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. At Twilio, he discovered that the primary obstacle was often not about losing to competitors but simply losing to inaction—companies deciding not to move forward with Twilio because they couldn’t fully grasp its ROI or how to leverage its suite of communication APIs effectively. This realization was pivotal, steering Twilio towards creating battle cards and objection-handling materials that refined their positioning.

Creating Tailored Marketing Strategies

Through collaboration with the product marketing team, Brandon helped craft a program that enabled Twilio’s sales teams to compete more effectively, catering messages specifically to company scales and industries. He talks about the approach that not only enhanced deal expansions but also accelerated enterprise sales cycles, demonstrating remarkable improvement.

Crafting ROI Calculators and Technical Blueprints

A highlight of our conversation is Twilio’s creation of ROI calculators and technical blueprints. These tools were designed to provide potential customers with tangible evidence of the value they could derive from Twilio’s solutions. Brandon explains how he and his team utilized internal benchmarks and customer case studies to build these calculators, allowing prospects to visualize ROI outcomes over several years. Simultaneously, technical blueprints provided a roadmap for implementing Twilio solutions, dovetailing each customer’s unique journey towards digital transformation.

Sponsorship and Successful Program Implementation

We also touch on the program’s official branding, Foundry. Initially a pilot effort to support sales reps, it quickly became integral to Twilio’s strategy. Foundry offered customizable sessions that showcased what clients could achieve with Twilio, eventually acting as a growth channel that continues to attract valuable leads.

Building a Customer-Centric Culture

As product marketers, putting ourselves in our clients’ shoes and focusing on their needs is paramount. Brandon emphasizes that every marketing tactic must be rooted deeply in customer understanding. Whether devising new programs or enhancing product offerings, centering decisions around customer pain points ensures genuine value creation.

The Message Critique Segment

Finally, we segued into a message critique of Default.com, analyzing its messaging strategies and drawing comparisons with Ramp.com. Brandon discusses the importance of clear, simplified messaging that easily communicates core value propositions. This discussion inspired our “barbecue test”—if your messaging wouldn’t make sense while bantering at a barbecue, it’s likely in need of simplification.

Brandon’s unique insights are invaluable for any product marketer eager to enhance their win rates, tuning into customer needs and thinking outside traditional frameworks to see impressive results.

LINKS

Connect with Brandon:

LinkedIn:https://www.linkedin.com/in/brandoncpenn/ 

Connect with Elle:

LinkedIn:https://www.linkedin.com/in/elle3izabeth/ 

This podcast was brought to you by GetWhys. 

Make research so effortless it becomes a habit. With GetWhys, you get immediate access to trustworthy B2B customer insights via a proprietary database full of real, verbatim feedback from your ICPs. Whether you’re updating messaging, building battlecards, or crafting a blog post… No more guessing, just actionable insights to support your strategic decisions.

Try it now: https://getwhys.io/?utm_source=elle