Tom Ebling is the former CEO of Demandware, a company that was acquired by Salesforce in 2016 for $2.8 billion. Today Tom is a Board Member and Advisor to SaaS companies. He joined Ryan to talk about how win-loss insights have driven him and his teams to make better, more strategic decisions.

From identifying a product gap that led to an acquisition, adding some much-needed nuance to buyer intel limited by seller bias, and proving one of his CEO-competitors was making stuff up, win-loss analysis has been a fundamental part of every company Tom has worked at.

You can watch the full interview on Klue's YouTube Channel

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Key Moments

(00:10) Ryan's first-ever customer at DoubleCheck
(01:29) How Tom leverages win-loss insights
(04:29) How big is the gap between seller intel and buyer intel?
(06:38) Using win-loss insights to drive decision making
(08:23) Gaining competitive intelligence through win-loss analysis
(12:15) Presenting win-loss insights at board meetings
(14:26) How Tom used win-loss insights to inform mergers and acquisitions
(18:13) Tom's advice for starting a win-loss program

Production Team:

Host: Ryan Sorley
Producer: Ben Ronald
Audio Editor: Michael Panes
Supervising Producer: Adam McQueen

CEO, Board Member and Advisor Tom Ebling