Chief Executive Assistant

Role Summary

Join Hire Hangar and work with fast-growing global companies while building a long-term career.

Job Title

Chief Executive Assistant

You are the CEO’s command center and execution integrator across a 3-business portfolio (luxury Caribbean vacation rental asset management, home services/insulation, and Boston real estate development). You translate fast-moving ideas into clear plans, systems, and follow-through—keeping operators accountable so nothing slips.

Responsibilities

• Own the CEO’s calendar, priorities, weekly planning rhythm, and daily execution check-ins
• Convert “brain dumps” into structured tasks, owners, deadlines, and follow-ups (with escalation when needed)
• Drive cross-business execution: unify plans, remove blockers, and keep momentum through rapid pivots
• Maintain a weekly portfolio scorecard (marketing, sales KPIs, project milestones, risks, next actions)
• Partner with key operators/partners (Ops, Sales, and Deal partners) to track commitments and accountability
• Coordinate across time zones and teams (including St. Martin ground support and remote VAs)
• Support light investor/client communication (owners/investors, not guests)

Requirements

• Experience working as Chief of Staff / Senior Executive Assistant / Operations Partner roles supporting a founder or CEO
• Proven ability to run execution systems end-to-end (priorities → plans → tracking → completion)
• Comfort enforcing accountability with senior operators and partners; clear, confident follow-up style
• Strong project management skills (ClickUp, Asana, or equivalent) and KPI reporting discipline

Non-negotiable: Prior remote work experience; fluent with remote collaboration tools (Slack, Zoom, Google Workspace, Asana/ClickUp or similar) and ideally experience working with US or UK-based companies—applications without this will not be considered.

Preferred Qualifications

• Experience supporting multi-business or portfolio operators
• Working knowledge of CRM + marketing ops workflows (email sequences, tagging, lead routing)
• Exposure to real estate development or home services operations
• Tools & Technology

ClickUp/Asana, Google Workspace, Slack/Zoom, Airtable/Google Sheets, CRM (HubSpot/GoHighLevel/Salesforce or similar), Zapier/Make, AI tools for writing/automation (e.g., ChatGPT)

Please NOTE

It is crucial that you complete the application form in full. As part of the application process, you will be required to record a video. If your application is successful, you will receive an email confirming next steps—the video is the first step of the interview process. If you do not record a video, we will not be able to consider you for ANY open roles

We connect top talent with vetted employers, competitive pay, and real growth opportunities.

• Remote
• Time Zone
• US Eastern (ET) preferred; must overlap core ET working hours

About the Company

Meaningful Engagement: Move beyond a script-driven call center approach—truly connect with clients, understand their needs, and help them access the right resources.

Flexible Work Style: Benefit from a part-time structure that allows for personal flexibility while still meeting crucial response times.

Ongoing Training: Learn in-demand tools.

Team Culture: Collaborate with a supportive group that values curiosity, empathy, and genuine care for client outcomes.

To Apply

Please send your resume or CV. We look forward to hearing from you!

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, or disability status.

We connect top talent with vetted employers, competitive pay, and real growth opportunities.