Reservations Manager
7 days ago
THIS ROLE IS (WEEKENDS ONLY)
Overview:
- Start in bookings — with the potential to grow into full-time reservations & expanded roles as we scale.
- You'll be our second hire—a high-impact, high-growth role with the opportunity to lead as we scale.
Preferred Location: United States or Toronto, Canada
Hours:
On call on weekends from EDT 8:30am-6:00pm (Saturday & Sunday)
- Ideally in EST/EDT timezone.
Compensation: CAD$25/hour, plus performance bonuses of up to $500, based on quality of work, reliability, and overall contribution.
Do Not Apply If:
- You're not fully fluent in English or can't communicate clearly and confidently on calls
- You're in a time zone that prevents you from covering 8:30 AM – 6 PM EST (weekends)
- You're not naturally enthusiastic
or engaging when speaking with guests - You make frequent spelling, grammar, or accuracy mistakes
- You have
no experience speaking directly with customers
or clients (phone, in-person, or live chat)
About:
- We're building what will be a go-to platform for booking luxury excursions in the Caribbean (and eventually worldwide).
- Currently, our main focus is in boat and yacht experiences — but we'll soon expand into the other incredible offerings: safaris, heli-skiing, retreats & more.
Growth Path
- This role begins as weekend coverage, but as our business scales there may be opportunities to grow into expanded positions such as full-time (weekday) reservations, or other leadership roles within the company.
Core Responsibilities
- Ensures every guest inquiry turns into a seamless, well-coordinated booking — with personal care, speed, and
accuracy
. - Answer all incoming calls during on-call hours with a
polite
,
energetic
, and
professional
tone. - Coordinate and forward bookings to partner operators accurately and promptly.
- Deliver high-touch customer service, offering a warm, trusted point of contact throughout the guest experience.
- Track and flag booking issues proactively, and ensure partner follow-through.
- During non-call hours, support with business development, research, scheduling, and other high-impact operational tasks as needed.
Essential Skills
- Exceptional attention to detail
— accurate, thorough, and precise - Highly organized
— keeps tasks, messages, and follow-ups in perfect order - Warm, energetic and enthusiastic phone voice
that guests immediately trust - Clear, polished communicator
— excellent grammar, spelling, and verbal delivery (no typos) - Fast and fluent with technology
— quick to learn tools, apps, and shortcuts - Calm under pressure
— thinks clearly and acts decisively in urgent moments - Skilled at communicating with multiple parties at once
— partners, customers, internal teams — and keeping everyone aligned.
Interested? Or know someone who might be? Shoot us a message — we'd love to hear from you.
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