What really goes into sourcing and closing an 8-figure enterprise deal? 

A lot. I’m about to dive into a real life example of how an enterprise seller closed a massive deal.

Traditionally, we think of sales starting with the cold outreach. But enterprise deals start long before that. There’s a lot of legwork that goes into planting the seeds for a deal; usually weeks or months of work before you even speak a word to one of the decision makers.

Last month, I shared a story on LinkedIn about how Ron Masi, a member of the Enterprise Sellers community, closed an 8-figure deal. There were three main components that made up Ron’s strategy:

1. Deep Research and Discovery
2. Crafting a Solid Point of View
3. Deal Orchestration

Let’s break down each one of those strategy points:

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Deep Research and Discovery

Usually when salespeople talk about research, they’re just talking about Googling the company for a few minutes and skimming a recent news article before making a cold call.

Do this in enterprise sales and you’ll look unprepared!

For Ron, deep research meant spending MONTHS reading 10-K’s, 10-Q’s investor day presentations, CEO interviews, and executive’s Tweets. He devoured information in the way that a potential investor would before committing capital to a company. 

Then he dug deep into his account and booked meeting after meeting with people up and down the organization to understand their current state, the core imperatives set by senior management and how those were being addressed in each business unit. 

It was nearly 50 meetings when all was said and done.

Why so many meetings?

All to craft the Point of View (PoV).

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Crafting a Solid Point of View

Put in other words, Ron was trying to identify the problem that his prospect needed solving. He started with his best guess and showed it to each person he spoke with from the organization to gauge their response. Each one added nuance to his understanding of the nature of the problem and helped him create a new evolution of his PoV.

As one of my best coachees (Dustin Brown, the #1 rep at Outreach) said:

“The point of view is your opener and the opener is the new close.”

If you nail the point of view, you are more than halfway to the conceptual sale, especially for an executive audience who will probably only pay attention for the first five minutes anyway. In other words, you need to understand the problem before you even make the cold call. An executive isn’t going to bother taking the time to explain anything to you if you haven’t done a lot of legwork.

The Point of View method differs from transactional selling that you may have learned earlier in your sales career. That method involves leading with the marketing slide deck prepared by your company mentioning a market-wide problem and then quickly moving on to pitching the features and benefits of your product. Enterprise prospects do not want to see that.

They want to know if you have correctly diagnosed their problem and can show them how to achieve a business outcome.

Business outcomes are driven by capabilities. Capabilities can be made up of human, financial or technical assets. Sellers make the jump from their product to customer business outcomes too fast, which is an incomplete story told without the customer’s unique context which turns off customer stakeholders immediately.

For crafting PoVs, I prefer to ditch the term “features” and instead think of your product offering in terms of capabilities.

Does your product have the capability to fix the prospect’s challenges?

If you are wondering where to get started creating your Point of View, here are some questions to ask yourself:

• What is the outcome your solution enables? (the measurable result)
• How does your solution impact the people involved in the business process? What does it enable them to do (or stop doing)?
• What capability does it enable? (the ability to perform a business function – mobile payments, integrate two specific systems, etc.)
• Why is that capability important? Does it change, shorten or improve the current business process?
• How can you describe today’s business environment where that capability creates winners? “Today’s environment of ungated content, analyst reporting and B2B software review sites means more than 80% of buying decisions happen before customers reach out to suppliers to engage directly. This has created an opportunity for SaaS companies who can reach and influence potential customers far before customers proactively contact them. Those who build that capability win the majority of market share (example 1, 2, 3) and those who don’t quickly become tier 3 competitors (examples of loser companies who do not have that capability)."

The best enterprise sellers are storytellers. They craft a story for prospects to see two potential outcomes: An overwhelmingly positive outcome if they work with your company, or a negative outcome if they choose not to.

The last part of the strategy that Ron nailed was deal orchestration.

Using his revised PoV draft as his guide, Ron set about building his expanded deal team and plan for deploying them to engage and build relationships with stakeholders across the landscape of business units that were in scope.

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Deal Orchestration

The deal multiplied in complexity, with dozens of people involved across the two organizations involved. Enterprise selling is often about staying organized and keeping all the stakeholders on track and informed. 

Ron orchestrated the entire effort to perfection, assigning entire workstreams to functional A-players on his team. He operated more like an air traffic controller than a seller.

He did it through delegation. In big deals there will always be multiple work streams executed simultaneously. You as the seller can’t be in multiple places or meetings at the same time. Do as Ron did and assign capable owners to each work stream. You are de facto becoming a manager by directing the actions of others on your team. Below is an example of delegation. The seller delegates ownership of two out of three simultaneous work streams, enabling the deal to move forward without the seller doing all the selling tasks or being in every meeting.

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Forget the typical 5 steps sales process for complex enterprise deals. Instead, think of your job in terms of the three components outlined above: Deep research and discovery, crafting a solid Point of View, and deal orchestration. 

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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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