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Product Marketing Adventures

Boost win-rates like a Twilio PMM

Product Marketing Adventures · 2025-04-15 · 37 min

Episode notes

As product marketers, we look at metrics from all over the business. One metric that's commonly tracked is win-loss. There are many factors that influence win-loss from sales effectiveness to positioning. Today, we’re talking about how one product marketer studied win-loss deals and turned it into a highly targeted pre-sales marketing program for Twilio. That product marketer is Brandon Penn, a B2B marketing and go-to market leader who has helped scale some of the biggest names in tech. He’s a force to be reckoned with in the tech industry, having scaled enterprise go-to-market programs during Twilio's hyper-growth phase and led pivotal marketing initiatives at Shopify Logistics and Runway. In this conversation, Brandon is sharing his incredible insights on crafting strategies that not only resonate with customers, but deliver tangible success. Understanding Win-Loss Analysis We begin by discussing the importance of win-loss analysis. For Brandon, it was about donning the customer’s shoes and identifying the reasons behind wins and losses.

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