Our Team

Scott Williams

Vice President, Brand & Creative

Scott is responsible for enterprise-wide brand architecture and positioning, development and marketing and communication initiatives and experience design. He was the Chief Marketing Officer of Morgans Hotel Group and Chief Creative Officer at both Starwood and Commune Hotels & Resorts. Prior to hospitality he worked in television at CBS, ESPN and HBO.

He is a member of the Academy of Television Arts & Sciences and serves on the programming committee at the Harvard Club New York. He received a BA from the University of Washington, a MFA from the American Conservatory Theater in San Francisco and a GMP from Harvard Business School.

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Shira Wilkofsky

Marketing Performance Manager

Shira was born and raised in Brooklyn, New York. She moved to Great Barrington in 2017 to escape the hustle and bustle of NYC life. As Marketing Performance Manager, she is responsible for the day-to-day implementation of hotel marketing and other performance-related initiatives across Main Street properties. In this role, she serves as the primary hub and clearinghouse for communicating and coordinating between properties and agency partners. She brings to the table more than a decade of Food & Beverage experience, having held every role from host and busser to server and Front of House Management. Prior to stepping into her current position, she served for three years as Restaurant Manager for The Red Lion Inn dining room and oversaw all of the hotel’s dining outlets.

Shira’s favorite destination will always be a sunny, sandy beach with a lounge chair, a great book and time with family.

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Rebecca Weinman

Corporate Operations Manager

Rebecca is a native of the Berkshires. As Corporate Operations Manager for Main Street Hospitality, she is the Swiss Army knife of the central office. Her role spans everything from executive support and project management to SaaS & IT Program Manager. She brings a diverse background to a career built around being a master of problem solving. After growing up in restaurants and earning a college degree in painting, she entered the museum field, accepting a job at The Clark Art Institute that ultimately led her to a job as Community Affairs Coordinator with Nancy Fitzpatrick, owner of Red Lion Inn and co-founder of Main Street Hospitality. In that role, Rebecca worked with leading cultural organizations from the Boston Symphony Orchestra and Norman Rockwell Museum to MASS MoCA and state and regional Economic Development Organizations. Prior to joining Main Street, she founded Blackford Studios, an independent Marketing and Event Services company with a focus on serving the arts, nonprofit and wellness sectors.

Rebecca is an avid solo traveler who has visited 39 of the 50 US states, and over a dozen countries. She loves exploring new places and off-the-beaten-path destinations.

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Jon Sterrett

Director of Culinary Services & Executive Chef, Red Lion Inn

Jon is responsible for culinary operations at The Red Lion Inn where he oversees all F&B Dining outlets including the Main Dining Room, Widow Bingham’s Tavern, the Courtyard (seasonal) and the Lion’s Den, a prohibition era speakeasy. As Director of Culinary Services, he provides support to the MSH leadership team to shape the Food & Beverage concepts, culinary processes, and the performance of our existing and future hotel properties.

Originally from Pittsburgh, Chef Sterrett got his start flipping burgers at McDonald’s and worked his way up through the ranks, becoming Executive Chef at Nordstrom Marketplace Cafe before moving on to the Fairmont Pittsburgh. He became Sous Chef at the award-winning Superior Motors restaurant followed by Head Chef at Senti Restaurant and Wine Bar and Executive Chef at or, The Whale in the Distrikt Hotel. He’s had the pleasure of working alongside Chefs from all over the world, exposing him to a variety of cooking styles and ultimately shaping his culinary ethos and team-oriented mentality.

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Brian Smith

Regional Director of Operations

As Regional Director of Operations, Brian manages the overall operations of a dedicated group of Main Street Hospitality hotels and restaurants, continuously optimizing performance while staying true to the brand’s core values. His aim is to support the strategic and operational vision, while empowering teams to elevate Main Street’s commitment to authenticity.

Brian brings previous management experience with Kimpton Nine Zero Boston, Hilton, and Hyatt Hotels & Resorts.

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Lindsey Slater

Assistant Director of Finance

Lindsey is from the Berkshires, where she has lived for most of her life. She brings a background in banking to her role with Main Street, drawing on experience gained from a range of positions starting from customer service and extending to senior branch operation assistant. As an Assistant Director of finance for Main Street Hospitality and Hammetts Hotel, she focuses on Treasury (cash) and generating monthly accounting statements.

Lindsey’s favorite places are at home baking with her kids, or reading a good book while camping with her family.

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John Siddall

General Manager, Port Cunnington Lodge

John Siddall brings more than three decades of knowledge acquired in the Club & Hospitality Industry to his role as General Manager of Port Cunnington Lodge. He has held senior management roles for numerous golf and country clubs, as well as with Georgian College, Muskoka Lakes Navigation & Hotel Company, and McMichael Canadian Collection Art Gallery. With a personal focus on Service Excellence, John brings an eye for detail, passion for Food & Beverage and a hands-on management style to his role, with a dedication to mentoring employees and inspiring his teams to exceed expectations.

John enjoys participating in fundraising for local hospitals and his communities’ worthy causes.

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Katie Myers

Accounts Payable Specialist

Katie is from Stephentown, NY, in Rensselaer County. Before moving into her current role, she worked as a Reservations Manager and Rooms Director at The Red Lion Inn, and as General Manager of The Seven Hills Inn in Lenox, MA.

Her favorite place is Keen Valley, NY, where she loves to hike the high peaks of the Adirondacks.

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Benjamin Moulton

Assistant Director of Finance

Benjamin hails Haverhill, MA. He began his hospitality career working in food and beverage at country clubs before transitioning to Auberge Resorts Collection. There, he worked on the accounting team for three luxury hotels in New England and managed the financial operations of opening a 140-acre resort in New York. He currently oversees property accountants and onboards all new hotels for Main Street Hospitality.

Benjamin’s favorite place is anywhere in the Pacific Northwest – in particular the Oregon coast, and the Redwoods in California.

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Randi Milewski

General Manager, Hammetts Hotel

Randi is from Rhode Island. She brings an entrepreneurial approach to her role as General Manager of Hammetts Hotel, drawing on experience in the operations of both independent properties and brands to build a solid foundation for the creation of standards and procedures.

Her favorite place in the world is anywhere where she is with her family.

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Rebecca Lilley

Human Resources Generalist

Rebecca hails from the town of Lee, MA, in the Berkshires. Prior to joining Main Street as an HR Generalist for Red Lion Inn, she served as General Manager of a small boutique inn in Lenox.

Her favorite places are the cities of York and Edinburgh in the U.K.

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Mel Karakaya

General Manager, The Porches Inn

Born and raised in Turkey, Mel has worked in the hospitality industry since 1994, with experience across a variety of operations roles both internationally and domestically. Prior to joining The Porches Inn as General Manager, she worked as Senior Guest Services Manager at The Breakers Palm Beach.

Her favorite places in the world are the galleries of MASS MoCA and the Clark Art Institute, and the Turkish cities of Istanbul and Antalya.

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Rhonda Hastings

Innkeeper, The Briarcliff Motel

From hosting breakfasts and firepit nights under the stars to impromptu lobby gatherings, Rhonda loves getting to make memories with guests that become friends (and the dogs of Briarcliff, of course). With a background as an Executive Housekeeper and Concierge, she brings a deep understanding of how to deliver the highest level of service to Main Street’s embedded culture of hospitality.

Rhonda loves traveling around the world, but her favorite destination is Cabo San Lucas Mexico. From Playa del Amor to El Arco, she loves the beaches and turquoise water of the Sea of Cortez – and the fresh seafood. Fish tacos please!

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John Harrison, CMP

Regional Director of Sales

John is from Narragansett, Rhode Island. With more than 25 years of leadership in sales and marketing for the hospitality industry, he has managed sales for some of the most prestigious luxury hotels in the Four Seasons Hotels and Resorts portfolio and led multi-property sales for Salamander Hotels & Resorts. He also has experience within the Historic Hotels of America network, founded by the National Trust for Historic Preservation. John is a Certified Meeting Professional and Notary Public.

His favorite place in the world is Tuscany, Italy.

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Elena Dwyer

Brand Director

Elena splits her time between New York City and Connecticut. Before joining Main Street Hospitality as Brand Director, she worked on the ad agency side for 25 years across a variety of clients including P&G, J&J, Visa, L’Oreal, Pernod Ricard and others.

Her favorite place is the Delta Sky Lounge, because if she is there it means she is about to embark on adventure.

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Andres Gutierrez

Area Director of Revenue Management

Andres hails from Houston, TX. Before joining Main Street Hospitality, he worked with a variety of branded and independent multi-property resorts, from Omni Hotels & Resorts and Nemacolin to The Biltmore Company.

His favorite place in the world is the Linville Gorge Wilderness in Pisgah National Forest, located in Western North Carolina’s Appalachian Mountains.

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Beth Diskin

Assistant Director of Finance

Beth is originally from Spokane, WA. She brings a degree in Business Administration and more than 35 years in the hospitality industry, from restaurant and hotel operations to accounting, to her role as Assistant Director of Finance for The Red Lion Inn, The Porches Inn, Briarcliff Motel and Fitzpatrick Retail & Realty Co.

Her favorite place in the world is Belgium.

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Simon Dewar

General Manager, The Red Lion Inn

Simon hails from the UK, where he served for 17 years in the British Army before transitioning into the hospitality industry. An experienced General Manager with a passion for leading high performing teams and boosting organizational revenues, he brings a range of expertise to his role. He is a graduate with high honors of Connecticut Culinary Institute and the co-founder of Charlotte Julienne, a food and lifestyle store.

Simon has previously served as General Manager for Relais & Chateåux’s Blantyre and Weekapaug Inn; The Lake House on Canandaigua Lake; and the Chatwal Lodge in the Catskills.

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Terry Coughlin

Hospitality Leadership Coach

Terry has been involved in hospitality since his very first job at age 16. He worked in various restaurants throughout high school and college, but truly recognized his love for the industry when he was hired as a waiter at Danny Meyer’s Gramercy Tavern. He spent more than two decades working for Danny’s Union Square Hospitality Group, ultimately earning the title of Managing Partner and Director of Operations; helping to conceptualize and open four restaurants, overseeing seven different businesses and mentoring dozens of young leaders.

Terry lives with his family in Great Barrington, MA, where they own and operate Granville House, a five-guest room Bed & Breakfast. He continues to share his passion for all things service related as a hospitality leadership coach.

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Jennifer Curtin

General Manager, The Beatrice Hotel

Jennifer is from Ashland, MA. She holds a bachelor’s degree in Hotel Management from Johnson & Wales University, with a minor in Eco & Nature Based Tourism. She launched her career with Kimpton Hotels, joining their Manager in Training program and working in Boston and Aspen. Prior to joining The Beatrice, she worked for Destination Hotels as Assistant General Manager of Woodmark Hotel & Still Spa in Seattle.

Jennifer’s favorite places are the beach in the summer, and the mountains in the winter. She loves a good beach day relaxing in the sun, or cruising mountains on her snowboard.

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Cate Colombo

General Manager, Chebeague Island Inn

Cate is an experienced Luxury Boutique Hotel Manager with more than two decades in the hospitality industry. Prior to coming to Chebeague Island Inn, she served as General Manager at The Hartstone Inn & Spa in Camden, Maine. She brings skills in sales, food & beverage, luxury goods, front office, and operations management to her role, with a focus on creating and maintaining a vibrant work culture.

Cate believes in the art of making every guest feel like a valued friend, and in embracing the employees, vendors and purveyors who are at the heart of hospitality culture.

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Carla Child

Director of Project Management

Carla hails from The Bluegrass State of Kentucky. With a background in entertainment catering, she brings people skills, creative thinking and problem solving skills to her role as Director of Project Management, along with a “can do, let’s do” attitude!

Her favorite places in the world are New York’s theatres & museums. In the last few years, she has come to love the natural beauty of Alaska.

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Tyler Carroll

General Manager, Hotel Downstreet

Tyler is from Taunton, MA. He brings more than a decade of experience in working at hotels across the Boston and Newport regions to his new role as General Manager of Hotel Downstreet.

His favorite place in the world is the Cape Cod National Seashore.

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Bonnie Bonn-Buffoni

Bonnie Bonn-Buffoni

Bonnie currently lives in West Stockbridge, MA. She has more than a decade of experience in the banking industry, and more than 18 years of experience in payroll & bookkeeping for firms ranging from construction and civil engineering to social welfare and financial law.

Outside of work, Bonnie’s life revolves around her five boys and their activities. She has coached soccer, basketball and baseball and sat on the board of directors for the Great Barrington Little League and Housatonic Youth Basketball League. She is a longtime Treasurer of the Stockbridge Sportsmen’s Club and has supported many booster clubs throughout the years for youth and high school sports teams. She is currently a member of the Berkshire Hills Regional School District’s school committee, and their finance and superintendent evaluation subcommittees.

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Mario Arakelian

General Manager, Canoe Place Inn & Cottages

Mario was born in Cyprus to an Armenian father and a Greek-Cypriot mother. He began his hospitality career with Four Seasons Hotels & Resorts, serving for a decade in various Rooms Division Management roles before making the transition to manage an upscale Mediterranean restaurant in Manhattan. Before coming to Canoe Place, he served for several years as General Manager of Hamptons Hotel.

The Parthenon in Athens, with its timeless beauty, is one of Mario’s favorite places in the world.

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Jennifer Usaty

Vice President, Finance

Jennifer is responsible for all financial operations and related matters. This includes hands-on financial leadership to further develop the organization by providing best-in-class accounting, financial reporting, treasury operations, short and medium range budgeting and forecasting, and new business development in partnership with hotel properties’ leadership and owners. Jennifer, who served as the Regional Director of Finance at Auberge Resorts. is a seasoned hospitality professional with a proven track record of success and growth in the Luxury Boutique sector.

During her free time, you can find Jennifer hiking, gardening, boating, surfing, or anything outdoor related. She strives every day to be a strong female role model for her three sons who she absolutely adores.

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Suzi Darre

Vice President, Human Resources

As Vice President of Human Resources, Suzi’s role is to bring Main Street’s purpose to life as it scales, overseeing its dynamic portfolio. She draws on extensive experience in human resource leadership, having served as director of talent across 11 states and notable hospitality names including The Carlyle, a Rosewood hotel; The Surrey, a Relais & Chateaux hotel; and the Auberge Resorts Collection.

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Joe Gallo

President

Joe leads strategic growth initiatives, development projects, strategic capital and acquisitions, financial relationships and investor development.  He is also responsible for Main Street’s corporate operations, administration, human resources and IT.  He brings 30+ years of finance and management expertise to his role. As Managing Director in Citigroup’s Investment Bank in New York, Milan Italy, and Boston, as well as other CFO and executive roles, Joe has worked with numerous lodging companies such as Marriott, Hilton, Starwood, Wyndham, Doubletree and Meristar.

Joe holds degrees from Brown University and NYU School of Law and is Chairman of the Board of Dorrance Dance Company. He hikes, skis and road trips in his free time in Tyringham, MA where he lives with his wife Ann.

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Greta Kipp

Chief Operating Officer

Greta is responsible for optimizing performance for all Main Street in areas such as business intelligence, pricing/distribution strategies, asset management, financial reporting/budgeting and business planning. She is a US Army veteran and following her service and university studies she began a hotel management career in leading independent hotels, including Topnotch Resort in Stowe and The Williams Inn at Williams College.

Greta serves on the boards of New England Inns & Resorts and the Turner House Living Center for Veterans. She partakes in dog-friendly travel, checking out up-and-coming nano breweries and exploring backroads and off-road.

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Sarah Eustis

Chief Executive Officer

Sarah Eustis founded Main Street Hospitality in 2014 with a vision that leverages three generations of family hospitality leadership. Now at the forefront of the independent hospitality landscape, Sarah evolved Main Street into an expanding collection of properties through her commitment to stewarding a meaningful and memorable guest experience, unique to each destination and hotel. Her hospitality career began at fourteen in the housekeeping department at the Red Lion Inn in Stockbridge, MA, which has been in her family for over 50 years.

Following a prosperous 20-year career rising to the role of designer, merchandiser, and brand developer for world renowned brands such as Ralph Lauren, Gap Inc., Limited Brands, and Etam in Paris, Sarah returned to the Berkshires to carry on her family business. With properties ranging from new builds to landmark establishments, Main Street now owns and operates five properties in The Berkshires, two in Rhode Island, and maintains a growing pipeline of projects in one-of-a-kind destinations throughout the Northeast. A passionate leader, Sarah pioneers the organization with a continued commitment to community and an approach to hospitality that focuses on connecting people in meaningful ways.

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