Master Your Up-Market Strategy Like A Unify PMM

Master Your Up-Market Strategy Like A Unify PMM

Landing your first enterprise deal feels like you cracked the code. Then leadership wants ten more, and suddenly “going upmarket” becomes the plan, even if your motion still looks mid market. This episode is about what actually changes when you move into enterprise, and why it is not just selling to bigger companies. It is a different buyer, a different story, and a different way of proving value. Quintin Smith joins me to break it down. He is a two time founding PMM, currently leading go to market at Unify, and previously helped scale CaptivateIQ during a major growth phase. He shares what it took to turn enterprise from a lucky win into a repeatable motion. We get into the enterprise buyer dynamics that most teams underestimate, including the importance of the full buy team and the narrative shift required to win at that level. Quintin also walks through his Four Rs framework for building an upmarket strategy that can actually run, from research and refinement through enablement and reporting. We also do a messaging critique of Profound, a company helping brands improve visibility inside AI platforms like ChatGPT and Microsoft Copilot. We talk about what they are doing well in clarity, and where a more future oriented narrative could help them own the category as search behavior shifts. LINKS Messaging Critique (Profound): tryprofound.com Connect with Quintin: LinkedIn: https://www.linkedin.com/in/quintin-smith-35b51582/ [https://www.linkedin.com/in/quintin-smith-35b51582/]  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/]

Tell Engaging Stories Like a PushPay PMM

Product marketing is split into two camps. One group relies on safe templates, stock imagery, and generic descriptors that blend right into the background. The other group treats creative storytelling as a strategic muscle, pushing past surface-level benefits to build a genuine, emotional connection with buyers. This episode is about how to break out of that first, stuffy camp and start driving real revenue impact with your content. Stefan Gladbach joins me for a deeply practical conversation on transforming content ecosystems from stuffy to unforgettable. Stefan has spent over eight years building product marketing playbooks across multiple industries, and currently leads content innovation at the church tech market leader, Pushpay. He shares how he moved his team away from static talking-head clips into dynamic whiteboards and narrative skits that capture authentic audience sentiment. Stefan breaks down his exact five-step creative playbook. We explore how to unearth real emotional pain points rather than hiding behind surface-level benefits like "saving time and money," how to turn up the creative heat gradually using the "frog in a boiling pot" method, and how to handle status-quo objections from internal leadership using hard empirical data. We also conduct a live homepage messaging critique of Vidyard, analyzing where their hero layout succeeds, how they accidentally trick users with integration logos, and why overloading copy with buzzwords like "AI-powered" dulls your product story. If you take one lesson from this episode, let it be this: creativity is an operational muscle that requires daily practice reps. Stop relying on safe frameworks and start bringing your product stories to life. Key Takeaways * Ditch the Boring Benefits: Surface-level claims like "save time and money" fail to trigger emotion. Dig deeper into the daily frustrations of your buyer persona to build a true before-and-after story. * Boil the Frog Domestically: Avoid pitching radical creative concepts immediately. Introduce micro-experiments to accumulate early metric wins and secure internal leadership trust. * Build a Customer Safety Net: Keep your boldest ideas grounded by testing wacky concepts against a tight, informal loop of trusted customer advisors before going live. * Defend Content with Data: Answer brand-guideline objections and executive hesitation by pointing directly to upstream click-through rates and downstream sales-call callouts. * Get Creative Reps In: Creativity isn't just innate; it's a muscle. Use side projects, LinkedIn posts, short fiction, or improv classes to keep your storytelling sharp for your day job. LINKS Messaging Critique (Vidyard): vidyard.com [http://vidyard.com]  Connect with Stefan: LinkedIn: https://www.linkedin.com/in/stefan-gladbach/ [https://www.linkedin.com/in/stefan-gladbach/]  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/]

Claude Code Your Next Launch Like A Vivun PMM

Product marketing is splitting into two groups right now. One group uses AI to move faster and crank out deliverables. The other uses AI to operationalize deep thinking, pressure test positioning, synthesize customer patterns, and build systems that keep working after the launch. This episode is about that second group, and what it looks like when it is done well. Ryan Radcliffe joins me to break down how he helped Vivun reposition at breakneck speed as the company evolved from serving sales engineers to launching Hero for sellers. Ryan’s approach was not “throw prompts into Claude and hope.” He built a 40 page messaging and persona manifesto grounded in research, stakeholder alignment, customer psychology, and voice of customer insights. We talk through how that manifesto became a real operating system for the company. How Ryan translated executive narrative into personas, positioning, proof points, and language guidelines that teams could actually use. Then we get into where Claude fits, and how constraints and inputs matter if you want outputs that stay on brand and avoid the usual AI mess. We also cover the moment the system proved itself when the team had to ship a hero website fast, plus a messaging critique of UserGems and why generic AI language is the quickest way to lose trust. The big takeaway is simple. AI is not the strategy, clarity is. AI just helps you scale it. LINKS Messaging Critique (UserGems): https://www.usergems.com/ [https://www.usergems.com/]   Connect with Ryan:  LinkedIn: https://www.linkedin.com/in/radcliff/ [https://www.linkedin.com/in/radcliff/]   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/]

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/]