So you want to move up to larger deals. Let’s say you’re selling $20k contracts and want to move up to selling $100k deals.

Or you’re at the $100k level and you want to move up to 7-figure deals. Here are a few tips I have from dozens of years selling over $160 million in enterprise deals:

We all know the game changes as you move up the ladder.

If you just take the marketing deck you’ve been given and parrot that to a potential buyer, you will never grab the attention of an executive.

There are two things you must master in order to sell mega deals:

1. Reaching and engaging executives
2. Crafting a customer-specific value story

First, let me clarify why I love working on large deals: Large deals are more stressful and take a longer time than small deals - but the added stress and time does not rise as fast as the potential deal size of larger deals. So you might make 3x the money for only 20% more stress and work. Working on large deals is a no-brainer.

But there are a few extra wrinkles you’ll need to understand when you move into the realm of large enterprise deals.

Number one is engaging executives. Plucking a couple of impressive-sounding stats from your company’s marketing deck and flashing them on the cold outreach won’t get you in the door.

If you’re positioning a deal in the $500k to $1 million (or higher) range, the buyers you’re targeting will expect you to have thought deeply about the implications of your solution in their business. 

What made me really learn this was when one extra-spicy executive reacted to my product-based messaging with, “I’m here to talk about important things happening in my business. You’re here to talk about your product. I’m gonna cut this one short.”

Which leads me to my biggest mega deal lesson which I learned years ago:

I’m sitting in a conference room at the customer’s HQ. This was one of my group’s largest customers, a $10 million annual contract. We were working to renew the deal. I’m sitting with my Head of Sales on my right, and my Head of Professional Services on my left. We’re sitting across from several people on the customer’s team, including the executive sponsor of the deal that I had been primarily working with.

The other side is not happy with us.

We’re missing SLAs. People on our professional services team have been churning. Lots of other things are going wrong. It feels like this $10 million deal may fall apart.

We’re trying to save face by offering to move some of the work from offshore to onshore teams and discussing potential discounts.

The executive sponsor on the customer side stops us and says, “Guys, this isn’t about discounts or moving team members around. This is about how we steward the most important IP that our company owns.”

There was a long pause as those words settled in.

And then the conversation completely changed.

Here’s how my Head of Sales broke it down as we walked out of the building to get our taxi to the airport:

“Either we’re going to lose this deal, or it’s going to be a much larger deal than we had anticipated.”

I was surprised. I assumed we’d either lose the deal or have to discount the hell out of it to win.

But our Head of Sales, a grizzled 20-year veteran at the company, corrected my thinking. 

“The buyer told us what’s important to him. Let’s listen.”

What I learned that day is that high-level strategic executives think much bigger than I thought they did.

Here I was trying to eke out some 5% marginal improvement for them. Of course he looked at the pricing, but it wasn’t his main concern. When you sell to middle managers and execs at smaller companies, the sales game is often about comparison. You likely have dozens of competitors with similar pricing, deliverables, and features. 

Often a small $20k annual contract will close because you throw in a discount or some freebie.

But the enterprise sales game is played much differently. Executives aren’t playing a cost-cutting game and they’re not trying to get the cheapest price.

If an executive at a large company is involved directly in the buying process, that means the problem they are trying to solve is complicated and abstract. The winning vendor won’t be the one with the best price or slickest case studies. It will be the seller who paints the clearest picture for the buyer about how their solution will solve this big, hairy problem. 

In this instance, I was lucky that the buyer made it so clear for me. In many other deals, you won’t be so lucky. The decision maker won’t voice their real concern if you don’t perceive that something is wrong, and the deal will die without you knowing why.

If you’re used to selling smaller deals and focusing on MRR, you’re likely dealing with decision makers at small companies, or you’re stuck “below the clouds” selling to middle managers, never getting to speak with the real high-level decision makers.

It may be comfortable to play in that arena, because middle managers can be much easier to connect with. You can proudly show your sales manager that you’re busy with tons of demos. But in reality, many of those demos won’t close (your contact doesn’t actually make the decisions) or you’ll produce a few small deals.

Here are my tips for working in the megadeal arena effectively:

• The absolute best way to do outreach for megadeals: Leverage your company’s executives. An exec is much more likely ro reply to a peer on the same level. Your other options, cold outreach and working bottom-up through the organization, take way longer. Ask your executive to help with large target accounts by crafting an intro message for them to send. Your execs might already have personal connections with key decision makers at your key target accounts. Most sales reps never even bother to check this.
• You must maintain access to the executive even after they kick you down to the project-level. Keep them in the loop and keep working with them to move the deal ahead. This is a tough line to walk, since executives are obviously busy and don’t want a seller updating them constantly on information they don’t really need.
• Your deals must be executive-driven. If you’re not working with an executive champion who’s driving your deal forward, you don’t have a megadeal that will close. While a middle manager could be a champion for a small to midsize deal, they may not have the real political capital to push a deal forward.

Thanks for reading. I’ll be back next week with more thoughts. As always, you can check out enterprisesellers.com for more resources.

Jamal

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When You Are Ready There Are 3 Ways I Can Help You Get To The Next Level In Your Selling Career.

1. ​Mega Deal Secrets​ – Get a free copy of the book that started the mega deal movement.

2. ​Enterprise Sellers​ – Surround yourself with the most ambitious enterprise sellers in the game.

3. ​Mega Deal Secrets Masterclass​ – Get me on your deal team by investing in my coaching program where I personally help you close the biggest deal of your career in the next 12 months.

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