After starting a new B2B enterprise sales role I was pleased to discover three great new books on the topic.

“Selling Above and Below the Line” by Skip Miller, “Selling Is Hard. Buying Is Harder.” by Garin Hess, and “Mega Deal Secrets” by Jamal Reimer each take a different approach to navigating a modern enterprise sales process, yet share various themes I believe compliment the many insights and strategies shared collectively.

Here is my biggest takeaway from each:

Selling Above and Below the Line

The primary lesson, neatly represented in the book’s title, is to always recognize and sell to your audience.

For example, according to author Skip Miller, c-suite executives are not motivated to buy for the same reasons as their middle managers and those on the front lines. Because of this, salespeople should understand that when they are selling into an organization they are actually selling two different value propositions: an “above the line” value proposition convincing of high return and low risk, and a “below the line” value proposition demonstrating increased efficiency and ease of use.

What is one basic tactic an enterprise salesperson can apply knowing this? Since executives live primarily in the future, our questions and value proposition when speaking to those “above the line” should be framed towards illustrating the impact of implementing a solution company-wide and years forward. Middle managers, on the other hand, live primarily in the present, so our questions and value proposition when speaking to those “below the line” should address the more immediate effect on their daily routines, specific roles, departments, and shorter term targets.

Selling Is Hard. Buying Is Harder.

As the focus on sales enablement grows ever stronger, Garin Hess proposes the true key to victory in a complex sale resides in buyer enablement. Said differently, the primary lesson for enterprise sellers is to realize our success or failure will often come down to our ability to effectively coach our champions through their own internal buying process.

A powerful tactic from Garin is to assist our champion in proactively involving their necessary stakeholders, i.e. those who inevitably enter towards the end of the buying journey, often halting our momentum and extending our sale cycle. So how can we achieve this? Once we have buy in and the sale is qualified we should enable our champion by sharing a list of stakeholder personas (Marketing, finance, legal, etc.) we know typically need to be involved from our own past experience as sellers. Further, asking the prospect who in their company occupies these seats and what might cause them to veto making a change. The role of the seller emphasized here by Garin is a highly confident leader, with tone of experienced guide.

Mega Deal Secrets

The primary message from Jamal: astronomical success in enterprise selling is best achieved through creating transformational mega deals 10x-20x the typical average.

A pillar of Jamal’s process for closing staggeringly large contracts is a technique he calls “executive whispering”. This involves gaining early participation from our own internal c-suite, and that of our prospect. Why is this so important? It’s all too easy to spin our wheels working our way up from the bottom of an organization, spending copious amounts of time with people who have neither the motivation nor power to make transformational mega deals happen.

Luckily, there is a better way. First, leverage our own executive sponsor to secure a meeting with the executive counterpart we are targeting, as they are more likely to engage with someone who is on their same level. Second, present them a “C-level insight” demonstrating a unique understanding of whatever challenge is most preventing them from achieving their top strategic initiative. While it is from here we still must establish a proof of concept around our value proposition, battle with procurement, and negotiate the final sale, mastering “executive whispering” is our linchpin for making mega deals happen.


While previous classics like “The Challenger Sale” have long provided assistance to those embarking on new enterprise opportunities it is encouraging to see many refreshing perspectives on complex B2B selling.

If there exists a core theme among them I believe it is as follows: to master the modern enterprise sale is to master the skill of managing executive participation early in the sales process, versus waiting or hoping for our executive savior to come.

These three resources provide generously in helping to develop this crucial ability and many others. If you are an enterprise salesperson, or even an aspiring one, I can’t recommend them highly enough.

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