you know, half-year starts and finishes. So tell me more about Medic. Methodology and just having powerful pattern recognition and habits, you know, across the process so that you can manufacture excellence, right?

Right, right. Yeah, I, look, I think there's some key characteristics that go with that, right? First off, you have to have passion for what you do, right? If you don't have passion, I would say go find something else to do because sales is hard to begin with. And if you don't have the passion for it, You will never be successful at it, in my opinion. You know, I always strive to be 1% better, you know, the Atomic Habits, right? You know, you're better each day, continue to learn. I think you've got to have some grit to be successful. And that is, I don't think is completely can be learned. I think you have to develop that along your younger years. For me, I developed it through my older brothers and my Sports background, playing competitive sport. And I think that needs to be cultivated. I don't think you just, you just have it or you don't. The other thing is you have to continue to want to learn, right? And then I was always very curious and want to be a sponge. And then along with what you say is you got to have a process, whatever that process may be. Mine was medic, right? But you need a process, a methodology to be successful, right? And And I think, you know, following medic, you're not going to close every deal, right? But what it helps you do is find the gaps in where you are and be more successful. So instead of maybe winning 10% of deals, you got to, you can win 70%, 60 or 70% of deals. And that's a big jump, right? And I think what I learned along too is with process, there was a great coach in the US named Nick Saban. I don't know if you've ever heard of Nick Saban.

Yeah.

He coached in the NFL. He coached Alabama to an incredible, I think, 3 national championships in 5 years. And he talked about, I saw at a very early age about his process. He said, look, I coached a team one year. It was 5 and 6, and we had to play the number 1 team in the country, Ohio State. And he said what he tried to take a different approach, because if he took the same approach, he said it would've been a loss. So his approach was he was going to Put 100% effort in on every play. And if the play wasn't successful, they'd line up for the next play and give 100% effort. And regardless of the outcome, right, he would give 100% effort for each play and not look at the scoreboard and focus on the present and each moment that they can control, right? Because they couldn't control the rest. And they actually upset and beat Ohio State in a very famous game. And, and that was the start of follow the process with, with, it's very big in the US and, and trust in the process, right? He actually defined that and he took that approach in his coaching career and was extremely successful. And I've tried to adopt that in my own career in sales and just focus on what I can control, which is not very much, but Focus on what I can control and each day try and give 100% effort for what I can do. And then hopefully good things come as a result.

So what you're just saying is absolute golden. I wish that this was mandatory for people, you know, getting into sales. I went, I got into sales through Xerox. You know, they ensured that, you know, before you set foot or talk to a customer, you were trained and you were retrained and then you were coached again. until everything was managed and measured. So, give me a quick rundown of MEDIC and how it has helped you, because for someone who doesn't know what MEDIC is.

Sure.

Yeah, sure.

Yeah, the M stands for metric, and that is a, if you can try and find something that's quantifiable, either a time savings with your solution or a dollar savings, that's really hard to get. But if you can do that, a benefit to the customer, then you show value, right? If you don't show value, then you have no chance. If you're gonna— I see a lot of reps talk about features and benefits, and there's a lot of toys out there that have features and benefits, and every product has good features and benefits. So you're just gonna be another commodity, another, another toy. But if you can find a metric to hang your hat on, some sort of savings you can provide the company, then you've got something to go on. And the E stands for economic buyer. So that's like the person that has power over discretionary funds that can actually sign the order form. A lot of time I've seen reps, including myself, you work and you think you've got a deal and you give a price even or a quote, and then the person says to you, I'm not the decision maker, right? You've got to talk to so-and-so. And then you go to that person, they say, I'm not even looking, this isn't even an initiative I'm looking at right now. So I found that out the hard way as well. So ideally you should top-down sell and work with finding that person that can do that. D is the first one is decision criteria. So how are they going to choose A over B? How are they going to evaluate your solution? And typically a lot of companies use a matrix or an RFP. There's a lot of RFPs in Australia. Unfortunately, I'm not a big RFP fan because they take up a lot of time and a lot of time they're very generic. In nature, so they're not really geared towards what you're selling. Sometimes, sometimes they are. And then the next one is decision process. What's the process that they're going to do to make a decision? So I like to say, and then what happens? They say, oh well, we're going to have this panel set up, and then what happens? And then we're going to meet and have demos from all the competitors, and then what happens? Right. So I like to. Find out what that process is. So, you know, is it 2 months? Is it 3 months? Is it 6 months? And that all goes into when you forecast a deal to having a successful forecast that you commit to management. You try to, I try to have a 10% variance on my forecast. So that helps you do it. And then the I is identify a pain. At the end of the day, if you can't identify a pain, you have nothing to sell them. So that's probably the most important is You know, what is their pain, right? And can you, does your solution help them with that pain, right? Because they're looking for something that's going to help them. And then lastly would be champion, right? So that's, do you have someone who's selling internally when you're not at that organization? Because 99% of the, 99.9% of the time you're not at that company, right? So who's selling on your behalf? Who's talking about your solution when you're not there, right? And sometimes there's no one and those deals are very I don't think I've ever won a deal without having a champion. Right. And often, you know, one of the big mistakes is people mistake coaches for champions. You think someone's a champion, but they're not really in the power base. A champion needs to be in the power base and can have influence. A lot of times I've talked to people and they're, I think they're a champion and they, let's get the deal done and they can't get it done or don't have the authority or power or influence. And that's a tough lesson to swallow as well. So that's probably a common mistake that I see as well. But then they've added some med pic, they've added a paper process, they've added another C, compelling event, why buy now? I've seen MEDIC with an extra C. So, there's been a lot of variations over the years to it and a lot of new systems that have been morphed from MEDIC, but that was my original understanding of MEDIC.

Fantastic. So, now we've got a process and now you bring the person to the process. So, what are some of the non-negotiable habits If I want to set up a year that is the start of the year, you know, want to make club, you know, you get the trip, you get the accelerators. You know, I remember, you know, my sales manager, this was the late '90s. This, my sales manager said, Pri, this is going to be the best job and the worst job you've ever had. Right. It just depends whether you're winning or you're losing.

That's true. That's true. Yeah.

Tell me, what are the non-negotiable habits that set you up for a club year?

Yeah. I would say the first one is consistency, right? Is consistency of your process, right? Whatever that process you have, it works for you. And they're, you know, everybody's different. So what works for me may not work for somebody else. So whatever that process is about consistency, I remember John Howard getting on A podcast I listened to, they said, they said, you walk every day, John. How do you stay so fit? He goes, I walk every day. You go, what if it rains? I walk every day. What if it's sunny out, too hot? I walk every day. So the point that he made was he was very consistent, right? He walked every day. That's why John Howard's so fit, even at his senior years, right? Because it's about consistency. So that's number one. So whatever your process be, I would say consistency. You know, I would say the other big thing is be genuine, right? That's for me, that's the most important. I'm talking right now on this podcast. I don't have any agenda. I'm, I'm, I'm, I'm, I'm me, right? I'm very raw. I'm not afraid to make fun of myself. I make mistakes just probably more than most people, right? So, so I don't claim to be anything that I'm not. You know, I would say I see a lot of people change personas when they get on a call or try to be something that they're not. You know, some people ask me, are you having a good day? And I'm on a call. I'll say, Actually, I'm having a pretty crappy day and I'll tell them why. And I think, I think that resonates because people like you to keep it real and be transparent. I've found that's the only way I know how to be. So that would be a big one. And then I would say, you know, my dad used to tell me as a kid, you can never please, you can please some of the people some of the time. You can never please all the people all the time. And that really stuck with me because I used to kind of be a people pleaser in my early days. And you want everybody to like you. And you know what, not everyone's going to like you and that's okay. Right. They didn't, maybe they don't like what I'm wearing that day or the look of my face or my accent or whatever it may be. Right. Or they've had a bad day. Right. There's lots of different reasons why, or they, or they're, they liked a competitor or they, you know, there's always different agendas and reasons and, you know, you're never going to please everybody. So I don't, I just am who I am. And if people don't like me, that's okay. Right. If they do like me, that's a bonus. And, you know, I just try to, to, to help, you know, to, to build their confidence that I'm a trusted advisor and a consultant and that I'm there to help them, right? And most of the time they can see that and sometimes they can't. And I, those are probably the deals that I don't win or I lose. And I just have, you just have to move on because you can only control so much.

So you've talked about consistency, you've talked about authenticity, you've talked about having a process. What else would you say? Is there anything else just set up for a year that if you do these things, you're gonna make clump.

Yeah. I would say another one is get comfortable with being uncomfortable.

Please.

Because the IT industry that we're in changes so rapidly. You know, if I look at in the last 6 months even, you know, there was no one was talking about AI, you know, 9 months ago, right? I should say, but now everybody's talking about AI and You know, not only are they talking about generative AI, but they're talking about beyond that, right? And what's next. So you can never, I would say you always have to constantly reinvent yourself. You constantly have to stay in tune with the nuances of the industry. So, you know, I'm constantly a ferocious reader and listener to your podcast as well and LinkedIn and whatever else you can pick up. Because I would say the biggest thing is you have to adapt to change. And you have to be willing and want to change. If you're not wanting to change or passionate for what you do, gets back to the passion, then it's gonna be hard to be successful.

Fantastic. The last thing that I'm gonna ask on from habits, you know, and whether it's with sport, whether it's with sales, tell me about activity and work rate. How does that sit in terms of setting up yourself for success?

Yeah. I look, I always took the motto myself that if I don't win, I'm okay with it as long as I haven't been outworked. Right. So I will try to outwork because I'm not the smartest. I'm not dumb, but I'm not the smartest guy in the room either. Right. I don't try to be, but my point is I have to really work hard because if I do, if I work 70%, I'll do 70% of my number, right? Or less, right? I won't be successful. So I have to give 110% every day for me to be, for myself to be successful, right? And that goes to if I'm supporting a customer, if I'm, you know, providing that customer information, you know, I'm very responsive. Customers and prospects who know me, I try to get back to them quickly with what they need and clearly and answer what they need, right? So, So I have to, you know, really work hard. My work rate is, is probably 70 to 80 hours a week. Everyone knows me in the company. They think I'm a bit of a, I probably annoyed a few people over the years. I definitely have with calls to the US at strange hours and, you know, but, but I, I do it all for the customer. Right. And, and, and all, if I'm in there, I put myself in their shoes and they need things quickly. A lot of times their, their job may be on the line or they're just, or their, their, their budget or their decisions. So I, I, I'm going to work fast. And I try to use that speed of velocity to help them get what they need. And in turn, if I can do that, then hopefully that makes me successful as well.

All right. Well, we're going to wrap up with this question. You've done the triple jump and triple jump, in my opinion, is change. You've changed countries. You've sold in 48 countries, but you've actually lived in multiple countries as well. Sure. changed functions. You know, you've been a leader, you've been an individual contributor, you work for some large organizations, you work for startup, you're currently in a, you know, pre-IPO, fast-growing organization. I guess the question is, how does— and you've made club in all of those situations, which is impressive. I can see that shelf behind you, and that is enviable. Envious. So What that, you know, how does each shape, you know, each transition shape you and how do you manage to, you know, cope with the change, continue with the change and still keep coming out, you know, in terms of achieving your numbers and the goals that you've set yourself?

Right, right. Look, I think early on in my career, it was fear of failure that probably drove me to be successful. I was so I was, I was always in survival mode, right? I was always trying to living in, living in the city, right? Big expenses, right? And trying to cover big expenses and, and, and have a bit of lifestyle as well, you know, because you can't, you can't bring it with you as they say, right? So you've got to enjoy a little bit of along the way. And so I think that was what really drove me. I think now later in my career, it's more the thrill of success. And I get that by providing, really helping a customer, right, to achieve something great, to get them a win, you know, finding out their— what's the win for them. And that really gets me excited when we get a deal together, because I always try to make my situation win for the client and win for myself, not just a win for me and a loss for the client. So it's always a win-win. We're in it together. You know, I try to be a good partner, not a vendor. And I think that that has been very successful for me, that approach over the years, whether I worked for a small company or a large company like an IBM, I've always tried to take a partnership approach. And, and that's resonated pretty well with, with customers over the years. And I don't, I don't profess to win all the deals all the time. I don't. I'm often on the, I don't tell you about, I did a billion dollars US in transactions over the years. I don't tell you about Probably the $2 billion that I've lost. But, you know, in terms of, in terms of, you know, all I can do is control how I react to situations, right? I've learned my reaction and that's, for me, it's about the process. It's about being a good partner, being genuine and, and, you know, my work rate is high.

Yeah. Yeah. Well, this has been an incredibly insightful conversation. I think that shelf behind you says it all. You cannot buy those things. You can only earn those things. They can only be earned. So, you know, you, what you've said today is all earned experience and that is worth, worth gold and more. So thank you. I appreciate you so much. And I, I love seeing your LinkedIn posts, you know, thank you customer in Sydney. Thank you customer.

Thank you so much.

But it's, it's been amazing. Thank you so much. Yeah.

Thank you. Thanks. Thank you for having me on the show. All the best.