Speaker 1:

Hi, and welcome to The Insiders by durhamlane, where we get perspectives from industry thought leaders about strategies that are unifying marketing and sales cycles to help accelerate growth inside your world.

Richard Lane:

Simon and I were delighted to be joined for this episode by Jamal Reimer, founder of Enterprise Sellers. Over the course of a 20-year sales career, Jamal discovered the secrets of mega deals, a mindset that delivers back in multiples. Listen on to hear Jamal’s story and his views on the characteristics of high-performance enterprise sellers, the Roger Bannister mindset, believing in the unbelievable, how to use executives effectively, and what to avoid when working with the C-Suite. There’s lots to unpack in this episode, so strap in and enjoy. See you again soon.

Simon Hazeldine:

Hello, and welcome to The Insiders by durhamlane, an industry podcast giving you the inside track on all things B2B, sales and marketing. I’m your host, Simon Hazeldine. I’m an author, sales expert and keynote speaker on all things sales and negotiation. I’m joined by my co-host, the CCO and co-founder of durhamlane, Richard Lane. Richard, great to be back in the studio with you for another Insiders episode. Do you want to tell us a little bit more about durhamlane before you introduce our guest for this session?

Richard Lane:

Certainly. And hi, Simon. Great to be back. Just in brief, durhamlane is an integrated sales and marketing agency. What does that mean? Well, we help our customers create [inaudible 00:01:33] on channels of meaningful and well-qualified sales opportunities that business development teams love to close, so everything demand and lead generation-based. We’re thrilled to be joined today in The Insiders’ studio by Jamal Reimer, founder of Enterprise Sellers. Jamal, welcome. I’m going to hand back to Simon and really looking forward to today’s conversation.

Jamal Reimer:

Thanks, guys. Great to be here.

Simon Hazeldine:

Wonderful. Thanks, Richard. Jamal, what we normally do with our guests, is just so our listeners can get to know you a little bit, could you just give us a bit of background and how you came to be in the role you’re in currently? And I think that’s going to be important for the topics around mega deal that we’re going to be talking about.

Jamal Reimer:

Sure. I was a 20-year individual contributor, enterprise seller. The first half of my career was very bumpy. So bumpy, I was fired twice in a row for underperformance. Early in the second half, that second decade of selling, I was fortunate enough to be mentored around how to sell really large deals. And over the course of that later decade, I was fortunate enough to close multiple, three different deals that were %50 million in higher of SaaS revenue. That’s a short story.

Simon Hazeldine:

That’s a three impressive deal numbers I think. So I’ve been reading your book Mega Deal Secrets. You can see from my bookmark, I’m about halfway through. So I think it would be really helpful for our listeners if you could define what you mean by a mega deal. So you’ve mentioned some numbers there, but what would be, in addition to those, how would you define that for somebody?

Jamal Reimer:

Simon, that’s a really great question, because when people read some of the posts that I do or the book, that eight figure number gets stuck in their head and that’s not how I see mega deals. What I see, is mega deals are deals that are significantly higher than whatever it is that you are used to selling in your selling reality. So part of what I do is coaching, and I’ve worked with coached reps who are used to doing 30K deals and help them get to 150, or some that are at 150 and they get to three or four million. So for me, the mega deal is not a nominal number or some kind of minimum number of zeros behind a number. It’s three X, five X, 20 X the size of what you’re used to doing or what’s typical in your role or industry.

Simon Hazeldine:

Yeah. So that’s going to be a little bit of a shift change for the seller and I guess maybe for their organization as well sometimes, that this seller suddenly starts bringing in revenue 10 times. That’s probably going to be an interesting, disruptive kind of moment for the individual and for the organization. And so you mentioned your first 10 years were a little bit bumpy and challenging and getting pushed a couple of times. Bless you for that one. But what was your first mega deal? What was that one that really shifted your perception and your approach?

Jamal Reimer:

It was in 2012 and it was an experience where we had a customer who had become a very dissatisfied customer and they were looking at options other than us, and it was a renewal year in what was typically three year contracts. And when I said I was mentored, I was literally taken by the hand by my head of sales and my head of professional services, both of whom were 20, 30 year veterans of our industry, which was pharma tech. We sold to R&D organizations within the global pharmaceutical world, mission-critical stuff, really big clunky stuff.

And it was over a nine-month period that the story really began, the story of the book, the book is the story of my first large deal. And things really solidified as the beginning of the story when we’re sitting in a conference room on site with the customer, my head of sales on my right, my head of professional services on my left, across the table is the customer team led by our executive sponsor, and we are almost fumbling around trying to say, “Here’s all the great stuff that we’re going to do for you to try to keep you as a customer.” And it was shifting out consultants from offshore to onshore, or a discount here and a discount there.

And pretty soon into that conversation, the executive sponsor put up his hands. He’s like, “Guys, guys, guys, this is not about changing out resources or discounts. This is about how we steward the most important IP of this company.” And it was a long pause and then the conversation really shifted. And after the session was over and me and the team were headed to the taxi to go back to the airport, my head of sales said, “Guys, win or lose, we are up for looking at a very large transaction here.”

And I just looked at him and I was like, “Where did you get that? They’re not happy, they’re going through all this pain and we are the source of it, and I don’t get it. I’ll be happy if we just keep them.” And he said, “Didn’t you hear what he said? He revealed the true importance of the nature of this project, of what we’re doing, whether we’re doing it well or poorly in this moment. This is critical to the company, not just him or the project or et cetera. It’s a massively important issue. And where there’s massive pain, there’s massive potential value.

Simon Hazeldine:

Well, what would you say were some of the key shifts that happened? So you’re looking at it as unhappy customer, “We’re going to be lucky to get a renewal,” and the perception of your boss et cetera was different. What was that shift like for you?

Jamal Reimer:

It showed me what I was used to doing was talking about products and what the conversation quickly became, they were on a big ship and there was a big hole in the side of the ship. And all of a sudden, your attention and your sense of what’s important in life gets very, very focused when you’re in a situation like that. And it made me realize that talking about products is like talking about how nice the wrapping around a package is, rather than what’s inside is this lifesaving medicine that’s going to help your infant son stay alive. That’s the two extremes of what kind of value proposition we’re talking about.

Simon Hazeldine:

That’s wonderful. I would’ve very much liked to have been a fly on the wall and seen that shift taking. Richard, for you, in terms of what Jamal said, resonate with durhamlane in terms of how you approach those conversations with customers?

Richard Lane:

Yeah, absolutely, Simon. We have our durhamlane mantra, and mantra number one is, “Business fit, business value,” developing long-term relationships. So absolutely understanding the defined needs. We spend our time at the very top end of the sales funnel looking for opportunity and qualifying that for our customers. So our job is to pique people’s interest and then convert that interest into meaningful opportunity. And for there to be opportunity, that has to be needs. So yeah, totally prescribe to what Jamal was saying there.

Simon Hazeldine:

And Jamal, I know you mentioned you do coaching, so through amongst other things, and as the founder of Enterprise Sellers, you must have seen a lot of enterprise sellers. The group I’m particularly interested in is what we might define as high-performance enterprise sellers. And what would you see as the characteristics, be that thinking approach or behavioral approach that would define them apart? These are the people who are going to possibly be able to do mega deals. So what are the kind of characteristics that you would commonly see?

Jamal Reimer:

Great question. Two very different categories, but they relate. The most consistent characteristic is in the mindset bucket, which is, they’re all trying to get to the top of a very tall mountain. They’re focused on the summit, they’re not focused on the middle part, they’re not focused on the low lands, they’re focused on the summit of a very tall mountain. It’s a mindset thing.

You’ve got choices in terms of who you prospect into. You could prospect into somebody in the low lands, I lovingly call them worker bees, folks who are button pushers. They do the jobs, they’re individual contributors, they’re moving pallets, they’re writing reports. You could prospect in at that level and you’d have a very limited conversation about what would be valuable to them as an… They’re looking for an easy button. If you can sell an easy button, they’re going to love that.

If you go to somebody in the midlands, the mid-level managers, they’re looking for value for a team, a team of five or 10 people, so to speak. But if you’re very focused on the top of that mountain, your value proposition, for the same product as these other two guys, is much more around an outcome that can move the needle for a business unit or for an entire enterprise.

So you say what are the characteristics of top performers? Number one is mindset. This kind of very, it’s almost grand thinking. “What is it that me or my company or products or any of this can do to significantly move the needle for the senior people within one of my accounts?” But everything else after the mindset piece can vary widely. So if you go with this mountain analogy, you get three different sellers who are all focused on the summit. They might choose to get there three different ways, either time of year or what year they use or which face they go up, which team to use. They can do it very different ways.

I’ve seen mega dealers who are extremely systematic and they really shine at running a great process. I’ve seen other mega dealers who are world-class relationship managers, particularly through crisis and almost brinksmanship. And then there are other mega dealers who are really good at putting together a team in a way that they’re mapping the right people and it becomes the most beautiful form of team selling. It’s like these two teams that are interacting in a way that bring together these things. So I hope that’s not too vague, but there really are these two different groups. One is very, very consistent about the mindset, and the other, they can all have different primary strengths in their methods, that meet their personalities.

Simon Hazeldine:

But grand thinking, in your words, seems to be a very important defining point in terms of perception. I guess that sounds like what happened in the taxi on the way back from the client to the airport. Your colleague was grand thinking and you were, “Oh my goodness, we’re going to be lucky if we keep this thinking.”

Jamal Reimer:

And the beauty of that, what you just called out Simon, is at the heart of that little snippet, is hope that lots of us sellers can do mega deals. We don’t have to be born with the mindset, we don’t have to be born with a personality of fearlessness or some kind of pixie dust that we can just magically throw on our customers to enchant them. We can learn this. I learned this. I, the seller who was fired twice in a row for underperformance and was just about to get out of the whole gig of B2B sales. So it’s absolutely fair dues to say, if I can do it… I don’t know if I want to say anybody can do it, but lots of us could do it.

Richard Lane:

Yeah. And I love that phrase, grand thinking. I was just wondering, I agree, Jamal, anyone can learn it. I wonder whether you can forget it as well? If the environment that you are in, perhaps you might end up not grand thinking?

Jamal Reimer:

That’s also a great point, Richard. I’ve seen reps who have done a single mega deal lose their grand thinking. And either the environment will change or their territory will change or their boss will change or there’ll be some change, and they allow that change to lock them into a lower level of thinking.

Richard Lane:

Yeah, interesting.

Simon Hazeldine:

I’m interested, Richard, as well. When you said that, I was just thinking about the importance of, you saw from Jamal, your example of your manager, that impact. And I’m just guessing if managers are going, “Hey Jamal, can we get this to 75K? Can we get this one to 100? Can we get this one to 50?” Rather than, “How do we revenue five million here?” And it will be the grand thinking, the managers starting to stimulate that thinking, which I guess is what you must have to do when you’re coaching people as well?

Jamal Reimer:

You’ll appreciate this. So there’s many kind of mindsets you can have. Some of it is about how to do something, “How am I going to approach this?” And the other is more positive thinking, “I can, I can, I can.” All things are possible, manifesting results I’m looking for,” et cetera. But one of the mindsets we talk a lot about is the Roger Bannister mindset. Incredible British story of the first person in human recorded history to run the mile in less than four minutes and I call it the Roger…

For those of us that might not know the story, Roger Banister was a medical student and an amateur runner who also went to the Olympics. So he was no beginner, but through his own unorthodox training methods and mindset, he simply disagreed with a growing perception that potentially, maybe physiologically it wasn’t possible for human beings to run a sub-four minute mile. And he just didn’t subscribe to that thinking and he had his own methods of training.

And on a subpar day at a track in the UK, on a soggy track, he made the decision 20 minutes before the gun went off to actually go through with it and he did it. And then I usually ask somebody, I’m coaching, I’m like, “Guess how long it took the next guy to do it? It was under two months.” And so once that record was broken, I think it’s thousands, it’s at least in the high hundreds, if not thousands of runners have broken the four-minute mile.

Richard Lane:

Just to credit my home track of Iffley Road in Oxford, that was where he did it.

Jamal Reimer:

Take a picture, put it in the show notes.

Simon Hazeldine:

Richard obviously would now lay claim to that result.

Richard Lane:

I used to run around it myself, but not that sort of speed.

Simon Hazeldine:

And in your book, Jamal, one of the phrases that really struck me was executive whispering. So we’re talking about thinking about the summit, aiming at the summit, and you’re going to be having conversations about moving the needle. So you’re talking to senior level people. So how do you approach coaching people around those kind of executive interactions, executive involvement?

Jamal Reimer:

It’s a bit of a process. It doesn’t happen all at once. The first level that we talk about is, “Hey, you don’t have to do this by yourself. You don’t have to overnight change your mindset to the point where you are comfortable establishing what I call peer business relationships. You’re not going to start feeling like you are a peer to somebody who’s been in an industry 20, 30 years and they got a title five levels higher than yours,” et cetera.

And so the way to leg into this is by leveraging people around you who are aligned with you in your efforts, who already have, or who are closer to that peer business status. And the first port of call is your own executives. So what we talk about is this executive whispering is the art or science, or mix thereof, of working with executives on both sides of the table, the customer side and in internal to your organization.

And even though I’ve been doing it for a long time, sometimes I still let my executive and their executive have one-on-one interactions and I’m not even around, don’t need to be. It’s a gradual approach. You can start by leveraging others, and then as you start to be in those rooms where those conversations happen, the next thing is realizing what it’s really like. It’s like getting a peek behind the curtain.

What happened with me is that when I started to get in those rooms, I started to realize, holy cow, executives are nowhere as intimidating as the mid-level guys who are using all this babble to credentialize themselves in front of large groups. And the executives tend to be, not everybody, but they tend to be plain talkers who use normal, everyday language to describe problems or opportunities or situations succinctly because there isn’t a lot of time and they’re not deep in the details, but they got to push the ball forward in the conversation.

Simon Hazeldine:

It’s an interesting thing about deploying your own executives. I’ve often come across it as an area for significant improvement. I’ve been working with a client for about a year now, rolling out a key account management complete program and solution, and their executive management team have been participating in a sort of condensed version. And we were talking about this concept and I said, “They may, because of what I’ve said to them, they might come and ask you more often to support them.” I had all of the C-level in the room and the CEO said, “Well, let me give you some feedback. I’ve been asked once in the last 12 months to go and visit a customer.” And he said, “I might not say yes, but they’re not asking me.” So I think it’s a real opportunity sometimes I think that’s missed, Jamal. And Richard, you might get your folks wanting to deploy your good self in their customers?

Richard Lane:

Try and keep me away, is the problem, the thing. Yeah. No, I think we have a good understanding of that exec level up and use it as best we can. We’re not a huge company, so we’re not an enterprise by any stretch, but we do our best to engage the right people at the right time. And I think we’ve shifted and probably moved from a place where we didn’t empower our execs enough, and the C-level took too much control and we’re moving away to become more supportive rather than to own. And that’s probably quite a big lesson as well.

Simon Hazeldine:

Jamal, you mentioned the process aspect. And with your client base and through Enterprise Sellers, you must work across all sorts of different sales processes, sales methodologies. At a meta level above that, what would you say are the common themes that you see, rather than about MEDDPICC or whatever as a methodology, some of the common themes that you think are helpful?

Jamal Reimer:

Well, there’s a few. Clearly, one is… So sellers who come to me are interested in doing outsized deals. They’ve reached some kind of a perceived ceiling in their own selling and they’re trying to break through to get beyond it. And so that’s the driver. And so if that’s the interest, then one theme is the larger the deal, the higher in the org you’re going to have to go to make it happen. And so if that is true, then the follow on is, “Well, how can we get higher in the organization as quickly as possible?” Because the other thing is that most… Well, sometimes they go faster. I was just talking with the COO last week about this. Sometimes the larger deals go faster if you’re at the senior level. So there’s all kind of reasons you want to get to senior people faster.

One, is that if you go to the middle level or lower, they tend to be more risk averse and that partially explains why they try to limit you or contain you and not let you engage with other parts of the organization or go above their heads. So it slows the process of engagement. But the other is just, as I said, senior people are accountable for outcomes. They’re not necessarily wedded to how those outcomes are being achieved today. So they’re more open-minded. So one huge theme is get to power as soon as you can, and once you get there, the second theme is, what are you going to say?

And what we can’t do is rely solely or parrot the sales enablement materials were given. They’re good. I’m not saying they’re not good, but they’re just a platform. Right? They’re like that Lego base that you’re supposed to actually build upon. And you can’t just take the Lego base and make something you need to put something on top. And something on top is based on lots of deep, what I call research and discovery reaches. Research is stuff you can read by yourself and access on the internet, like annual or quarterly reports or investor day presentations and stuff like that. Discovery are things that you have to actually discuss with people. They could be employees within the account you’re selling into or they could be people within the ecosystem around that account, SIs, board members, former employees or executives. There’s all kinds of people around the account who are not direct employees.

The biggest theme is the importance of getting to senior stakeholders quickly. The second thing is once you get there, having a compelling story to tell. What I learned from one of the greatest sellers I’ve ever met, and her name’s Marcie Akers, she’s at Oracle. She said, “I don’t even use the word software anymore. When I’m having a presentation or a conversation with executives, I don’t even use the word software. I either talk about the asset or I’m just talking about the outcome.” So those are two big themes that I would say.

Simon Hazeldine:

I guess you may have partially answered some of my next question is, some of the common mistakes and failings that you see? And I guess we’ve probably going to know, aiming for the middle, not getting to power. What specifically, when people are in front of the power, when they are rat executive level, what are some of the… Sure, one big mistake I think is to take in your sales collateral and expect that to do the job for you, which is quite dangerous place I think to be when you’re operating at… In fact, taking in your PowerPoint slides at all would probably be a good idea to maybe give that an avoid. But other thoughts about what maybe some of the failings you’d see, the common things that you have to coach people around to improve?

Jamal Reimer:

Two are really close to each other. One, is staying in presentation mode instead of conversation mode. And very closely related to that is simply talking too much. A lot of sellers, particularly when they feel they’re not feeling confident, they feel that the way to add value and credibility is to say more. And they talk. Not only are they talking about the product, but they’re talking a lot about the product, and deeply. And there’s this misconception that that kind of, “Well, if you like this feature, you’re really going to love this one.” And they feel it’s kind of like loading up a grocery cart full of goodies, when instead, you’re just pushing that senior person further and further away.

The opposite of that is to ask a lot of smart questions, pose some challenging or engaging concepts, and that’s what ignites executives, they’re like, “Ah, she’s got a great idea here and this is something that we want to talk about. And she’s letting me do some talking, too, because I got thoughts.” Now, you’re engaged. And that’s the opposite of the failure that a lot of reps have, which is, let me just rat-a-tat, get my machine gun of features and functions out.

Simon Hazeldine:

It’s Forrester research. I think it’s been out a little while, Jamal, it would probably line up almost exactly. 88% of executive decision makers said they would rather have a conversation than a presentation when they’re dealing with sales-related matters. So they understand the meeting is around selling something, but they’d rather have a conversation, which I think absolutely backs up your approach. Richard, durhamlane’s conversational selling approach, how would you… Because I guess that’s one way, it’s my words for it, not Jamal’s words.

Richard Lane:

Yeah. So our methodology selling at a high-level is very similar in terms of, I said earlier, business fit and business value. We typically prospect into C-level and they’re going for, “This is why I’m writing to you. This is why we think you should be interested and this is why I’d like to happen next.” So that’s a little framework that we use, whether it be voice or email. So going in for research and discovery, I think discovery is so important, isn’t it? And I was once taught 95/5, so in that senior stakeholder session, if I can talk for 5% of the time and they can talk for 95, then I’m in a winning place. And I don’t actually think I’ve not won a deal where I’ve managed that at the early stages with the right level of contact. So it’s free consultancy to qualified prospects, isn’t it?

Simon Hazeldine:

Yeah, 70/30 is the one that I keep hearing about, normal sales conversations. So I would definitely say the higher up you’re going, the percentage needs to be changing quite significantly. Jamal, just a slight change of topic. You’re also the founder of Outboundless, which is described as a creative outbound marketing company. What does Outboundless do differently, would you say, to other outbound marketing companies?

Jamal Reimer:

I guess we come with a premise. So I’m a co-founder. I’m one of the, I would almost say the main co-founder’s name’s Nathan Offner. And I’m a career seller who’s always trying to find creative ways to engage people of capacity who have lots of gatekeepers around them. An absolute title wave of fairly typical messages coming to them, primarily through email or phone. And those are what I feel to be, they’re so commonly used, they’re overused, and executives build up a lot of callous to those mediums. And Nathan is a career outbound specialist. And basically, what we’ve done is create uncommon approaches to connecting with people who we don’t have any current relationships with, which are primarily a mix of creative items sent through the mail, linked to a digital experience that’s personalized to the individual. And so if you can imagine getting a fedora and a bullwhip in a box, you could imagine what kind of adventure you might be setting yourself up for. And interested to see what’s the next thing that’s going to be coming. So without giving any further details, that’s the nature of what we do.

Simon Hazeldine:

Yeah, don’t give away the recipe to your secret sauce, Jamal. We thank you for your generosity in joining us on The Insiders, but I guess there’s some secret source there that the people will have to contact Outboundless if they want to know some more. I’m just envisioning that particular chief executive officer that I was mentioning earlier, receiving that in a box on their desk. I think that will be an interesting moment that I would probably pay money to see. So that’s absolutely wonderful. Thank you. Richard, you’d normally give us the Richard Lane summary of some of the key points from our conversation with our guests.

Richard Lane:

You keep building this up, Simon. So I feel under pressure, but Jamal, I loved your honesty at the beginning, 20 year sales career, ups and downs. I wrote down, “Ups and downs equals experience.” Perhaps you wouldn’t have got to be doing what you do now if you hadn’t had the ups and the downs. So I always think that’s worth reminding people, that when times are tough, dig in. And the great thing about the world of sales is that if you put the effort in and you think hard enough, then you will ultimately be successful.

Understanding the criticality of the issue. I think so many people focus on product. This is brilliant timing because I’ve just come out of a big renewal conversation internally about one of our customers and so it’s got me with my grand thinking hat back on, which is appreciated. But we talked about that shift from product to strategic business and we try and practice that here at durhamlanewith our first mantra.

Really enjoyed the conversation around mindset. I think mindset is such a powerful tool across so many different walks of life, but sales, as much as many other professions, particularly if you think about sports. Grand thinking, creating the right environment as a business owner, then it’s my job to create the right environment for people to be able to think in a high-performing way and to be empowered to have that grand thinking. And then believing in the unbelievable. So the Roger Bannister mindset, I think that was a great thing to remind ourselves on, is that just because something maybe is thought to be not possible, doesn’t mean that that is the answer.

And then we talked about getting to power ASAP. So some of the, I guess from a methodology point of view or from an approach point of view, what are the things that our listeners can take away and do immediately? I love that idea of getting to power ASAP, but then also knowing what you’re going to do when you get there. It’s that research and discovery before you get there. It’s about not being in presentation mode and definitely not talking too much. So listening, being that consultative advisor, I think that advisory role is so key. And here at The Insiders, we talk about being the sense makers and the storytellers and I think that’s pretty much in tune with what we’ve discussed today. Jamal.

Jamal Reimer:

Definitely. No, a great rundown and I agree with everything.

Simon Hazeldine:

That’s wonderful, Richard. Thank you. And Jamal, just before we go, we’ve got a final question for you. We are building The Insiders Spotify playlist, and we’re asking every guest to add a song to the very eclectic collection that we’ve gathered so far. What is your chosen song?

Jamal Reimer:

Hands down, Eye of the Tiger.

Richard Lane:

Yeah, very good. What a cracker. Almost burst into song then. That would have been embarrassing.

Simon Hazeldine:

It’s the classic motivation before the sales pitch kind of music, is it? I think.

Richard Lane:

You’ve done your research and you’ve done some discovery, and then you’ve got your senior C-level exec meeting sorted out, you press play in the car park before you walk in and you’re away.

Jamal Reimer:

That’s it. That’s it.

Simon Hazeldine:

Wonderful. Well thank you very much, Jamal, for joining us on this episode of The Insiders by durhamlane. Thank you to my co-host Richard, and thank you to you for listening in, as always, folks. If you’d like to subscribe to The Insiders podcast on your preferred podcasting site, you’ll be notified of new episodes as and when they’re released, which they are on a regular basis. And visit durhamlane.com to learn more about selling at a higher-level. In the meantime, we’d just like to wish you all good luck and good selling folks.

Speaker 1:

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