The Ops Drop

S2.E5 Why You’re Really Losing Deals - And What to Do About It


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Why You’re Really Losing Deals - And What to Do About It Most companies think they know why they’re losing deals. In reality, they’re relying on generic Salesforce picklists and half-hearted notes that offer zero insight. The truth is, win-loss data isn’t just for Sales or GTM. It’s strategic intel that fuels smarter product decisions, sharper messaging, and more accurate forecasts. If you’re ignoring it, your product roadmap, marketing spend, and revenue targets are probably off-track. Brady Jensen, Founder of Clear Go-To-Market, joins us on The Ops Drop to talk about why most closed-lost analysis falls short - and what high-performing teams are doing instead. With a background spanning sales and product marketing, Brady now helps businesses uncover the real reasons behind lost deals and use that data to drive measurable growth. If you’re serious about product-market fit, cross-functional alignment, and building a business that actually wins - this episode is for you.

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The Ops DropBy Darren Fay and Mackenzie Hughes