217: Maintaining Member Retention & Engagement with Tayler Cusick-Hollman

The Laylee Emadi Podcast — For Speakers, Coaches, and Course Creators

If you’ve ever launched a course, membership, or product and wondered why your people aren’t engaging with the resources you worked so hard to create, this snack-size episode is for you. Pulled directly from a live Q&A inside the Educators Lounge, this conversation with Tayler Cusick-Hollman reveals what really goes on after the sale.

During our call, Tayler highlighted that many of us are facing similar issues in the education space, where we struggle with onboarding, retention, and having to spoonfeed your community—even when it feels redundant.

We also dig into the mindset shift that needs to happen after the sale. Because keeping people engaged is just as strategic—and important—as getting them in the door in the first place.

The Hidden Challenge After the Sale

We put so much effort into launching: building funnels, perfecting messaging, and creating amazing content. Then when that sale comes in, we celebrate!

But what often happens next? Often silence.

And suddenly, we’re in our heads wondering why our new members aren’t as hyped about our program as we are. Why aren’t they showing up? Why aren’t they interacting?

The hard truth: the sale is only the beginning. What comes next is a different kind of work.

What We Miss About Engagement

The simple but game-changing truth? Just because the thing is there, doesn’t mean people are gonna know it’s there.

While sharing about my own experience with building a membership, I asked our members to also chime in with their own. Tayler is building a membership around a low-cost software product (Enji), which means she’s had to be especially thoughtful about member retention. Her biggest lesson? We all need to be spoonfed.

Yep. Even if it makes your inner educator roll her eyes. Even if it feels redundant. Because people are overwhelmed, distracted, and juggling a million things.

If you want them to experience the transformation you promised, you have to guide them through the process. Step by step.

The Case for Spoonfeeding (Even When It’s Annoying)

You might be thinking, “Shouldn’t they just read the welcome email?” or “Isn’t it obvious what to do next?”

But think about your own habits. How many programs or courses have you purchased and never opened? How many community platforms do you ignore because no one is actively prompting you to come back?

This isn’t about being patronizing, it’s about creating clarity and ease. Your members aren’t lazy, they’re just human, and humans need reminders.

So tag them in the group. Send the extra email. Create that “Start Here” guide—even if it feels like you already said it.

Repeating yourself doesn’t make you a bad educator. It makes you a smart business owner.

Retention Marketing: The Missing Piece

Tayler dropped a term that more creators need to know: retention marketing.

It’s the marketing that happens after the sale. The nurturing, the reminders, the personalized check-ins. It’s onboarding with intention. It’s engagement that feels personal. It’s all the things that keep people coming back—not just for the content, but for the community and transformation they signed up for.

If your members aren’t engaging, it’s not a personal failure. It is a cue to revisit your systems.

Are you assuming too much? Are you relying on a one-time welcome sequence instead of an ongoing strategy? Are you prioritizing post-sale support the same way you prioritize launch week?

It’s not about doing more. It’s about doing the right things, consistently.

Mentioned in this Episode

layleeemadi.com/educatorslounge

Connect with Tayler

enji.co

instagram.com/enji_co

instagram.com/taylrd_designs

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