Sales Hustle is now Sales Transformation
March 30, 2022

#275 S2 Episode 144 - From Being Fired to Selling Mega Deals with Jamal Reimer

A 20 year veteran enterprise seller who cracked the code and sold exponentially large enterprise deals, and now the owner of Mega Deal Secrets, Jamal Reimer surely knows what it’s like to be pounded by rejection, and what it takes to succeed. Jamal joins Collin in this latest episode of Sale Transformation, to share his sales journey and how he was able to close deals valuing up to a whopping $160 million!

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  • Humble beginnings in door-to-door sales
  • The journey to SAS Sales
  • How Jamal started selling mega deals
  • Jamal moves again from working to entrepreneurship
  • Jamal’s book: Mega Deal Secrets
  • Utilizing executives and the right people for mega deals


Jamal: “I sucked my first year, I worked 80 hours a week for 13 weeks, and I came home with 2200 bucks. Well, I was so scared of the experience, I was so beaten up by the rejection, that I actually had an interesting response, I said ‘ ‘I just can't let something that I'm that scared of, to exist’ ’. So I gotta go back. And I kind of do it again. And so I'm not that scared. And so I did.”

Jamal: “I got into a rut where I got fired twice in a row for underperforming. I just couldn't get my arms around how to sell what I was selling.”

Jamal: “A high quality, buying and selling process can lead to the establishment of a relationship and a model that almost has its own moat around it. That would be tough as nails for a competitor to come in and try to eat down. “

Jamal: “I want to stay with the executives. It's more fun, it's simpler, you get more done in like a fraction of the time. And that was kind of the permanent change in my mindset. I'm like, I want to go to the top, because that's where stuff gets done.”

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell. And this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:29] Hey, before we start today's episode, I wanted to bring you in on the best kept secret in B2B sales. If you're serious about social selling and your only strategy is cold DMS through LinkedIn, you're missing the mark big time. Learn how I fully managed revenue generating podcasts can change your life and your

[00:00:56] All right. Welcome to another episode of sales transformation today. I've got Jamal Reimer. Uh, he is the owner over at mega deal secrets. Jamal is has 20 year veteran of enterprise seller who has cracked the code to selling exponentially large enterprise deals. Having closed 160 million in sales. Revenue as an individual contributor for small vendors and top global SAF software, SAS software providers.

[00:01:26] I can't speak today. Jamal. How are you doing? I'm doing well. I'm going to be here. Yeah. Thanks so much for coming on the show. Um, take us back a little bit. Like where did your sales journey start? And then let's go from there. Uh, I had a very illustrious beginning to sales, um, when I was a freshman in college.

[00:01:46] I had maybe the year before that returned from Africa, my parents were living in Africa. It was South Africa. The currency had plummeted and they couldn't pay for college. So I had to come up with a way to do that really quickly. And I was basically recruited by a fellow student to go sell books, door to door and long story short.

[00:02:13] That was my first experience in selling. I sucked my first year, I worked 80 hours a week for 13 weeks and I came home with $2,200. Oh wow. I was so scared of the experience. I was so. Beaten up by the rejection that I actually had an interesting response. I said, I just can't let there be something that I'm that scared of.

[00:02:35] To exist. So I got to go back and I got to do it again. And so I'm not that scared. So I did, and it turned out to be a kind of a, a student career. I did it for five summers and just got better and better every year, by the end of it, I, I, I made enough money to fund a service project, which was to do a video, traveled to these different places around the world where young people were doing, uh, acts of service.

[00:03:03] And I made a video about that to promote young people access services. That was cool. Wow. Okay. Kind of crazy. Most people would have. You know, ran, ran for the fences. They're having an experience of getting beat up from door to door selling, right? Yeah. Yeah. It was traumatic. I'll leave there. It's it's funny though, because I've talked to a lot of people that have had very successful careers in sales, you know, like yourself.

[00:03:31] Um, and many of them started door to door, you know, whether it's selling Cutco or books or magazine subscriptions, like you name it. Um, Yeah. I mean, it's, it's one thing to cold call on a phone and get hung up on are called, you know, Some certain names, you know, but door to door, like, you know, it's a whole different story.

[00:03:57] I mean, the, the, the short kind of essence of what that experience is like is my first summer we went to the Midwest and it was small towns in Kansas and evidently. Every other type of door to door seller had already been through this area. And it was my first year and I had no thick skin whatsoever, you know?

[00:04:20] And I went, I was getting beaten up right in the left for a whole week, was like my first week at doing this. And at the end of that week, I went into this one older home that had a porch and a screen door. No, it is blazing hot, a hundred degrees, really humid. And I knocked on the door and I could hear the.

[00:04:43] And then just through the screen, I could see through the shadows kind of a half a face come forward. And this whisper was like, what do you want? I started my little approach in my little spiel, and then I just heard, I don't know. That you have,

[00:05:06] uh, that was kind of one of the lowest points of the summer that I had to learn how to rebound from. And I'm glad that I did cause, uh, it, uh, it left the door open to have a great career in sales. Yeah. So, all right, so let's fast forward a little bit. Tell me when, when did you get into SAS sales? Uh, it was after I was a failed startup.

[00:05:29] Wow. My, uh, my, my partner and I, uh, I, I left San Francisco where I had a beautiful life as a, uh, a banker. I was, I worked at Citibank when I worked in the CD bank, private bank, taking care of superly, uh, rich people. And I left that to go to Seattle to start a startup. We did it for two years and it failed.

[00:05:50] And then I moved to Chicago to be close to some people, uh, some really good friends of mine. And I got a job at a software company that wanted somebody to sell for them to open up the financial services market. And I got the job because, uh, the startup was about financial services. My background was in banking, but I never sold a thing other than books in adult life.

[00:06:13] Okay. And so, and, and so the, that, so, uh, After the banking, then you went into SAS sales or was that where you were you a founder of that company? Part founders. This is before SAS sales. I'm a hundred years old. I'm 53 years old software at that time was on-premise software, right? Discs that you put into your servers within your firewall and fire it up and use it as you like SAS wasn't invented for almost another decade until after that.

[00:06:45] Got it. Okay. And then what, um, when, when did you, what ha what went wrong with, with entrepreneurship for you? Um, our, our market idea was, uh, our, our, our business idea was market sensitive. We, we were kind of like Carta, you know, if you know, Carta, they're the ones that hold all of your equity-based compensation and you can see how many shares do you have?

[00:07:08] How many options have you been granted and how many of them are. Uh, our, our, uh, uh, have you exercised or had vested, et cetera? We had that idea in 1999. And when the market crashed, nobody wanted to emphasize their equity based compensation because everybody was underwater. So we didn't have a business.

[00:07:29] We folded that just bad times. Yeah. Yeah. Okay. And then, so then after, after that, um, well I'm curious though, from going, you know, from, from previous roles into entrepreneurship, like how do you think that helped you? Did you, what did you learn through that experience? I mean, um, so you, you, you move from having to take care of everything to having a very narrow purview, but when you are talking with.

[00:08:01] Um, executives or, or management, you, you have a wider perspective and it's easier to make that jump from talking about features and functions and software into business outcomes and what they're trying to achieve and earnings per share and how you, the deal with that. Wow. Okay. And I'm curious if that, do you think that experience helped.

[00:08:27] Kind of shape, you know, the work that you do today, helping people close mega deals. Um, yeah, but it got worse before it got better. Okay. Tell me more. Um, the first career, the first decade of my selling career, excuse me, was, uh, was really miss. I started out with a bang. And then, um, I got, uh, there was a series of smaller companies that I worked for and there was a w I got into a rut where I got fired twice in a row for underperforming.

[00:09:06] I just. Yeah, my arms around how to sell what I was selling. So twice in a row I was, I was fired. And then after that, I was like, is this really for me? Am I, am I the right guy for it? And all that kind of stuff to the point where the recruiter that I was begging for to help me get a job, he looked at my resume and he said, well, You saw me going like your year and a half year and a half to all these places.

[00:09:35] It's not like you worked at Oracle for the last 10 years and sure enough, the next job that I got was working for Oracle.

[00:09:46] How did you manage that? Uh, Uh, it turns out that I got hooked up with a desperate manager who turned out to be the worst manager of my life. And he couldn't say why you weren't kidding when you said it got worse before it got better. So I worked for this guy for two years. He impacted my health. I got anxiety, cold sweat chills at night, all kinds of stuff, because he was using intimidator and he reps, he was very successful and he helped some of his reps to be successful.

[00:10:17] And we close a few sizeable deals, but in the process he just turned me and other reps inside out. Wow. Um, and then I met my future wife, who is a Swedish doctor who was visiting her family nearby. And we met through mutual friends a year later, we decided to get married and I moved to Sweden because she can't practice medicine in the U S trained and certified.

[00:10:46] And once I moved to Europe, I, I stayed with Oracle in a different business unit. And that's where my big deal experience really took off. And what was the leadership like that for you? Oh, well, the first manager was definitely better than the other one and then the next manager was better. And then the last manager was great.

[00:11:11] He was the one that I stayed with until. Uh, I left a couple of years ago. Okay. So, I mean, I'm just curious in that timeline, right? From getting, let go at two jobs, really questioning like is sales for me, um, to moving, you know, to another country. Um, and then. Things starting to turn around and get better and certainly to get experienced, closing larger deals.

[00:11:40] What do you think shifted or what did you learn in that time to go from somebody getting fired from under performance to closing large deals? There were definitely some aha moments. And, um, uh, I recently wrote a book. I'll tell you about the book a little bit later, but I tell this story in the book. The watershed moment among several watershed moments.

[00:12:04] Um, I was brought into an account, um, that was an existing customer, uh, but they really hated us. And especially in that moment, um, we had recently acquired the tool that they were using. And as so often happens, there's lots of turnover in the wake of an acquisition and all the folks from the smaller company lead.

[00:12:25] Cause they don't want to work for the big company and that had happened. So, uh, the company with the, the relationship was in disarray, the customer was extremely dissatisfied looking around at alternatives. And I was basically mentored by my head of sales and my head of services and were. 20-year olds veterans of the industry, you know, salty, foul mouth, you know, they knew the insides and the outsides of every bit of this space.

[00:12:56] And we were sitting in a meeting with the, the executive sponsor of this. And we were going through. So there was software and there were services involved. And so we were going through how we could discount this or that, or we could move an offshore team to be on shorty at higher quality. Isn't it. And the customer stakeholder, you just put up his hands.

[00:13:17] He says, guys, guys, guys, this is not about just, and on shore, off shore, it's all. This is about how we steward the most important IP of this.

[00:13:34] That was this long pause kind of looked at each other and the whole conversation shifted from there. And we, and it was a, just a, it was a different journey from there when we understood the importance and the urgency of the matters at hand and what that led to was. Us hearing them to the point where we, as a team got in the Fox hole with the customer and sales led the way we didn't throw this over the fence to customer success or services or anything like that.

[00:14:10] And we stayed with them and we redid everything. We did a non-standard commercial model. We did a non-standard operational model. We changed the who and the how and everything about this thing, which is really where I learned around how to get around rules. And so they're just rules and guidelines and anything can be broken if it's in there, if it's the right thing to do for the customer.

[00:14:37] And then the punchline of the story is that we took the customer who used to be a dissatisfied $10 million account. And in nine months, Help them to renew for three years or $50 million.

[00:14:55] And that was the experience that opened my eyes to this whole nother world of selling that I had never been exposed to when I was what I now call a run rate seller. And you know, you get that first of you over the mountain, you see this other valley you'd never knew was there. It's like holy cow. That's what I want to do.

[00:15:16] That's what I want to do for the rest of my career. Now it's interesting because in that situation, right, trying to renew the client, talking about discounts and features, right. And.

[00:15:37] You would have thought you, you, you in, was that the way that people were still mainly selling at that time, at least in your organization or in your unit to keep an over an overly simplified answers? Yes. Yeah. And then all it took was that one buyer being brutally honest, you know, the situation to realize that there was a better way and it did change the way we sold, um, to the point where that customer stayed with us for, for years.

[00:16:21] And I did multiple mega deals with this one customer because of the nature of the relationship. We're able to establish the nature of the model. We were able to establish. It's almost like it be a high quality barring selling process can lead to the establishment of a relationship and a model that almost has its own motor.

[00:16:49] That would be tough as nails for a competitor to come in and try to eat down. So it's interesting. You can use sales as a competitive advantage in building a unique relationship and the relationship is kind of the, the, um, the bus word, but the pillars of. Th th the technical architecture and the team in place and how it's run and how are you charged for it?

[00:17:17] All that stuff goes to the partying. I guess you could call it initially, it's the buying experience, but then it turns into the relationship experience. How was it for them using your stuff? Do they get value from it all? Cause that's, that's the issue with SAS, right? You always get, got to be bringing success to the customer because it's not a one-time sale.

[00:17:40] Over and over. Right. Right. And then how did that change? How you sold generally or even like, okay, so we've talked about the one deal went from 10 to 50 and then they renewed multiple times, but how did that help you and change the way you sold generally? And what did you bring to other deals to close more deals similar to that one?

[00:18:04] Um, it, it, it set that dividing line between there's books out there that talk about, you know, selling above the line. Right? So there's that line. And that line below the line are folks who are lower in the organization. I lovingly call them worker bees, right? They're on the shop floor, they're doing the tasks and they're making the donor.

[00:18:28] And above the line are the folks who manage everything. And once you get to that level of management, you're not doing the tasks anymore. You're watching folks and you're helping teams get things done. Then the higher you go, the broader your scope, and sitting there in that first meeting and having other meetings like it, where I just listened to my execs, talk to their execs.

[00:18:50] I'm just saying. These guys are talking like their neighbors talking over the backyard fence, you know, it's just so plain and so simple and all the mid-level and the lower level folks, while I'm in meetings with them, everything's all complicated. They use long-terms and they get into these crazy details that don't really matter.

[00:19:11] And so I'm like, I want to stay with the executives. It's simpler. You get more done in like a fraction of the time. And that was kind of the permanent change in my mindset. I'm like, I want to go to the top because that's where stuff gets done. And that's where important conversations happen. I don't want to get bogged down with these lower things.

[00:19:33] I mean, not that you'd never want to talk to them, but it's, it's just a focus, right? It's it's where do you, where are you looking wherever you look, that's where you're going to learn.

[00:19:44] Wow. And, and, and then, so then you were at Oracle for how long. 13 years. And then what, what was, uh, what, what was the transition after that for you? Um, there was a, there was a short period where I said, okay, I'm done working for companies and I'm gonna go out on my own. And I started to consult with a number of companies and then one of them really kind of took off.

[00:20:11] And then they said, Hey, we need you full time. So I took that on for about a year, year and a half. And then, um, and then it was time to move on from there too. And so now got it. And when did you write the book? Uh, the book took a year and a half to write and it came out.

[00:20:38] What's what's the response been so far? Uh, it's been really great. Um, uh, I keep a little folder of the feedback that I get. Mostly people just give me feedback on, on LinkedIn. Um, but now the reviews are starting to come in from Amazon. So they've just been really positive. The general feedback is that, um, the format of the book is engaging because it's written like a novel, it's like a salesman.

[00:21:05] It's the story of this first big deal that I ever did. And it goes through all the colorful characters and all the ups and downs and the uncertainties that I had and the areas we didn't know we were doing. And then the areas that we really knocked it out of the park, up to the big climactic finish. And then it tells the whole.

[00:21:26] It's always a, it's a page Turner. It's actually fun to read. It's not like here's the metric of how you do this process.

[00:21:37] Yeah. Yeah. And, and so, and then do you, you work with individuals or teams on like how to implement these types of things to close bigger deals? Or tell me a little bit more about that. Yeah. When I started doing podcasts to begin with and to have a lot of sellers follow up after a great episode, I'd love to do big.

[00:21:57] How do you do? Can you teach me? You know? Yeah. And that started, um, I took a group of sellers and I said, okay, I'll get on zoom with you guys once a week, or as long as it takes to get out everything I know about. And that has morphed and iterated into a, a multi-month masterclass. And so it also started with individuals, but now managers are starting to notice the difference in their sellers.

[00:22:28] And they're starting to come around now. Uh, I do some for individuals and now I'll be doing more for that are private for pretty big brands. Scale-ups what are, what are, if you, what are a few things that are maybe covered in the book or just Keith Key ingredients to people that want to, you know, have the, you know, have a seat at the table to have those conversations too.

[00:22:57] Um, Just get started with selling bigger deals. If they don't have a lot of experience or really just are trying to go upstream. Um, the, the first thing is just mindset. I had this mindset experience that I just kind of explained through these initial stories and my mindset shift was okay, there's this line and there's folks below and there's folks above and everything happened.

[00:23:24] At the above level, that's oversimplifying, but that's kind of what I was left with. And as soon as that was made clean and clear to me that changed everything about how I sold. And then I started to think, well, how can I get high? I'm just a lowly salesman. And so I started to then get into the whole concept of leverage.

[00:23:45] And so I started to leverage my executives or our, um, our board of advisors or our board of directors or the managing director of whatever, uh, SSI we were working with at that time, anybody who I was like, who is probably already got relationships with the senior folks, I'm trying to get. And how can I befriend them or guilt them or whatever,

[00:24:12] and so cost to leverage them. Right? Yeah, exactly. I mean, but, but, um, and, and then I took a cue from, well, and as part of this, I took a cue from somebody who, you know, the person who I watched the first time I saw somebody actually do mega deals and she said, Jamal, I'm an extremely needy. I need others for everything.

[00:24:36] I go get executives to knock down the door and to establish the executive relationship. I get the eight players on the pre-sales team to run the demos and the discovery. I get the strategy people to engage with. Um, they're kind of big thinkers about where we're going to go in the future. And so I'm like great.

[00:24:55] If then that must be a part of the playbook. Um, I'm just going to start to do that. Um, and then that rolled into getting these folks involved early in the sales cycle. Lots of sellers are used to the idea of bringing in their executives, but they do it late when things are almost kind of wrapped up.

[00:25:14] Maybe dealers do it right upfront, you know, hourly. How are we talking? Uh, I have conversations with Marie executive. As soon as I smell that there could possibly be an opportunity if I've done enough research to say, yeah, okay. We still buy the seat and we sell to sales organizations and they've got a budget million sellers.

[00:25:36] So if they bought, they could buy big. Okay. That's almost enough. And then I go to somebody who I want to use his lip. If I don't have any relationships in that customer, I go to somebody super senior in my organization or somebody who I know, knows people over there. And I say, I smell smoke. I need you.

[00:25:55] Will you come and help me start a fire. This thing is not totally qualified yet. We do not have it all buttoned up, but I want to find out really fast if we could get a big deal here and it ain't going to happen fast unless we get really high really quick. So will you come along with me for this ride?

[00:26:14] Hmm. So you got to know a couple of things, right? You got to know how to sell it internally, properly, right. To get buy in for the executives to show up. Right. And, and, and the second part is you gotta make sure it's a good, solid opportunity, right. Because after you do it a few times, and there's no opportunity, it's going to be a little bit harder to sell it internally.

[00:26:37] Right. Yes, but you don't have to win every time if you have a good batting average, especially when in, as you're working with these, I don't want to use it as you work with these executives to be involved. All of a sudden you you're in the same boat. So if you're in the same boat and you're all rowing, it's not like they can all pull at you and say, Jamal you're you're, you're the, the weakest link here.

[00:27:03] And you are why this thing didn't. It becomes our deal. And then, um, yeah, you can't, you can't have a big goose egg after three attempts for sure. But you don't have to win every one of them. You just, um, if you're going about it the right way. And if you're it's like babe Ruth, you know, everybody respected him so much for his home home runs and pretty much ignored the massive number of strikeouts he had.

[00:27:33] People forget that even, you know, the best say this since we're talking baseball, right? I mean like a good batting average is, is, is what 300. You know, 300 in the, around there, which means, you know, you're still not hitting how many times, like more times than you're hitting. Um, so yeah, well, awesome. I mean, I really enjoyed this conversation.

[00:27:59] I really enjoyed learning your story a little bit. Um, the ups and downs of it and all of it. And, uh, I think that there's a lot of people that can benefit from implementing these, trying to sell bigger deals. Everybody's. I'm trying to think of how they can sell bigger deals, where can they connect with you?

[00:28:15] Where can they get the book? What are we going to include in the show notes for them so that they can learn more? Yeah, I mean, the gateway to all my stuff is my LinkedIn profile. So if folks, you know, checking that you can, we'll put that link for the show notes. And then if you go to the featured section, there's a, there's a link in the feature section on where to get that.

[00:28:35] And there's a link to my webinar, right? The webinars. Um, what does it, what does it take? What are the five it's called the five shifts, which are the five things that sellers need to do to transform themselves from. Run-rate sellers into something much, much bigger than a deal. Awesome. Thanks so much, Jamal.

[00:28:59] Really appreciate it. If you enjoyed today's episode, please write us a review. Share the show with your friends. It really helps us out. I'm always listening for your feedback. You can go to sales,, drop me a voice DM, and I will get back. Hey, you stuck around that tells me you're serious about your own sales transformation.

[00:29:17] If you're tired of doing things the old way and want to get started in your journey with other people on the same path, head over to sales,, and crush your numbers on your leaderboard. Yeah. It's free sales cast, doc community. Send me a DM with your best pitch and mention this ad. And I might even give you free access to our best temples.