Annie Roberts is the Senior Vice President of Owner Services at Travel + Leisure Co., where she leads the product development, owner onboarding, call center, and club management teams.  

Annie started her career in timeshare in 2003, when she was brought on as a temporary worker for contract filing at Trendwest, which was acquired by WorldMark by Wyndham, in Seattle. “I was a political science major, so vacation ownership was not something I knew a lot about initially,” said Annie. “I did know that everyone in the Seattle area knew about Trendwest, and almost everyone knew someone who owned with them,” said Annie.

While her first venture into timeshare might have been unplanned, Annie quickly discovered that the industry and the enthusiastic team at Trendwest were exactly the right fit for her career. “I have always been passionate about leadership,” she said. “It started in high school when I became senior class president and then in college when I was the student body vice president. When I got the job at Trendwest I thought, ‘I can really see myself as a leader here, so I’m going to learn more about this company and this industry and go for it.’”  Over 21 years later, Annie is still in the timeshare industry, and has since transitioned to work across the enterprise at Travel + Leisure Co.  

Annie eventually joined the consumer finance team, where she learned valuable lessons about the owner journey. After relocating with the company to Orlando in 2007, she moved through various departments, learning how all areas of the business work in tandem to create a positive owner experience. That cross-functional understanding led to Annie assuming the role that she has now, which connects resort operations and customer service.  

“One of the things I love about the timeshare industry is the unique career path it provides,” Annie said. “In the last 21 years, I’ve worked in finance, marketing, sales, process improvement, customer service, and new product development. There are so many opportunities to expand and improve your career. Especially at Travel + Leisure, if you raise your hand and volunteer for something new, we will find a way to help you and make you successful. There aren’t too many companies out there that give you that many options.”      

Another reason Annie has stayed in the timeshare industry for more than two decades is her commitment to putting owners on vacation. “Every time an owner makes the decision to buy a timeshare, they’re investing in their family,” said Annie. “I try to remind our customer-facing teams that every interaction with an owner is a chance for us to invest in their family, too. That is a really good reason to get up and go to work every morning.”

When it comes to offering advice to team members who are newer to the industry, Annie says that having patience with yourself is the first key to success. “Traditionally, new employees are put on a 90-day plan, but timeshare is tough to learn,” she adds. “Still set your 30, 60, and 90-day goals, but understand that in your first six – nine months, you will learn something new daily. I still had those learning moments when I took over customer service in 2019, even after years in the industry. So, stay humble and keep an open mind to figure out all the nuances.”

Annie also has advice for young women joining the industry in particular: “Say yes to things. This organization and the broader industry want to help you. Look for peers to connect with to grow and learn together. There is more than one available seat at the table for women. “

Outside of work, Annie enjoys traveling with her two children. “I was born in Santa Barbara, so anything that takes me back to Southern California is at the top of my travel list,” Annie said. “Luckily, Travel + Leisure Co. has an amazing portfolio of properties in San Diego. I try to go as often as I can!”

Another top travel destination for Annie is Hawaii. “My kids fell in love with the islands when we went a few years ago,” she said. “They are my favorite travel buddies. It’s amazing watching them experience new cultures and realize there’s not just one way of living. Vacation breaks down so many barriers in that way.”

No matter where her travels take her, Annie appreciates the experience her family has every time they stay at one of Travel + Leisure Co.’s resorts. “Timeshare is such a great way to travel as a family,” said Annie. “Having the added space and the ability to do things like cook a meal in our suite makes such a difference. Now, when we go anywhere, my kids are like, ‘Where’s my own private room?’ Timeshare has given us so many fantastic and unique memories.”