EA & Operations Support Specialist

About the job

About the company

Hi there! I’m Trish, and my husband Brad and I run Ocean Getaways – a boutique yacht charter company that curates unforgettable ultra-luxury vacations aboard stunning crewed yachts all over the world.

We’ve been in the travel industry since 1985 and have had the joy of working with high-net-worth individuals, Fortune 1000 companies, and top-tier travel advisors to make dream vacations a reality.

We’re passionate about creating once-in-a-lifetime experiences with the highest level of service and personalization.

We’re a small, tight-knit team that values excellence, proactivity, and making things better for our clients and our internal systems.

If you’re the kind of person who thrives on details, loves bringing order to complexity, and enjoys working with smart, service-focused people, we might be a great fit for you.

About the role

We’re looking for an EA & Operations Support Specialist who’s detail-obsessed, tech-savvy, and comfortable juggling executive admin tasks with operations support. You’ll help manage the full charter process from inquiry to post-trip follow-up, while also helping us fine-tune and improve our internal systems and workflows.

In this role, you will:

🗓️ Manage executive calendars, schedules, and travel logistics

✉️ Draft and respond to high-level communications

📝 Prepare meeting agendas, reports, and summaries

📂 Coordinate internal projects and follow-ups

📃 Assist with client proposals, contracts, and charter documentation

🚤 Coordinate charter logistics (guest preferences, provisioning, transportation)

📇 Manage CRM entries and ensure all records are up to date

📊 Track charter milestones, payments, and communication timelines

🧭 Document and map existing workflows and SOPs

⚙️ Identify inefficiencies and recommend improvements

🛠️ Assist with implementing tools, processes, and automation

🧪 Help test and train team members on new systems

🗂️ Use project/task tools like Asana or Trello to manage deadlines

📁 Maintain digital checklists and shared docs (Google Workspace, Airtable, etc.)

🤝 Liaise with tech providers to optimize tool usage.

You’re someone who communicates clearly, thinks in systems, and thrives on organizing chaos into smooth operations.

You’re meticulous, proactive, and trustworthy – especially when handling sensitive information.

You’re also a team player who enjoys making things better, working independently, and delivering excellent service with polish and professionalism.

Working hours: Full-time role working from 5:00 am EDT to 14:00 pm EDT, with an hour lunch break. Note, there is some flexibility, depending on the day.

About you

You’ll thrive in this role if you have:

✅ Bachelor’s degree preferred (Business, Communications, Hospitality, or related)

✅ 3–5 years supporting executives or business owners (luxury/service industries preferred)

✅ 2+ years of experience in operations coordination or admin management

✅ Experience reviewing or implementing new systems and workflows

✅ Familiarity with working with HNW clients or luxury brands

Brownie points for:

🌟 Experience in luxury travel or working with UHNWI clients

🌟 Comfortable with tools like iCloud Drive, MS 365, OneDrive, QuickBooks, Zoom, Dropbox

🌟 Experience with CRMs like HubSpot or Zoho

🌟 Familiarity with Asana, ClickUp, Lucidchart, or Miro

🌟 Basic knowledge of automation tools like Zapier or Make

Benefits

What’s in it for you?

💰Salary: $1800 – $2200 per month*

🕒 Full-time: Fully remote

🏖️ Paid time off: 20 days per year

*Please note that this is a gross salary and that you are responsible for any tax-related procedures in your country of residence. We kindly ask you to apply only if you are happy to work remotely as an independent contractor.

EA & Operations Support Specialist