A Masterclass in Closing Big Deals with Steve Waugh

20 snips

Sep 4, 2025

In this engaging discussion, Steve Waugh, a legendary enterprise software salesperson with a remarkable track record at companies like Blade Logic and BMC, shares his insights on closing big deals. He emphasizes the critical mindset for success, the importance of identifying champions and detractors, and how to articulate value over cost to influence executives. Steve also dives into the necessity of strong executive support and navigating internal challenges while mastering the art of building relationships, making this a goldmine for aspiring sales professionals.

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ADVICE

Map Champions And Detractors Early

Focus on C‑suite entry and then go broad to map champions, neutrals, and detractors across the organization.
Identify detractors early because they can derail big deals if left unchecked.

ADVICE

Isolate Detractors Without Burning Bridges

Treat detractors kindly and test them repeatedly while elevating champions to the top.
Use your wider team and SEs to uncover undermining behavior that appears when you're not in the room.

ADVICE

Carry A Clear ROI And Test Buyers

Quantify and carry an ROI/business-impact case to every conversation and test executives on it.
If they still fixate on cost despite massive ROI, challenge fit or escalate to different decision-makers.

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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."

Hosted by five-time CRO John McMahon and Force Management Co-Founder John Kaplan, the Revenue Builders podcast goes behind the scenes with the sales leaders who have been there, done that, and seen the results.

This show is brought to you by Force Management. We help companies improve sales performance, executing their growth strategy at the point of sale.

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