Marketing teams across industries face similar challenges in reaching their audiences with relevant, timely offers that support overall acquisition and retention. Some organizations, however, face additional hurdles because their audiences are savvy to marketing tactics and may have an especially high standard for what it takes to truly grab their attention and earn their trust.
In this #ContentChat conversation, Erika Heald was joined by Maureen Jann, a marketing strategist with deep experience connecting with marketing-skeptical audiences, including IT leaders, startup founders, and marketers themselves. They covered how to build trust with skeptical buyers, why generic outreach backfires, and what it really takes to stand out when everyone’s been burned before.
Watch the full conversation on YouTube, or read through the highlights below.
What Makes an Audience Difficult to Market To?
Maureen and Erika both work with audiences who’ve seen it all—marketers, IT professionals, and startup founders. Those audiences have been misled by empty promises, buzzword-heavy pitches, and performance marketing campaigns that didn’t deliver.
“It’s not that they’re marketing resistant—it’s that they’re bullsh*t resistant.”—Maureen Jann
That skepticism means you need to come in with transparency and clarity. If you pretend you’re the smartest person in the room or promise the moon, you’ll lose their trust immediately.
“If your content can be written by anyone, it won’t be trusted by anyone.”—Maureen Jann
“Credibility should not be declared. It should be conferred.”—Maureen Jann
“Being a thought leader isn’t about being the best BS’er in the room. It’s about how much real-life experience you have doing the thing.”—Maureen Jann
Building Trust With Transparent Marketing
So how do you earn attention from audiences that are tired of being sold to?
- Lead with transparency. Maureen signs off her emails as a “Marketing Director and IT Translator.” She builds trust by making it clear she’s not trying to speak over her audience.
- Show, don’t tell. One of our favorite ways to prove credibility? Sharing behind-the-scenes how-tos and customer stories that highlight real success without bragging.
“If you show credibility, you don’t have to tell everyone how good you are.”
—Maureen Jann
- Don’t chase vanity public relations. Maureen and Erika both ranted (lovingly) about people being misled into thinking a paid Forbes contributor post equals press coverage. Spoiler: it’s not.
- Value > virality. A sponsored session can be memorable and meaningful, but only if it’s genuinely useful. If it feels like a sales pitch, people will tune out fast.
“When it feels like help, it works. When it feels like a pitch, it falls flat.”—Maureen Jann
Ideas That Still Resonate Years Later
Maureen shared how her team created a horoscope quiz for marketers, complete with a plastic flamingo and disco ball. It cost $5K, was packed with expertise, and five years later, people still take the quiz.
It worked because it was:
- Audience-specific
- Memorable
- Backed by real value
That’s the magic formula: delight + expertise = results.
Why Format and Channel Matter
Not every organization wants to be edgy—but you can still differentiate. That might look like:
- Turning a case study into a customer-narrated blog post
- Running a sponsored session that teaches instead of sells
- Building diagnostic tools or assessments that help people self-identify their gaps
All of these tactics prioritize helpfulness over hype.
Content Marketing Solves Problems to Earn Trust
Marketers are not here to game audiences into liking us. We’re here to help solve problems and share real stories. If you do that consistently, the right people will engage.
📘 And ICYMI: Erika’s new book Content Foundations is now available! Head to contentfoundationsbook.com or search for it on Amazon.
