Guest & Operations Specialist

Job Description

Job Description

Location: Brewster, MA (Hybrid option – Cape Cod & South Shore preferred)
Type: Full-Time, Year-Round
Schedule: Includes weekends and holidays during peak season; on-call rotation required during summer. Flexibility for a Tuesday–Saturday or weekend-inclusive year-round schedule.

About the Role

We're hiring for multiple full-time Guest & Operations Specialists to support our fast-growing vacation rental business. This is a hands-on, core role focused on guest experience, reservations, and internal operations coordination. You’ll be part of a close-knit team where clear communication, follow-through, and ownership matter. We work hard, share a lot of laughs, and are genuinely excited about where we’re headed. If you're looking to build your career, want to contribute meaningfully, and are ready to jump in wherever needed—you’ll thrive here.

What You’ll Do

• Handle guest operations from reservation inquiry through post-stay follow-up—including bookings, communication, and in-stay support

• Be a go-to contact for both guests and homeowners—keeping things smooth, calm, and professional

• Manage and maintain accurate property listings and internal systems

• Assist with vendor coordination, seasonal staff scheduling, or office logistics as needed

• Join the summer on-call rotation and be prepared for shifting schedules during peak season

• Pitch in wherever the team needs support—this is a role where no two days look the same

What We’re Looking For

• Organized, detail-oriented, and able to follow through on tasks without micromanagement

• A problem-solver who can anticipate issues and stay calm under pressure, with the ability to navigate difficult conversations with tact and confidence.

• Comfortable managing high-demand customer service situations with professionalism and resilience—especially during peak season

• Comfortable with tech, communication tools, and open to using AI or automation tools to work smarter

• Interested in growth—but also excited to be part of the core team that runs the business day to day

• Willing to work weekends and holidays in season, and possibly a Tuesday–Saturday or weekend-inclusive year-round schedule. A “GSD” mentality is a must

• Cape or South Shore candidates who can be in the Brewster office at least 3 days a week, with some flexibility based on the time of year

Why Work With Us

We’re a small, committed team that values accountability, clear communication, and high standards. The work can move quickly—especially in-season—but we support each other and take pride in what we deliver. There’s exciting room to grow here, and we aim to promote from within when we see team members stepping up.

Focus Areas & Growth Potential

Guest services is the foundation of this role, but we’re also looking for team members who can contribute in other key areas from day one. As we scale across the Cape and improve our systems and operations, there’s room to grow into areas like:

• Office operations & vendor coordination

• Sales & Marketing support

• Process optimization & systems thinking

• New tech implementation & automation

• Guest services management

• Staff onboarding & training

These aren’t the only directions—we’re building a well-rounded team with complementary strengths. Let us know where you’d be excited to contribute now, and where you see yourself growing next.

Compensation & Benefits
Competitive salary based on experience
401(k) with company match
Paid time off & paid holidays
Hybrid work setup (in-office + remote)
Additional benefits are under evaluation as we grow.

How to Apply

Email [email protected] with your resume and a brief note about why this role is the right fit. We get plenty of generic applications—take a minute to tell us something real. Bonus points if you include a reference to “GSD” or tell us about a time you owned a process or solved a tough problem. We're looking for contributors, not just task-takers.