Over 30 Years of Luxury Travel Expertise
As the recent Executive Director and Head of Brand Culture for Chase Travel Group, she is recognized for her leadership in luxury mindset development, generational readiness, and serving ultra-high-net-worth travelers. Her strategic vision and deep understanding of luxury client psychology have earned industry recognition and positioned her as a trusted travel industry expert for leading hospitality brands, including Travel+Leisure, Celebrity Cruises, and Rosewood Hotels & Resorts.
A YPO member who understands luxury clientele intimately, Kimberly’s thought leadership in inclusive hospitality ensures extraordinary transformation for her clients. Her philosophy of leading with curiosity rather than assumptions has reshaped how luxury travel brands approach everything from service delivery to multigenerational family travel. Whether working with family offices, luxury travel brands, or multigenerational businesses, Kimberly’s approach centers on one transformative question: “Why?” — the gateway to creating organizational cultures that not only meet expectations but change lives.
When not working or traveling, Kimberly loves spending time with her husband, two adult children, and their Bernadoodle, Tusker (named after the Kenyan beer). She is passionate about volunteering and creating a world that embraces kindness, grace, and non-judgment. She attempts to lead by example in all aspects of her life. Her philosophy: lead with an open heart and mind, and let transformation begin with “Why?”
Kimberly’s Why
“i okay”
Two simple words from my three-year-old changed how I think about leadership forever.
As our family explored the world together, I watched Ash’s little legs struggle with steps too tall for their stride. But instead of asking for help, they’d dust themselves off and declare with fierce determination: “i okay.” That phrase became our family mantra—not because everything was always okay, but because it reminded us, we could move forward with courage and curiosity, even when the path seemed impossible. After 30 years in luxury travel and brand leadership, I realized most organizations face the same challenge: they are trying to navigate steps that are not designed for them. Generational workforce shifts. Evolving consumer expectations. The demand for authentic inclusion. But instead of pausing to understand these new realities, they default to old solutions and quick fixes. The hospitality industry taught me that extraordinary experiences begin with deep listening – understanding what someone truly needs, often before they realize it themselves. Yet I watched companies implement diversity programs without understanding inclusion, mandate new policies without asking why their current culture are not connecting, and rush toward solutions for problems they had not fully grasped.
That is when this question began haunting me:
What legacy are you building with the questions you are not asking?
Why We Exist
The most powerful leadership transformations begin with “Why?” Keep Wondering Why (KWW Inc.) exists because the leaders who will shape the next decade aren’t those clinging to what worked yesterday. They are the ones brave enough to wonder why their current approach is not enough, and curious enough to build something better.
As the first thought-leadership consultancy to combine 30+ years of luxury travel and hospitality expertise with authentic generational and LGBTQ+ perspectives, we empower luxury brands, executives, and family businesses to achieve sustainable competitive advantages through generational readiness, a luxury mindset, and inclusive leadership.
We don’t just provide answers—we cultivate curiosity-driven cultures where “Why?” becomes your greatest strategic asset for enduring success.