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/

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/

Getting your pricing strategy right can make or break market share. Great product marketers know that a well executed strategy doesn't just drive revenue; it shapes perception, influences adoption, and can determine whether your product wins or loses in the market.

Joining us on this journey is someone who knows all about turning the tides with pricing—Nupur Bhade Vilas, who heads up product marketing at Kustomer. She's a force, well-known for pushing AI-powered customer experiences and driving go-to-market strategies that make waves. Having led game-changing initiatives at places like Twilio, Nupur brings this incredible insight in our conversation on aligning pricing with real customer value.

The Underrated Power of Pricing

Nupur highlights a vital point: in many companies, pricing is this often-overlooked lever that doesn't sit with product marketing. Instead, it lives in finance or sales. But when PMMs get to steer the ship, it’s magic. She stresses that pricing must evolve alongside the market, especially now with AI shaping the landscape.

4 Phases of Pricing Transformation

Together, Nupur and I explore the essential phases of transforming your pricing strategy: Discovery, Research, Design, and Operationalization:

1. Discovery: This phase is all about clarifying the problem you aim to solve, leveraging insights from leadership to uncover the roots and shape your strategy.

2. Research: From diving deep into competitor tactics to customer surveys, it’s a journey of learning and understanding industry norms and disrupters.

3. Design: This is where you build your pricing packages with precision, ensuring clarity and safeguarding margins, guided by a solid, data-driven approach.

4. Operationalization: Moving from concept to execution—this phase requires tight collaboration across departments to ensure consistency and avoid customer confusion.

Securing Stakeholder Buy-In

We face the reality of winning over stakeholders, from the executive level to the operational groups. Nupur speaks about the clever use of a ‘SWAT team’ post-rollout to maintain nimbleness and keep the strategy aligned and responsive.

Embracing Evolution and Flexibility

Nupur emphasizes that pricing isn’t a ‘set and forget’ aspect of product marketing. It requires ongoing feedback and the freedom to adapt. Her comparison with Netflix’s paced transition from DVDs to streaming nailed the point—you’ve got to give change its space, allowing customers to ease into it.

Ultimate Takeaways for PMMs

For any PMM on the brink of a pricing transformation, remember: flexibility is key. Stay customer-focused, and let your strategy grow with your business dynamics. Keep tweaking based on feedback and ensure that your pricing approach continually aligns with customer needs.

A Nod to Creativity and Authentic Branding

Before signing off, Nupur shares her take on Pierre, a company that grabbed her attention with its audacious branding around code review collaboration. It’s a brilliant reminder of how creativity and authenticity can redefine market norms. We also talk through ideas about beneficial next phases for Pierre’s new product rollout, and Nupur discusses her thoughts on how they could more clearly convey what they have on offer.

So, here’s to all product marketers—embrace change, step into your customer's shoes, and inject your strategy with the boldness and creativity that define leaders like Nupur.

LINKS

Connect with Nupur:

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

Connect with Elle:

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

 Online communities are a goldmine for finding customer advocates who can supercharge your product launch - but too often companies rely on things like email blasts and paid campaigns, completely overlooking the power of engaged customers.

Within your own community are passionate advocates, ready to champion your product and influence others.  Leveraging these voices in a launch isn't just about buzz - it’s about creating credibility, driving adoption and igniting that word of mouth growth that sustains long after the launch.  

In this episode, I have the pleasure of sitting down with Kaavya Gupta, who currently leads a product marketing team at Reddit. Her specialty is caring for products that make it easy for anyone to find and engage with communities on Reddit.

In our conversation, Kaavya gives us the inside scoop on community-driven product launches and why they’ve become a model for most of her team’s launches.

Understanding the Role of Community in Product Launches

Kaavya believes that the true heartbeat of a successful launch lies not in what the brand dictates, but in what the users themselves express. Kaavya walks us through a recent launch that capitalized on community advocacy, demonstrating the importance of bringing users into the fold early through co-creation. The result was an enhanced product experience, validated and refined by the very community it was meant to serve.

The Process: From Research to Execution

For those wanting to replicate this community-driven model, understanding your audience deeply is the first step. Define who your product touches, quantify the impact and empathize with what matters to them.

Once you have this foundational understanding, Kaavya recommends outlining the key phases of your activation strategy: collecting user feedback, enabling internal teams and launching the product while always keeping an ear to the ground to gauge community sentiment. She steps us through the process of hypothesising, researching, segmenting and continually refining your messaging based on feedback from your community and stakeholders.

The Art of Messaging and Engagement

Kaavya emphasizes the crucial role that messaging plays in product launches. Messaging isn't just about the right words; it's about creating a narrative that resonates with your audience on a deeper level. This narrative acts as the backbone of your strategy, guiding the advocates to communicate the product’s value effectively. By crafting messages that speak to emotions and needs, you empower your advocates to become true evangelists of your brand.

Remember, at the heart of groundbreaking product marketing is the passion and authenticity driven by your community. Kaavya shares so many valuable insights with us, and  I hope this episode leaves you with inspiration in taking the next step in your own PMM journey!

LINKS

Connect with Kaavya:

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

Connect with Elle:

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