Jan Barrow never set out to become a leader in the timeshare world—but her journey from hospitality’s front lines to the executive team at Lemonjuice Solutions reveals a career defined by grit, vision, and an unwavering commitment to people. Barrow’s steady rise to senior leadership at Lemonjuice Solutions reflects a career built on trust, determination, and adaptability.
In a recent interview with TimeSharing Today, Barrow spoke candidly about her evolution—from bussing tables in Florida to helping legacy resorts reimagine their futures. Along the way, she's become a trusted advocate for owners, a strategic force behind resort transitions, and a voice of integrity in an industry at a crossroads. Her insights offer a rare, behind-the-scenes look into the challenges facing today’s timeshare boards and how strategic solutions are helping reshape the future of vacation ownership.
Rooted in Hospitality, Powered by Purpose
Growing up in the Sunshine State, Barrow absorbed the culture of southern hospitality early on. Waiting tables, cleaning guest rooms, and handling the front desk weren't just jobs. These roles formed the foundation of her lifelong passion for serving people. "I learned a lot about how to treat people," she recalled. "And that never leaves you."
A practical education shaped her early career. Mastering floppy disks and early office software in the 1980s opened the door to administrative roles. But Barrow wasn't content to stay behind the desk. Her professional aspirations would expand far beyond that. As a single mother in her early 30s, she returned to school with determination and purpose, earning a business degree and a minor in psychology from Florida Southern College. She noted with pride that the campus holds the most extensive collection of Frank Lloyd Wright-designed buildings in the United States. Years later, her son would graduate from the same college, a milestone that deepened her connection to the institution and its values.
FlightSafety International and a Pivot to People-Centered Work
Barrow's decade at FlightSafety International—a Berkshire Hathaway-owned aviation training giant—offered her a fast-paced role. Starting as a secretary and rising to become a product marketing manager, Barrow was at the helm for product development, B2B sales, and program coordination. She even learned how to fly. When upward mobility began to mean selling planes instead of solving problems, she knew it was time for a change.
That change came from a newspaper ad and a leap of faith.
Finding Her Calling in Timeshare
That newspaper ad led to an interview with Interval International. Though initially hesitant to take the job, Barrow was drawn to flexibility and the opportunity to earn vacation benefits. She accepted the role of on-site account manager in Marriott’s offices, where she served as a liaison between Interval and the Marriott Vacation Club working directly with owners and troubleshooting service issues.
"Once I got into the timeshare industry, I fell in love with it," she said. "I loved helping people go on vacation, and I loved that no two days were the same."
Barrow climbed quickly, eventually serving as Regional Director for the Southeast. Her work spanned Florida to Texas, Missouri to Virginia. Her accounts included industry giants like Marriott, Disney, and Westgate, as well as respected independent developers like Spinnaker and Kings Creek. Travel was constant—up to 70% of the time—but she thrived on variety and human connections.
Guided by Mentors, Grounded in Values
Barrow’s collaborative approach earned her deep respect from resort developers, many of whom became long-term business partners and friends. Guiding her through the intricacies of the timeshare industry, her mentors equipped her with the expertise and confidence to lead. Many were always willing to answer questions, explain technical details, and provide support.
"My time at Interval was inspiring and energizing—it showed me just how vital our members and timeshare owners are. They weren’t just part of the business; they were the heart of it, the reason we did what we did every day."
A Changing Industry Landscape
The 2008 financial crisis rattled the timeshare landscape. Capital markets froze, consolidation accelerated, and exchange companies began to shrink. Owners struggled with rising fees and fewer options. The traditional model of vacation ownership was under pressure.
Barrow began to explore new opportunities. Interval had acquired Vacation Resorts International (VRI) and Trading Places International (TPI), expanding its footprint into resort management. Barrow transitioned to VRI as Director of Business and Corporate Development, and she learned to approach resort management from a different angle. She deepened her understanding of budgets, reserve funding, and operational oversight—skills that would prove invaluable in the years to come. This experience would prove pivotal, especially when COVID-19 upended everything.
A New Chapter with Lemonjuice
After being furloughed and ultimately laid off during the pandemic, Barrow could have stepped away from the industry. Instead, she stepped into a new chapter. Lemonjuice Solutions founder Alex Krakovsky and SVP Jeff Ingram saw something in her – the empathy of a listener, good instincts, and the resolve of a leader. Those initial conversations led to a series of interviews, including one with Scott MacGregor, Chief Operating Officer, and with Perry Creek Capital, Lemonjuice’s major investors. By January 2021, Barrow had joined the company as Vice President of Development.
Barrow could have stepped away from the industry. Instead, she stepped into a new chapter. "It felt like the early days of Interval," she said. "Creative, fast-paced, full of potential and fun."
Driving Growth, Delivering Value
Barrow quickly set out to lead a brand transformation. While Lemonjuice had earned meaningful recognition for its work with distressed timeshare properties and converting them to wholly owned condominiums, that reputation was too narrow. Barrow helped introduce the “Resorts Reimagined,” a trademarked initiative focused on repositioning properties for long-term sustainability through full conversions, partial repurposing, or strategic management.
Since 2021, Lemonjuice has grown to triple its size. The title department alone boasts more than 40 specialists. The company now manages 17 resorts and is actively reshaping dozens more through its redevelopment program.
Now serving as Senior Vice President of Development, Barrow oversees business development, outreach, and program innovation. Her work bridges legal, financial, and emotional complexities—always with owners in mind.
A Vision for the Future of Legacy Resorts
Today, Lemonjuice provides a full spectrum of services. The company has returned more than $100 million to timeshare owners with much more on the way.
Barrow noted, “Our approach has always been rooted in putting owners first. We never charge owners to get out of their timeshare—we compensate them. Rather than offering one-size-fits-all solutions, we take the time to understand each resort’s unique situation and provide tailored options that reflect the specific needs of the property and its community.”
Her vision for legacy resorts is clear-eyed and compassionate.
"Boards have fiduciary responsibilities,” Barrow said. “And in today’s environment—with rising insurance costs, aging infrastructure, and shrinking owner bases—those responsibilities mean exploring every option."
Barrow's ability to guide communities through difficult decisions with clarity and care makes her a rare force in the industry. “I never thought I’d spend my life in the timeshare industry,” she admitted. “But now, I can’t imagine doing anything else. This work matters. It helps people. It delivers great vacations. It saves communities. And it gives owners the dignity they deserve."
For Jan Barrow, this journey was never about titles or transactions—it's about transformation and creating a future that honors the past and welcomes what comes next.
About Lemonjuice Solutions
Lemonjuice Solutions is a leader in strategic management and reimagination for legacy timeshare resorts. With a team of industry experts and a proven track record, the company offers comprehensive and tailored solutions. To learn more about Lemonjuice’s commitment to preserving the value of timeshare resorts, visit lemonjuice.com or contact Jan at 863-602-8804 for a strategic consultation.