Mega Deal Secrets: Jamal Reimer (ex-Oracle) on Closing $50M+ Deals in a No-Budget World

Jamal Reimer – author of Mega Deal Secrets, ex-Oracle Key Account Director, and closer of multiple $50M+ deals – joins MarTalks for a masterclass on landing uncommonly large enterprise deals.

• Why pipeline building is brutally hard in 2025 (and the simple fixes most reps miss)
• The #1 mistake sellers make with executives – and how to speak their language with financial value stories
• How to turn any financial reality (margin pressure, working capital lockup) into a compelling point-of-view that wins sponsors
• Why executives ghost you, how to earn trust fast, and the exact questions that create “aha” moments
• Selling to executives vs. users: the mindset shift that 10x’d Jamal’s deal size
• Bonus: Free Point-of-View Trigger Document (link in show notes) – your cheat sheet to instantly craft executive-level POVs from any financial trigger

Perfect for CROs, enterprise reps, founders, and anyone tired of small deals and endless demos. Steal the playbook Jamal used at Oracle to dominate the largest accounts – and start closing mega deals today.

Get Jamal’s book Mega Deal Secrets and the free POV Trigger Document in the show notes.

#EnterpriseSales #MegaDeals #SalesTips #ExecutiveSelling #ValueSelling #MarTech #MarTalks

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Transcript

SPEAKER_00 0:03

Welcome to Mar Talks, the number one podcast for e-commerce and marketing applications. Mar Talks is devoted to covering the latest technology developments that drive the global commerce ecosystem from advertising to last mile. Enjoy all of our content at Rosenstein Group.com slash Mar Talks-Podcast.

SPEAKER_02 0:27

Well, hello everybody. Welcome to another episode of Mar Talks. My next guest today is an incredibly successful enterprise sales executive, product lead, founder, investor, and author of the book Mega Deal Secrets. Everybody meet my guest, Jamal Reimer. Welcome to Mar Talks, Jamal. Great to be here, Daryl. Well, to kick things off, tell us a little bit about yourself. You know, how did you get saddled with the unbearable career of being an enterprise software sales?

SPEAKER_01 0:57

How to summarize, it started selling books door to door in college, took a winding turn until I got my first right out of the gates. What was it, 20-ish years ago? There was no SDR role. So there was no kind of starting at the bottom and working up. My first B2B role was in selling to quote unquote enterprise accounts in financial services. And that led to a very bumpy road for the first 10 years. And sometimes I made my number most of the time. I didn't. And then through a circuitous route, I wound up at Oracle. And through my 13-year journey at Oracle, I was always an individual contributor, never went into management. And I just ultimately was hell-bent on learning the art of the complex sale and the large sale. And I was able to do that. And in the second half of my 20 years, I actually figured it out, took a nice long time. And then I was able to do a number of deals at or above $50 million and became a key account director, which was kind of a thing at a work hole. It was kind of like the Uber selling. It was the thing. And for the past six, almost seven years, I've just been putting my own shingle out and I help individual contributors as well as teams learn the same. Learn how to do uncommonly large deals and uncommonly large accounts.

SPEAKER_02 2:13

Well, you know, having closed a couple of $50 million deals last week, I've got to say, you know, that took uh I wish that would have been great. We wouldn't be talking right now. Well, I think I'd be on a plane somewhere. But those are earth-shattering software deals. You know, you just don't see those. Uh, you hear about them in legend, and here we are talking to somebody that's actually done it. So you've said the biggest challenge today sales executives have is just starting that conversation. Why is pipeline building so much harder today than it was five to ten years ago?

SPEAKER_01 2:48

I think we're going to revisit this theme a few times in in this episode, this conversation. What I really see happening is that there are just a number of forces that are converging to create a very messy, very difficult environment. One, clearly, we're in an economic downturn and there's lots of uncertainty in the market. Which always constrains corporate buying. It doesn't stop it, but it constrains it. And then secondly, we're out the almost unbroken chain of downturns before and after COVID, we've seen increasingly decision-making power for almost any purchase rise to senior levels. So it used to be that low-down folks could make small purchases and middle-tier managers could make to do middle-sized deals, and then the big ones had to be done by execs. Now it's almost everything needs to be at least approved, if not really vetted, and every T crossed, every I dotted at the executive level. Sometimes even the board. So there's a smaller number of people who can say yes. There's a larger number of people who can they can only say no. And then the third component is that technology is really changing the landscape, at least from a couple of big fronts. One's already hit and the other one's hitting now. God bless them. The gongs and the sales loss and the outreaches of the world have created a great capability, but it's largely misused or overused. And so it's enabled sales teams to absolutely carpet bomb the buying landscape to the point where I routinely talk with executives who have three, four, five hundred emails per week, unsolicited sales emails, just clogging their inbox. So with these forces at play all together, it's no wonder why almost everybody has difficulty getting any message through, you know, because that's like being on Highway 5 in LA in rush hour, right? There's no move, no movement, no forward progress. And you're pretty hot and sweaty. Exactly. It's an uphill battle. It's an unfair game, you you could say, because it's just such a trying to start conversations is such a crowded activity right now. And everybody, almost everybody's doing it the same way. It's just this carpet bombing email. And one of the mistakes that management, I think, is really making is holding on to this idea of velocity sales that goes all the way back to predictable revenue model from Salesforce, and everybody says, okay, this is the way we're going to do it. And it really hasn't changed since then. And all of these forces together are creating this cacophony that's making it really tough for everybody.

SPEAKER_02 5:35

Well, I certainly understand companies wanting to be uh to hold on to metrics, they want predictability, they want to be able to make forecasts. That's essentially why you're hiring your CRO, is to make sure that those targets are hit. So given that, if your company is targeting major enterprise transactions, what's the first thing you want to tell that management team in terms of the average sales cycle? If uh, and for the purposes of our discussions, most of our listeners are selling true enterprise software with an ACV of a quarter million dollars and above. Those qualify in this for the for the purposes of this conversation as enterprise software deals.

SPEAKER_01 6:21

I think a lot of this is kind of known and out in the open, but I think a lot of management teams are either fearful or almost unable to make decisions like this, pressure from the board, pressure from investors, uh, pressure from not really seeing, not knowing an alternative to do business as it has been done. And so the common thing, so I see this from the perspective of the sellers in the field on the ground, and they're coming to me and they're saying, I want to sell in a more strategic way. But my manager or my VP or my CRO or the powers that be have mandated that I sell in a higher velocity way. So I don't have the bandwidth to do things that are more strategic. I have many accounts, I don't have few accounts. And they're asking me to go up market and just do more, right? More emails, more voicemail, more phone calls, more meetings, more demos. And it just leads to burnout and it's ineffective because of the first problem that we just laid out.

SPEAKER_02 7:23

Yeah. Volume without true hyperpersonalization, doing the research, understanding your customer obviously isn't playing because they're dead to that. So what you've developed as throughout your career, career journey, and now that you're sharing with hundreds upon hundreds of sales executives, some of which I know this quarter have closed eight-figure deals for major enterprise software sellers and for mid-sized software sellers, I should say, is financial fluency being the new language of credibility that enterprise software sellers should use. Why is that so critical? And how should sellers build that into their day-to-day conversations?

SPEAKER_01 8:08

You know, there's that old saying, you get access to who you sound like. And there are so many sellers that have been trained on either a sales process or product knowledge. Product knowledge is great when you want to talk to users. And so that gets you, you know, if you think of it, I use this analogy that our accounts are like mountains, you know, there's lots of worker bees at the bottom, and then there's the middle layer, and then at the top there's fewer, but at the top there are the executives, right? And so if you want to talk product, you're gonna be talking with users and admins and you know, of systems, maybe system owners. At the middle layer, they want to talk about operational outcomes, right? Am I going to improve my process by X amount of time or cost or what have you, operational issues. But the executives just want to talk about financial outcomes because everything at the operational level ultimately rolls up to a financial metric that somebody in the C-suite is watching. And so when you can couch a conversation, a theme, a story in financial terms, it's gonna basically be, oh, the executives are gonna say, oh, this must be my scope. This is my language. I'm tuning in a little bit more to that. If you say, hey, I can change your process from six steps to four, the midlayer is gonna tune in, but the executives are gonna tune out. So let me just pause there. That's kind of the base level. It you get access to who you sound like. And if you're not using financial terms, if you're not counting your value in terms of helping them achieve financial results that they're on the hook to achieve, it's like, okay, this is not my scope. This is not what I'm looking for. So I'm not going to talk to this person. I'm going to push them down.

SPEAKER_02 9:54

Yeah, I was always taught that you're supposed to dress like who you want to do business with, which is why I had to stop wearing overalls. And I still regret that choice those 30 years ago. You've described a football stadium versus whisper analogy when it comes to marketing. Why is personalization at the financial and strategic level so much more effective than this volume outreach from a gong?

SPEAKER_01 10:22

Yeah, it's um what I tend to see as, you know, because I'm in the buyer market too, because my name is on my company as the owner. So I get lots of inbound from SDRs, BDRs, etc. And the vast majority of them are basically saying some flavor of we help companies like you with problems like X. And that's their version of personalization. That's about as or I saw you wrote something on LinkedIn, or I saw that you have this type of a company, and that's it. There's no story there, it's simply an observation, and using that observation as an excuse to ask for some time or a next step of some kind. The analogy that we discussed before, this whole idea of being in a stadium, if you're in a big football stadium and the crowd is roaring, you're not really gonna pay attention to that because that's just normal. And then it becomes background noise, even though it could be deafening. But somewhere around you, if somebody just whispers your name, right, Daryl, if you just hear just a peep of that, you're gonna crane your neck looking who's talking to me, who's who's addressing me specifically? That's just the analogy that I use because when we craft a point of view, right, which is a statement, kind of a visionary statement on why the customer would benefit by investing heavily in an approach that our widget, right, our product or our solution, if we can get that across on why it's in their best interest, this is the best option that they have to achieve X results. We don't have to yell, we just have to put it into terms that they care about specifically addressing their situation, not companies like them, them specifically.

SPEAKER_02 12:07

So I'm always interested about personal experiences, and I try to get as many of those as I can into the show. And I was just curious from your own experience, can you recall where getting in front of the right executive decision maker changed the trajectory of a deal? And it could be where you'd already, you know, in entered in it, one executive and been pushed down. But I'm just curious if you could share one example of where you got into that C-suite and it changed the trajectory.

SPEAKER_01 12:40

I would rather tell a more recent example from a uh a seller that I've worked with, which is really and and it was just within the last 12 months. Cool. So this seller was selling cybersecurity and he was a coaching client of mine. And for almost a year, he was stuck in this one account because both the head of engineering and the CFO didn't want to talk to him because they had an incumbent in place. A compelling event you could say happened, and the CFO left, they needed to get a new CFO. And this seller really leaned into financial fluency and working with executives and finding out what's really important to them. And he really leaned into the earnings call. He was selling it to a public company. He went so far as to start to follow the individual analysts who were on those earnings calls. And he identified the analyst that worked at Morgan Stanley. Morgan Stanley was the investment banking firm for his target account. He struck up a conversation with the analyst about improvements that could be made in the business. This led to a series of introductions between Morgan Stanley and the target account and this seller's account. It got to the CEO of the seller's company and the incoming CFO of the target account. And this completely changed the conversation such that the next part of the story is when the seller and his executives were able to engage the incoming CFO. The CFO quickly said, you know, I spend like 4% of my attention on cyber. And the seller was like, Holy cow, what am I going to do now? This guy doesn't really care that much about what I do. And he said, right then and there, I stopped selling cyber. And I started trying to find something that I could sell him that was the achievement of what he's trying to achieve. Turned out that he cared about IBIDA through cost savings. And so I crafted a financial story. Hey, Mr. CFO, I can see you care about IBITA. You set it on earnings calls, etc. You want to increase IBIDA by reducing costs across the board by 10%. I think I've got a way to give you three of those points. I can give you three of the 10 points that you're trying to reduce overall costs. If you want to talk about that, let's do that. That causes attention. That started a conversation. Turned out that the punchline of the conversation was that he could do it through fraud prevention. So he removed his product from the headline. Hey, I want to talk to you about cyber. I want to talk to you about fraud prevention. And he removed that. And instead, the headline was, let's talk about how you can reduce expenses across the enterprise. And then he turned that headline into the punchline at the end. And that's what got him in the door. And he did an eight-figure deal in less than a quarter based on getting to the right executive and having the right financial story.

SPEAKER_02 15:33

Outstanding. So getting in on that earnings call and listening, figuring out who the analyst at Morgan Salem was, looking them up, striking up that conversation, getting those. That is not classic enterprise sales where you're working within an organization. It's at a whole different level. It's engaging influencers for the account. And that takes a lot more time to devote to listening to and reading and researching an account before you approach them. But I love the fact that he jettisoned his entire product conversation and totally focused on here's what the financial impact is going to be. And that is what his audience was most interested in and solely focused on is that financial impact. So do you think a traditional ROI conversation really has that same resonance?

SPEAKER_01 16:32

It does, but that conversation is a I mean, it I built something I call the value maturity model. And you can see that a value story grows and matures as the engagement with a prospect deepens. It starts by doing really deep account research just to get your own as a seller, you get your own understanding about the sell the business reality of what's going on in the account. And then you put together your first nascent value hypothesis. It's not proven, it's total theory, but it's credible, right? And then you start to socialize that with internal and ecosystem players in and around that account. And every time you do that, the audience, the listener, they're either going to agree, disagree, or add or change your hypothesis. And all of those are good. Because with every conversation that you have that tests and deepens your understanding of how to get to the financial outcome, it gets you closer to perfect. A lot of sellers are fearful. They're like, okay, if I show up with my shiny idea and they shoot it down, I'm dead in the water. So I've got to hold on to my idea. But the truth is, you we we want to teach our sellers that getting corrected is just magic. Because when that happens, one, we get closer to the real truth. And two, it's an exercise in having the audience who is a customer stakeholder. This is them starting to take ownership of the idea. You know, hey, Daryl, your idea is okay, but you need to move it a little to the left because you're not quite on track. It's more like this. That's them adding their almost their identity to an idea. And as they do that, man, if you continue to do that, ultimately the point of view will be the customers, not yours. And that's when you truly are building champions, because that's when they sell your idea when you're not around because it's their idea at that point, it's not yours.

SPEAKER_02 18:44

Well, by giving them something to work with that's a construct instead of a presentation, it's inviting their commentary, it's inviting them to engage, it's inviting them to share additional information. It's like the classic open-ended question. Like, this is what I think your situation is. Do I have that right? And if they're saying anything, it's positive because it's it's feedback. It's saying, I'm gonna continue this conversation, I'm gonna continue. Yeah, you're thinking about me. Thanks. I appreciate that. I'm gonna give you some insight.

SPEAKER_01 19:21

Yeah. I mean, oftentimes if we can move away from a presentation mindset and into a conversation mindset, and then into a co-crafting or collaborative mindset with a lot of the sellers or the teams that I work with, I talk about can you achieve your goals in terms of getting across a message and starting a conversation without a deck? And that they kind of freeze up on that. And then I say, Let's try an alternative. How about a whiteboard? Can you start a conversation using a whiteboard and then at some point hand the marker to the prospect and say, where is this off track? What would you add or change to this? And they take that. It's like passing a baton in a relay race, right? They're they're gonna run, they're gonna go with this, and that's a part of a physical exercise that helps them take on this idea. And now you're collaborating, and pretty soon they're leading, and that's right where you want to you want to go there.

SPEAKER_02 20:21

That whole term collaborative sales, I mean, that is the highest form where you actually enable that buyer or that sponsor, because they're it's a committee for enterprise deal to champion your idea and to actually play the key role in crafting what that final deliverable is going to be. Well, this is a lot of conversation that you know, quite frankly, I can't think of how you would report it in Salesforce or any sales uh SFA that's out there. So for the CROs that are listening right now, what should they be coaching their sellers to do differently to get these meetings in the C-suite?

SPEAKER_01 21:03

So before you can coach the sellers, you have to make some changes. Uh, what do you want to call it, like institutionally, right? I think we might go a little bit deeper into this as we go, but some things that CROs can do is to mandate how do we treat the segments differently? What often happens, especially in the younger companies, is there's so little footprint in the market, they're giving their sellers vast territories, huge lists, which totally most sellers do not know how to do great territory mapping or territory account management in terms of picking, okay, who am I gonna go? I got a thousand accounts, who am I gonna go after? So, step one is just figuring out how are you gonna treat the segments differently. And realistically, if you want to go up market and start to do larger deals, well, you know. One thing that's going to help doing that is obviously go to larger accounts because each one of them has a bigger TAM, right? So addressable market in that one account, the total amount that they could buy from you, your widget. So if you're selling into bigger accounts, volume messaging, volume tactics do not work. So what's the alternative? Have them focus on fewer accounts to give them the runway that they need to do the needed exercises just to break down the door, which is enough account research, not a Google scan and maybe getting the contact details from Zoom Info or whatever service you use, but really getting into what's going on in the business. How does this account make money? Is it one big fat product that's the golden goose, or is there a portfolio? What are the trends that are going on that set the goalposts for their business reality this year or these five years or the decade ahead or behind them? When a seller can start to understand this stuff, you're prepping them, you're enabling them to get higher in the account. And then it goes back to all the stuff that we already talked about, all the decision making, all the budget control, it's all very high up. So you've got to come in sounding more like Accenture than an SDR. So if I were a CRO today and I had the ambition to do larger deals, go after larger accounts, however, I define going up market, one of the first things that I would do is take a good hard look on how do we treat the different segments, right? Because so many organizations, especially when they're younger in their maturation, there's not much footprint of them, or you know, maybe the brand isn't out there, et cetera. They let the first line managers or maybe the second line give these long lists or huge territories to a few sellers. And then that totally is very difficult for the sellers to figure out of the 500 or 1,000 accounts that I have, which ones I'm gonna am I gonna go after? And mentally, the way that I would think of it is I would find some 80-20, right? The Pareto law, 80% of the revenue is gonna come from 20% of these accounts. How do we split out whatever we consider to be below that, call them smaller accounts, to what's gonna be the list of the larger, more target accounts? And we sell to them differently. And it's more okay to do the volume sale to SMB and mid-market, even though it's still very convoluted there. But with the larger accounts, you just need a different play with different expectations of activity, like volume of activity, type of activity, and expected time to outcomes. So I would give the larger accounts to experienced sellers. You can grow mid-market and commercial sellers some of the time, but that's an organic process, it takes a long time. If you need outcomes this year, go get you some folks that really know the space and have already done enterprise selling, it's just go buy it instead of grow it. And then I would give them the bandwidth to do what they need to do because selling to these larger accounts is very front-loaded work. And so much of the effort in today's go-to-market plays are in getting the first meeting with anybody, but rather it should be how can we set up to go higher in the account earlier so that we don't have to spend much time with the lower folks and the medium folks who are more likely to block our way to the senior folks and make our ability to get connected with senior people a long, drawn-out journey. If we can find the right message with minimal activity at the lower and middle layer, and we can get that senior message down soon, if it matches with something they need to get funded and done this year, they will sponsor us all over the organization with the right people. So we don't have to herd the cats. The internal sponsors will. But let me take a pause. I could talk about this forever.

SPEAKER_02 26:13

I love that from the standpoint that so much of what you're discussing may be unique to an account and thus not repeatable. But the methodology for doing this research, for going to Edgar, for listening to the earnings call, from reading analysts who are covering the space that your client is in, that's abundantly repeatable. And learning those core messages that you have to understand what the financial situation of your client is and come at it from that angle, that can be you could scale the hell out of that. There's absolutely no limitation on that. That is a great methodology for any company, is to get focused on how they financially impact their clients and have that be their sole message that the sellers are delivering. One group that is listening in and we haven't talked about is well, what the hell does marketing do? What does marketing do during all of this? Are they involved? Do we need marketers? Yeah, I think so. What do they what's the role of marketing?

SPEAKER_01 27:20

I'm seeing the role of marketing change. And you know, everything's a pendulum. There's nothing new, there's new flavors, but there's nothing new. And it just swings in one direction and the other. And I think the direction of the pendulum swing right now is squarely with how do we put a face to the message and the air cover that marketing can help their company give to the sales force on the ground. That face could be the CEO, the founder, somebody who's seriously, you know, deep into the product or the offer or strategy who can take to podcasts, take to social media, and be this beacon with a thoughtful, you know, thought leadership message or series of messages that will draw people in. It's outbound to inbound. And you see it from really talented CEOs and founders, and the uptake of the message is just so much faster. And it's doing more with less. It's a shift of these players' time. And some of this, I don't know if the right word is ghostwriting, but like take me, I'm not a CEO of a big company, but with the small company that I have, which is coaching and software, we just put out a new product. And this product was launched in June. And in less than three months, we're almost to 10K MRR. The average SaaS company takes 12 to 18 months to get to 10K MRR. And the way that we've done it is just a part of my content cycle. And so I'm messaging on LinkedIn and through my email list about themes that are important. These themes, right? Financial fluency and working with executives, and you know, getting to you get access to the people you sound like, things like this, with a call to action to look at a product. So marketing can be a huge assistance by setting up and enabling and scaling the voice of the face or the faces of the company. That's I think the biggest thing that marketing can do right now.

SPEAKER_02 29:29

Give the CEO the thought leadership. You had a product, you had a marketing uh a bully.

SPEAKER_01 29:34

Yeah. Now, the pushback that I think any audience is likely and understandably to give is hey, I'm a CEO or hey, I'm a CRO, I got a day job. I don't have time to invest in content creation. That's absolutely valid. But if you look at the Adam Robinsons of the world, if you look at the Gal Agas at Alliant, right? He's the CEO of a company in Israel, they are trouncing virtually all of their competition in their space, which is digital deal rooms, right? And he's doing it through crushing it on LinkedIn. And it's just a such a good use of his time. It's such a good use of a founder or a CEO's time. And it doesn't have to take over their job, but they do have to put hours into it. But there are some of the most profitable hours they could do.

SPEAKER_02 30:25

Yeah. I think everybody has to be a content creator in an organization now as part of what they do. It's just if you're not creating content, you're not helping perpetuate your message. Well, what would an enterprise seller in one of these organizations tell their SDR? And what's the role of SDRs now? I certainly know that you know we're increasingly seeing the adoption of AI agents to do inbound SDR work. 80% of the sales cycle takes place before a sales executive even talks to or communicates with, I should say, the buying committee at their client. So where does the SDR fit into this?

SPEAKER_01 31:04

It's a great question. For one thing, we're all seeing that the SDR, the total number of SDRs in roles today is dwindling. And I think it's going to survive. It's not like there's not going to be any more SDRs, but I do think that they're going to be right-sized. We're going through a right sizing of the role. And one of the best sellers in my community, I got a community of like about 100 sellers that are senior sellers, and you know, we share best practices. And one of them did a whole session with his former BDR, who's now an AE. But you know, they talked about what they did the other couple of years ago. And they did such an amazing job of dividing and conquer to do, yes, it was outreach, but you know, they really thought of it as multi-threading to build the story. And the way they went at it is that the AE really was quarterbacking the building of the story. And he started with the hypothesis and he had a certain direction he wanted to go. And he really partnered with this BDR and he said, okay, I'm going to go directly after these folks, and they're the senior folks. I want you to go to all these middle folks and some low folks, fully knowing that some of these conversations were going to be one and done. But we need their input, their perspective on an issue. So the basics premise that they were getting these meetings was, hey, Daryl, you don't know me from a hole in the wall. I'm from X Company, and we've got a meeting with Y VP coming up. And the topic is X. Does this topic even hit your world like at all? Like, does this topic touch on what you do every day and what you're, you know, on the hook to deliver? And some said yes, some said no. If they said yes, they'd get their perspective on how that topic impact them. They didn't raise the issue of a product. There was nothing about a product sale on tap. It was just a conversation about an issue, maybe a pain. And they were trying to find who did it impact and what were the multiple perspectives across lines of business about this issue. More than half of them they never spoke to more than once. But at less than half that were really ready to engage, the BDR was enabled over and over. And the BDR would update the AE, the AAE would update the BDR, and together they grew their understanding of the account around this issue. So the BDR was not their primary goal, it was not just to get meetings. Their primary goal was to advance the sales team's understanding of the issue from many perspectives. And it's a lot easier to get a phone call, even a 10, 20-minute phone call, to talk about an issue rather than talk about a product.

SPEAKER_02 33:48

Absolutely. Absolutely. What's the burning issue on your desk? That's what they're going to want to talk about, and they'll give you the time. Well, you know, we're talking a lot about process and financial fluency and getting above the noise and what air cover marketing is supposed to provide. I'm interested a bit more in the people. You just mentioned, you know, an AE came and talked and came on with his BDR and talked about how they collaborate to engage an account and discover who's in charge and of a particular problem who it impacts most directly. In your coaching career as well, you know, you you talk to guys that are closing eight and nine, even nine-figure deals. What's the biggest difference between those reps and the average Joe or Janet?

SPEAKER_01 34:35

If you really want to distill it down, it is the classic owner employee divide. The typical seller sees themselves as an employee. Even if they've got a performance-based compensation plan, they still see themselves as an employee. They knock off at a certain time or at a certain level of activity. Then there's a separation both between them and the company and them and the customer as well. These highly successful sellers have an owner mentality. Maybe it's not that they feel that they're an owner of the company that they work for, but they are the owner of the relationship between them and their prospect or their customer. And they're able to think like an owner of their prospect or their customer. Because when they think, okay, I'm selling to a tire company, and I got to get into the shoes and the mind of the person I want to sell to. Because if I don't know what they're going through and what they're on the hook to deliver and everything that's between that, how am I ever going to hit that bullseye of value? And again, that's another thing that I could talk about for hours, but that is the essential difference. It's not whether they're relationship people or not. It's not whether they're challengers or not. It's not whether they're lone wolves or any of those other classifications. It's the mentality of can they think like an owner or do they think like an employee?

SPEAKER_02 36:06

Well, I'm trying to think about how do you qualify that during the interview process. Like quick question. What questions you are? Okay. Okay. So do you feel like you're on your territory? You know, that kind of flies in the face of what most major enterprise software companies do, which is they have verticals and they have the subject matter experts, so that that ownership of a major account, a global account, is diluted. You've got the chief seller, and then all of the folks that are selling their add-on piece under them that do not own the account. And that quite honestly is the most consistent gripe that I hear from them is that yeah, we don't control whether or not this deal happens at our account. We've actually got to have an internal account owner green light our deal process. Like, how do you maintain satisfaction or sanity as a seller in that kind of environment? I don't understand.

SPEAKER_01 37:04

So I come from Oracle, which is an absolutely crazy matrixed organization that does compound deal after compound deal. What I mean by compound deal is there's multiple products being sold, represented by multiple sellers in need of Uber uh coordination at some level. And I learned the most about that when I was a key count director. So I didn't have any direct reports, yeah, but I used to say, you know, nobody reports to me, but a lot of people work for me because there's all these kind of sellers beneath you. If you're wondering, how does somebody who I guess that the word co-prime is out of favor, but you get the idea, you know, a seller who's not is not the core rep, they really do have to work with the core rep. And there will always be decisions in their territory, which accounts is the core rep totally dialed in on and just you know marking up their whole territory because they feel a great sense of they need to control it because they got to get a deal done, versus which ones are out of there, which are more in their peripheral vision, where I could actually get their buy-in. So if you're the core rep and I'm the a peripheral rep, I'd say, Daryl, you got three big accounts, two of them are mine. What are you doing? And you'd say, Well, in the blue one, I'm way in there, don't touch it, and come to me before you even write an email and all that kind of stuff. And I'm like, Great, I'm either I got to go lockstep with you or I go elsewhere. How about the yellow one? Oh, the yellow one, nothing's going on there. You mind if I just do my thing there? Yeah, no, no, that's fine. So it's just like you know, stepping into the the shoes of your buyer, you got to step into the the shoes of whoever you're trying to influence their thinking and behavior. That's the way that I coach on how to deal with those issues.

SPEAKER_02 38:52

Well, let's talk a little bit more about coaching. You know, what books or resources or practices or diet or exercise regimen do you recommend for sellers who want to develop executive fluency early?

SPEAKER_01 39:03

The best book that I could recommend is called Financial Intelligence, and it's by Karen Berman and Joe Knight. It's an excellent, excellent book. Of course, it's available on Amazon. And the audience is not sellers per se, but the audience is basically anybody that needs to understand the basics of financial intelligence, financial fluency without being a finance professional. Excellent, excellent book. A lot of the teaching and courses and all these kinds of stuff that we've developed are based on the ideas that we got from that book. So that's my number my top pick.

SPEAKER_02 39:39

And you actually, as we've mentioned on multiple occasions throughout this podcast, you actually do consult with enterprise sellers and through your own program and through engagements with enterprise software companies. Can you provide us a link or some information about that?

SPEAKER_01 40:00

Certainly. I'll leave some information that we can put in the show notes. But long story short, whether it's individuals or teams, we tend to stay on the more enterprise side, commercial side, and helping companies go up market and train their reps to get there. That website's elite sales secrets. I would say the the well, number one, you can just kind of reach out to me, but other than that is JamalReimer.com.

SPEAKER_02 40:26

JamalReimer.com. There we are. You know, since we have a little bit of time here, I'm I'm awfully curious, and I'm sure the people that are listening are as well. It's like uh learn a little bit more about Jamal. Jamal, I assume you weren't hatched out of a pod. You were born somewhere and grew up somewhere. Am I right about that?

SPEAKER_01 40:45

That would be right. I I did grow up somewhere. I was mostly in North Carolina, and then we started to live internationally, moved to Africa, and then when I was on my own as an adult, lived in China and Chile. I'm now in Portugal and spending after spending the first 15 years of my marriage in Sweden, and then we moved to Portugal just last year.

SPEAKER_02 41:10

Wow. So what led to all of that travel?

SPEAKER_01 41:14

Wanderlust, right? When I was in graduate school, I was interested in finance at the time, and the emerging markets of South America were really where it was at. And so I decided to go to my, like any good sales guy would do, I went to all my professors and I got a list of everybody that they knew in Argentina, Brazil, uh, Chile, and the in the area. And then I went and I tried to meet with all of them on an actual trip and met them face to face. And it I wound up getting a job at Citibank on a trading desk in uh Chile. And so that's what kind of started my country hopping. How many languages do you speak? Two English and Spanish. That'll work. But so you moved to Portugal is kind of pretend you speak Portuguese or starting. Starting, it's not as similar as I thought it would have been, but it gives me a good uh leg up as we went. When you were a little tight, did you want to be a CFO? I didn't know for the longest time what I wanted to be. Even most of the way through university, I thought I was going to be a psychologist, some kind of counselor. And then uh about halfway through, I saw I had something for sales, and so that's what I what I leaned into.

SPEAKER_02 42:23

Got well, very cool. Well, Jamal, it has been an absolute pleasure having you on the show. Do you have any parting thoughts that you'd like to leave with our audience?

SPEAKER_01 42:33

Learning how to sell to executives is probably one of the best skills that anybody could learn. And if if your audience is CROs, they already know that, right? They're one of them and that that's how they got to where they are. But transferring those skills to their sales teams is uh number one, it's hugely valuable. Number two, it's not obvious. It's not something that you can really deliver in nice, clean, discrete steps. And one of the things that I encourage is wherever possible, is to invite or allow reps, like one at a time here or there, to join executive meetings in any internal following other reps, whatever it is, because it's such a fast experience to have this aha moment when you see executives talking to each other. So, of everything that we talked about, I think the two things that are extremely important and move the needle the most are learning how to work with executives and couching those conversations in financial terms with financial value stories. When you have those two things, those are two massive pillars in doing much larger deals that are and establish very sticky relationships.

SPEAKER_02 43:48

So, in other words, get your people out there in front of the client so that it demystifies what those folks are talking about. Jamal, thank you so much for joining us today. We're gonna have all of your contact information in the notes. And I wish you the best.

SPEAKER_01 44:06

One thing I wanted to leave you with is a tool that you can use, which is one of the hardest things to do to create that aha moment for sellers, is okay, once you find a financial reality that is going on within an account, what does that do to your point of view? How do you make that leap? So I'll put this, I'll give this to you for your show notes. It's just a document that we call a point of view trigger document, which can enable a rep to see, okay, if they're having margin compression, this is how I can turn that into a point of view. Okay, if they got a lot of money wrapped up in working capital, this is the direction that I should take my point of view. So I'll leave you that. You know, that's a cheat sheet that can quickly help rep see, aha, this is actually what I can do to build a point of view from whatever financial reality is happening in an account.

SPEAKER_02 45:00

Outstanding. Adding value to the end, Jamal. Take care.

SPEAKER_01 45:04

Thanks for having me, Darrell. Be well.

SPEAKER_00 45:09

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