5 Shifts to Move to Mega-Deal Thinking & Catch Whales


5 Shifts to Move to Mega-Deal Thinking & Catch Whales: Overcoming Small-Deal Syndrome (Summit Replay)

This video training was originally presented at the 2019 Sales Hacker Success Summit. In it, Strategic Account Manager and top 1% performer at Oracle, Jamal Reimer, shows you how to think big and close on mega deals.

What You’ll Learn

  • You’ll see behind the scenes of an actual mega deal
  • Why mega deals aren’t just for sales superheroes
  • 5 mindset shifts you need to make to become a whale hunter

The Video


Download the Mega Deal Playbook Here

Outline, Timestamps, and Transcript

Who is Jamal Reimer (00:00)

Jamal’s first ever big deal (04:11)

The 5 shifts to big deals (10:43)

1. Integrity and authenticity (11:12)

2. C-level insights(13:35)

3. Leverage your executives (21:46)

4. Pump up the deal size (31:15)

5. Invest in mentoring (41:01)

The Mega Deal Playbook (43:07)

Key Takeaways (48:44)

Who is Jamal Reimer (00:00)

Hey, my name’s Jamal Reimer, and I am an enterprise sales rep at Oracle. Today, on the Sales Hacker Success Summit, I’m going to be talking about doing deals of uncommonly large size.

Let’s jump into the content. I’m going to share my screen, and we’ll get going. The title of this work is called, 5 Shifts to Move to Mega Deal Thinking, and it’s really about the steps that I had to take, and the shifts in my attitude, my mentality, and the processes that I used to move from doing average and smaller sized deals to really hunting whales.

In the next 45 minutes what I’ll do is take you behind the scenes of an actual mega deal by telling the story of the first large deal I ever did, and also we’ll talk about each one of the five shifts to become a whale hunter.

Now, the biggest thing is going to be at the end — and it’s also something that I’ll leave you that you can download — which is what I call, How to Find and Close a Mega Deal in 12 Months When the Conditions are Right. It’s my playbook on all the steps that I take from beginning to end, how to find a mega deal, how to work it, and how to close it, within 12 months when the conditions are right.

A little bit about me. I’m a 1% top performer at Oracle, and have been on and off for the past seven years. Since 2012 I’ve closed over $160 million dollars in SaaS revenue, and I did most of that by doing multiple deals that were over $50 million dollars. I did that within two different roles. Both were individual contributor roles as an individual sales contributor. The first was as a Strategic Account Manager where I had a handful of named accounts. And the other was as a Key Account Director, when I only had one account, and I was kind of like an uber rep over many other reps that all sold into the same account globally.

I’m also a community builder. I have a LinkedIn group that’s called “The Sales Tribe,”d and you’re all welcome to join if you’re an enterprise seller. And, I’m also a coach. I help sales reps and sales teams become whale hunters.

Now, I wasn’t always a big deal sales rep, and I remember very clearly what life was like before I ever got to do my first mega deal, and I had a lot of fears and doubts about my abilities. I mean, the first one was every year I wondered how I was going to make my target.

In all of the companies that I’ve ever worked in, the target for the year has never been something that is negotiated, it’s always given to us. I would always get that number and I would look at it and I would say, “How am I ever going to make that number?” It was just an ongoing fear. I still sometimes feel it, but much less than I ever did.

I also feared I’d never break out of small deal syndrome. For the first several years of my enterprise selling career, I was doing fairly small deals over, and over, and over. I was never able to break out of what I saw as the small deal range, and I just didn’t know how to get there.

I also feared being fired for under performance. That’s a real fear in our industry and in our role. In many cases they run the sales group in such a way that if you’re not performing on a certain basis — not only annually, but sometimes quarterly or even monthly — you can be out. That was a real fear that I had for a long time.

I also secretly worried that my so-so quota attainment, which was like once every second or third year, and I feared that rate was going to be the best that it ever got for me in my sales career.

One of my biggest fears was that I was never going to reach my financial goals.

If you’ve felt any of these fears, welcome to the tribe. I have felt them, and sometimes they still bite at my heels. But, many of them have kind of taken a backseat after I learned how to do much larger deals.

Jamal’s First Ever Big Deal (04:11)

The first shot that I ever had about a mega deal, let’s talk about what that was like. Firstly, it was with a customer that we already had. They were doing some business, a certain kind of a run rate amount of business on an annual basis. And, they would do a multiyear agreement with us to work together for a number of years, and then we would renew that contract from time to time.

But, this customer, I just got this customer. I had it at one time, it was taken away, given to another rep, and then I got it back. When I got it back they were in a crisis situation. The customer was very, very unhappy, the customer was considering alternative providers.

What had happened was, we had gone through an acquisition of a product that the customer was using, and during that acquisition what many times what happens is many people in the acquired company tend to leave and go do something else. And that turnover was creating a lot of inconsistency in our delivery, and it was really creating mayhem for the customer, which created this whole crisis situation.

We would meet with the customer every week for several weeks in a row. And at the beginning of that process, when we were just setting up to go through making all the changes needed to get through the crisis, we were sitting down with the executive sponsor for the program, the executive at the VP level.

We were talking with him about, “Hey, maybe we could do some discounts over here, and we could move some team members around in a certain way.” We were trying to start the process by creating a cost savings. This VP basically put up saying, he says, “Guys, guys, guys. This is not about moving around a few people or a few prices, this is about how we steward the most important IP in our company.” There was a long pause after he said that.

The conversation shifted quite quickly into a very different kind of conversation. I remember that after that meeting when we were going to get into the cab to go back to the airport after, because we had to travel to get to the headquarters of the customer. My VP of Sales turned to me in the taxi and he said,

“You know, today’s meeting changes everything.”

I said, “Okay, how’s that?”

He said, “This is no longer a run rate deal, I think this is going to be a deal of a much larger size.”

I said, “Why is that?”

He said, “Because by telling us the great import of this project and the need to get it right, he’s basically saying that he wants a very ambitious result, far beyond anything we’ve done in the past. He’s really opened the door for us to come back with a very ambitious solution. And the ideas that I think we’re going to be rolling around are going to be, they’re going to take a lot more resources. I think the overall deal size is going to be much, much bigger.”

To make this story a little bit shorter, there were some key outcomes that happened over the next monument period. Firstly, we transformed the operational and commercial models that we were working, the assumptions that we were working with this customer.

From an operational standpoint we completely changed the nature of the team, and I’ll give an example of that a little bit later. We moved from using more offshore people, we moved to onshore people. And we brought in some of our very best resources, and we dedicated them to this customer in a way that we hadn’t done before.

In the commercial model we did things that were extremely special, but we were able to do it and get the approvals to do it because of the potential size of the deal.

We also, by making those changes to the operational model, were able to ensure a higher level of quality and on time delivery of each one of the projects that we were tasked by the customer. And by delivering significantly greater capabilities — by changing the team, by doing some special things both at the software and with the services — it justified a much higher price, which is what my VP of Sales had eluded to at the very beginning of the process.

The result was that, that mega deal turned out to be over 50 million dollars, and it was by far the biggest deal that I have ever done, and it was the biggest deal in the area of business that I worked for several years before that.

It was through that process, it was through the journey of the first mega deal that I ever did, that I really learned, and I’ve discovered that there are these five shifts that I needed to go through to move from being a small deal sales rep, into a large deal sales rep. And once I made them, everything was different.

My deal sizes tended to grow from a few million, to tens of millions. My commissions also grew. They moved from 100K, to 200K, to 400K, and beyond. And, I began to get a lot of recognition for the work that I was doing, sometimes in front of thousands of reps and sales leaders like at our annual kickoff meetings, or at the awards trips that we would go on, the Presidents Club, a lot of awards and things like this. And everything changed for me — financially, professionally, and I became what some people called an elite rep. I don’t say that to brag, but rather to show the level of transformation that can happen once we tap into these five shifts that we’re going to go through.

And, maybe the biggest lesson of all, that I really want to share with anybody who will hear this message, is that I used to think that doing huge deals was really for superheroes — the only people who I had seen do it. I just looked at them with such awe because I had no idea how it was done. But, the reality of the matter is that mega deals are not for superheroes, they’re for normal human beings like you and me.

If I can do one, I would like to say that almost anybody can do one. And, I’d love to see that proved out if you guys can really kind of harness some of the power of the shifts that we’ll discuss.

The 5 Mental Shifts To Big Deals (10:43)

Let’s get into those shifts.

The first one is basically very foundational, and to many of us this might be obvious. But, it’s worth stating it again and right at the outset….

To operate and to lead with integrity and authenticity is the basis of any solid foundation that you’re going to build with a customer, that would support doing a significant transaction that would lead to a long term relationship between two companies, or two institutions.

Integrity and authenticity (11:12)

Let’s break this down a little bit. Let’s first talk about what we mean by integrity and authenticity. For this case, what I mean by integrity is the quality of being honest and having strong moral principles. Being very forthright with the customer and with your own stakeholders about how the transaction is coming along is extremely important.

Because, if you don’t have trust, and if people don’t take you at your word, then there’s really no foundation to work upon, you’re building castles in the sand.

And authenticity is representing one’s true nature or beliefs and being true to oneself. I think that is so key as a foundational principle that we need to use it as a kind of our behavioral model, because I know what it’s like to think that I needed to put on a kind of a salesman’s mask or a persona. It used to be that when I’d get on the phone my voice would change, and I’d use that funny sales guy voice.

I know most of you will know what I’m talking about, but especially through the process of doing this first large deal I saw, for example, how my executives, and how the executives of our customer were very plain, and open, and honest with each other. And sometimes, would make massive progress on one component of the deal in like half an hour, because they were just speaking so plainly about what was possible, what was not possible, what they were willing to do, what they were not, and justifying why.

It’s that level of authenticity that really makes significant business transactions happen.

Without integrity, your words have no impact. It goes back to what I was saying about building castles in the sand. If there’s no rock-solid foundation, that everyone who hears us knows that what we say is true. If that’s not the case, then there’s no solid foundation, because why would anybody believe what we say?

From an authenticity perspective, without authenticity we’re just another one of those stereotypical reps, who’s kind of parroting a script or some kind of canned presentation that has no level of real ownership. It’s like we don’t even really know what we’re talking about, we’re just reading from a script.

2. C-level insights(13:35)

Okay, the second shift is what I call C-level insights. I think most of us are quite familiar with insights and what that really means, but let’s give it a definition. For the terms of this discussion, an insight is the ability to have a clear, deep, and sometimes sudden understanding of a complicated problem or situation.

I became much more conscious of insights in the past 10 years or so. Some just from working in the industry, and others from reading.

One of the books that I’ve read that was very impactful in terms of my understanding of insights was a book called, The Challenger Sale. I think many of you have read it, and if you haven’t I would recommend you doing it. Which is basically the idea that the market in the enterprise sales world, buyers and sellers, we come from a place where we (sellers) used to start conversations by asking lots of questions, general discovery questions. And there for a time, that was something that worked at every level. But now, that has become so commonplace — to ask lots of discovery questions — the higher you go in an organization, especially at the executive layers, they are just so tired of having to answer lots of questions.

They simply don’t have time to do that kind of activity, and they really, what they really want, if an executive is going to take a meeting or a session with a sales person, they’re doing it because they think that they can learn something new.

Let’s talk about the level of impact of what a C-level insight is all about. So first, kind of a baseline. There are two kinds, let’s say that in the world of impact that we could have on a customer, there’s two ends of a spectrum.

On the one end of the spectrum is incremental improvement, and a lot of us have experience in expressing a value proposition that would improve a current process, or would decrease the pain of a certain stakeholder type by X amount. And that is usually like, we can make your life a little better, or a little faster, or a little cheaper by 15-30%. That kind of a pitch, that kind of a value proposition is an incremental improvement at best.

Yet, on the other end of this spectrum of value is a transformational capability, which is basically bringing a completely new capability, offering a company something that they couldn’t do before, that they didn’t have the tools, or the wherewithal, or the resources to be able to do something in a certain way. It’s somewhere along this continuity where we find various sizes of deals because of their impact.

I would be willing to say that almost every deal of significant size is much closer to a transformational capability, than an incremental improvement. That’s part of the shift of understanding what a C-level insight is.

How can I get the insights that I bring to my customer?

How can I get that insight to be much closer to something that they’d never been able to do before, rather than just making something that they do today a little bit faster or cheaper, etc.?

Let’s give you another example of what I mean by a C-level insight. Let’s say that there are different levels of insight in a different way. We talked about this continuum of transformational capabilities or just incremental improvement. Let’s look at it a different way in terms of what kind of stakeholders are going to respond to what kind of insight.

Let’s say the base level of insight would be at the director level. Kind of a first line manager, you know? Below a VP, somebody who manages a team. You might bring to them an insight by saying,

“Hey, if you look into this part of your business, what you might find is there’s an issue, or there’s a problem that you may or may not be aware of. Here’s a process, or here’s a tool that can fix that for you.”

A director has a certain scope of work and responsibility, and that’s typically around a team, or a small number of teams. That’s about the size of the insight that they could bite off, or buy into, because that’s the only mandate or vision that they really have is, how to take care of their team.

Yet, the next level up, let’s say there’s a VP. If you have a higher level of an insight, a VP would be interested in something that might impact an entire business unit, because that’s the scope of the VP’s world.

She’s in charge of the entire customer success group, and if the insight that you bring about something that’s going to move her business forward, or her part of the business forward across an entire business unit, she’s going to be able to digest that because that’s a part of her world and her mandate.

Yet, if you want to really interest the C-level in something that you’d have to say, you need to bring an insight that is going to impact the entire enterprise. Now, let’s just say if you brought a C-level insight to a director, I would say there’s a high chance that you’re not going to get very far because they might say, “Well that’s really wonderful, but dealing with things at this level is far above my pay grade,” and they might not even sponsor you up to move your thoughts forward.

But, if you get the attention of the C-level by having that kind of an insight across the enterprise, that’s a conversation that they’re going to be much more interested in having, if you can get their attention.

Let’s do some case studies.

Gunner Shock is an actual person, and he’s a Field Sales Rep for a publicly traded provider of an application monitoring tool set. Before we started working together, Gunner was a sales rep that would go for the director level insight, and he found success at selling at that level, and he was closing deals between 50K and 250K, [that] was kind of the range of the deals that he was doing.

But, after he realized a problem, and that problem was that he was quite ambitious, still is. He realized that he was never going to crush his number at that rate and size of deals.

So, we worked together to up his level of insights, and he stopped producing director level insights, and he upped his game to have a VP level insight.

And just an example of that is, in one of his accounts. Instead of just offering the value of his tool for one set of stakeholders, this set of stakeholders had many internal customers that they needed to serve. And so he said,

“Well, why don’t you become a data broker, and you could leverage our solution to be able to offer our services not only for your business unit, but for all of the customers, the internal customers that your business unit serves?”

And the VP really got interested in that idea. It was hard for the directors in his group to see how that was possible, or it was something that they could do. But, the VP was much more interested because that was the scope of his world, he wanted to have greater impact internally, and so he heard a higher level of insight.

As a result [Gunner] is in the process of closing a, between one and two million dollar deal. I need to check up with him and see how he’s doing on that, but that’s the significant increase that he had by selling a higher level insight, he was able to sell at a higher level in the organization and talk about deals that were also larger.

3. Leverage your executives (21:46)

Okay, the third shift is what I call leveraging your executives. I can’t stress enough that, that’s probably the greatest secret in doing large deals that’s right out there in the open. You may have heard many times your executives saying, “Get me involved early, get me involved early.” But in many times, there’s not a process in place to be able to raise your hand and say, “Hey, I need an executive in this one deal please,” right? It’s kind of a one off process where you go and try to chase them.

Let’s use the analogy of mountain climbing. I like to use this analogy because I think we’ve all lived it, and there’s two very different ways to get to the top. If you look at trying to do a large deal as climbing a really big mountain, at the summit of that mountain are the executives at your customer. It’s the executives that are going to either have the budget or the decision making power or the influence to be able to approve and sponsor deals of size.

Most reps, me included for the longest of times, we see the journey to those customers and interacting with those customer executives as a long mountain climb from the bottom to the top, that we do ourselves. Basically, we think of ourselves as mountain climbers, but what I learned, and what really shifted my mentality, is that we don’t have to do that.

Why not instead of being mountain climbers, we become heli-skiers?

How does a heli-skier get to the top of the mountain? They rent a helicopter, which takes them to the top in about 10 minutes. In this case what would the analogy be for our helicopter? Who is that? That’s our executives.

The reason why they can serve in that role is because our executives and the customer executives already have peer status. There is a huge psychological effect for all of us when we, in society, when we’re interacting with somebody. One of the quick checks that our brain does is, who am I speaking to? Is this person a peer? Or if we’re in a hierarchical structure, are they a peer, are they a superior, are they a subordinate?

That has some influence in how we interact with them, and it’s much faster to connect two peers together than it is in any other kind of a mismatch. And in basically every case, if you think about it, we as sales reps, we are seen as individual contributors. We’re not even managers in most cases.

For us to establish a peer relationship to have a serious business dialogue with an executive, it takes a lot of time. We have to earn the trust, and earn our seat at the table by displaying lots of credibility. Well that’s great, and we still will need to do that, but, we don’t have that much time to get a deal done if we’re trying to get something done within 12 months.

So, what I do is I leverage other people’s position, influence, expertise, bars on their shoulders, whatever it is that I need. If I don’t have that capability or that branding myself, I go leverage it from other people within my organization to accelerate getting in front of the right people within the customer, and most cases I’m trying to get in front of executives.

I hope that was helpful in terms of an analogy. Be a heli-skier, not a mountain climber.

Case study number two is about this topic of how to be a heli-skier, not a mountain climber. Mark Coombs is also a Field Sales Rep, and he’s with a late stage company that has an AI product for automated contracts review. So you can, instead of manually looking through contracts to see if there is a common term across all of our contracts that we need to change, [see] are we at a certain amount of risk because we’ve got too much limitation and liability in too many contracts etc.?. You can do this in an automated way much, much faster, and a much lower cost.

Mark used to chase 15 to 20 deals per year, all of them quite small. 50 to 100K most of them, 250k tops, quite similar to Gunner before him. Again, all of his deals were done at the director level or even lower.

What Mark did, was he developed his internal brand with his own executives — we call that building a well before you need it. Even before he needed their assistance, he started to give his own internal executives value.

So, he was tasked with going to open a new market segment for his company, and so what he would do is he would set up monthly market updates, and he invited everybody in the C-suite of his company. They could come if they had time, and if they were too busy, they didn’t have to come. But he would update them on this new market segment because it was such a priority for the company, and the executives found it very informative. And they really appreciated that, and they started to view him differently as well.

He not only did the monthly updates, he became an expert in one specific use case that nobody else within his company was really looking at. By becoming the expert in that one use case, there came a time when his CEO basically said, “Mark, I want you to run with all of the …” it was kind of a time sensitive use case based on a regulatory issue.

He basically said, “I want you to run with all the opportunities across our company where this comes up as the reason why they’re getting in touch with us.” All of a sudden he had a whole bunch of high quality opportunities that were given to him, on top of the ones that he was already working.

And thirdly, once he started to get to know his own executives and just deliver them value with their priorities about getting to know this new market, he started to do executive mapping. He would start to go to his customer and say, “Hey, my CEO is going to be in town to speak at a conference next week, I’d love for you guys to have lunch.” He would start to get the mappings done with an executive on his side who he thought would be a good match within one of his customers.

That vaulted forward the serious business conversations that he was trying to have. Whereas before, he’d still be trying to climb up that mountain working with directors that may or may not have the vision, or the mandate, to be able to deal with issues, and try to change business processes in a way that would be needed to get the value out of what Mark was selling.

Now, Mark is running the biggest opportunity in his company’s history, and he’s got a deal team that’s made up not only of the normal players like his pre-sales engineer, and customer success teams, et cetera. On his deal team is also his CEO, his CPO (which is Chief Product Officer), as well as a senior partner of a global consulting firm. And together, they are trying to close a deal that’s worth six million dollars. Quite far away from his normal 50K to 100K deals, so good on Mark. I hope he’s able to close that.

Strategic use of executives has absolutely changed the nature of my deals from $10-50 million. I like to say that larger deals can happen faster with appropriate executive engagement. Because when you get the right people in the room, it’s just amazing what can happen, and the speed with which it can happen.

If you find an insight into an area of the customers business that they’re not aware of and not focused on, and if you can demonstrate that it will really move the needle for them, sometimes they can take action extremely quickly.

My first mega deal took place in nine months. The other two that I did took much longer, but that’s what I mean when the conditions are right. You can do amazing things in a short period of time.

I’ll leave this section with a question.

How much more confident would you feel if you had one or more of your senior executives from your company on your deal team? How would that change the nature of the conversation, and with whom you’re having it within the customer stakeholders?

All right, so let’s do a quick recap. So far we’ve talked about three shifts.

The first is, it’s absolutely necessary to lead with integrity and authenticity, to establish this foundation of principled communication and behavior.

Secondly, we need to up our game to find not just any insight, but a C-level insight if it’s a large deal that we’re looking for.

And thirdly, we need to get better at learning how to leverage our executives. Because it’s through executive engagement and mapping with customer executives, that we accelerate very serious business conversations, and we get them on the table in the early part of the year, not at the end of a potential deal that’s taken 18 months just to reach the executive level.

4. Pump up the deal size (31:15)

Okay, so let’s move on, the fourth shift is what I call, how to pump up the deal size. Many of us who are listening to this are in technology related fields, a lot of us are in the SaaS world.

It’s been my experience in selling SaaS, professional services, and technology that these are all IP based businesses largely, and on the one hand there’s a very strong … it’s a great business to be in because you can, if it’s software, you can write the code once, and you can sell it many times. That’s a beautiful sales model and revenue model.

But on the flip side, if you’re in the procurement department of one of our customers, they can also say, “It’s just one set of code that you’ve already written once. It doesn’t cost you anything more to give us a larger number of seats, or units,” or whatever metric you’re selling by. “So if you’re going to charge me $100 a seat for 10 users at $100 each, and if I want to buy 10,000 users, I don’t want to pay you anywhere near $100 a seat, I want to pay you nine cents. I want a 91% discount because it doesn’t cost you anything more.” It’s not like a capital good, that you have all these fixed costs that you can’t get rid of.

We need strategies that are going to help us set and defend really large numbers, because the larger the number gets, the easier, the more confident the procurement teams and our customers feel that they can ask for larger and larger discounts. If they’re successful in doing that, we’re never going to get the large deals that we’re trying to get to.

There are many ways to set and defend a high price, most of them are in one of these three, and in this session I’m going to go through one type. I broadly call these areas, they are defense strategies that are based on value of the solution, the volume of how much is being sold, and the variety (how many pieces of value that can be identified) that would be delivered to the customer.

I’ll do one example, that’s probably as much as we have time for today. And talking about the value example, let’s look at value. Let’s talk about mega deal value. Value can have, we can define value in many different ways, but let’s say that there’s another continuum, right?

We’re looking for very extreme levels of value, either really positive or negative. What I mean by that is, on the negative, a mega deal could have a huge value to a company if it helps them avert some unspeakable disaster, like losing their license to operate, or having a connectivity failure for more than 24 hours, you know? Something that would absolutely kill the business or its brand and have long, long lasting impact on revenue, on goodwill, on relationships, and ability to grow. That’s one type of mega deal or value that’s far kind of on the negative side, averting unspeakable disaster.

On the other extreme, is how to achieve ultimate victory. If our products or services can show a customer how they can become far and away the number one choice of the market vis-a-vis any of their other competitors, that’s another mega deal value.

Companies will pay through the nose to take great strides in front of the rest of the competition, because of the swarm effect that their customers will have when making buying decisions by having that kind of lead in the market.

This is mega deal value, it’s extreme. It is transformational. It is not incremental. Let’s use that as the basis for the rest of the discussion on how to defend our price from a value standpoint.

I’m going to give you an example from one of the deals that I did. These are not the real numbers, and I’m using round numbers to prove a point. But, the argument holds true.

Before we did our first large deal, one of the components of the relationship that we had with this customer is they bought service. They bought software from us, and they also bought services.

In that services engagement, they were using our general consultants, and our general consultants are a pooled group of resources and of people who we had. It was our bench, right? Our consultant bench, and they would be ready to service any one customer when they had availability, and they’d get booked, and then they’d go and do a project. During that time they were unavailable, and then when they had availability they could go onto the next customer.

We had both onshore and offshore resources, so the onshore tended to cost more because of the cost of living that it took to hire them, and they were in India and Europe. And then we have offshore which were really great resources, but they were in much lower cost countries, so the hourly rate was just lower. They were using lots of offshore resources in our pooled set of consultants, these general consultants.

The solution that we said would really make a big change in our ability to ensure quality and on-time delivery of project after project was moving to our specialist consultants and creating a dedicated resource.

That was basically shifting to be much less offshore, and to be much more onshore consultants. And not only taking more onshore consultants, but making them dedicated. So now if they were available, or if they were engaged with the customer, the customer would still have to pay for them because they were not going to be available to work for any other customer.

So they were paying many more hours, or committing to pay for many more hours to use our best resources. That average rate was more than twice what it used to be. It would jump from $100-250 per hour, so that’s a massive increase in price, and we knew that it wasn’t going to be easy for the customer to justify that jump.

What we mapped the value to was an outcome which was a decrease in risk. The big risk that they feared, and it was a very real risk, was a risk to mission critical deadlines. There were real impacts if any one of these projects did not hit one of these deadlines. And we showed them convincingly that by changing the model from general consultants to specialty consultants, from going from offshore to onshore, and from pooled resources to dedicated resources, we would be able to reduce that risk 78%. 78% is a huge number, so let’s look at what it actually looked like.

If we take the numbers, they were going to need about 10,000 hours worth of work for the next agreement. If they did it at $100 an hour, that would come to a million dollars. But, to make the jump to the dedicated model, they would not only have a higher price per hour, they would also be signing up for more hours, because they would take all of the hours of the consultants, not just the ones that they knew they were going to use. To do that, that would create a fee of five million dollars, 5X what the old agreement looked like. How could they justify a 5X increase in one line item in a deal?

Well, so let’s recap what the value is. The value is a reduction in risk, a 78% reduction in risk. The incremental cost is four million dollars, remember? Because we’re jumping from one million, to five million. That’s a four million increase in a contract. How in the world is that worth it?

Well, the customer agreed with us when we showed them the numbers that the impact of missing a deadline in one project was $10 million dollars. It was a lost time to market, and a loss of revenue because they aren’t able to monetize that project in a timely fashion. They agreed that every project was at least 10 million dollars in loss if they were not on time, and if we were not on time in delivering that project. They were doing multiple projects per year.

So even if they only did one project, by paying four million extra they were avoiding a loss of 10 million dollars, so there’s six million dollars for the better just with one project. If you multiply that across many projects, they got into the hundred millions of dollars of potential savings by doing this. It was through that, that we convinced them that a five X increase just in the professional services cost made sense.

That’s the end of the example of how to use value to measure why it makes sense to do such large leaps forward and creating deals that are much, much bigger.

5. Invest in mentoring (41:01)

Now, the last shift in some ways may be the most important, because that’s made the biggest difference in my career, by having mentors. I strongly advise that all of us invest in mentors. Everybody should have a mentor, multiple mentors if possible. Mentors, they really bring three things.

Number one, new ideas. New ideas, things that we’ve never tried before, doing things that we know how to do, but doing them in a completely different way. Just fresh, fresh ideas is the first thing that mentors bring.

Secondly is accountability. If you’ve got a mentor, and if they take that role seriously, they’re going to hold you accountable to the things that you’ve asked them to teach you. And so, having accountability maps very well with the third and maybe the most important thing, which is….

Having a mentor vastly accelerates your success. Summing this up, I would get a mentor who has done the thing that you’re trying to do. I used to say, “Hey, I want you to be my mentor because some day I want to be you. I want to do the things you’ve done, and have the success that you’ve had.”

The next slide here is just an example of how I can measure the value of mentors for me.

This is more or less a representation of my numbers, my attainment every year since I started back in 2002. The big spike, this blue quadrant is the nine month period that I had the greatest mentors ever in that first mega deal that we did. And ever since I learned this new way of selling, I’ve never gone back. I’ve had some variation up and down, but I’ve continued to have made deals every few years, and things have been completely different.

That was my own transformation that I went through, all because I had really good mentors that had done the thing that I wanted to do.

The Mega Deal Playbook (43:07)

Now, now is the best part of all, and this is something that you can download, and I’ll show you how to download it later if you want to get this after this session. It’s my playbook on how to find and close a mega deal in 12 months, when the conditions are right. I’ll show it on the next slide, and you can download it after.

This is my mega deal playbook (Download above). You’ll see each one of these layers is a step in the process that takes you from the very beginning all the way through to close. I’ll walk you through it briefly, but this would take weeks, and weeks, and weeks to go through in detail. For now, use it as a conceptual model so you can set up your next deals maybe in a similar way.

It starts by looking through your territory, and picking what accounts do I have that could even be candidates to do a mega deal? Then the advice that I would have is, start with the path of least resistance by going to current customers, whether they’re happy, or super in crisis, anywhere in between, they can be good candidates.

If you remember, my first big deal was done with a customer who was in a great crisis, and it was an opportunity for us to turn things around, and then we spring boarded it into something much larger than it used to be.

Secondly, the next step is to partner with an internal executive. To do this you have to have a good brand, right? You have to have a good reputation internally, and you do that by giving value to executives even before you have a deal on the table.

I mentioned at least one or two ways to do it, and there’s many, many more to do that as well. Once you have at least some kind of a relationship with an internal executive, then you bring them into an executive conversation based on the unique insight. There’s a ton of upfront work to be done to be able to create the insight based on research about what you know about the customer and the customers market, as well as developing your relationship with internal executives.

Once you’ve done those, and you deliver this impactful C-level insight at the executive level, you invite them to initiate some kind of an investigation, some kind of project to prove out these great claims that you’re making through the insight. And to do that, you do some kind of an assessment.

Your company might have different names for it. It could be a Proof Of Concept, a POC, a pilot, offering them a sandbox environment, or running through a set of use cases in a structured way. There’s many different forms that an assessment can take.

But if you can offer a free, or a near free assessment, and you can quantify the outcomes to show them how much better their future state would be with your solution rather than their current state without it, that is a massive leap forward in not only being able to get a mega deal, but be able to get it within 12 months if your assessment period is short enough.

After the assessment period then there’s the… Let’s say you’ve had a great outcome in the POC, and the numbers are all there. Then you’ve got to go around to all the different stakeholders which are going to be needed to get a … because big deals are political. There are the business stakeholders which would benefit from it, there may be business stakeholders which would not benefit.

Let’s say your solution knocks out the need for 50 people. Well, the owner of those 50 people in terms of whose team they’re on, they’re not going to want to lose those 50 people, so they could see your solution as a threat. There’s a process that you need to go through to filter out who are the friends and foes among all of the needed stakeholders who are going to need to bless this deal before it will actually happen. There’s much more to it, but that’s the next stage of the process.

Then after you’ve got buy-in from the critical mass of the required stakeholders needed to get the deal done, then you move onto the close. The close is basically a negotiation of all of the deal points. The terms, the price, the policies, the legal language, compliance and security, all of that stuff has to be vetted.

When the conditions are right, when there’s a compelling event on the customer side that they see a sense of urgency, they can move through this process within a 12 month period. It’s happened to me, and I’ve seen it happen elsewhere. This can absolutely be done. But even if it can’t be done in 12 months, most of my mega deals take more than a year to do.

And so, that’s another mind shift that we all need to go through. Not only the reps, but also our management giving us the time to not only do the run rate business. We’re always going to have to do run rate business. We can’t only do mega deals all the time, because if we tried to do one once a year and then we failed, we have a big goose egg for that year.

That’s just not going to work. But our management does need to give us some kind of a ratio of time to be able to grow the deals that can be grown into a mega deal size, rather than closing them at the first closing opportunity before they’re at the maximum possible value.

In a nutshell, that is the mega deal playbook. On the last page in the contact page, you’ll see where you can download this and get a hold of it.

Key Takeaways (48:44)

Let’s wrap things up. Here’s the final recap. The five shifts to become a mega dealer are number one, deal with the customer and your internal stakeholders with integrity and authenticity. Number two, deliver, create, uncover, and deliver C-level insights that have massive impact across the entire enterprise. Thirdly, leverage your executives to be able to interface with customer executives in an accelerated fashion. Number four, pump up the deal size by having a plan to establish and defend really high numbers based on data. And lastly, find experienced mentors. People who have done this before, they are the ones who are going to be able to accelerate your learning and success more than anybody else out there.

That’s pretty much it for me. The last thing that I wanted to add is that a lot of people have come to me in the past six months or so asking for advice and mentorship in terms of how to do mega deals.

For them, I’ve created a masterclass. If you’re interested in this masterclass, it’s an eight week program where we do two sessions a week to get you to the next level as soon as possible.

You can find more information at MegaDealSecrets.com.

My contact information is here. You can also see my website, and how to get a hold of me either on LinkedIn, email, or on Twitter. Thanks a lot everybody for listening, and I look forward to connecting.

Hit me up, I’d love to be connected on LinkedIn, and happy selling.

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