Senior Executive Assistant & Strategic Ops (Remote)

Squared Away; Northern (KY); Remote; USD 30,000 - 33,000; Full time

Benefits offered by this job

Fully remote

Job summary

Squared Away is seeking an experienced Chief Executive Assistant to support senior executives in a fully remote, national-capacity role. You will manage calendars, communications, and travel, while driving process improvements and ensuring discretion with sensitive information.

This is a long-term position with potential transition to W-2 in 2027 and ongoing client support. You will work across multiple time zones, prioritize competing demands, and build trusted relationships with

Qualifications

• Administrative experience supporting senior leaders is required.
• Experience supporting executive-level roles is strongly preferred.
• Ability to operate in ambiguity and take ownership without constant direction.
• Strong judgment and discretion with confidential information.

Responsibilities

• Manage executive calendars across time zones and coordinate scheduling.
• Draft and triage executive communications and emails.
• Coordinate domestic and international travel end-to-end.
• Prepare meeting materials, agendas, and reports; track action items.
• Identify and refine workflows to improve efficiency and reduce friction.
• Conduct research on competitors, tools, and market trends to support decision-making.

Skills

Executive support

Calendar management

Time-zone coordination

Remote work experience

Discretion and confidentiality

Communication

Tools

Microsoft Office

Job description

Squared Away is seeking an experienced Chief Executive Assistant to support senior executives in a fully remote, national-capacity role. You will manage calendars, communications, and travel, while driving process improvements and ensuring discretion with sensitive information.

This is a long-term position with potential transition to W-2 in 2027 and ongoing client support. You will work across multiple time zones, prioritize competing demands, and build trusted relationships with