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Boost win-rates like a Twilio PMM

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

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Topics in this episode

PositioningMessagingproduct marketing

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.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • 25 Years of (Product-Led) Growth: Actionable B2B Lessons From Leah TharinEveryone Hates Marketers · on Positioning96 / 100
  • Event ROI for Early-Stage Startups: Lessons Learned the Hard WayA Go-To-Market Perspective · on product marketing88 / 100
  • Clear Expectations and Skill Capacity: A Sales Leader's Balancing Act with Chris OrlobPillar Talk · on product marketing88 / 100
  • B2B SaaS Marketing: No progress after Series A without product marketing (episode #148)How I Made it in Marketing · on product marketing88 / 100
  • Why Some SaaS CMOs Flourish in PE-Backed Orgs, and Others Flame OutThe Get · on product marketing86 / 100
  • EPISODE 11: Michele Nieberding Shares Her Top Use Cases and Future Predictions for AI in Product MarketingThe Last Word on Product Marketing · on product marketing84 / 100

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