Product Marketing Adventures

Go Bold with Competition Like a Sybill PMM

If you are a startup PMM staring down a category leader, this episode is for you. We use the David and Goliath story as the setup, not to be dramatic, but because it is real. You are not going to outspend the incumbent, and you probably cannot out muscle them on brand. So the question becomes, where is the opening that actually matters? Collin Mayjack joins me to break down how Sybill went head to head with Gong and turned it into real pipeline. Collin leads product marketing at Sybill, previously worked on growth and adoption at GoFundMe, and brings a rare trust building lens from his background before product marketing. He shares how to compete without trying to become the market leader. We walk through Collin’s competitive playbook, including how to get painfully clear on differentiation, how to pull real customer frustrations from the places people are already venting, and how to build a full funnel system that backs bold claims with proof. We also talk about why putting a real person at the center of the narrative can make competitive messaging land harder and feel more credible. Finally, we dig into the guardrails. How to go bold without being reckless. Plus, a messaging critique of Zendesk’s “Call Your Mom” campaign and why empathy matters when you are trying to create contrast in the AI era. Key Takeaways * Do not try to outspend the category leader. Find the opening that matters and go all in. * Competitive positioning only works when it is specific, defensible, and rooted in real product differences. * Customer frustration is a goldmine, but only if you use the language customers already use. * Bold top of funnel content needs bottom of funnel proof, or it will not convert. * A human face can make competitive messaging feel more credible and harder to ignore. * Guardrails matter. Be bold, but stay truthful, fair, and empathetic. LINKS Messaging Critique (Zendesk): https://www.zendesk.com/ [https://www.zendesk.com/]  Connect with Collin:  LinkedIn: https://www.linkedin.com/in/collinmayjack/ [https://www.linkedin.com/in/collinmayjack/]  Connect with Elle: LinkedIn: https://www.linkedin.com/in/elle3izabeth/ [https://www.linkedin.com/in/elle3izabeth/]  Website: https://www.productmarketingadventures.com/ [https://www.productmarketingadventures.com/]

Know the "So What" Like a Digital Science PMM

Ever been hit with the classic, “We’re launching next week. Ready? Go.” moment? In this episode, we talk about why that scramble happens, what it costs, and how the best product marketing teams avoid it by getting clear on success, ownership, and the difference between a release and a real launch. Doug Kimball joins me for a practical conversation on one of the biggest moves a PMM can make: rebuilding the go-to-market function from the ground up. Doug has led global marketing and product marketing teams, run major field kickoffs, and helped teams improve pipeline impact and collaboration using Pragmatic Institute principles. He also recently published a book on B2B positioning and messaging called So What? Why? Who Cares?. Doug breaks down how he approached rebuilding GTM at Digital Science without overcomplicating it. We get into how to look back at what worked and what did not, align PMM work to revenue outcomes, clarify roles across product and marketing, and put frameworks in place so launches stop feeling like one-off fire drills. We also do a messaging critique of OppTrack, a win-loss and competitive intelligence company, and talk about the difference between messaging that is clear and messaging that creates urgency. If you take one thing from this episode, it is this. Before you build the plan or ship the launch, nail the “so what.” LINKS Messaging Critique (OppTrack): https://www.opptrack.com/ [https://www.opptrack.com/]   Connect with Doug:  LinkedIn: https://www.linkedin.com/in/dougkimball/ [https://www.linkedin.com/in/dougkimball/]   Book: https://sowhatwhywhocares.com/ [https://sowhatwhywhocares.com/]   Connect with Elle: LinkedIn: https://www.linkedin.com/in/elle3izabeth/ [https://www.linkedin.com/in/elle3izabeth/]  Website: https://www.productmarketingadventures.com/ [https://www.productmarketingadventures.com/]

Write Your Product Narrative Like a Zapier PMM

Your company has outgrown the thing it is known for, but the market has not caught up yet. New launches land like add-ons instead of the next chapter, and suddenly you are trying to scale a bigger story with old positioning. In this episode, we talk about what it actually takes to evolve brand perception as your product expands. Wade Burrell joins me to break it down. Wade has 15 years of experience across product, go-to-market, and growth, with time at Worldpay, Square, and Intuit Mailchimp. He led SMS expansion across 37 countries and helped shift Mailchimp from being seen as an email tool to being understood as a multi-channel marketing platform. Today, he is at Zapier, leading product marketing for critical infrastructure in the AI era. A big part of our conversation focuses on Wade’s work repositioning Mailchimp’s SMS product. It started as a standalone MVP and was initially treated as useful but optional. Wade shares how they worked to shift that perception, connect SMS to the broader platform story, and make it feel like a strategic priority instead of a bolt-on. Wade also walks through a practical narrative playbook for PMMs, including how to audit your existing platform assets, run open-ended customer research, bring insights into roadmap discussions, and sharpen positioning through real constraints. Plus, we close with a messaging critique of Cursor and where their story could expand beyond developers to speak to larger engineering organizations. Key Takeaways * Platform expansion creates narrative lag if your positioning does not evolve with the product * New products need to feel like the next chapter, not a bolt-on * Strong narrative shifts start with an audit of what you already own and can credibly claim * Open-ended customer research helps you find the gaps that matter, not the story you want to tell * Sales feedback is a fast reality check on whether positioning holds up in the real world * Great messaging can still get sharper by building a second layer for new decision-makers LINKS Messaging Critique (Cursor): https://cursor.com/ [https://cursor.com/]   Connect with Wade: LinkedIn: https://www.linkedin.com/in/wadeburrell [https://www.linkedin.com/in/wadeburrell]  Connect with Elle: LinkedIn: https://www.linkedin.com/in/elle3izabeth/ [https://www.linkedin.com/in/elle3izabeth/]  Website: https://www.productmarketingadventures.com/ [https://www.productmarketingadventures.com/]

Boost Product Adoption Like A GoFundMe Pro PMM

Most adoption problems are not product problems. They are behavior change problems. In this episode, we dig into status quo bias and why customers often stick with what they know, even when your product is clearly better. If you have ever struggled to get users to switch, upgrade, or adopt a new workflow, this will feel very familiar. Keith Blazek joins me to break down how to drive adoption at scale across an entire customer base. Keith has spent over 13 years driving growth across SaaS and financial services in both B2B and B2C, and he helped scale Classy, now GoFundMe Pro, through major growth and transformation. During that time, the platform grew from $1B to $2.6B in annual nonprofit donation volume. Keith walks through his adoption playbook, starting with the step most teams skip. The audit. What assets and channels do you actually have, where does the product fit in the lifecycle, and what is really happening in onboarding and usage. From there, he explains how he builds a repeatable system rather than relying on one big campaign. We also get into practical segmentation, targeting, and positioning for buying committees, plus his Gain, Logic, Fear framework for getting different stakeholders on board without changing the core message. And in the messaging critique segment, Keith audits Wealthfront and shares why specificity and clarity matter even more when you are asking people to change. LINKS Messaging Critique: https://www.wealthfront.com [https://www.wealthfront.com]  Connect with Keith:  LinkedIn: https://www.linkedin.com/in/keith-blazek/ [https://www.linkedin.com/in/keith-blazek/]  Connect with Elle: LinkedIn: https://www.linkedin.com/in/elle3izabeth/ [https://www.linkedin.com/in/elle3izabeth/]  Website: https://www.productmarketingadventures.com/ [https://www.productmarketingadventures.com/]

Leverage Your Community Like An Expedia PMM

Everyone seems to be talking about community right now, but what does it actually take to build one that people want to be part of? In this episode, Cara Gravett joins us to unpack why community matters more than ever in a landscape full of polished, AI-generated noise, and why belonging can be far more powerful than attention. Cara brings deep experience from Expedia, where she worked across product, partners, and revenue, helping shape growth in complex B2B ecosystems. She now advises companies on how to make product marketing more strategic, and also runs Between Launches, a community built for product marketers to learn from one another and grow together. In our conversation, we explore the difference between an audience and a true community, why smaller and more intentional groups are often more effective, and what Expedia’s Travel Agent Affiliate Program can teach us about building something genuinely useful. Cara also shares a practical lens for approaching community strategy without the fluff. We also touch on where AI can support community building, where it falls short, and why human connection still sits at the centre of it all. Plus, in the messaging critique segment, Cara breaks down Maven Clinic’s positioning and shares a smart reminder about the value of sharper audience focus. LINKS Messaging Critique: https://www.mavenclinic.com/ [https://www.mavenclinic.com/]  Connect with Cara:  LinkedIn: https://www.linkedin.com/in/cara-gravett/ [https://www.linkedin.com/in/cara-gravett/]   Connect with Elle: LinkedIn: https://www.linkedin.com/in/elle3izabeth/ [https://www.linkedin.com/in/elle3izabeth/]  Website: https://www.productmarketingadventures.com/ [https://www.productmarketingadventures.com/]