I’ve always loved The Wizard of Oz. There’s something timeless about Dorothy’s journey, a young girl swept up by a tornado, dropped into an unfamiliar land, and told the only way home is to follow a winding Yellow Brick Road to the Emerald City. She doesn’t know exactly what she’ll find there, but she knows it’s her destination. Along the way, she meets companions who each have their own needs: the Scarecrow seeking a brain, the Tin Man longing for a heart, and the Cowardly Lion desperate for courage.
What strikes me most about this story isn’t just the adventure, it’s the clarity of the path. Dorothy knew where to go. The Yellow Brick Road was visible, intentional, and purposeful. She wasn’t wandering aimlessly through Oz; she had direction, even when obstacles appeared.
Now, think about your senior living community’s website. Are your prospects following a clear Yellow Brick Road, or are they lost in the poppies, unsure which direction to turn?
At Waypoint Converts, I’ve spent years helping communities create that Yellow Brick Road, a clear, guided path that turns curious website visitors into engaged prospects and, ultimately, into residents. And just like Dorothy’s journey, it requires the right companions, courage to embrace change, and a strategic destination in mind.
Meet Your Marketing Characters
Every great journey needs companions, and in senior living marketing, these “characters” represent both the challenges you face and the solutions you need:
The Scarecrow (Strategy): Remember the Scarecrow? He believed he didn’t have a brain, yet he was the one who consistently came up with clever solutions throughout the journey. In marketing, we often see communities that feel like they lack strategy—great intentions, beautiful communities, passionate teams, but the website feels aimless. Or we continually want to drive them to a tour when they may or may not be there yet. Visitors arrive but are unsure of where to go next. There’s no clear path forward.
I see this all the time: communities invest in gorgeous websites, but without structured, data-driven pathways for every type of prospect. The Scarecrow teaches us that having a “brain”—a smart strategy—means understanding your visitors’ needs and creating intentional routes for them to follow. That’s exactly what we do at Waypoint Converts. It is important to consider a full funnel approach, meeting your visitors no matter where they are in their search and exploration journey.

The Tin Man (Connection): The Tin Man’s quest for a heart is perhaps the most emotionally resonant part of the story. He already had the capacity for love and empathy; he just didn’t believe it. Your prospects are craving that same connection, that heart. They want to feel understood, valued, and guided with compassion.If your website doesn’t engage prospects emotionally or provide instant, helpful answers, they’ll click away and look elsewhere. This is where our Virtual Sales Assistant (VSA) becomes your Tin Man, adding warmth, personality, and guidance to every interaction. It answers questions at 2 a.m., provides reassurance when families are anxious, and builds trust even before the first phone call. The Waypoint VSA helps the sales teams by allowing consumers to get questions answered quickly. We are an “I want it now society.

The Cowardly Lion (Fear of Change): The Lion thought he lacked courage, but he proved his bravery time and again when it mattered most. I understand that trying new technology—especially automation and AI—can feel intimidating. What if it doesn’t work? What if it feels impersonal? What if our team can’t adapt?
But here’s what I’ve learned: courage isn’t the absence of fear; it’s moving forward despite it. Waypoint Converts makes adopting these tools easy and natural. We empower your team to act confidently, knowing that technology isn’t replacing them, it’s supporting them, handling the repetitive questions so they can focus on the meaningful, human moments that truly matter.

The Yellow Brick Road: Your Customer Journey
Dorothy’s Yellow Brick Road wasn’t a shortcut—it was a carefully laid path that required patience, persistence, and trust. Your customer journey is no different. Every step matters, and every twist in the road serves a purpose.

Here’s how I see the Yellow Brick Road playing out in senior living marketing:
- Awareness (Leaving Kansas): Just like Dorothy’s house landing in Oz, prospects “land” on your website, often through search, ads, or referrals. They’re in unfamiliar territory, trying to orient themselves. This is your first impression—make it count.
- Engagement (Meeting the Munchkins): In Oz, Dorothy immediately encounters helpful Munchkins who point her toward the Yellow Brick Road. On your website, personalized messaging and VSAs serve the same purpose—quickly helping prospects find relevant information and feel welcomed.
- Consideration (The Journey Through Oz): Dorothy faced forests, poppy fields, and the Wicked Witch’s castle. Similarly, prospects navigate doubts, questions, and comparisons as they consider their options. This is where nurturing matters—tailored content, guided interactions, and consistent communication keep them moving forward on your Yellow Brick Road rather than wandering off the path.
- Consideration (The Journey Through Oz): Dorothy faced forests, poppy fields, and the Wicked Witch’s castle. Similarly, prospects navigate doubts, questions, and comparisons as they consider their options. This is where nurturing matters. Tailored content, guided interactions, and consistent communication keep them moving forward on your Yellow Brick Road rather than wandering off the path.
- Nurturing (Staying on the Path): Here’s something critical that Dorothy teaches us: she didn’t make the journey in one day. She needed rest stops, encouragement from her companions, and multiple touchpoints to keep moving forward. The same is true for your prospects. In partnership with SeniorLiving SMART, we’ve learned that meeting the necessary touchpoints along the journey is essential to help prospects continue toward the Emerald City.
As Deborah Howard, founder of Senior Living SMART, explains: “Marketing automation is a must-have. With a long sales cycle requiring 22 to 28 touchpoints, a salesperson can’t manage this alone. Marketing automation bridges the gaps by delivering content, inviting prospects to events, sending guides, and providing testimonials, videos, and virtual tours.”
This is where Marketing Automation becomes your guide, ensuring no prospect is left behind in the poppy fields. Automated nurturing keeps them engaged, informed, and moving forward, even when life gets busy or fear creeps in.
- Conversion (Reaching the Emerald City): The Emerald City represented hope, answers, and transformation. Your conversion point (whether scheduling a tour, contacting admissions, or requesting information) should feel just as momentous and welcoming.
With Waypoint Converts, I’ve designed tools that make your website a seamless Yellow Brick Road, leading prospects from curiosity to commitment without confusion, friction, or dead ends.
Defeat the Wicked Witch of Marketing Challenges

Let’s talk about the villain of the story. The Wicked Witch of the West didn’t want Dorothy to reach her destination; she threw up obstacles, spread fear, and tried to keep Dorothy trapped. In senior living marketing, your “Wicked Witch” takes many forms:
- Slow or no responses to inquiries
- Generic, one-size-fits-all website experiences
- Leads that slip through the cracks
- Prospects who ghost after initial contact
These challenges feel insurmountable sometimes, don’t they? But just like Dorothy had her ruby slippers and loyal companions, you have tools to conquer these obstacles:
- Instant engagement: Our VSAs respond to questions immediately, 24/7—even when your team is asleep or busy with tours.
- Personalized experiences: Visitors see content tailored to their specific interests, whether they’re exploring memory care, independent living, or simply researching options for a parent.
- Staff support: Automation reduces repetitive workload, freeing your team to focus on the personal interactions that matter most—the phone calls, the tours, the hand-holding moments that can’t be automated.
I’ve seen communities transform when they stop fighting these battles manually and start using smart technology strategically.
Reaching the Emerald City: Conversions That Matter
Here’s the twist in The Wizard of Oz: when Dorothy finally reaches the Emerald City and meets the Wizard, she discovers he’s not magical at all; he’s just a man behind a curtain using tools and ingenuity. But that doesn’t diminish her journey or her success. She still gets what she needs.
The same is true in marketing. The “magic” isn’t smoke and mirrors; it’s smart strategy, the right tools, and consistent execution. When your website effectively guides visitors, engages them emotionally, and nurtures them at every step of their journey, your community sees real, measurable results:
- Higher lead engagement rates
- Increased tour requests
- More move-ins and faster occupancy growth
Waypoint Converts ensures your Yellow Brick Road isn’t just scenic—it’s strategic, measurable, and effective. I’ve built these tools because I believe every senior living community deserves to reach its Emerald City, whatever that looks like for them.
Start Your Journey Today
Dorothy had one more powerful realization at the end of her journey: she’d had the power to go home all along. She just needed guidance to discover it.
Your community already has incredible stories, compassionate care, and dedicated teams. You have the power to convert prospects; you just need the right tools and strategy to unlock it.
Don’t leave your prospects wandering in the land of Oz, or worse, lost in the vast, overwhelming internet. Let me help you build your Yellow Brick Road with Waypoint Converts’ customizable Virtual Sales Assistant and website personalization tools.
Your Emerald City awaits.
Schedule a Demo and start guiding your prospects today.


