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/