May 15, 2024

Crafting Your Sales Persona With Jamal Reimer

In this Sales Therapy episode, Jamal Reimer and Alper Yurder discuss Jamal’s enterprise sales journey. They highlight relationship-building, meaningful conversations, and adapting to industry shifts, such as the rise of CIO influence. Touching on digital tools, they stress the need for adaptability in modern sales.

Meet our guest:

Jamal Reimer, Founder and CEO at Enterprise Sellers

Jamal Reimer is a seasoned enterprise seller with over twenty years of experience, renowned for his expertise in closing exceptionally large and intricate enterprise deals. With a career highlight of securing his first $50,000,000 deal at Oracle in 2012, Jamal now shares his wealth of knowledge through his Mega Deal Secrets masterclass and book, empowering ambitious sellers from top tech companies to achieve unparalleled success in the world of enterprise sales. 

Key takeaways:

  • Continuous persistence and a commitment to self-improvement are crucial for success in the sales profession.
  • Enterprise sales can be likened to a novel, with its highs, lows, and diverse characters, emphasizing the importance of embracing its complexity.
  • Building genuine relationships and engaging in meaningful conversations are foundational to successful sales strategies.
  • Understanding industry shifts, such as the transition in influence from CFOs to CIOs, and adopting a transformative mindset focused on innovation are essential for thriving in the evolving sales landscape.
  • Leveraging digital tools enhances stakeholder collaboration and alignment, facilitating more effective sales processes.

Prefer audio format? Listen on Spotify!

Watch the highlights

From adversity to sales success

In this episode of "The Therapy Chair," host Alper Yurder interviews Jamal Reimer, an expert in complex selling and enterprise sales. Jamal shares his journey, starting with his idyllic childhood in Asheville, North Carolina, followed by a challenging move to Southern Africa during apartheid. These early experiences, including a period of financial hardship during university, shaped his resilience and career in sales. 

"I had to start my university basically penniless. And that was another set of challenges that hit, you know, and so all this stuff happened during a time where I was feeling very alone and I tried to have to kind of go it on my own."

Jamal recounts his start in door-to-door book sales, which taught him crucial survival skills and set him on his career path. The discussion highlights the evolution of sales from repetitive tasks to strategic, relationship-building endeavors, emphasizing the fulfillment found in complex, long-term sales processes. 

"I learned about a much more strategic type of selling that really changed the game. And when I found that, I was like, this I could do for a super long time."

Jamal likens this to a hero's journey, filled with challenges, decisions, and growth, ultimately leading to professional and financial success.

Navigating the complexities of sales

In the next section of the podcast episode, Alper Yurder and Jamal Reimer discuss the dominance of tech sales conversations, the challenges of transitioning to complex sales, and pivotal moments in their careers. 

Alper expresses his curiosity about moving from advisory roles to sales and reflects on the rarity of experiencing large, enterprise deals. Jamal agrees, emphasizing the importance of persistence and personal development in achieving success in complex sales. 

"Persistence and patience have kind of come together... I was continuing to try to better myself and I was investing time and effort in not just selling but becoming better at selling and seeking out mentors."

They also share insights on navigating challenges, learning from mistakes, and trusting one's instincts in the sales journey.

"The biggest piece of advice that I'm thinking, the very top of mind now is you know more than you give yourself credit for... Trust your gut more often."

Insights into modern sales strategies

In the section of the dialogue, Alper Yurder and Jamal Reimer discuss various aspects of modern sales strategies. They delve into the importance of emotional intelligence in sales, the shift towards more human-centric approaches, challenges in complex sales deals, the role of digital sales rooms, and the mindset needed for sales success. 

"It's the emotional intelligence of just being able to talk with somebody human to human."

Reimer emphasizes the significance of empowering others, shifting perspectives, and aiming for transformative changes rather than incremental improvements.

"The bigger deals... were just a crucible of pressure against the timeline... But what it taught me was shifting away from what I knew was the sales role in the past into the complex sales role, which is much more about delegation.”

Full episode transcript

Alper Yurder:: So all that is fine. All right, so today in The Therapy Chair, we have Jamal Reimer, who is one of the OGs when it comes to complex selling and enterprise sales. And he shares it with them with the world through his work with enterprise sellers. And you can, you know, I found him on LinkedIn, obviously. Many of you have as well, but we'll be talking about his success, the joy, the pain and the journey. Welcome to Sales Therapy, Jamal. How are you feeling today?

Jamal Reimer: Great to be here, Alper. Thanks for having me.

Alper Yurder: My pleasure. Any Good Therapy starts with childhood and growing up. So I'm gonna go there very quickly. And in the warmup to this session, we had a very personal, very informal chat and we talked about not just work, but also human behavior, psychology, what makes people do the things that they do and they don't. So today I think we're gonna touch on those a little bit as well. But before we go into that, Any Good Therapy starts, as I say, with childhood and growing up because it shapes the person we are today as a person.

Can you tell me a little bit about the very young you, maybe up until the university or age of 18?

Jamal Reimer: Um, most of my childhood was spent, um, in the southeastern US in, in North Carolina. And it was a fairly idyllic, you know, upbringing in the mountains, uh, you know, the Appalachian mountains in a, in a town called Asheville. And everything was fairly, uh, you know, picturesque until we moved to Southern Africa. My father and my mother both got jobs in, um,

It was a part of Africa that was within the contentious years of South Africa's time under the apartheid government. We went there to serve one of the new countries that was kind of born, you know, they're called the homelands. And we were there, my parents were there for five, six years. And we were together for three years during the end of middle school, junior high and the beginning of high school for me.

Alper Yurder: What were they doing?

Jamal Reimer: Well, my father's in public health. My mom was in development. And then the tests and challenges really started for me personally. It was a bad time to leave. You know, I was really into friends at 12 years old and then, um, uh, 13 maybe. And then we went from this nice idyllic mountain, you know, town to kind of a dust bowl.

Alper Yurder: Oh, wow, how interesting. Mm-hmm.

Jamal Reimer: And it was not the prettiest part of South Africa. South Africa is gorgeous, especially on the southern coast, but where we were, it was quite, you know, sub-Saharan. And I had a lot of challenges for the two, three years that I was there.

Alper Yurder: Hmm, adapting.

Jamal Reimer: And then I came back prematurely because I really was not having a great time. And I said, I want to go back one way or the other. And we, I wound up living with a family who was friends of ours, you know, kind of lifetime friends, and that was difficult living in somebody else's house for my senior year of high school.

Alper Yurder: Oh yeah, it's already hard enough to live in your own parents' house. Are you an only child, by the way? Ah, okay.

Jamal Reimer: Yeah. And then I know I have a younger brother about five, five years younger. And then I started university and right around that time, the currency that my parents were earning dropped 75% in value so they couldn't really help me with college. So I had to start my university basically penniless. And that was another set of challenges that hit, you know, and so all this stuff happened.

Alper Yurder: Hmm.

Jamal Reimer: during a time where I was feeling very alone and I tried to have to kind of go it on my own and that was kind of the beginning of premature beginning of adulthood you could say.

Alper Yurder: Hmm. Losing your money right before uni is not a great experience, which I've gone through as well. My father went through a huge bankruptcy and I was in Paris. Like, I remember crying on the street. Anyway, this is your therapy session, so we're not going to be talking about my crying stories. But it sounds like you had a brother. Like, why did you feel alone though? It feels like a pretty OK child. OK, childhood. OK, you grew up for the three years in somebody else's house. But where's that lonely, that feeling coming from? Loneliness.

Jamal Reimer: Um, it was, I mean, living in a, in a family's home, that's not your own is really, really different, even if it's a loving family or, you know, or things like that, I had to make all the universities about, uh, I had to make all my decisions about university on my own. I didn't have my parents around to counsel me on that. And then once I arrived at university, um, I, I lit, I think I had $800 in my account that was supposed to last for the whole semester to cover, um, tuition, books, food, lodging and everything. And it just didn't fly. So, and I didn't really want to tell my parents how bad it got because they did what they could, which was very little. And I knew that they probably couldn't do more or at least so I thought. So I was kind of carrying a lot of stuff on my own at that time.

Alper Yurder: Where were you at this time? Where did you go to uni?

Jamal Reimer: In North Carolina, I went to the University of North Carolina in Chapel Hill.

Alper Yurder: Did you go to the top of the tallest building and you said like I'm gonna conquer you Carolina or any moment movie moment like that?

Jamal Reimer: Um, I, I guess the closest moment to that is, um, I, so the story that I've told before, but it's been a while since I told this story is that, um, that the bank account dropped so low, uh, I had applied for student loans, but it was going to take several weeks for that money to be approved and to arrive. And so I had this kind of danger zone of several weeks.

Alper Yurder: Yeah, of course.

Jamal Reimer: And there was a, one of the most popular restaurants on the main street in my university, it was called time out. There was a fried chicken place and they were famous for their chicken biscuits. And what they would do is they would take fried chicken on the bone, like a breast of chicken, and they would rip off the chicken breast from the bone and put the chicken on the biscuit. And then that's what they were saying. But they had this bone with a little bit of chicken on it and a whole lot of breading on it still left. And they saw, they called them bones.

And they sold them for 10 cents a piece. So for a few weeks, most of the nights of the week, my dinner was two bones and a glass of water and a plain biscuit.

Alper Yurder: I never mentioned this conversation would go to down the road. We was poor so fast, but I had I remember a moment In my father's bankruptcy. I don't this was 15 years ago. Luckily But I think it shaped a man who I am I'm the most frugal founder you'll ever see unfortunately And I remember like you know how you leave a tip or whatever to the cab driver like I had such little cash or such little coin like every little

It was lira by the time I was in Istanbul, but like one lira, which is basically a quarter of a cent or something. I don't know. Even then I couldn't leave. I remember like this. This could be important for me at some point in this next week or whatever. Um, so I think it teaches a very different lesson about money when you go through that situation, doesn't it? What was the lesson I taught you then?

Jamal Reimer: It actually sent me on my career path. Um, because during that year I was approached by, I was on a fencing team. I was, I was athlete and one of my, um, team members invited me to come to a meeting that wound up being a pitch to sell books door to door the next summer. And, um,

Alper Yurder: Mm. Okay

Jamal Reimer: through a whole other series of stories. I wound up doing that for five summers and the first summer was a terrible experience and I was a terrible seller to becoming quite successful.

Alper Yurder: but you were a door-to-door seller. Let's establish that.

Jamal Reimer: I was, I was indeed.

Alper Yurder: OK, great. So, cliche number one tick. OK, I didn't do the door to door selling, but I love it when, you know, it's these very typical salesperson stories. This was may I ask how many years ago?

Jamal Reimer: Oh, this was 1986.

Alper Yurder: Okay, so the world of sales has changed from back then, I would imagine. But I think some things stay constant. Like when you compare what you did throughout your career to that door-to-door experience, to today's social selling and all this virtual stuff, you know, it's no longer about how many meetings did you go to physically per month. Some things must have remained constant. Like, do you feel like some things are constant and what are those for you?

Jamal Reimer: A little bit. The, it's almost the backend has remained constant, which is my why, right? Why am I in sales? Why do I, why is sales such a central component of my professional life is because in that, in that kind of crisis period of having nothing or next to nothing, it was sales that got me out of that.

And it was something that I could control. I didn't, you know, I got a little bit of scholarship, but nowhere near enough to cover all the costs. I went to my parents and they helped what they could, but that was not sufficient at the time. And so I had to take it upon myself.

And so I was able to do it the first summer just barely because I was so poor at it. But then the following summers, I got better and better and better and better. And by the fifth summer, I made 10 times the amount that I made the first summer. And so it's always stuck with me that, you know, sales is my, is my way to survive in the, in the material world.

Alper Yurder: Hmm. Also, I guess enjoy and thrive, since you've been doing it so passionately for so long. It mustn't be only about survival, it must be about, you know, the joy of it as well. I don't know, like what, what? Ah, the front end, yeah! Okay. The subconscious. Gotcha.

Jamal Reimer: That's the front end, the back end, right? The back end is this is what I do to survive. And there were years when I, in my frontal cortex, I was like, this sucks, I hate this job, I hate the repetitiveness of it. And that sales, I hate, I hate that sales, that form today. But I learned about a much more strategic type of selling that really changed the game. And when I found that, I was like,

Alper Yurder: Eh... Ah, yeah.

Jamal Reimer: This I could do for a super long time.

Alper Yurder: Okay, I think I know exactly what you mean. The high-velocity repetitive one demo after the other is horrible, but when you have those long conversational relationship building, there is like a million down the road. Those kinds of stuff are really cool. And you also make friends, you connect with smart, interesting people, and you have great conversations. Is that kind of what you're alluding to as the repetitive versus the fun bit?

Jamal Reimer: I, it absolutely is. And I finally realized like two weeks ago that what I appreciate about the longer cycle, the more complex enterprise sale is it is the hero's journey of B2B selling. It's a novel, right? It's not an instruction book with formulaic steps that are repeated ad nauseam. It's like a Russian novel. They're a great novel, right? There's ins and outs and many colorful characters and there's parts of the journey where you have to choose what a fork in the road and then you take a path. It turns out to be the wrong path. You gotta go back to the fork, get a backtrack and start over and take the other fork. Um.

And yeah, that path became incredibly fulfilling, both just with, like you said, the relationships and the complexity and the learnings, as well as financially, it was a much better route.

Alper Yurder: Yeah, I love that. And you talk about it a lot, obviously, like some of the more attention-grabbing headline is how I made the X or how I made the commission and whatever. And unfortunately, yeah, it is, it is what grabs the attention, but I guess the journey to that is what's really interesting and you talk about it quite a lot. So I'm interested in one thing, particularly for my own learning. So I, my sales career, I started as an advisor, strategic consulting, et cetera. So that was, you know, problem-solving, helping others to solve their problems, like very complex, et cetera, et cetera. 

And then I realized I actually love selling an idea, pitching an idea. And then I transitioned more to a sales, quota holding, blah, blah. But this was 10 years of non-SAS sales. So it was more traditional, you know, selling training, selling, um, real estate, uh, whatever's, um, but it wasn't this, this shiny world of software as a service, which seems to dominate a lot of the conversation, especially on LinkedIn or on more visible places. 

I feel like a lot of literature comes from that world of tech sales. First of all, do you agree with that statement that a lot of that conversation is dominated while there's a whole world of sales out there, which we can say traditional. Do you agree with that statement at all or not really?

Jamal Reimer: I'm told it. LinkedIn is dominated by SaaS sellers and gurus and various players, 100%.

Alper Yurder: Yeah. And that therefore a lot of the learning and conversation comes from it. So after that long-tailed explanation, my question is this. It's sometimes hard for me to imagine those because I never sold, I sold a $5 million, you know, training program to a bank, which had digital components, but I never saw the $5 million tech tool to a whatever. 

So those big deals, that really fun, interesting experience that you tell me now that we both enjoy about sales, it feels like is preserved to a very 1% or whatever of the sellers in this spectrum, only like the elite of the elite get to experience it. I don't know if that was clear at all for you or if it made sense what I'm trying to say.

Jamal Reimer: It does feel that way to me too. And a big chunk of my mission is to break that assumption because I really am of the mind, if I could do this, lots of people could do this because I'm not that special. I mean, I have some level of intelligence, I have some level of discipline, and I definitely have persistence.

Alper Yurder: Mm. Mmm. Of course.

Jamal Reimer: Persistence and patience have kind of come together. Just keep trying. Just keep trying don't give up that kind of attitude and I didn't I didn't have big success until like the 12th or 13th year of my career those first 12 or 13 years I was always looking over my shoulder. I made my number like every second or third year

I was like, I feel vulnerable and this is harder than it should be. And you know, it's like trying to run through mud. Um, so anyway, I might've lost the thread here.

Alper Yurder: No, no, but what do you think is the what made that pivotal? What is that pivotal moment where it felt, oh, OK, just falling into place and I'm actually becoming better and probably I'm going to be making more money now.

Jamal Reimer: I mean, so I had glimmerings of it every few years. I was like, oh, I learned something enough to get this deal over the line, and it was a good size deal. Okay, great, I must be making some progress. But then the next year, things would kind of fall apart, and I was like, all that great stuff that happened last year isn't happening now, and now I feel out of control again.

And so there was that those bumps, right? It wasn't all the first 12 years wasn't all terrible. It was like very spiky and very unpredictable. And I felt out of control because of it. But the big turning point was when I did that first large deal and I don't take credit for it at all. Um, I was pulled into the deal. Um, it was an account that I had for many years and then it was taken away from me when new management came in a year later, the customer asked for me during a kind of a critical time because the company that we had acquired that put this new management in was a product that we didn't have, it was a new product for us, but for the customer, they were in crisis with this product and they were gonna think to turn. And this turned into a super large deal. And we took it from like 10 ish million up to 50 million in a nine-month period. And I was completely tutored.

I'm a head of sales and my head of services at the time. And it was through that process of learning on the ground with 20 year veterans in our field how to do this. And it was an amazing, life-changing experience, but some reps can have that life-changing experience and then they can never reproduce it. Fortunately, I was able to do it two more times over an eight-year period.

Alper Yurder: I'm going to say, okay, maybe a bit controversial. I feel like, okay, there might be somebody listening to this conversation now and saying like, you know what, I'm trying my best to, but I'm kind of, you know, stuck in a role or similar roles. Like how do I make the transition to more like enterprise complex sales, large sales? Like first you can start with, you know, developing yourself, I guess. But also there's a huge part of like luck and chain of events that lead you to a deal like that.

Jamal Reimer: Yes.

Alper Yurder: For me, it was similar, like my very first like multi-million dollar, 50 people stakeholder, whatever, which actually led me to build Flola eventually was it happened to me, like I finally at my fourth sales role or whatever, I was given an opportunity to sell to somebody and somebody coached me to sell it, you know? So it was, I was still the same me eager to learn and whatever, but it was the universe finally handing me an opportunity. So there's things we cannot affect.

Like that opportunity and whatever. But what are the things we can? Like, do you feel like there's things that we can prepare ourselves for those bigger deals, better roles, higher commissions?

Jamal Reimer: Yes. So I kind of truncated my part of the story. It didn't just happen that I was a...

Medium-ish grade seller and then I got this opportunity and it's a huge hockey stick. It wasn't as simple as that There was a there was a road along the way where I was continuing to try to better myself and I was investing time and effort in Not just selling but becoming better at selling and seeking out mentors and all that good stuff reading books everything that you could typically do to take control and improve and along the way

Alper Yurder: Yeah, it never is. Of course. Mm-hmm.

Jamal Reimer: I might have a small success, but it started to get noticed by my management. And then there was this, there was a period where this new management team that had come on that had taken the account away from me, it was during that year that I did not have this big account, but I was working on smaller accounts. And I could have been bitter and just like coasted and try to look for another job and get out, but I was in there, man, I was slugging away and I was trying to, you know, fight the good fight and, um,

Alper Yurder: Yeah, believing the good days are coming.

Jamal Reimer: Yes, yes, tomorrow. I love you tomorrow. And I remember I took my manager who I didn't know that way. He didn't know me that well. I took him into an account and I said, you know, come and see what I'm doing and I need you to, to get involved. And so he flew up to Denmark and we saw one of the accounts that I had. It wasn't a big account. It was medium ish. And we had a conversation with their IT group.

And this manager was his only background was applications, business applications. And he had only, he, he grew up for 15 years having business application conversations. And I was at Oracle, right? And you can't live at Oracle without knowing something about the backend and infrastructure and databases and things like that. So I was far from a tech person, but I was having this conversation with the IT team and we were talking about the backend and the infrastructure and all these kinds of things. And my manager was totally silent. And I wasn't thinking about it. And then we, when we left, we were walking to the car. He was like, wow, Jamal, that was amazing. I'm like, what? He said, but you, you took the conversation from talking about the app and you, you went toe to toe with these guys all the way into the backend and how it's going to fit into the architecture and all this stuff. I've never seen that before.

And so I didn't think it was a big deal, but evidently I had done something right that kind of changed my brand with one player, my manager to shorten the story that ultimately got back to our VP. And then I was on a trip to the US, I was with another big customer and the phone rings and I leave the meeting to pick it up because it was my VP and he said, the big company that I had lost before, he's like, they want you back. And I need to know right now, are you ready to take on this account or not? Because we're in a renewal year and it's gonna be tough.

Because they are really not liking us right now. And instantly I said, absolutely, I want it back, let's go.

Alper Yurder: Mm-hmm. I want to talk about that renewal experience for sure. So I should make a memory note for myself, but I want to touch on one or two things that you share that one is you invited your manager to this conversation, probably to elevate, to learn, to understand, like because you need to explore and open up this account. And you know what you know, but you don't know what you don't know. So you invite somebody else to the conversation, hopefully to give you another perspective, open up, teach something. If I'm right, then I guess.

The beauty of that is that safety that you felt to be able to bring your manager into this conversation without feeling worried like, okay, if I bring them in, they will see what I'm not doing right. They will probably tell me off about this, that I think that's a huge part of it. Like you can only thrive when you have that sort of feeling of safety, can't you?

Jamal Reimer: Yeah. Yes. And I guess both of us can acknowledge how rare that feels sometimes. Like with so many sellers that you talk to, so many sellers that I talk to, there's a lot of looking over your back, right? A lot of insecurity, a lot of fear, a lot of living in the crock brain, right? We're so many sellers are living in fear, so they're not able to think and be creative because they're just trying to survive. So yes, I was.

Alper Yurder: Yuff. Yeah.

Jamal Reimer: blessed at that moment, being able to feel safe enough to be vulnerable enough to bring my first line manager into something where maybe I was doing it right and maybe he was going to ding me.

Alper Yurder: Yeah. I think one of my most fascinating learnings and I had a manager who was the founder, who was a very interesting type. And I was always very intimidated by him, everybody as well. But at the same time, I'm always a challenging person, blah, blah. I wasn't as scared of him as probably he would love for me to be, but probably my biggest fuck up. I pushed the client. This was my biggest deal then. Push the client to the brink of writing a note to my manager to say, like, can you get this guy off of my back? Because it's like enough is enough. And I never do that, never do that. 

And I learned my lesson and all that. But he walked in the door and he told me, OK, I have some news for you. Probably you won't like it, but it's OK. That's how he opened the conversation. You know, he didn't say, like, how dare you fucked up this huge account for us? And no, because I don't know. And it was like a big fuck up, but big learning for me as well. Did you have any of those?

In your time, I'm sure you have had.

Jamal Reimer: Absolutely, all the time.

Alper Yurder: Can you share one with us? Like your biggest one maybe.

Jamal Reimer: Um. I mean, the ones that are coming to mind are when some mistake that I had done would come to light.

Alper Yurder: Mmmm

Jamal Reimer: And the way that management would react, it'd just be very telling. Let's just say at Oracle, I got fewer, or at least in the early days at Oracle, I got fewer understanding managers like yours. You make any screw up in kind of bulge bracket Oracle at that time.

Alper Yurder: Oh.

Jamal Reimer: What was it? The early 2000s and it was just, you know, you get knocked, you get knocked over the head. You keep moving, but you get knocked over the head.

Alper Yurder: Mm-hmm. Yeah. Yeah, you do. You do. You do. And you learn. Um, yeah.

Yeah, but those things, I think they're quite pivotal. Like for me, that is pivotal. So, you know, since then, the last decade or so of coaching people, it's always been like, I'm a very people person, client centric. They come first and et cetera. And I feel like I did my everything. I was very kind, blah, blah. But at the same time, this pressure of quota and, you know, success and like, I have to make it sunk cost, you know, I've spent already 70% of my whatever on this, this has to happen. So then you push, push.

Jamal Reimer: Yeah.

Alper Yurder:  and you don't know what your client is going through. And then like the sweet lady, she just, you know, backfired in a big, big way, big way. Yeah. Looking back then, what advice probably would you offer to your younger self with the wisdom you have today? Like, what would you do differently?

Jamal Reimer: Yeah. Mm, 100%.

The biggest piece of advice that I'm thinking, the very top of mind now is you know more than you give yourself credit for. Because as I look back, I would always have like a gut feel about how something should go. But I would immediately say, well, I'm young in the role or I'm not that experienced in the role, so I'm not sure. And I'm going to abdicate my own decision-making

Alper Yurder: Oh wow! Hmm.

Jamal Reimer: powers to somebody else like my manager, somebody else in the line of management, or the customer to dictate how, I'm giving away all of my power. And now, at 55 years old, I'm saying, my gut is actually pretty good, and it always has been. And human interactions, if you grow up with a half-decent sense of right and wrong,

Alper Yurder: Mm. Good. Hmm.

Jamal Reimer: propriety and politeness and things like that, that stuff does translate. There was that, what was that book? It was like, everything I needed to know I learned in kindergarten, right? That concept is sound. So the biggest piece of advice I would give is, trust your gut more often. Do take advice from others who may have been through a specific experience that you haven't been through before. But… you're probably not far off just using your gut. If you've got, all of us have a fairly decent gut.

Alper Yurder: Yeah, I guess I would have to agree, but I don't think I can still confidently say, well, you just said, maybe I need a bit more, a few more years, maybe, and I'll get there. One question I want to ask you is when I see an amazing salesperson in action, whether it's in a client call, what they're doing behind the scenes, building consensus internally, externally, it's just a joy to watch.

Especially like a great discovery is just amazing. It's a conversation that feels so natural. You know, the client might be a little bit grumpy and they meet me like cut to chase and et cetera. And, you know, you're just doing your thing, enjoying the conversation, you know, walking them gently towards that tunnel. So for me, those discoveries, the nurturing, those are great moments when I see a great salesperson in action. I love it. Like this person is great. I want to work with them, et cetera. Do you have any of those like favorite things about good salespeople that they do really well?

Jamal Reimer: Hmm. Um, yeah, I, I talked to her work with sellers every day and you can tell it right away, there's this, it's the, it's the, um, you know, uh, not the IQ, the EQ, right? The emotional intelligence of just being able to talk with somebody human to human.

There's such a clear bifurcation between somebody who has that emotional intelligence and comfort in their own skin and the other person who is, I guess the best word is scripted. It's a scripted, stereotypical sales persona. And there's a lot of connotations. The wording that they use are trying to get everything right.

Alper Yurder: Yes, unfortunately.

Jamal Reimer: It's also in a promotional tone rather than a conversational tone. You know, I think all of us know what we're talking about. And being, being talked at, uh, being, you know, listening only to be able to respond or defend.

Alper Yurder: Yeah. Yeah, being talked at rather than talked with.

Yeah, no, I hate that too. I think that's what sort of the last 10, 20 years of to the moon growth and predictable revenue model, I think. I mean, I never had it. So I was trying to learn it so I can make it because I guess that was the only risk before scaling and growing. Do you feel like it's changing now? Like it's no longer just that, you know, onto the next demo, these robotic things, these automated things are being felt by the buyer, so it's not working anymore. Or it's still.

The recipe for success.

Jamal Reimer: I mean, let's put it this way. What are the facts? And what facts do I have access to? So I am not on the ground in every company of every rep that I work with, but I am in touch with the reps themselves. And the reps are saying, hey Jamal, I'm coming to you because I like how you think and your content. And I want help to go in that direction because what I'm getting in my current company, either the management,

Alper Yurder: Or scaling, I guess. Hmm. Hehehe

Jamal Reimer: or the model isn't working. I'm being asked to go, to have more complex conversations with more senior stakeholders in larger accounts. And I'm not being shown how to do it. I've never done it and I'm being asked to do it, but I'm not getting anything extra in terms of knowledge tools process.

And so I think there's a huge, I think that there are certainly people who are waking up and there's an awful lot more content that I read, let's say on LinkedIn about, Hey, that's the old way. And this is the new way. Um, but I'm not getting kind of this wholesale feedback that, Oh yeah, everybody, all the companies are waking up and every, and the companies are changing their, um, motions.

Alper Yurder: Mm-hmm. Mm. Yeah. Approach in the model. Yeah. Oh, yeah.

Jamal Reimer: to be able to be more selling in a human way instead of the scripted sales way. And I want to pick up on something that you said. You talked about predictable revenue. I think there's a real similarity with the predictable revenue experience that we have had and the challenger sale experience that we've had. Both of them have a lot of sound principles. Both of them...

Alper Yurder: Hmm. Mm-hmm.

Jamal Reimer: have largely or at least significantly been misapplied. So I think a lot of people already know, like with the challenger sale, a lot of reps or organizations got the concept of challenging, they got it wrong. It became that kind of sales bro challenge, that kind of take control and just make them understand kind of a challenge.

Alper Yurder: Just for the sake of challenging, I guess.

Jamal Reimer: which was never intended, right? And to do the challenge of sale well is to sell well. But I would knock its application in the field by many sales organizations. The same is true with predictable revenue.

Because there are a lot of great elements. And yes, it's true. The more leads you have, the better off you're going to be. But it doesn't translate into just having great leads. Means that the sales will close and margin will be there, et cetera. And there's some assumptions in the model, especially like.

how much your SDRs know, how much your BDRs know to be able to warm up conversations with real conversations to get the referral, right? Cause a lot of their model is go high, get somebody to refer you internally to have that conversation with the appropriate person and that'll be your entree in. But it breaks down with massive amounts of sequencing, right, massive amounts of outreach.

Alper Yurder: Mm-hmm. Yeah.

Jamal Reimer: I'm kind of an executive now just because I own my own little tiny company. So I'm getting all that outbound. I'm seeing, I'm on the other end of it. And it's just like, this is absolutely, it's like being in a windstorm all day when you're trying to be at the beach.

Alper Yurder: Of course. Horrible. Yeah. Oh yeah, tell me about it. I mean, I think I'm inundated by those two. You already started talking about some of the more current issues that you speak with or the type of reps that you speak with. What are those two, three things that you speak about on a day-to-day basis or what is top of mind for you or what are you trying to crack these days?

Jamal Reimer: Um, everybody is in the belly of the beast of remaining in this downturn. And that's having all the impacts that we already know, which is, you know, the CFO for a while there, the CFO became the new CEO and it just had control of everything because the VC or private equity owners said it's time to tighten everything up and that's going to happen through the CFO. But now I'm starting to hear, um, evidence that…

At least with most of our world, as you said, there's a really big world of selling, but so much of us are in the tech world. In the tech world, now the power is shifting from the CFO to the CIO. When the CIO is having more and more power, getting the mandate, hey, you gotta work out our tech stack. Either we bought too much in the past and we need to consolidate, or...

There are unaddressed projects, because we've been in spending lockdown for two years. And now we're kind of coming out of it, but we want to spend on technology in a much smarter way. So now the power is starting to shift. So the things that are top of mind with the reps that I'm working with are, how do you determine who has the real power? How do we have the conversation with that group or that individual or those key individuals. And how do we have a conversation that's not about your product? The punchline of the conversation is, okay, the product can help you do this. The meat of the conversation is, what's the root cause of what you're doing? What would be the bullseye about where you wanna go? And what's wrong with the current… condition that you need a new approach, but we need to understand that deeply.

Alper Yurder: Yeah. A lot of that is so intuitive to me. Like it's just simply if you're genuinely interested in the other party's problems and day-to-day, so I think it's a natural conversation, but then I guess a lot of people are not, therefore it becomes the scripted thing that you mentioned. But I guess if you have that craving for the elite seller status or that, you know, 1% and the bigger deals and et cetera, then you naturally have to go in that direction, there's no other way.

That's the only way people will start caring about what you have to say, because you're actually talking about them rather than yourself or your product.

Jamal Reimer: 100 percent.

Alper Yurder: And in terms of, you already mentioned some of those current things and the changes. So until six months ago, I think the whole conversation was like, oh, the CFOs are now involved, new stakeholders, blah, blah. So now, and even in a new kind of department you have to use up. So how, my question is one or two tactical questions before we come to the end of the show. Um, how have you built consensus? How have you, like, what were your tips or your golden nuggets?

In building consensus with multiple stakeholders, pulling different people into the conversation. Like, what have you done in your career that you feel like has done really justice to that building momentum, building consensus, building alignment between different stakeholders? What should people do to be able to do that?

Jamal Reimer: So what's coming to mind, I'm not sure if this is a personality thing or if it's something that you can say, oh, everybody should do this. So I'll just say what's really worked for me is giving people power and then guiding them with that power. Because that old mentality of you got to get your sales cycle in control, you got to get your customer stakeholders in control is really falling flat.

Alper Yurder: Hmm? I love it. Yeah.

Jamal Reimer: Um, so the first thing that I do is basically whenever I'm talking with anybody, you know, is basically say, here's what I understand, or I'd like to get your perspective, or you know, I'm ready to talk about X, Y, and Z, but why don't you kick us off? What do you want to get out of this half hour?

So there's many ways to express, hey, I'm interested in whatever it is that you want, and I'm going to put whatever I want on the back burner. And then when they get that, when that comes across sincerely, then they're like, I'm ready to invest some time with this guy, because I believe that he's here for me and not him. He's also here for him, but he's putting me first.

Alper Yurder: Yeah, that you want, yeah. Yes. Yeah, I love that. Yeah?

Yeah, but that's the only way. If you will only get to him yourself, if you are actually first interested in the other party, but have you experienced like, for example, one of the main reasons why I started building Flolo was like, I was in large enterprise sales, trying to teach my team to multi-thread complex sales. I don't have any idea about where the deals are going, like which stakeholders should be included. Are they interested? All these questions. And then as a leader, you depend on your weekly pipeline conversation.

To get all those juicy bits from the rep and they're telling you, yeah, it's going well, it's going well, but you don't really have any data, et cetera. Like, what were the disappointments about running those large complex deals and how did you overcome them?

Jamal Reimer: The bigger deals that I was exposed to, for whatever reason, and regardless of how much planning either side would try to do in advance, they were just a crucible of pressure against the timeline. So that created a, what do you want to call it? It's like a deal culture.

Alper Yurder: Hmm, timeline, yeah.

Jamal Reimer: You know, you can have a culture on a specific deal. And if it's infused with a compelling event, then it's positive because everybody's like, yes, we have to get to a yes or no or whatever by X date. There is upside in having that.

Alper Yurder: Yeah.

Jamal Reimer: But when there's so much to do, it's such a really short period of time, then it becomes just a source of stress. But what it taught me was shifting away from what I knew was the sales role in the past into the complex sales role, which is much more about delegation. And so the up and coming sales rep takes on a lot of responsibility and says, I have to do all the selling tasks.

Alper Yurder: Mm-hmm.

Jamal Reimer: I've got to do prospecting. I've got to start the conversation. I've got to get their attention. I've got to do the mapping. I have to do X, do, do. And that is the mentality of being the star on the field or on the stage, making the performance or the winning of the game possible. But what I found I needed to do when the complexity rose,

I needed to come off the field altogether and become the coach or the director of the show and deploy the best sports people or the best performers for their role on the stage or on the field. And it's a very different perspective because now I'm not even on the field, I'm putting other people in front. And sometimes it happened simultaneously because I couldn't be everywhere at once. And it was a whole new skill set.

Alper Yurder: Yeah, yeah, you mentioned it before. Give the power. Mm-hmm. Yeah.

Jamal Reimer: And that's one of the skill sets that we work on. And that's one of the skill sets that I'm convinced are really necessary for whatever's on the other side of what we're calling the complex sale.

Alper Yurder: Yeah, I love that. So you're doing the coaching bit and I was doing the coaching bit and I was trying to, you know, create minimis and like, you know, like this is how I invite another person to the conversation without even them realizing it or offending the other party and then I was like, Oh God, like it would be really great if there was a, you know, I was using JIRA for internal.

I don't know if you have ever heard of it, like Jira is like a tool that is like internal processes from finance to HR to legal, you know, like the ball runs and then the momentum keeps building, but it was so UX unfriendly and I was working on deals with like, you know, really 50 stakeholders, you would think somebody's the champion, but then somebody will pop out of nowhere, blah, blah. And all of that told me, okay, you need to build Flola, which is this, you know, hopefully a bio-enablement tool to help build consensus and stakeholder alignment more easily, everything in one place. 

Then I discovered I'm not the first genius to build this tool, which is actually a category of its own digital sales rooms. It exists. Others are building it too. So my question is like, what's your experience of these digital sales rooms space or mutual action plans? Do you sometimes use them, advise their usage? Do you get them, not get them? What do you feel about them?

Jamal Reimer: I think they're great. I think that you're right. There is a category with now many players. I think that their usefulness increases with the complexity of the deal. The complexity can be either number of tasks or number of players.

Alper Yurder: Mm-hmm. Yeah.

Jamal Reimer: I don't know if there are standouts who are taking the front runner. You know, right now it feels like it's still kind of a diverse group. But they can, they are absolutely what I would think is a part of modern day selling because they give more intelligence to the customer and they give more intelligence to the, to the selling team, the buying team, both sides have more data in front of them that they want.

Alper Yurder: Yeah, everyone's game, yeah. Mm-hmm.

Yeah. And as we start building it and putting it in front of people, we see new use cases now onboarding, retention, et cetera. That becomes like very intuitive because, you know, you ask your buyer to do a hundred things. So now here's a tool that can enable you to do it, but it's so funny. As a first time entrepreneur, I'm building something from my own pain point. I see it resonates with some, it doesn't with others at all, which is really interesting, and then try to follow what the market trend is like.

So it is something relevant for people's day to day. It's relevant for you. It might be very relevant for you as the seller, but not for the hundreds of people you're trying to sell to. Um, so my last question therefore is what do you feel like salespeople need to help them to do their job better these days? And it can be training processes, coaching tools. What do you think they are?

Jamal Reimer: The biggest thing that moves the needle is a different, you could call it a mindset or you could call it a perspective, but it's how do you get your chin up and stop looking kind of for the rocks at the bottom of the mountain and how do you look at the summit?

Alper Yurder: I think it's for everyone. It's true for everyone, not just the salespeople. So how do you do it? How do you do it yourself? How do you keep your chin up?

Jamal Reimer: I'm always thinking is that as big as it could get? Not in terms of deal size, but in terms of impact or influence or what's the highest thought? What's the highest thought possible in this scenario? Are we trying to, is our goal a 15% improvement on a process or is our goal

Let's completely change the process to something that makes a lot more sense that we could do today through technology that was not really possible a few years ago and completely change how this works and take something that would take days and turn it into minutes. That's a transformation. It's a different way of thinking.

Alper Yurder: Yeah.

Jamal Reimer: There's an incremental perspective, which is how much better can I make it in single digits, in single percentage points or double even. But the other thing is how can I completely change how this is done?

Alper Yurder: Yeah, love that. Well, so now, our time is over and I'm going to need to cut it on the clock just like any good therapist. But is there anything that I should have asked you that I've forgotten to ask or I haven't asked?

Jamal Reimer: There's many long conversations that you have asked about, but I would absolutely, I am firmly entrenched in the enterprise segment, and I would encourage everybody, if you're thinking about what the heck is my career gonna look like, what's the trajectory? A lot of people think that the trajectory in sales is to be an AE for a while.

I don't know, start as an SDR and then become an AAE, and then become a bigger AAE, and then go into sales management. And my experience is really different. And there's a lot of sellers who are like, I want permanently or for the vast part of my career, want to be an individual contributor seller. And there's a whole destination route in doing that, but that most people never hear about. So I'll just plant that as a seed rather than go into the details of what it could look like.

Alper Yurder: Yeah. Yeah, it's so funny. It can start a whole new conversation because that was the path that I was envisioning for myself, then I ended up being a founder, but life. Um, I think that's a great path to be like a senior esteemed, elite seller, etc. Well, that was a great conversation. Thank you, Jamal. Nice to meet you. Uh, I think you are definitely the cool, humble person that you look like from your LinkedIn profile and sharing a lot of great wisdom. So it was a great chat. Thank you for being on Sales Therapy.

Jamal Reimer: Alper, thanks for having me.

Alper Yurder: All right, so if you enjoy the show, subscribe to us on Spotify, YouTube or whatever you are listening us to. And thank you very much again, Jamal Reimer for being with us today and see you on the next episode, everyone. Bye bye.

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