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Our Team

Vaystays is the premier professional vacation rental marketplace, offering beautiful vacation homes in the best destinations across the globe. Every property listed on Vaystays is individually verified by our team and professionally managed, giving you peace of mind. So all you have to do is kick back and enjoy your vacation, stress free.

Wes Smithe


Wes helped launch in the summer of 2009 after earning his Bachelor’s degree in Entrepreneurship from Saint Mary’s University. Following a few years in account management at Leo Burnett and FCB Global, two of the top advertising agencies in Chicago, Wes joined the team full-time as a partner in the spring of 2011, and co-founded Vaystays in 2014.

He has a passion for branding and good web design, and oversees the company’s marketing and sales teams. In his spare time he enjoys travel, live music, and spending time with his wife, dog, and family.

Chad O'Farrell


Chad joined the Vaystays team in June of 2015 as Director of Business Development after working in the Travel industry for a number of years. He graduated from Daniels College of Business at the University of Denver, and spent several years working in the sales & marketing world, most recently as Senior Regional Sales Manager for Groupon Getaways. Chad is responsible for developing strategic relationships for Vaystays and growing the business exponentially.

In his free time, he enjoys woodworking, travel, music and most of all, adventures with his wife and 2 dogs.

Bill Hinderman


Bill is a product leader with a focused experimentation and optimization engineering background and a taste for analytics-driven MVP delivery. He has led engineering efforts within optimization and experimentation at Expedia Inc., Orbitz Worldwide, and Raise Marketplace. The teams he has built are responsible for creating both the framework for, and the mindset around lightweight A/B experimentation within these companies' eCommerce experiences.

Bill is the author of Building Responsive Data Visualization for the Web. In his free time, he runs and mixes cocktails.

Bailey Gordon

Account Executive

Bailey has been an Account Executive at Vaystays since August 2015. Having grown up in Chicago, she decided to haul herself to Southern California in 2013 where she began to enjoy 75 degree weather year round and started grad school at USC. She studied global communication and focused her thesis research on utilizing technology for travel platforms.

In her free time Bailey enjoys yoga, cooking, and playing with other peoples dogs.

Rocco Larose

Account Executive

Rocco joined the Vaystays team in the summer of 2015 as an Account Executive after receiving his degree in International Business with a minor in Italian from Loyola University of Chicago. He was fortunate enough to study abroad in Rome during his time at Loyola which further solidified his love for travel and experiencing of new cultures.

When Rocco isn't at work you can find him trying new restaurants throughout the city, hanging out with his English Bulldog Tank, or getting too emotionally invested in Cleveland sports.