Executive Assistant

Direct Supply•Milwaukee, WI

4d•Onsite

About The Position

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. In the Executive Assistant position, you’ll serve as a trusted partner to multiple Vice Presidents and Directors, providing proactive executive support that enables leaders and teams to operate effectively. You’ll manage complex calendars, coordinate travel and meeting logistics, support executive communications, and streamline workflows using both traditional and AI-enabled tools. This role is ideal for someone who thrives in a fast-paced environment, is a heavy user of AI, anticipates needs before they arise, and excels at balancing multiple priorities while maintaining exceptional attention to detail.

Requirements

5+ years of experience providing executive or senior-level administrative support in a fast-paced business environment.
Proficiency with Microsoft Office Suite and comfort with AI-enabled tools, cloud systems, and virtual collaboration platforms.
Strong written and verbal communication skills with the ability to clearly present information and ideas.
Proven ability to manage multiple priorities with exceptional organizational skills, attention to detail, and follow-through.
Demonstrated ability to anticipate needs, manage competing priorities, and operate independently with minimal direction.
Demonstrated discretion in handling confidential and sensitive information.

Nice To Haves

Bachelor’s degree in Business, Marketing, Communications, or related field preferred.
Experience with dashboards or reporting tools such as Power BI, Salesforce, or Smartsheet.
Experience supporting Vice Presidents, Directors, or senior leadership teams preferred.
Experience coordinating executive meetings, events, and travel logistics across multiple stakeholders.

Responsibilities

Provide confidential executive support to multiple Vice Presidents and Directors, serving as a trusted partner in managing priorities, communications, and day-to-day operations.
Manage and prioritize complex calendars, coordinate domestic travel, and oversee logistics for executive meetings, events, and leadership activities while proactively identifying scheduling conflicts and opportunities to maximize leader effectiveness.
Anticipate leader needs, proactively resolve administrative and operational challenges, and ensure leaders are prepared for meetings, presentations, customer interactions, and key business activities.
Plan and coordinate internal events, off-sites, customer meetings, and department-wide sessions, including communications, agendas, catering, meeting materials, and space logistics to ensure seamless execution.
Prepare polished customer-facing materials, business reviews, executive presentations, and meeting materials under tight deadlines.
Leverage AI-enabled tools to automate workflows, draft communications, generate reports, and improve day-to-day team efficiency.
Serve as a key point of coordination across leadership teams and cross-functional stakeholders, ensuring clear communication, alignment, and follow-through.
Capture meeting notes and ensure action items, deadlines, and stakeholder responsibilities are tracked and completed.
Continuously identify opportunities to optimize processes and improve leader and team efficiency.
Collaborate across internal teams to support initiatives and ensure smooth execution.
Exercise exceptional judgment, professionalism, and discretion while handling sensitive information, shifting priorities, executive requests, and confidential business matters.