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Our Team.
At SmartStay Coaching, we’re a team of experienced short-term rental experts dedicated to helping homeowners succeed in the vacation rental space. As investors and operators, we bring real-world expertise, proven strategies, and hands-on guidance to help you maximize revenue and streamline operations. Meet the team behind SmartStay Coaching—your partners in building a profitable rental business!
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Since 2016, Jason has had the privilege of hosting memorable guest experiences for thousands of travelers, including their furry companions, in beautiful and comfortable vacation rentals.
He's one of the very few
30x Airbnb Superhost and
28x Vrbo Premier Host!
Originally from just north of
New York City, Jason has called Boston and its surroundings home for 20 years, he brings a profound understanding of the region's unique spirit and allure.
Kory is the founder of 603 BnB, a vacation rental management company that works exclusively with New Hampshire homeowners to maximize revenue through AirBnB & VRBO.
Kory is 4-time AirBnB Superhost and VRBO Premier Host, and leverages his 10+ years of experience working in technology & data to help homeowners optimize their performance & processes to ensure a seamless guest experience.
Rachel and Alex are the founders of Shore Way Management, a premier vacation rental management company on Boston’s North Shore. Since 2022, they have grown their management portfolio to over 40 properties and have been recognized by AirDNA as one of the top management companies in the Boston market.
In addition to managing rentals, Rachel and Alex own an 10-unit boutique hotel, combining their expertise as both investors and managers.