[Hiring] Executive Personal Assistant @Winning Assistants

Role Description

Our client is seeking a highly organized, proactive, and dependable Executive Personal Assistant to support daily operations, communication, and executive-level coordination. This role is essential in helping leadership stay focused, organized, and efficient while ensuring that priorities and tasks are managed seamlessly.

As an Executive Personal Assistant, you will take ownership of:

• Calendar management
• Email correspondence
• Task tracking
• Document organization
• Supporting operational needs

You will act as a trusted partner to leadership, ensuring that day-to-day responsibilities are handled efficiently and nothing falls through the cracks. This role requires someone who is comfortable working independently, adapting quickly to shifting priorities, and proactively identifying opportunities to improve workflows.

Strong communication is essential, as you will interact with internal team members, external partners, and stakeholders. Bilingual proficiency in English and Spanish is preferred, as it may support communication with certain stakeholders, but it is not required.

The ideal candidate is a self-starter who anticipates needs, communicates clearly, and executes tasks with precision. You should be detail-oriented, reliable, and comfortable handling confidential information with professionalism and discretion.

Qualifications

• Strong experience as an Executive Assistant, Personal Assistant, or similar role supporting leadership
• Excellent organizational and multitasking abilities
• Proactive, self-starter with the ability to work independently
• Strong attention to detail and follow-through
• Ability to receive feedback and adjust quickly
• Excellent communication and problem-solving skills
• Ability to manage priorities in a fast-paced environment
• High level of discretion and confidentiality

Requirements

• Must be proficient in speaking and writing English very clearly
• Must have relevant work experience
• Be able to submit an NBI clearance and/or Local Police Clearance background check before onboarding (mandatory)
• Must be available for video meetings with your camera on (when needed)

Benefits

• Dedicated HR & Contractor Support Team: Access to world-class support for questions, guidance, contract matters, and client communication.
• Premium VPN Access (Optional): A secure VPN license can be provided upon request to enhance privacy and security for client-related tasks.
• HIPAA & Cybersecurity Training + Certification (Provided): Access to our internal HIPAA compliance training, cybersecurity modules, and certification to help you confidently handle PHI for U.S. healthcare clients.
• Top 1% VA Performance Training: Access to our proprietary training on communication, client management, productivity systems, and best practices to help you become a top-performing VA and increase long-term client retention.
• Client-Approved U.S. Holidays: Contractors may take U.S. holidays off according to the client’s needs and schedule.
• Client-Approved Paid or Unpaid Time Off: Time off may be granted by your client. Paid time off is optional and only if offered by the client.
• Access to Tools & Resources: Templates, workflow guides, productivity tools, and client-specific SOP support to help you perform at your best.
• Optional Performance-Based Incentives: Some clients may offer bonuses, incentives, or increased hours based on your performance.