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

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
• (04:22) - - What is Win/Loss analysis and why it matters
• (06:59) - - Why companies obsess over lost deals (and why that’s a mistake)
• (09:17) - - The real value of analyzing won deals instead of just losses
• (11:48) - - How to identify your best customers and find more like them
• (13:40) - - The power of competitive intelligence in shaping positioning and sales
• (15:53) - - How to ethically gather insights from former competitor employees
• (19:03) - - Common mistakes companies make when running Win/Loss programs
• (21:18) - - How to structure a Win/Loss interview for maximum insights
• (24:49) - - The key questions to ask during Win/Loss interviews
• (28:07) - - Why sales and marketing alignment is critical for Win/Loss success
• (31:32) - - How Win/Loss analysis can influence product roadmap decisions
• (34:17) - - The best way to present Win/Loss findings to executives
• (36:47) - - How to turn insights into action and drive real business impact
• (39:52) - - A step-by-step guide to launching a Win/Loss program
• (42:59) - - Final takeaways and advice for product marketers

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