Senior Executive Assistant & Strategy Partner — Remote

Squared Away; Washington (District of Columbia); On-site; USD 33,062 - 49,593; Part time

Benefits offered by this job

Fully remote (1099)

Flexible schedule

Job summary

Squared Away is seeking an experienced Chief Executive Assistant as a fully remote, 1099 independent contractor to support senior executives. You will manage complex calendars across time zones, handle confidential correspondence, and anticipate needs with proactive, discreet execution.

This role requires 20+ hours weekly, weekday business hours, and a reliable home office. You’ll work with diverse clients, maintain high standards, and build efficient processes while preserving confidentiality.

Qualifications

• Permanent U.S. address in one of the listed states.
• Available during normal U.S. business hours (Mon–Fri, 9 AM–5 PM in local time).
• Minimum of 20 hours per week, with flexibility for extra hours.
• Administrative experience supporting senior leaders; executive support preferred.
• Experience working remotely is preferred.
• Reliable home office setup (Mac/PC with webcam, high-speed internet, smartphone, quiet workspace).

Responsibilities

• Manage executive calendars across multiple time zones.
• Draft, respond to, and triage correspondence for executives.
• Coordinate domestic and international travel end-to-end.
• Prepare meeting materials, agendas, and reports; track action items.
• Create and refine workflows to improve efficiency and reduce friction.
• Conduct research on competitors, tools, and market trends; provide concise summaries.
• Maintain confidentiality and exercise sound judgment in all matters.

Skills

Proactive thinking

Executive calendar management

Strong written communication

Cross-time-zone coordination

Discretion and confidentiality

Remote work experience

Tools

Microsoft Office

Job description

Squared Away is seeking an experienced Chief Executive Assistant as a fully remote, 1099 independent contractor to support senior executives. You will manage complex calendars across time zones, handle confidential correspondence, and anticipate needs with proactive, discreet execution.

This role requires 20+ hours weekly, weekday business hours, and a reliable home office. You’ll work with diverse clients, maintain high standards, and build efficient processes while preserving confidentiality.