Join Our Team
We’re always interested in talking with a potential next rockstar member of our team! If you’re thinking about a career change, or just want to see what’s out there - contact us! Even if there isn’t a current open position, we’re growing quickly and make hiring decisions fast - so get in touch to learn more about us, and to tell us more about you! We are an inclusive, fun, and values-driven company with an incredible culture to match.
Please send all employment inquiries to [email protected]. We look forward to hearing from you!
Current Opportunities
Executive & Personal Assistant
Location: Duxbury, MA
Schedule: Full-Time (3-40 hours/week)
Compensation: $25–$35/hour, based on experience
About the Role
Right hand to the Founder of a growing Cape Cod vacation rental company, a new AI services company, and father of 3.5 and 7-year-old girls. You’ll manage 20+ active threads across business, personal, and family — from coordinating vendors to running errands to helping manage kids’ schedules. Local to the South Shore, gets things done without being told twice, comfortable switching between business operations and a grocery run in the same afternoon. Real autonomy and trust from day one.
What You’ll Do
Scheduling & Task Management
- Schedule meetings, calls, and appointments; follow up on open items until resolved
- Help manage the task list — adding, updating, and closing out items
Household, Property, Office & Vehicles
- Coordinate vendors (cleaners, landscapers, handymen, contractors)
- Organize and maintain the office, home, property, and vehicles
- Grocery/supply runs, mail sorting, home organization, seasonal prep
- Monthly property walk-throughs (Duxbury home + occasional Cape Cod trips)
Kids & Family
- Help manage kids’ activity schedules, coordinate with co-parent on logistics
- Research and book camps, lessons, and activities; handle clothes and gear as needed
- Occasional pinch-hit babysitting
Errands
- Vehicle drop-off/pickup (inspections, detailing, service), pharmacy runs, package returns
- Meet vendors on-site; ad-hoc errands as they come up
What You Bring
- EA, personal assistant, office manager, or household manager experience
- Local to Duxbury, Plymouth, Kingston, Marshfield, Halifax, or nearby — in-person regularly with a car
- High discretion — you’ll handle personal matters
- Strong follow-through and independent judgment
- Eager to learn and use AI tools daily — we’ll train you, but curiosity is non-negotiable
- Comfortable with tech (Google Workspace, apps) and around kids
Growth & Comp
$25–$35/hour, 30–40 hrs/week, hybrid. Significant upside based on impact. Start as the get-everything-done person and grow into operations or chief-of-staff as the business scales. We’re AI-forward — you’ll use AI tools daily for research, drafting, and getting organized. We’ll teach you, but you need to be excited about that, not intimidated by it.
How to Apply
Email [email protected] with your resume and a brief note answering one of these:
- Tell us about a time you juggled 5+ things at once and nothing dropped.
- Describe a situation where you anticipated what someone needed before they asked.
- What’s the most satisfying task you’ve ever crushed? Why?
Keep it short and real. We’d rather hear your voice than a polished cover letter.
Guest & Operations Specialist
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.
