Executive Assistant

Summary

You’ll be the founders’ right hand and the engine behind our executive operations. Day to day, you run the calendar, inbox and projects, keep launches and buildouts moving, handle business admin and logistics, and lead the VA, so the founders stay focused on growth. You’ll also help standardize operations with SOPs and smarter systems.

About Us

At Chill & Thrill Retreats, a stay is never just a stay. We create immersive, experience-driven retreats like our Nautical, Forest, Beach and Stargazing Retreats, each professionally designed to be our guests’ vacation, not just a place to sleep. The destination is the bonus. Our stays are designed to provide our guests a place to build memories that last for years to come!

We’re owner-operated and powered by smart systems and automation, with 5 live properties, all in the top 1%, and 2 more coming. We sweat the details so every guest gets the WOW from the first message to after checkout. If you love hospitality, love a good system, and want to help build something with meaning, you’ll fit right in!

What You’ll Own

• Calendar, inbox and travel: protect the founders’ time, triage email, book travel and meetings.

• Weekly rhythm: prep the weekly review of all launch boards, keep the priority queue current, and make sure decisions get made.

• Launch and buildout support: keep timelines, budgets and open decisions moving on each new property; surface blockers early.

• Business admin: invoices, receipts, handoffs to the CPA and bookkeeper, entity renewals, insurance and licensing paperwork.

• Logistics: appointments, errands, events and vendor coordination.

• Special projects: vendor and market research, summaries, owner and investor updates, decks.

• Lead the VA: assign work, review output, keep SOPs current.

What Success Looks Like

• The founders’ calendar and inbox run without them.

• The weekly review is prepped before anyone asks.

• Launches and buildouts stay on schedule, and blockers surface early.

• Admin items close on time, with no deadline surprises.

• The VA runs on clear SOPs with minimal rework.

• The founders are no longer the bottleneck.

Who You Are

• 3+ years as an EA, chief of staff, or office manager for a founder or small business.

• Reliable, with transportation, and happy working in person with the founders.

• Writes clearly, stays calm when priorities shift, and follows through every time.

• Discreet: you’ll see financial and business details and treat them as private.

• Fluent with Google Workspace, Google Meet and monday.com; picks up new tools fast and uses AI to work faster. Experience with Claude is a plus!

• Brings solutions, not just questions.

• Bonus: hospitality, real estate or short-term rental experience; bookkeeping basics.

Why This Role

• Direct access to the founders and real trust from day one.

• High ownership and real impact on a fast-growing business.

• Room to grow into a bigger leadership role as we add properties.

Pay: $25.00 - $35.00 per hour

Benefits:

• Flexible schedule

Work Location: Remote