Episode EightyTwo

How to Close $50+ Million Mega Deals

Guest: Jamal Reimer, Strategic Account Manager at Oracle

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About This Episode

Jamal Reimer has closed over $150 million of SaaS revenue in his career.

I’m going to let that sink in for a minute.

That revenue total includes a string of wins over several years, but it also includes giant mega deals for Oracle, where Jamal is a Strategic Account Manager.

That made him the perfect person to interview about how to close massive deals. And his advice did not disappoint.

Here’s what he told us.

Get the Right People in the Room—And in Your Life

The reps who can go find, hunt, and kill a mega deal on their own . . . you could probably count them on one hand. And they’re tremendous individuals.

Most of the time, though, to get to the point where you can close a massive deal, salespeople need to be mentored. Jamal includes himself in the second camp.

He’s been through two growth phases in his career:

  1. Getting thrown into the fire, not knowing what he was doing until he could run instead of crawl. (He experienced tons of rejection in his first sales experience selling books in college.)
  2. There was a shift after the first mega deal he was a part of, when he was fully the student, to taking on the leadership role. He knew the words to the song on subsequent deals, and he could even add a few of his own.

His first mega deal changed his life, more in terms of perspective than commission or glory. He remembers sitting in a conference room with his two VPs and two very senior executives on the customer side. He felt like a fly on the wall listening in on somebody else’s conversation.

The talk was so natural, so matter-of-fact. But the progress made in 45 minutes between those levels of people had taken him months with more junior professionals. He had a breakthrough.

“Some of the greatest secrets are that the basics really work,” he said.

The 45-minute story is a testament to the power of getting the right people in the room. When you hit the sweet spot in tennis and the ball goes over the net at the right spot and the right speed… that’s what happens when you get the right people in the room for the right conversation.

It’s not necessarily about the numbers of meetings or hours you get: it’s about setting up a small number of interactions that are choreographed just right so you hit the sweet spot.

Blue Ocean/Red Ocean

Perhaps you’ve heard of the book Blue Ocean Strategy. Originally, the premise of the book was about market share and competition, but it has been interpreted in many different spheres of business. Jamal readily admits he’s adding to the number of reinterpreters, but he has a fascinating application for the book in sales.

If you go after the easy targets in the bloody red ocean, you’re going where all the other reps are, too. But fishing in the blue ocean means “go as high as you can go” in an organization isn’t just a mantra: it’s a real opportunity that you shouldn’t pass up.

There’s an inexplicable barrier to entry for sales reps on LinkedIn. Plenty of people aren’t willing to do it. So it’s still a blue ocean.

The same is true for “swimming” with the executives. If you figure out how to do it, how to get in there and be credible, there’s so little competition.

It’s the dream.

How to Get Mega Deals Started

There are two types of experiences getting mega deals started.

  1. The likely suspect is a current customer. Even if you only have a tiny engagement, there’s something there. If you have some kind of a toehold, you can continue a conversation or begin a later conversation based on an earlier one.
  2. If you don’t have that, you take your best shot with a prospect. Either with someone who has moved companies or with someone completely fresh.

The way Jamal’s had the most success is what some reps would call “cheating.” His “cheat” is using his own executives.

It’s no huge secret, though. It’s human nature. If you’re an executive, and you get emails from two people, one from a sales guy and one from the COO of Oracle… which one do you think you’re going to read?

If you can get to someone at your COO’s level, that’s a win in itself. But you can’t just march in and ask an internal executive you help you out. You have to do a lot of work building up your personal brand internally with stakeholders.

After you’ve built up the trust, you can go to one of those stakeholders and say, “I smell some smoke over here. Let’s go make a fire.” As long as you lay out the reasons you think the pitch will work in detail, you have a good chance of getting them to agree.

“I’ll do the legwork,” you can tell them. “You just show up and do the glory work.”

All they have to do is send an email you wrote (or tweak it) or show up to a meeting that you’ve organized. If you do the heavy lifting, they’ll be much more willing to agree.

Jamal says he’s never been turned down by any internal executives ever when he requests their help to go on a pursuit like that. No, the deal won’t catch every time, but the probability certainly goes up.

Parting Wisdom

You can move from a red ocean to a blue ocean just between your ears. And that happens by just being your human self.

It’s so hard for most salespeople to do, because we feel there’s a persona to go with the role. It’s not true.

The moment you’re just you, people will be able to tell. They may not know what you’re talking about, but they’re going to listen because they know you’re in your integrity zone.

Your audience will instantly take note, and you’ll have conversations that peel back the sales veneer.

This post is based on a podcast interview with Jamal Reimer from Oracle. To hear this episode, and many more like it, you can subscribe to The Sales Engagement Podcast. If you don’t use iTunes, you can listen to every episode here.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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