Remote Executive Assistant to Founder | AI-Driven Ops

Inside Out Hiring; United States; Remote; USD 22,000 - 28,000; Full time

Job summary

Inside Out Hiring invites an experienced Executive Assistant to support the founder of a NY-based nursing home management company. This remote role covers inbox triage, scheduling, travel coordination, and later onboarding and compliance tasks. You will leverage Claude and Microsoft 365 to optimize back-office workflows.

The ideal candidate has 2–5 years supporting senior leaders, excellent English (C1), and a proactive, secure, detail-oriented approach to operations in a fast-paced environment.

Qualifications

• 2–5 years supporting senior executives or business owners in a high-level admin role.
• English fluency at C1 level with polished written and spoken communication.
• Demonstrated critical thinking and structured problem-solving abilities.
• Adaptability and ownership in balancing executive support with daily ops tasks.
• Hands-on experience with AI productivity tools, specifically Claude.
• Ability to operate securely within systems for sensitive business records.

Responsibilities

• Inbox & Calendar management: triage emails, schedule, protect executive time.
• Travel & logistics coordination for meetings and events.
• Employee onboarding administration: benefits, health insurance, 401(k) setup.
• Compliance & license tracking for medical and facility operations.
• Spreadsheets & dashboards: maintain and optimize operational metrics.
• Document workflows into SOPs and leverage Claude/AI to streamline procedures.
• Vendor scheduling and follow-up for interviews and deliverables.

Skills

Inbox management

Calendar management

English fluency (C1)

Problem solving

AI mindset

Tools

Claude

Microsoft 365 / Outlook

Job description

Inside Out Hiring invites an experienced Executive Assistant to support the founder of a NY-based nursing home management company. This remote role covers inbox triage, scheduling, travel coordination, and later onboarding and compliance tasks. You will leverage Claude and Microsoft 365 to optimize back-office workflows.

The ideal candidate has 2–5 years supporting senior leaders, excellent English (C1), and a proactive, secure, detail-oriented approach to operations in a fast-paced environment.