Who We Are



We are a small start-up with lively and diverse backgrounds. Our operations are out of Lake Geneva, WI and Dallas, TX. What binds us together is our love of travel and not just any travel but the experience of vacationing at a rental home. We believe that essentials like groceries and home products should be a commodity of convenience. By taking the stress out of where to find coffee, not having to pack a large bottle of sunscreen or diapers our mission is to empower travelers to focus on what their vacation is really about. Immersive experiences shared connections with loved ones and time for adventure are just a few of the things we hope you’ll have more time to do.



Meet the Tailored Stay Team

Kristin Fitzgerald - Founder and President

Kristin Fitzgerald possesses a background in business development, digital marketing, and e-commerce web development. Having worked with multiple brands in hospitality she has a passion for serving the guest elevated travel experiences. As a Mother of three, who is used to being on the go, Kristin embraces the chaos and the continuous learning that comes with wearing multiple hats. A city girl at heart, she loves to travel to places like Paris and NYC but she can just as easily rest her feet on a lakeside dock in Northern WI.

Tera Bennett - Founder and Brand Officer

For Tera Bennett, it rings true that ‘the key to success is customer service and building personal relationships’. Tailored Stay originated from an arrival experience she found lacking at a vacation rental stay. As a certified Esthetician, Tera has built up a loyal clientele base and has managed an upscale salon. She often speaks to her clients about their travel and gains insights into the products and branding of Tailored Stay. Tera has an eye for beauty but don’t let that fool you. You may find her out ‘mudding’ with her husband and two dogs.

Stephen Fitzgerald - Finance/Ops Guy

Stephen Fitzgerald has spent the last few decades driving growth for multiple consumer and hospitality brands. He’s been involved in leadership for sites like Travelocity and Hotwire, hotel connectivity platforms and large hotel brands. Stephen’s linear thinking and ability to always be calm under pressure helps balance the passion of other team members, most notably his wife, Kristin. Stephen heads up the finances for Tailored Stay and lends a hand anywhere it’s needed. His favorite places to travel include London and Hong Kong.

Nicholas Armstrong - Everything IT

Nicholas Armstrong comes to Tailored Stay with over twenty years as an IT professional. His experience with grocery e-commerce, large databases and programming are essential to the inner workings of Tailored Stay. While Nick speaks the language of tables and SQL, he can also recant in vivid detail the battle of Hastings, key events in the Roman Empire, and well, all of history really. When Nick travels he is looking for adventure and physical exertion whether that means scuba diving off the coast of Barbados or slaloming down the white slopes of Vail.

Anna Arrow - PR & Communication

Anna Arrow has experience in both the entertainment and hospitality industries. She’s schooled in Hollywood style event production, having spent a decade in Los Angeles and Beverly Hills. As one of the most traveled members of the team, Anna’s wanderlust has taken her as far as Thailand and the United Kingdom culminating a wide world view and a strong standard of customer service. Anna focuses mostly on the guest experience.  Having stayed at dozens of rental homes herself, Anna understands exactly what Tailored Stay guests need.

Mark Dominic Grosso - Defender of the 'Law Signal'

Mark Dominic Grosso is a general practice attorney who has handled cases from criminal defense to civil litigation in TX for nearly ten years. Prior to that, Mark was a Sr. Marketing Manager at a major telecommunications company. Inspired by comic book heroes of his youth, Mark embraces ‘The Law Signal’ providing equal justice to clients who sometimes may not have the means for costly representation. A true people person, Mark looks to Tailored Stay as a way to be part of celebrations and the best times of people’s lives.

Cecilia Cuff Hospitality Director

Cecilia Cuff has devoted her career to service, creating next-level consumer experiences for brands such as NCAA, Frito Lay, B Corp, Essence Festival and Captain Morgan as well as curating high-end private events for a wide range of clients. She’s done everything from overseeing culinary experiences for Emeril Lagasse to production and hospitality for Sheryl Crow, Brad Pitt and Angelina Jolie, Rihanna and many more.

Cecilia’s breadth of experience includes the development of brands all over the United States and beyond, including The Grand Lux & Gin Bucks in Chicago, Hyatt Hotels in Lake Tahoe, Curacao, Miami, and New Orleans and most recently, Taos Ski Valley.

When not buried in a spreadsheet, Cecilia can be found running her multidisciplinary art space for underrepresented artists, Parse Seco, or surfing!

Pat Parker - Website Lead IT

Pat keeps things going. She has been in the IT business for the last 25-years, dedicating the last 12 years  to WordPress sites, specifically Woocommerce, E-Learning, Membership sites, plus building custom coded solutions.

When not at her computer, Pat can be found on the trails in the White Mountains with her dogs, Cinnie and Ollie!

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