Guest Experience & Operations Specialist

Full Time Brewster, MA (Hybrid up to 3 days in office) $45,000-$60,000

About the Role

We're looking for sharp, motivated people to join our team as full-time Guest Experience & Operations Specialist.

This is a core role. You'll be the connective tissue of our operation: managing guest relationships, keeping reservations running smoothly, and jumping in where ever the business needs you. We're a small, committed team that works hard, communicates clearly, and genuinely enjoys what we do. If that sounds like your kind of environment, keep reading.

Our office is in Brewster - a great place to work if you're on the Cape or South Shore. We have a hybrid schedule, with most of our team working in the office Mondays, Wednesdays, and Fridays. Schedules shift during peak season, and some weekend and holiday availability is expected in the summer.

What You’ll Do

• Own the guest journey from first inquiry through post-stay follow-up -- bookings, communication, in-stay support, and everything in between
• Serve as the primary point of contact for both guests and homeowners, keeping things calm, professional, and moving
• Keep property listings and internal systems accurate and up to date
• Assist with vendor coordination, seasonal staff scheduling, and office logistics as needed
• Participate in the summer on-call rotation and adapt to shifting priorities during peak season
• Fill in wherever the team needs you. No two days are the same.

What We’re Looking For

• Organized and detail-oriented, you follow through without being chased
• A natural problem-solver who stays calm under pressure and handles difficult conversations with confidence and tact
• Genuinely excited about the growth stage of a small business, you understand that building something means the job description will evolve, and you are energized by that, not unsettled by it
• Comfortable with tech, communication tools, booking platforms, and open to using AI or automation tools that help the team work smarter
• Willing to work weekends and holidays in-season, and comfortable with a schedule that includes Saturdays year-round
• Based on the Cape or South Shore, and available to be in our Brewster office at least 3 days a week, with some flexibility based on the time of year
• A GSD mindset, you take ownership, finish what you start, and don't wait to be told twice

Compensation & Benefits

• $45,000–$65,000 salary based on experience
• 401(k) with company match
• Health Insurance Stipend
• Paid time off and paid holidays
• Hybrid work schedule
• A real seat at the table as we grow, we promote from within when people step up

How to Apply

Email [email protected] with your resume and a brief note, not a form letter. Tell us something specific: a time you owned a process end-to-end, solved a tough problem on the fly, or tell us about a time you helped a team or business get better. Bonus points if you include a reference to GSD. We read every application and respond to the ones that stand out.

Pay: $45,000.00 - $65,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Paid time off
• Professional development assistance

Ability to Commute:

• Brewster, MA 02631 (Required)

Work Location: Hybrid remote in Brewster, MA 02631