AI-Enabled Strategic Executive Assistant to Senior Leaders

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

Benefits offered by this job

Generous benefit package

Job summary

Direct Supply is seeking an Executive Assistant to support the EVP, General Managers of our technology platform businesses, and senior leaders in Milwaukee. You will manage calendars, prepare materials, coordinate leadership reviews, and drive efficient operations.

You will leverage Microsoft Office and AI-enabled tools to enhance productivity, coordinate travel, and maintain discretion for confidential information across the organization.

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

Executive support

Calendar management

Travel coordination

Communication

Attention to detail

Relationship building

Discretion

Tools

Microsoft Office Suite

AI-enabled productivity tools

Virtual collaboration platforms

Job description

Direct Supply is seeking an Executive Assistant to support the EVP, General Managers of our technology platform businesses, and senior leaders in Milwaukee. You will manage calendars, prepare materials, coordinate leadership reviews, and drive efficient operations.

You will leverage Microsoft Office and AI-enabled tools to enhance productivity, coordinate travel, and maintain discretion for confidential information across the organization.