Episode #221: Strategy | In this episode, Matt Carnevale sits down with Drew Giovannoli, founder of Buried Wins, to dive deep into Win/Loss analysis and how product marketers can use it to drive better sales, positioning, and competitive strategy. Drew shares how he helps B2B companies turn customer insights into revenue-driving decisions, plus the three key changes every product marketer should make to get promoted.

Matt and Drew cover:

Why you shouldn’t obsess over lost deals - and how to focus on winning more of the right customers instead.
How competitive intelligence can shape your positioning and sales strategy.
How to structure Win/Loss programs to influence product, sales, and marketing strategies.

Timestamps

(00:00) - - Introduction to Drew
(04:13) - - What is Win/Loss analysis and why it matters
(06:50) - - Why companies obsess over lost deals (and why that’s a mistake)
(09:08) - - The real value of analyzing won deals instead of just losses
(11:39) - - How to identify your best customers and find more like them
(13:31) - - The power of competitive intelligence in shaping positioning and sales
(15:44) - - How to ethically gather insights from former competitor employees
(18:54) - - Common mistakes companies make when running Win/Loss programs
(21:09) - - How to structure a Win/Loss interview for maximum insights
(25:27) - - The key questions to ask during Win/Loss interviews
(28:45) - - Why sales and marketing alignment is critical for Win/Loss success
(32:10) - - How Win/Loss analysis can influence product roadmap decisions
(34:55) - - The best way to present Win/Loss findings to executives
(37:25) - - How to turn insights into action and drive real business impact
(40:30) - - A step-by-step guide to launching a Win/Loss program
(43:37) - - Final takeaways and advice for product marketers

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Win/Loss Analysis: How to Turn Customer Insights Into Revenue

The Dave Gerhardt Show (from Exit Five)