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 (02:49) - - What is Win/Loss analysis and why it matters (05:26) - - Why companies obsess over lost deals (and why that’s a mistake) (07:44) - - The real value of analyzing won deals instead of just losses (10:15) - - How to identify your best customers and find more like them (12:07) - - The power of competitive intelligence in shaping positioning and sales (14:20) - - How to ethically gather insights from former competitor employees (17:30) - - Common mistakes companies make when running Win/Loss programs (19:45) - - How to structure a Win/Loss interview for maximum insights (22:12) - - The key questions to ask during Win/Loss interviews (25:30) - - Why sales and marketing alignment is critical for Win/Loss success (28:55) - - How Win/Loss analysis can influence product roadmap decisions (31:40) - - The best way to present Win/Loss findings to executives (34:10) - - How to turn insights into action and drive real business impact (37:15) - - A step-by-step guide to launching a Win/Loss program (40:22) - - Final takeaways and advice for product marketers Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more