Most PMMs pride themselves on being customer obsessed, but there's another critical audience we often overlook—our own sales teams. If you want your product to win in the market, you have to win over the people taking it to market. Today we're exploring how to move beyond handing off enablement decks to truly influencing how your sales team operates, transforming them from order-takers into strategic partners who genuinely understand your product's value.

Sharon Markowitz joins us with experience leading product and partner marketing at Atlassian, LinkedIn, Intuit, and Zoom. Named a top 100 product marketing mentor by ShareBird, Sharon's also founder of Your Career Wings, coaching marketers on upskilling and career development. At Zoom, she encountered a classic challenge during rapid expansion—standard functionalities weren't meeting customer expectations, creating conversion bottlenecks that required innovative solutions beyond traditional PMM approaches.

Sharon's breakthrough came when she stepped outside conventional PMM roles, establishing a sales incentive program funded by the marketing budget. By listening to sales reps who wanted simple perks like company swag, she built a program that energized the sales force and propelled deals forward. Her deep engagement wasn't just about meetings or chat channels—it was fostering genuine relationships and maintaining alignment with sales objectives, ultimately driving millions in new customer value.

We also dive into Sharon's four-step playbook for sales influence: listen attentively to both external customers and internal teams, embed yourself in sales calls to understand their needs, build initiatives collaboratively with the sales team, and be bold enough to step outside your lane when business demands it. Plus, we explore our messaging critique of Time Left, a B2C app connecting strangers for midweek dinners, and Sharon shares insights on keeping messaging simple while identifying growth opportunities.

For those looking to tap into Sharon's expertise further, she is offering personalized coaching with Your Career Wings & a 20% discount with PODCAST20 on your first paid booking of 1:1 Career Coaching Session through August 31, 2025.

This is an incredibly insightful conversation with Sharon, and I hope you're inspired to transform your approach and break creative boundaries in your own career.

LINKS

Time Left (messaging critique): https://timeleft.com/

Connect with Sharon Markowitz on LinkedIn

Connect with Elle:

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

Most PMMs don't track customer lifetime value, but we absolutely should. When you understand CLV, every trade-off becomes crystal clear—you know exactly where to focus your energy and can shape strategies around what actually retains your best customers.

Today we're diving into how Visa built their lifecycle marketing practice from scratch, turning one-and-done transactions into proper repeat engagement.

Terry Setiz joins me with 20+ years at Coca-Cola, HBO, Hasbro, and Visa. Here's what surprised me: Visa isn't a credit card company—they're a payment tech powerhouse (obvious, once you think about it!). Terry’s team embraced e-commerce with Visa Checkout, smashed down silos between marketing and IT, and created the genius 'One Hand' campaign featuring NFL stars making touchdowns while checking out simultaneously.

Terry's golden advice? Stop treating product launches like tick-box exercises. Think long game, experiment like a mad scientist, and don't be scared to pivot when data tells you to. His approach proves that understanding your market and solid KPIs keep everyone aligned whilst building for both today's wins and tomorrow's growth.

For our messaging critique segment of the show, Terry chose Modelo Beer as our subject. He praises their authentic tagline 'Brewed for those with a fighting spirit' for genuinely resonating with working-class audiences who take pride in hard work. However, he warns against generic sponsorships and endless product extensions that could water down their strong brand identity.

Terry brings us a masterclass in turning CLV insights into actionable strategy. Consider this your guide to understanding how your customers' true long-term value can transform every strategic decision you make as a PMM.

Key Takeaways:

• CLV clarity transforms every PMM decision because you finally know the actual long-term payoff, not just vanity metrics.
• Breaking down silos between marketing and IT creates go-to-market magic that addresses real needs whilst making life easier for users.
• Treat launches as continuous journeys focused on repeat engagement rather than forgettable one-time events.
• Creative campaigns with relatable stories demolish feature-focused messaging, especially when solving actual pain points.
• Strategic KPI alignment with executives keeps long-term vision intact whilst smashing immediate growth targets.

Terry’s Formula:

Customer Lifetime Value = (Average Purchase Value x Purchase Frequency x Customer Lifespan)

LINKS

Modelo Beer: https://www.modelousa.com/

Connect with Terry:

LinkedIn: https://www.linkedin.com/in/terry-seitz-57aa654/

Connect with Elle:

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

Here's the truth about meaningful growth: you either sell more of your current product to more people, or you build something entirely new to attract fresh customers. The second path is where innovation meets strategy, where positioning becomes an art form, and where go-to-market plans can make or break your future. Today's story centers on Ember—yes, those temperature-controlled smart mugs you've seen at Starbucks—but here's the twist: they didn't stay content as a coffee mug company.

This episode unpacks exactly how Ember executed their bold leap into an entirely different category, chasing new audiences with completely different products. I'm joined by Daniel Alvarez, who's led product strategy at Ember, Dole, and Jacuzzi, bringing that rare mix of engineering depth and business acumen. Also with us is Connor O'Neill, who's spent over a decade crafting brand stories that genuinely resonate with luxury customers, from Ember to Babylist and Jaguar Land Rover.

Daniel and Connor reveal the four critical moves that transformed Ember's market expansion from risky gamble to roaring success. We also dive into our messaging critique segment, dissecting the Oura Ring's complex challenge of translating intricate health insights into relatable, digestible messages for everyday users.

The wisdom bomb from our guests? Market expansion isn't just about being different—it's about being meaningful. Remember that even the most cutting-edge innovations must connect through clear, compelling storytelling. Ready to explore new market spaces and dare to innovate beyond the usual boundaries? Let’s go!

Key Takeaways:

• Consumer insight drives everything - Deep analytics and behaviour understanding form your foundation for connecting with untapped market desires

• Leverage proven technology - Innovation doesn't mean starting from scratch; build on what works to create smooth transitions for existing customers whilst attracting new ones

• Craft aspirational narratives - Authentic storytelling that speaks to your audience's dreams and lifestyle aspirations is essential for market expansion success

• Simplify complex messaging - Even cutting-edge innovations must translate technical benefits into relatable, digestible messages that everyday users can understand and connect with

• Be meaningful, not just different - Successful market expansion focuses on addressing real customer needs rather than simply being novel or disruptive

LINKS

Oura Ring: https://ouraring.com/

Connect with Daniel and Connor:

Website: https://revelhorizon.com/

Instagram: @revelhorizon

Connect with Elle:

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

Ever wondered how product marketers can thrive when everything's constantly changing? This episode explores exactly that with Stephanie Sosa, a product marketing powerhouse who's worked at Slack, Airtable and Credit Karma. We dive into how embracing cultural moments can transform challenges into game-changing opportunities, using Slack's Huddles as the perfect case study. Remember 2020's chaotic shift to remote work? While most were scrambling, Stephanie's team spotted opportunity. Huddles wasn't just a new feature—it captured our collective need for connection in virtual spaces, born from understanding genuine customer needs during massive change.

Stephanie shares her practical blueprint for capturing these moments. Spot the signals by watching your customers and market closely, do your homework on competitors and industry shifts, stay present during beta phases to test messaging, and keep everything customer-centric from start to finish. The magic happens when you craft stories, not just launch features. Huddles positioned Slack as the ultimate digital headquarters—a promise about how work could feel meaningful in a virtual age. We also critique Sierra AI's messaging, noting their refreshingly human language but suggesting they need stronger differentiation in the crowded AI space through "show don't tell" interactions.

Stephanie has mastered the art of learning from customers and using those insights to guide launches that actually resonate because they're built on real needs. Her approach is a masterclass in timing, adaptation, and creating messaging that connects authentically. The world's ripe with possibilities for product marketers willing to pay attention—keep your ears open, connect genuinely with your audience, and the next big cultural wave might just be your defining moment.

Key Takeaways:

• Cultural moments create massive opportunities for product marketers who know how to spot and seize them
• Success comes from understanding genuine customer needs during times of change, not just following trends
• Beta phases are crucial for PMMs to gather insights and test messaging before launch
• Effective product marketing tells stories, not just features - position your product within your customer's real-world narrative
• Clear, human language beats jargon every time, but differentiation is essential in crowded markets
• Customer feedback should shape product development from start to finish

LINKS

Sierra AI: https://sierra.ai/

Previous episode mentioned: Find Product-Market Fit Like an OpenAI PMM

Connect with Stephanie:

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

Connect with Elle:

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

Finding product-market fit is like striking gold—when you hit it, your product practically sells itself. But how do you know when you’re onto a winner, or when you might be barking up the wrong tree?

I recently chatted with incredible product marketer Pranav Deshpande, whose journey through Twilio, Modern Treasury, and now OpenAI offers a treasure map for this elusive quest. At Twilio, he saw both stunning success and timing missteps. At Modern Treasury, he learned the power of a laser-focused customer profile. Now at OpenAI, he's riding the wave of perfect product-market fit with ChatGPT.

In our conversation, we dive into the signals that show you've struck gold: repeatable sales patterns, evolving customer feedback, and the delicate balance between being your product's champion and critic. Plus, we analyze Notion's AI strategy—brilliant in execution but sometimes missing the mark in messaging.

Perhaps the most important insight? Product-market fit isn't a destination but a moving target. Markets evolve, competitors emerge from nowhere, and customer needs shift constantly. What fits perfectly today might need serious adjustment tomorrow—making the journey more marathon than sprint.

Actionable Takeaways

• Schedule regular "reality check" sessions to honestly assess your product-market fit
• Study your happiest customers like they're rare specimens—what makes them tick?
• Know your pivot triggers before you need them—what market signals would make you change course?
• Remember that even revolutionary products need solid execution—brilliance without follow-through is just a good idea
• Accept that finding product-market fit is an ongoing journey of tweaking and refining, not a one-time achievement

LINKS

Notion: https://www.notion.com/

Connect with Pranav:

LinkedIn: https://www.linkedin.com/in/pranav808/

Connect with Elle:

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

Let’s be honest—every product marketing manager dreams of having a hand in shaping the product roadmap. But what’s the secret to actually getting a seat at that roadmap table? It all starts with trust.

Today, I’ve got the perfect blueprint for you, thanks to our special guest—Sheryl Li, the brilliant product marketing leader at Confluent. Sheryl isn’t just any PMM. From turning her science fair win into an asteroid named by MIT (yes, seriously!) to spearheading game-changing projects at Twilio and Confluent, her story is incredibly inspiring. Sheryl’s scientific mindset—think curiosity, experimentation, and pattern recognition—has become her superpower in crafting killer product strategies.

Drawing from her experiences at both Twilio and Confluent, Sheryl reveals her methodical approach to boosting product adoption through deep customer understanding and cross-functional collaboration. She emphasizes the critical role of trust-building with product partners and the importance of maintaining regular dialogues with product and data science teams, especially in consumption-based pricing models. Through her work with Confluent's cloud connectors, Sheryl demonstrates how combining investigative research with strategic storytelling can drive meaningful product improvements.

The episode concludes with an analysis of two fascinating case studies: Apple's Dynamic Island feature marketing and Dust's approach to AI messaging. These examples showcase how different companies, from established tech giants to emerging startups, can craft compelling narratives that resonate with their target audience while maintaining clear differentiation in crowded markets.

Key Takeaways:

• Build trust with product partners through consistent collaboration and shared ownership
• Maintain regular check-ins with product and data science teams to monitor adoption metrics
• Use customer interviews to craft compelling narratives that influence product strategy
• Follow up with customers to maintain relationships and gather ongoing feedback
• Transform technical features into customer-centric stories that drive engagement
• Balance innovation with clear, focused messaging that cuts through market noise

Resources mentioned:

Apple Dynamic Island Feature video: https://youtu.be/rFB7uSgFEsY

Dust AI: https://dust.tt/

Connect with Sheryl:

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

Connect with Elle:

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

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/

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/