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Our “Male Ally of the Month” column focuses on the men going out of their way to support women in the hospitality industry. While we all know they don’t have to help, these guys want to help, and this column takes the time to find out how and why they are determined to help us reach gender equality.
Matthew Upchurch is the founder and CEO of Virtuoso®, the world’s leading luxury travel agency network. Since launching Virtuoso in 1986, Matthew has transformed it into a global powerhouse with over 1,200 travel agency locations, 20,000 advisors in 58 countries, and $35 billion in annual sales. Known for its exclusive relationships with the world’s best hotels, cruise lines, airlines, and tour companies, Virtuoso has redefined what it means to deliver luxury travel.
This month, we’re celebrating Matthew as our Male Ally of the Month—Mr. January—for commissioning the amazing Generations of Impact, a powerful video series honoring and interviewing the women who shaped the travel advising profession. These stories showcase resilience, entrepreneurial brilliance, and the experiences of trailblazing matriarchs who built multi-million-dollar businesses. Their wisdom and leadership continue to shape the future of travel—and their insights are as inspiring as they are game-changing.
Matthew chats with us about the impetus behind Generations of Impact, the lessons he’s learned from women leaders, how their vision, ingenuity, and grit have shaped the travel advisory business as we know it today—and what the future of luxury travel looks like as women are set to take control of $30 trillion in the Great Wealth Transfer.
What inspired the creation of the Generations of Impact video series?
It was a long time coming. My only disappointment is I didn’t do it sooner! The idea originated during an event in Fort Worth focused on smaller, boutique agencies. I heard five different origin stories in quick succession, and they all had a similar theme: these women were often dismissed in their roles as they supported their husbands’ careers.
Back then, if a woman started a travel agency, it was often thought of as a “cute little hobby.” But decades later, these same women became the stars of the industry. These women faced barriers, carved their own paths, and built something extraordinary. Their stories are remarkable, and I felt a responsibility to preserve and share their legacy, not just for what they accomplished but for the lessons in resilience and entrepreneurship they can teach future generations.
I really hope everyone takes the time to watch. The amazing ladies we spoke with include:
Nancy Strong – Strong Travel Services
Mary Ann Ramsey – Betty Maclean Travel
Phoebe Weinberg – Greatways Travel
Valerie Wilson – Valerie Wilson Travel
Cher Roscoe – Travelcall
Ange Wallace – Wallace Pierson Travel
Ruth Turpin – Cruises Etc
What made this even more special is that my daughter, Evan, produced the series. She handled the interviews, coordinated with the video team, and reached out to these women personally. Hearing how quickly they responded to her requests just filled my heart. It was incredibly meaningful for me to see my daughter take on such a personal role in celebrating the women who’ve been such an important part of Virtuoso’s history.
What lessons have you learned from the women of Virtuoso over the years?
The women who mentored me taught me the importance of purpose-driven work, community, and creating a meaningful legacy. They had an intuitive leadership style that balanced toughness with empathy, and they were often more willing to mentor and collaborate.
One of my favorite definitions of leadership is the ability to inspire people to set aside some self-interest to achieve something greater together. These women exemplified that, and their resilience and creativity continue to influence how I approach leadership.
How has the travel advising profession evolved, especially for women?
Fast forward to today, and travel advising has transformed into a true profession, driven by expertise, creativity, and relationship-building. In the past, travel agents were essentially biological user interfaces for airline reservation systems, navigating complex platforms introduced in the 1970s. But as technology evolved and self-service platforms replaced those tasks, the profession shifted to one of delivering advice, building relationships, and crafting meaningful experiences.
Many early travel advisors were educators—teachers, administrators, or professors—who brought a natural curiosity and a passion for learning and helping others. Those skills translated beautifully into the advisory role, and that foundation has only grown stronger as the profession has evolved. Today’s travel advisors are more like trusted wealth managers. They’re not just booking trips; they’re delivering highly personalized, transformative experiences.
Women have been at the forefront of this evolution, using their strengths in networking, connection, and creativity to redefine the role of a travel advisor. Their resilience and entrepreneurial spirit have elevated the industry into one that is respected and thriving.
Why do you think women are still underrepresented in hotel leadership roles?
One reason is the historical bias toward finance and operations roles as pathways to leadership. Many women in our industry have traditionally been funneled into marketing or sales roles, which aren’t as commonly seen as stepping stones to CEO positions.
That said, things are changing. We’re seeing more women in top leadership roles. Barbara Muckermann is now the CEO of Kempinski Hotels, Andrea DeMarco leads Regent Seven Seas Cruises, Anna Nash is the President of Explora Journeys, and Cristina Levis is the CEO of A&K Travel Group, which includes Abercrombie & Kent and Crystal Cruises.
The entrepreneurial spirit among women is also incredibly strong. If the traditional pathways aren’t accessible, women will create their own.
Looking ahead, women are set to control an increasing share of global wealth. How do you see this impacting luxury travel?
This is such an important trend. When I started working with Ken Dychtwald in the late 1990s, one of the mega-trends he identified within the baby boomer generation was the increasing power of women as the core consumer. Ken, a psychologist, gerontologist, and founder of Age Wave—a company that studies the implications of population aging—has long been a thought leader on how demographic shifts reshape industries. His insights have been invaluable in understanding how this transfer of wealth will reshape consumer behavior.
By 2030, American women are expected to control at least $30 trillion in assets, driven by The Great Wealth Transfer. This massive shift refers to the inheritance of wealth as baby boomers—who currently hold about half of all U.S. wealth—pass their assets on to their spouses or children over the next 20 years. Now, we’re seeing this trend come to fruition in a big way, with women becoming the primary decision-makers for this generational wealth transfer, particularly in estate management.
For the travel industry, it’s critical to deeply understand how women think about spending, what motivates them, and the language that resonates with them. What we’re finding is that emotional connection is key. This goes beyond basic customization—it’s about creating meaningful, personal experiences that make people feel seen, valued, and inspired. As women increasingly control global wealth, this focus on connection and personalization will only grow more important for the luxury travel industry.
What should hoteliers be thinking about to meet the future of luxury travel?
The role of the General Manager (GM) is more important than ever. A truly exceptional GM—someone who excels at both back-office efficiency and front-of-house relationship-building—is invaluable and should be compensated accordingly. However, not every GM will have the skills to do both at a high level.
In those cases, it might make sense to rethink the structure of the GM role and consider splitting it into two positions: one focused on financial operations and the other on relationship-building and guest engagement. Properties that prioritize emotional connection and invest in building strong relationships with their teams and guests are the ones that consistently stand out in a competitive market.
Ultimately, the future of luxury travel lies in creating meaningful experiences for both guests and employees. Hoteliers who embrace innovation, prioritize human connection, and foster inclusive cultures will set the standard for success in the industry.
Thank you, Matthew, for your time and for shining a light on these legendary women, whose stories and advice are truly priceless. Their resilience, ingenuity, and leadership have not only shaped Virtuoso but also the travel advisory profession as a whole. To hear these inspiring matriarchs in their own words, be sure to watch Generations of Impact.