Want to boost your sales without coming across as pushy? The art of cross-selling isn't about bombarding customers with products—it's about striking when the iron is hot. Just ask Leah Brite, Head of Benefits Product Marketing at Gusto and three-time Top 100 Product Marketing Mentor, who's turned this delicate dance into a science.

In this conversation, Leah and I explore her winning strategy which lies in the customer readiness score—a game-changing approach that combines data-driven insights with human intuition. Her team identifies key triggers that signal when a business might need additional services, such as reaching specific employee thresholds or experiencing significant growth phases.

The proof is in the pudding: Leah's methodical approach, which includes multiple call-to-action options and a 50% holdout strategy for campaign validation, resulted in an impressive 20% lift in new sales opportunities. This success stems from meeting customers exactly where they are in their journey, whether they're ready to buy immediately or just starting to explore their options.

I’m so grateful to Leah for sharing her time, knowledge, and warmth with us - her insights are absolutely invaluable for any product marketers seeking inspiration or guidance in the realm of cross-selling.

Key Takeaways:

• Focus on customer readiness signals rather than pushing products

• Use the RICE model to prioritize cross-selling opportunities

• Offer multiple engagement options to match different customer needs

• Validate campaign effectiveness through controlled testing
• Build cross-functional teams for comprehensive strategy development

Twilio Segment: https://segment.com/

Connect with Leah:

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

Sharebird: https://sharebird.com/profile/leah-brite

Connect with Elle:

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

This podcast was brought to you by GetWhys.

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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/

Have you ever launched a campaign that went nowhere, or spent months chasing accounts that never convert? That's what happens when you don't have an ideal customer profile (ICP). When you’re marketing to everyone, you’re truly connecting with no one.

Today, I’m bringing you a product marketing expert with an amazing ICP story, Chris Piwinski. As product marketing lead at Adobe's Frame io, he is someone who truly gets both sales and product marketing at a deep level - because he's lived both worlds. Starting his career in sales at LinkedIn, Chris learned from some of the best sales leaders in the game while selling sales navigators to sales leaders. That experience gave him an inside look at what makes high performing sales organizations tick. He’s spent years perfecting the art of aligning sales strategies and marketing initiatives with customer needs—and he’s here to share it all with you.

He takes us through his strategy around:

• Data-Driven Foundation: thorough win-loss analysis
• Customer Voice Integration: Using tools like Gong to capture authentic customer insights
• Internal Alignment: Focusing on getting stakeholder buy-in with data-backed narratives
• Targeted External Engagement: Delivering tailored messages to key personas

The success of Chris's approach lies in its practical simplicity: creatively using existing content, maximizing brand assets, and equipping sales teams with targeted messaging. His golden rule? "Be customer obsessed." This philosophy drives better marketing campaigns and builds lasting customer relationships by letting customer needs guide all marketing efforts.

Chris’s expertise has been shaped by a community of remarkable product marketers, which he shares with us, and I know you’ll be incredibly inspired to take his insights into the next steps of your own journey.

LINKS

Connect with Chris:

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

Connect with Elle:

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