In this episode of the Sales Hacker Podcast, we have Jamal Reimer, Commercial Vice President at Saama and author of Mega Deal Secrets, a book about the principles that unlock the biggest deals of our career. Join us for an amazing conversation about building an achievable, repeatable roadmap for elite performance for any sales team or individual rep selling enterprise solutions.
If you missed episode #195, check it out here: 3 Steps to Focus on Your Customer’s Customer, with Ashley Welch
What You’ll Learn
- Go straight to executives
- Leverage your internal resources
- Make good pre-sale connections
- Ensure you are talking to people with influence
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Show Agenda and Timestamps
- About Jamal Reimer & Saama [2:13]
- Secrets of landing mega deals [8:39]
- A word on authenticity [12:21]
- Tools to help close huge deals [16:39]
- How to know if you’re on track to close [21:25]
- Paying it forward [27:19]
- Sam’s Corner [29:31]
About Jamal Reimer & Saama [2:13]
Sam Jacobs: Hey everybody, welcome to the Sales Hacker Podcast. Today on the show we’ve got Jamal Reimer, the author of Mega Deal Secrets, and a VP of enterprise sales himself.
Before we get there, we’ve got three sponsors:
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Only a few years ago, Jamal was a typical enterprise software sales rep barely making his number, he struggled to close the bigger deals that he knew were possible. Then he cracked the code for selling ultra-large deals and has since sold over 160 million in SaaS revenue.
He’s refined his secrets into an achievable, repeatable roadmap for elite performance for any sales team or individual rep selling enterprise solutions. Participants get access to the exact same system inside the masterclass. And the book is called Mega Deal Secrets: How to Find and Close the Biggest Deal of Your Career.
We like to start with your baseball card, your background. You’re VP of sales at a fast-growing, well-funded startup, and you’re also an author. Tell us a little bit about the book, and what you do during the day.
Jamal Reimer: I sell all day. It’s a niche SaaS company that deals with AI and machine learning, specifically in the R&D space for pharmaceutical companies. Long sales cycles, small community. I run a masterclass for ambitious sellers to help them find and close mega deals.
I got into sales out of desperation when I was in university. My family lived in Southern Africa in the mid-’80s, we lived inside of a country that was inside of South Africa. It was a country that doesn’t exist now, called Bophuthatswana. My parents, their savings, and income were meaningless in the US, so I had to pay for university.
I started working for a company selling books door to door, 80 hours a week, every summer, for five summers. That’s where I got all the hard knocks. You take a lot of rejection, it’s the most basic form of sales. That’s where it started.
Every summer it was some town or city or suburban area in the Midwest.
It ultimately got me into software sales, then into SaaS. My first decade of selling was sketchy. Some years I was doing pretty good. Other years I was very mediocre. I was fired twice in a row for underperformance.
The transformation happened after I moved to Europe. I married a Swedish citizen, a physician. It was so hard for her to start over with her credentials in the US, I moved to Sweden.
I was given an account in distress, they were thinking of leaving. We took that deal and we turned it from a 10 million run rate deal into a $50 million transformation. That’s where this whole mega-deal thing really came from.
Secrets of landing mega deals [8:39]
Sam Jacobs: Would you be willing to share some of those secrets?
Jamal Reimer: The biggest secret about doing mega deals is right out in front of us. There are a few principles.
One principle is that the bigger the deal, the higher in the organization you have to go. There’s almost like a barrier to entry to selling very high into an organization. It’s not comfortable. There’s this big perceived mismatch. The executives don’t want to talk to sales reps. The sales reps are like, “they have all these gatekeepers around.” If you’re going to get a mega deal done, you got to get there fast otherwise it’s a long trek to executives if you’re starting at the bottom floor.
You got to do discovery. You got to know the organization and its problems. There’s a real dance to do – getting good discovery with lower down folks without getting stuck there. If they start to feel like they are your main contact, they’ll get bent out of shape if you go above them without their sponsorship.
That leads to the next principle, which is the principle of leverage. Wherever I need an asset, something that I don’t have myself, I try to go leverage it from someone else or something else that already exists.
I go to my executives with a different idea, which is, “I know something about this account. I see some smoke, let’s go make a fire. But I need your help. This isn’t qualified, but here’s what I got.” I lay out the reasons why I think there’s a shot at doing a good deal because there’s a fire in the engine room over there.
I work with them to go fail fast. We will go together to my senior person, have their admin reach out to the admin of a super senior person within the account. If you’re matched with title and status, it’s a very different ask than a sales guy trying to get into a senior person.
A word on authenticity [12:21]
Jamal Reimer: Another principle that has served me well is authenticity. If you’re doing good discovery, how do you map the right person from your side to speak with the right person from the customer side? The first thing is you go through the steps of figuring things out. The last thing I would do is throw an email over to my executive and say, “send this.”
If all that happens is a rote mapping process with some kind of template email, that’s the same as an SDR sending an email that isn’t personalized. It’s going to land flat.
If you want to get into the millions, you got to be more like the field marshal of a Roman Legion. You’re going to be bringing the A-players from your organization at different levels. You’re going to be pulling in folks from products and the C-suite.
When you start looking at doing really big deals, the risk is higher. There’s more investment on the table. Failure and success have bigger impacts in either direction. More eyes are going to be on the evaluation. You need to bring your best and cover all the question areas that crop up.
RELATED: The Key is Personalization at Scale with Appy Choudhary
Tools to help close huge deals [16:39]
Sam Jacobs: Do you have tools, sophisticated mutual action plans, things like that, to facilitate the navigation through the enterprise so that you can close these mega deals?
Jamal Reimer: Very much so. I call it power map. I use it in conjunction with an org chart. The org chart is our attempt to capture the players within a unit we’re selling into. A power map is a graphic representation of the influencers and decision-makers who are going to move the needle in a yes or no sales cycle. I try to keep the tools as simple as possible because complexity just kills clarity.
Sam Jacobs: Are you 100 percent focused on mega deals?
Jamal Reimer: What I do is unique because I have a mandate to go for the big guys. Whether we get large deals or small deals to start with is a different story.
Between 20% to 40% of a rep’s time should be focused on a mega-deal because they have the small deals and the medium deals that they’re working on as well.
How to know if you’re on track to close [21:25]
Sam Jacobs: How do you confirm that you’re on the right track over the course of a very long sales cycle?
Jamal Reimer: You ask yourself some hard questions. A mistake that I’ve made in the past, and continue to make, is falling in love with what you think is a champion. They give you lots of intel about what’s going on and you make progress. At some point, communication slows down, or they start to reveal that they don’t have as much influence on the decision as they thought that they did.
At that point, two things happen. One, I ask for more stuff to see if they will or if they can. Secondly, as I question their willingness or ability to continue the cycle forward, I start to spend more time with other players in the game who can also be as influential.
Typically with large deals, there are at least two conversations going on. One with the project team on the ground, the other at a more senior level. If you set it up right, you’ve got both of those lines of communication are open.
These big deals are a lot like chess. You always need to be thinking two or three steps ahead. If this outcome is positive, what do we do? If this outcome is negative, what do we do?
Paying it forward [27:19]
Sam Jacobs: What are the ideas that we should be aware of? Books, mentors, or people that have been really influential?
Jamal Reimer: I get a lot of encouragement and good ideas from the sales community. I got to give a shout-out to people on LinkedIn. There are some people who are also influencers, Ian Koniak is one, Brandon Fluharty is another.
In terms of books, Selling to the C-Suite was a big influence on me. The Challenger Sale and The Challenger Customer were big influences. There are other books, everything from Atomic Habits to The Power of Moments, how you can craft a moment to be memorable and impactful long beyond when the meeting or the presentation is over.
Sam’s Corner [29:31]
Hey everybody. Sam’s corner. Great conversation with Jamal Reimer. He’s doing global sales and closing mega deals, all from Sweden.
Megadeals require a lot of structure and process. Jamal gave us so many great tips and insights. The first and biggest is you got to start at the top.
Make sure that you have the right champion in place, that you’re talking to people with actual power. You have to be careful that you don’t get caught talking to people that don’t have any actual influence in the organization, that’s a waste of time. How do you get around that? You have to test them. You have to ask them to do things and see if they’re capable of doing them. Closing a $50 million deal means moving things around on behalf of the company.
Give us five stars and get in touch with me, sam@joinpavilion.com is my email.
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