DiscoverRevenue BuildersA Masterclass in Closing Big Deals with Steve Waugh
A Masterclass in Closing Big Deals with Steve Waugh

A Masterclass in Closing Big Deals with Steve Waugh

Update: 2025-09-04
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Description

In this episode of the Revenue Builders Podcast, hosts John McMahon and John Kaplan are joined by Steve Waugh, a legendary enterprise software salesperson. Steve shares his journey from starting at IT resellers to executing some of the largest deals in enterprise software at companies like Blade Logic, BMC, and Medallia. He outlines strategies for identifying champions and detractors, the importance of mindset, belief in one's product, and understanding the customer's business impact. Additionally, Steve discusses the critical role of executive support in closing big deals and offers insights into navigating internal challenges within one's company. This episode is a treasure trove of wisdom for anyone looking to understand the art and science of selling large enterprise software deals.

ADDITIONAL RESOURCES

Connect and learn more from Steve Waugh:
https://www.linkedin.com/in/steve-waugh-4833b57/

Watch Force Management’s Panel Discussion on Growth, Valuation and Execution: https://bit.ly/4p6kyGS

Read the Guide on Winning Government Contracts: https://bit.ly/3UYAOvO

Enjoying the podcast? Sign up to receive new episodes straight to your inbox: https://hubs.li/Q02R10xN0

HERE ARE SOME KEY SECTIONS TO CHECK OUT

[00:02:19 ] Steve's Early Career and First Big Deal
[00:04:30 ] Breaking into Financial Services
[00:07:36 ] Mindset for Selling Big Deals
[00:11:50 ] Identifying and Handling Detractors
[00:22:21 ] Cost vs. Value in Sales
[00:32:10 ] The Importance of Content in Sales
[00:32:50 ] Embracing Your Unique Style
[00:34:53 ] Believing in Your Product
[00:36:39 ] Navigating Company Challenges
[00:37:55 ] The Art of Big Deal Selling
[00:46:33 ] Uncovering Hidden Opportunities
[00:51:21 ] Mastering Executive Communication
[00:53:43 ] Career Pathing and Leadership

HIGHLIGHT QUOTES

[00:20:49 ] "You have to believe that everybody gets up and puts their pants on the same way."
[00:24:26 ] "If a customer's constantly looking at cost, you haven't got 'em converted—you gotta get 'em to forget cost and look at the value."
[00:33:09 ] "You gotta know who your friends are, but you gotta know your enemies better."
[00:46:46 ] "Executives don't care how you do it—they care about the 'so what.'"
[00:54:17 ] "If my own leader doesn't believe me, it makes it uber hard for me to accomplish it."
[00:56:48 ] "It's a two-way street. The company has to support their people to believe they can do it, and they have to have that same courage."


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A Masterclass in Closing Big Deals with Steve Waugh

A Masterclass in Closing Big Deals with Steve Waugh

Force Management, Revenue Builders Podcast, John Kaplan, John McMahon