At Timbers Company, the journey to vacation home ownership often begins long before a sales conversation. It starts with a destination that captures someone’s imagination, a story that resonates, or a vision of how a family might spend meaningful time together.
Creating that connection requires a thoughtful approach across both marketing and sales—from building awareness and articulating the Timbers story to understanding prospective Owners and guiding them toward the residence and destination that best fit their lives.
Leading that effort is John Fitzgerald, Chief Sales & Marketing Officer at Timbers Company. With more than three decades of experience in vacation ownership and luxury real estate, John oversees the company’s integrated sales and marketing strategy across its portfolio of luxury residence clubs, private residences, and resort communities.
John shares his perspective on building enduring brands, creating meaningful customer journeys, developing high-performing teams and bringing sales and marketing together to support the continued growth of Timbers.
Q: Can you share an overview of your role as Chief Sales & Marketing Officer at Timbers Company?
A: My responsibilities include leading our sales and marketing strategies across the Timbers portfolio, working closely with executive leadership and our property teams to drive awareness, generate demand and connect prospective Owners with the Timbers experience. Bringing sales and marketing together allows us to think about the customer journey more holistically—from the first time someone encounters the Timbers brand through their conversations with our sales teams and, ultimately, their experience as an Owner. Every touchpoint should feel connected, intentional, and reflective of the level of service they can expect from Timbers.
Q: How has your career shaped your approach to luxury real estate sales and marketing?
A: Before joining Timbers, I spent five years with Hilton Grand Vacations and then 27 years with Marriott Vacations Worldwide, working across vacation ownership, fractional ownership, and whole ownership products. My experience also included leading sales and marketing efforts for The Ritz-Carlton Club & Residences for 7 years as well as international leadership in London where I led fractional sales for a fractional project in Mayfair. Working across different brands, markets and ownership models taught me that successful marketing and sales begin with understanding the customer. You need to know what motivates them, what they value and what creates an emotional connection to a destination or brand. Marketing helps establish that connection and sales deepens it through personal relationships and thoughtful guidance.
Q: What makes the Timbers brand and ownership experience distinctive?
A: Timbers combines extraordinary destinations and residences with a highly personalized approach to hospitality and ownership. But what makes the brand truly special goes beyond the physical product. It’s the relationships Owners build, the familiarity of returning to a place that feels like home and the traditions families create over time. From a marketing perspective, our opportunity is to tell that story authentically and help people envision themselves within it. From a sales point of view, it’s about taking that initial connection and understanding what it means for each individual family. When we do both well, we’re not simply marketing real estate—we’re introducing people to a lifestyle and community they can become part of for generations.
Q: How do you see sales and marketing working together to drive growth?
A: The strongest organizations don’t treat sales and marketing as separate functions. Marketing creates awareness, builds brand equity and generates qualified demand. The sales function brings insight into what prospective Owners are seeking, responding to that need and earning their trust to join the Timbers family. That feedback loop is incredibly important. The more effectively we share data and insights across the two disciplines, the better we can refine our messaging, target the right audiences, and create more relevant experiences throughout the customer journey. Ultimately, both teams are working toward the same goal: connecting the right people with the Timbers brand and building relationships that last.
Q: You describe the business as both an art and a science. How do you balance the two?
A: The science comes from data. We look at performance across the marketing funnel—how audiences are engaging with our messaging, where leads are coming from, how prospects are progressing and where opportunities exist to improve conversion. Those insights allow us to make smarter decisions about where we invest and how we communicate. The art is understanding why someone connects with Timbers in the first place. Luxury real estate is an emotional and highly considered purchase. Data can tell us a great deal about behavior, but it can’t replace a thoughtful conversation or the ability to understand what a family truly values. The most effective sales and marketing strategies bring both together.
Q: What is your approach to building high-performing teams?
A: Teams perform best when they understand the strategy, have clear expectations and are empowered with the tools and information they need to succeed. My role is to establish that direction, support their development and create an environment where people can challenge ideas, share insights and continually improve. Alignment is particularly important across sales, marketing and operations. The customer doesn’t experience those as separate departments—they experience Timbers as one brand. When our teams are connected around the same story, goals and understanding of the customer, we can deliver a much more consistent and compelling experience.
Q: Your guiding principle is “Be Authentic.” What does that mean in practice?
A: It means being genuine in how we communicate, following through on our commitments and making sure the experience we promise is the experience we deliver. That applies to both our marketing and our personal interactions. Luxury consumers are incredibly discerning, and authenticity matters. Our storytelling should reflect who Timbers genuinely is, and our conversations with prospective Owners should be grounded in understanding what is right for them. Ultimately, we’re building relationships, not simply completing transactions. That relationship begins with the first impression of the brand and continues long after someone becomes an Owner.