Executive Assistant

Direct Supply; Milwaukee (WI); On-site; USD 65,000 - 90,000; Full time

Job summary

Direct Supply seeks an experienced Executive Assistant to support the Executive Vice President, General Managers of our technology platform businesses, and other senior leaders in Milwaukee.

The role requires proactive executive support, strong attention to detail, and the ability to anticipate needs, manage complex calendars, coordinate meetings, travel, and confidential information with discretion. Collaboration across leadership teams and adoption of AI tools will improve efficiency.

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.
• Strong written and verbal communication skills with the ability to develop executive-ready communications.
• 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 and protect focus time.
• Prepare leaders for meetings, customer interactions, and reviews.
• Coordinate leadership meetings, business reviews, and planning activities.
• Prepare executive communications, presentations, and briefing materials.
• Coordinate priorities across leadership teams to remove barriers.
• Arrange domestic travel, executive meetings, and leadership events.
• Handle confidential information with sound judgment and discretion.
• Leverage AI and productivity technologies to streamline workflows and improve information management.
• Identify opportunities to improve executive support processes and operational efficiency.

Skills

Executive support

Calendar management

Travel coordination

Communication

Discretion

AI productivity tools

MS Office

Cross-functional collaboration

Tools

Microsoft Office Suite

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.