Jamal Reimer's Secrets to Breaking into Enterprise Accounts and Closing Mega Deals

A 6-figure deal can change your quarter, but a 7-figure deal?

That can change your whole life.

Just ask Jamal Reimer—closer of a $56,000,000 Oracle deal (yes, you read that right) and the world’s leading expert on megas deals.

After 20+ years of selling to enterprise companies, Jamal uncovered the winning strategies for how to close the biggest deals of your life in our most recent Apollo webinar.

Keep reading to learn how to land meetings with executives, create a pitch that captivates your most important prospects, and seal the deal on your biggest enterprise accounts.

Break out of the matrix into enterprise sales

What’s life like for a run-rate seller?

It's filled with high-volume activity, low-level stakeholders, tiny, time-consuming deals, and small commission checks. 

While these things can still be a reality for enterprise sellers, enterprise sales often revolve around the opposite—high-level strategy and intentional action. 

Jamal points out that individual contributors often have a great chance at success on paper but the system is gamed to make overperformance nearly impossible.

According to Jamal, the only way to break out of the game and get what you want out of your sales career is to think bigger, think bolder, and set your sights on the mega-deal.

Leverage your executives to access decision-makers

Breaking into enterprise accounts is a game of chess.

You can’t win by focusing on the pawns. You need to go after the queen.

“I've never seen a mega deal done without executive sponsorship. There's too much entropy and mid-level people don't even have the mandate to make big investments,” says Jamal.

Executives are the driving force behind any mega deal and if you can’t get to them, your deal is over before it's begun.

Here’s how you can use advanced filters in Apollo to find verified contact information for C-suite executives:

You have any executive’s contact information now, but like many reps, you might feel intimidated to reach out; like you don’t know their language or are not worthy of your time.

One of your best strategies will be to leverage your own executives. Go to them with your book of accounts and ask them for any and all mutual connections and support. They are going to be your golden ticket into the room of C-Suites.

Jamal puts it this way: “Don't walk up the mountain. That takes weeks. Go leverage a helicopter to take you to the top of the mountain in 10 minutes. This is the way of the mega dealer—and your executives are your first port of call to be your helicopter.”

Get executives intellectually chasing you

The last thing that a senior executive wants to hear is a discovery question like: “What are your biggest pains?”.

You're supposed to know that in advance and package it together with the customer’s ideal reality in mind.

Jamal calls this The Mega Deal Premise.

“A mega deal premise is a value story that senior executives are going to listen to and have not heard before,” Jamal says, “It helps them satisfy a big spend based on measurable justification of value.”

A Mega Deal Premise has three key components:

1. Core imperative: What the C-Suite needs to achieve this fiscal year

2. Distinctive value proposition: Your company’s secret sauce

3. C-level insight: An undiscovered or unappreciated reality about their business

You need to show that your distinctive value prop is the better, faster vehicle to get them to their core imperative, using the C-level insight as the rationale behind why a “yes” makes sense.

Work with your execs to think creatively when you reach out to deliver this information.

“Cold email and cold calling are like super highways that are bumper-to-bumper jam packed. We need to get off of those super highways. We need to go to other channels.”

Jamal gives examples of:

• Sending greeting cards

• Delivering physical gifts for special occasions (birthdays, anniversaries, etc.)

• And handwriting notes

Thinking outside the box to capture the attention of busy decision-makers will set you apart from the swaths of people banging at their door.

The Apollo team regularly features top sales experts like Jamal in webinars that cover everything from email deliverability and cold outreach to key sales trends and tools.

Follow Apollo on LinkedIn to get updates on all future events. 

If you’d like to replay the full-length webinar with Josh Garrison and Jamal, you can watch the recording here.