From Boring to Bold: B2B Storytelling at its Finest

This case study was created from an episode of the Product Marketing Adventures Podcast. It has been adapted into Dusted's case study format to preserve and showcase the guest's real-world experience. Written to preserve the voice of the true author, Stefan Gladbach.

I joined Pushpay a little over a year ago as a product marketer—my first time in church tech after eight-plus years across other industries. Pushpay sits in the church tech space as a CRM mixed with payment processing for donations, built for churches and nonprofits. Churches function like small communities with schools, groups, events, and sometimes thousands of congregants, so they need substantial software to run it all. Our product marketing content at the time was extremely safe: stock photos and videos of people hugging in churches, overused clichés like “transform” and “revolutionize,” and generic benefits around saving time and money. Competitive research showed our competitors were doing exactly the same thing. You could swap the logos on the content and not tell the difference.

Engagement on launches was weak across Pendo guide notifications, email open rates, and social—our product videos might get one or two likes. Pushpay is the market leader, yet a competitor whose product wasn’t half as good was generating real buzz and attention. Their young, brash founder sold a compelling vision that made customers feel part of a movement to reinvent church tech. The core task became clear: make customers care about our marketing, feel something when they saw our content, and actually engage—while figuring out what we could get away with. We market to churches, so certain lines can’t be crossed, even though church administrators scroll TikTok and memes like everyone else. I needed to find that line, stand out from endless lookalike competition, and tap the same human elements that were working for the competitor, without simply copying a founder-centric playbook.

I started by building credibility with quick wins across departments—updating sales enablement pieces and improving communication. One to two months in, I sat down with my boss and other stakeholders, shared what I’d learned from market and competitor analysis, and floated a couple of ideas for making product videos a little more fun. I’m a big believer in the frog-in-boiling-water analogy: go crazy all at once and stakeholders shut you down. Instead I turned the heat up gradually. I partnered with our videographer and slowly moved away from stiff talking-head videos and stock footage—adding more movement and playfulness, then using a whiteboard with fun drawings to explain concepts. From there we graduated to more complex skits that put us in the customer’s shoes and told stories in a fun, engaging way.

Step one was always deeply understanding the customer. Humor is powerful, but what lands varies by audience, especially a more conservative one. I interview customers, hop on sales calls, attend events, and keep a few close customers I can run wackier ideas by first (“Would you find this funny?”). Their feedback has stopped bad decisions. I dig past surface-level “save time and money” benefits to the real emotional layer—for example, the sales-manager story of being trapped in meetings and unable to coach reps, then regaining time to become the caring manager they wanted to be.

I treated the shift as mini-experiments: dial up boldness, measure, establish credibility, then push a little further. Internally and externally this protected us from shock or blowback. I prepared for the inevitable objections (“Is this off-brand?”) by accumulating metrics from each test and standing my ground with data instead of caving at the first pushback. Collaboration mattered too—our videographer Mary Ann had mostly done corporate-style work while I make wacky LinkedIn videos, so we had to find a groove. After 70–80 videos together, tweaking each time, we ended up in lockstep. Creativity is a muscle; I keep getting the storytelling reps in with my own silly LinkedIn and YouTube videos so breaking down a product story on the job becomes easier. The process is never-ending refinement as ICPs shift.

We leaned on Pendo for in-app guide notifications, email for launch communications, and social channels where early videos lived. Straight talking-head and stock footage gave way to whiteboard drawings for explaining concepts and then full skits. I tested ideas with a small set of trusted customers before anything went live and tracked early signals plus downstream impact. Collaboration with videographer Mary Ann was essential for filming; LinkedIn (and my own YouTube channel) served both as a distribution and practice ground for creative reps. Vidyard is a tool I use regularly for video hosting and tracking in my day-to-day work.

The first good sign was qualitative: people started talking about the content. Comments like “that whiteboard was pretty cool—I love how you explained that complicated concept” began rolling in. Metrics followed—email click-through rates increased, average time spent on our in-app guides went up, and launches started generating more leads. Even more rewarding, a prospect messaged me on LinkedIn saying a recent skit video was hilarious and that they liked Pushpay so much more now. When a prospect brings the content up unprompted, you know it stuck. Those small human signals, paired with the harder numbers, confirmed we were building real trust and emotional connection instead of adding to the noise.