Executive Assistant

Direct Supply, Inc.; Milwaukee (WI); On-site; USD 55,000 - 85,000; Full time

Benefits offered by this job

Generous benefits

Job summary

Direct Supply, Inc. seeks an Executive Assistant to support an Executive Vice President and senior leaders, enabling strategic focus by managing complex calendars, preparing materials, and coordinating meetings and travel.

You will leverage AI and productivity tools to streamline workflows, handle confidential information with discretion, and collaborate across functions to move key initiatives forward within a fast-paced, results-oriented environment.

Qualifications

• 5+ years of experience providing executive or senior-level administrative support.
• Proficiency with Microsoft Office Suite, virtual collaboration platforms, and AI-enabled productivity tools.
• Ability to manage multiple priorities, anticipate needs, and consistently deliver high-quality work with strong attention to detail.
• Strong written and verbal communication skills with the ability to develop executive-ready communications and presentations.
• Demonstrated judgment and discretion in handling confidential business information.
• Experience coordinating executive meetings, travel, and cross-functional activities involving multiple stakeholders.
• Ability to build effective relationships and collaborate across all levels of the organization.

Responsibilities

• Manage complex executive calendars by balancing priorities, protecting focus time, and adapting quickly to changing business needs.
• Anticipate executive needs by preparing leaders for meetings, customer interactions, presentations, and business reviews.
• Coordinate leadership meetings, business reviews, and planning activities while tracking decisions, action items, and follow-up.
• Prepare executive communications, presentations, reports, and briefing materials that support informed decision-making.
• Partner across leadership teams to coordinate priorities, share information, and remove barriers that keep work moving.
• Coordinate domestic travel, executive meetings, customer visits, and leadership events to ensure seamless execution.
• Handle confidential information with sound judgment, discretion, and professionalism.
• Leverage AI and productivity technologies to simplify workflows, improve information management, and increase executive effectiveness.
• Identify opportunities to improve executive support processes and enhance operational efficiency.

Skills

Calendar management

Communication

Discretion

Time management

Travel coordination

Tools

Microsoft Office Suite

Virtual collaboration platforms

AI-enabled productivity tools

Job description

Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. The Executive Assistant is a trusted partner to an Executive Vice President, General Managers of our technology platform businesses, and additional senior leaders. This role provides proactive executive support that enables leaders to focus on strategic priorities by anticipating needs, managing complex operations, and ensuring key initiatives, decisions, and commitments move forward.

What You’ll Do and Impact:

• Manage complex executive calendars by balancing priorities, protecting focus time, and adapting quickly to changing business needs.
• Anticipate executive needs by preparing leaders for meetings, customer interactions, presentations, and business reviews.
• Coordinate leadership meetings, business reviews, and planning activities while tracking decisions, action items, and follow-up.
• Prepare executive communications, presentations, reports, and briefing materials that support informed decision-making.
• Partner across leadership teams to coordinate priorities, share information, and remove barriers that keep work moving.
• Coordinate domestic travel, executive meetings, customer visits, and leadership events to ensure seamless execution.
• Handle confidential information with sound judgment, discretion, and professionalism.
• Leverage AI and productivity technologies to simplify workflows, improve information management, and increase executive effectiveness.
• Identify opportunities to improve executive support processes and enhance operational efficiency.

What You’ll Bring:

• 5+ years of experience providing executive or senior-level administrative support.
• Proficiency with Microsoft Office Suite, virtual collaboration platforms, and AI-enabled productivity tools.
• Ability to manage multiple priorities, anticipate needs, and consistently deliver high-quality work with strong attention to detail.
• Strong written and verbal communication skills with the ability to develop executive-ready communications and presentations.
• Demonstrated judgment and discretion in handling confidential business information.
• Experience coordinating executive meetings, travel, and cross-functional activities involving multiple stakeholders.
• Ability to build effective relationships and collaborate across all levels of the organization.

Job to be performed in the location listed.

Generous benefit package available.

© 2013 to 2026 Direct Supply, Inc. All rights reserved. Direct Supply delivers solution-driven platforms, products and services to help solve the toughest challenges facing Senior Living and Healthcare. For more than 35 years, we’ve grown consistently while expanding our offering of innovative solutions for virtually every critical area of senior health across the continuum of care. If you asked our 1,200+ Partners what separates Direct Supply from other applied technology companies, it’s that we are 100% employee owned and driven to work with a purpose. Every day, we strive to honor our mission of enhancing the lives of millions of seniors and healthcare professionals in a results-oriented agile environment that gives our Partners the necessary tools and flexibility to truly bring what’s next to Healthcare.

Ready to make a difference?