Ocean Getaways - EA & Operations Support Specialist

JobRack; United States; Remote; USD 60,000 - 80,000; Full time

Job summary

Ocean Getaways is seeking an EA & Operations Support Specialist to support their boutique yacht charter operations. This full-time, remote position requires detail-oriented individuals with strong organizational skills, a background in luxury service sectors, and proficiency in various project management tools. You will manage executive tasks and streamline operational workflows while delivering exceptional service to high-net-worth clients.

Benefits

20 days paid time off per year

Flexible working hours

Qualifications

• 3–5 years supporting executives in high-end environments.
• 2+ years of experience in operations coordination.
• Familiarity with luxury brands or HNW clients.

Responsibilities

• Manage executive calendars and travel logistics.
• Draft high-level communications and prepare agendas.
• Coordinate charter logistics and internal projects.

Skills

Organizational skills

Communication

Attention to detail

Proactivity

Tech-savvy

Education

Bachelor's degree

Tools

Google Workspace

Asana

Trello

QuickBooks

CRM tools

Job description

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.

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's lunch break. Note there is some flexibility, depending on the day.

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

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.

The JobRack team are working with Ocean Getaways to help them find their new team member.

The hiring process for this position will include the following steps:

1. Completing the application form on JobRack.
2. Recording a short video introduction of yourself.
3. If shortlisted, completing test tasks.
4. Attending video interviews to discuss your previous experience and the new role in more detail.

The JobRack team has gained a full understanding of Ocean Getaways’ needs and will review, filter, screen and test candidates in line with this.

To ensure your application is considered, take the time to carefully read the job description and submit a high-quality application.

We will, of course, provide you with feedback throughout the process.

At the request of Ocean Getaways, applications for this position must be submitted through JobRack and direct contact with the employer is not allowed.

We are committed to maintaining a respectful and professional environment for our jobseekers, our clients and the JobRack team. Any form of abuse or disrespect towards our team will result in immediate disqualification from this and all future opportunities through JobRack.

Please note that this position requires 100% commitment and is not suitable for those seeking a side job, freelance work, or part-time employment. It is important to only apply if you intend this to be your primary and only full-time job. Any attempts to work multiple full-time jobs without the knowledge of your employer may result in termination and a ban from applying to other jobs on the JobRack site.

Got questions about working remotely? Check out JobRack’s FAQ for answers to everything you might want to know. https://jobrack.eu/jobseeker-faq