Strategic Executive Assistant to CEO & Leadership Team

Dr. Comfort; Milwaukee (WI); On-site; USD 65,000 - 90,000; Full time

Job summary

Dr. Comfort, a leading footwear company focused on diabetes care, seeks an Executive Assistant to the CEO & ELT to orchestrate administrative operations.

You will manage calendars, draft communications, coordinate meetings, and oversee travel, events, and office workflows from our Mequon HQ. This role demands discretion, superb communication, and the ability to juggle multiple executive priorities with poise.

Qualifications

• 5+ years supporting a C-level executive.
• Discretion with confidential information.
• Exceptional written communication.
• Strong judgment about priority and urgency; the ability to say no on the CEO’s behalf.
• Proven ability to run competing priorities for multiple executives without dropping details.
• Professional presence and etiquette; front door to the executive team.
• Advanced Microsoft 365 (Outlook, Word, Excel, PowerPoint, Teams), video conferencing, and expense and travel platforms.
• Able to work on-site in Mequon, WI.

Responsibilities

• Own the CEO’s calendar end to end: schedule, reschedule and prioritize competing requests.
• Screen incoming requests and sort what needs the CEO, what can be delegated, and what can wait.
• Coordinate calendars across the ELT for recurring leadership meetings, reviews and offsites.
• Triage the CEO’s inbox: flag, draft responses, and follow up on open threads.
• Serve as a first point of contact for the executive team with employees, customers, providers, vendors and ownership.
• Draft and proof correspondence, memos, announcements and presentations.
• Handle confidential information — personnel, compensation, financial, legal and strategic — with complete discretion.
• Prepare agendas, pre-reads and briefing materials ahead of every significant meeting.
• Coordinate quarterly board and ownership reviews: scheduling, materials, logistics and follow-up.
• Capture action items and chase them to completion across departments.
• Book domestic and international travel, including trade shows, factory and supplier visits, and customer meetings.
• Build detailed itineraries with contingencies, and be reachable when travel goes sideways.
• Coordinate leadership offsites, company events, sales meetings and customer entertainment.
• Process expense reports and track recurring renewals, contracts and deadlines.
• Keep the Mequon office running: reception and visitors, mail and deliveries, supplies, kitchen and common areas.
• Serve as day-to-day contact for building management, facilities and office vendors; manage the office budget and purchase orders.
• Coordinate new-hire logistics with HR and IT — workspace, equipment, badges and first-day plans.
• Maintain organized digital files and confidential records.

Skills

C-level support

Discretion

Written communication

Priority management

Multitasking

Professional presence

MS 365 / Teams

On-site work

Tools

Microsoft 365

Video conferencing

Expense & travel platforms

Job description

Dr. Comfort, a leading footwear company focused on diabetes care, seeks an Executive Assistant to the CEO & ELT to orchestrate administrative operations.

You will manage calendars, draft communications, coordinate meetings, and oversee travel, events, and office workflows from our Mequon HQ. This role demands discretion, superb communication, and the ability to juggle multiple executive priorities with poise.