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Remote Personal Assistant (Milwaukee)

Five Below
Milwaukee, WI Remote Full Time
POSTED ON 4/3/2026
AVAILABLE BEFORE 5/31/2026
About the Role:
We are seeking a highly organized, resourceful, and proactive Executive Personal Assistant to provide exceptional support to our executive leadership. The ideal candidate is a polished communicator who excels at multitasking, maintains strict confidentiality, and thrives in a fast-paced environment. In this role, you will ensure the seamless execution of daily operations by managing both personal and business-related responsibilities for the executive.

Key Responsibilities
Provide high-level administrative support, including calendar management, travel arrangements, and meeting coordination

Serve as the point of contact between the executive and internal/external stakeholders

Manage confidential and time-sensitive information with the utmost professionalism

Handle personal errands, reservations, scheduling, and travel for both business and personal matters

Draft, edit, and proofread emails, reports, presentations, and other correspondence

Organize and maintain digital files and documentation

Coordinate with vendors, clients, and service providers as needed

Assist with project coordination, tracking timelines, and ensuring deadlines are met

Proactively ensure all assigned tasks are completed efficiently and accurately

Required Qualifications
Proven experience as an Executive Assistant or Personal Assistant supporting senior leadership

Exceptional written and verbal communication skills

Strong organizational abilities and capacity to manage multiple priorities

Tech-savvy; proficient with MS Office, Google Workspace, Zoom, Slack, and similar tools

Demonstrated discretion, confidentiality, and professionalism

Ability to work independently, problem-solve, and perform under pressure

Legally authorized to work in the United States

Preferred Qualifications
Previous experience supporting C-level executives

Degree in Business Administration or a related field

Familiarity with hybrid/remote work tools and best practices

Compensation & Benefits
Salary: $65,000 – $75,000 annually, commensurate with experience

Benefits Include:
401(k) Retirement Plan

Health Insurance

Dental & Vision Insurance

Life Insurance

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Salary : $65,000 - $75,000

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