Executive Assistant to the CEO & ELT

Dr. Comfort; Milwaukee (WI); On-site; USD 60,000 - 70,000; Full time

Benefits offered by this job

Medical, dental and vision

401(k)

Paid time off and holidays

Job summary

Dr. Comfort is seeking an Executive Assistant who supports the CEO and ELT, keeping calendars, communications, and meetings running smoothly. This role requires proactive coordination, discretion with confidential information, and a professional presence to act as the front door to the executive team.

On-site in Mequon, WI with occasional travel. The ideal candidate will have 5+ years of C-level support experience, advanced Microsoft 365 skills, and the ability to manage multiple priorities

Qualifications

• 5+ years supporting a C-level executive.
• Discretion with confidential information.
• Exceptional written communication.
• Strong judgment about priority and urgency.
• Ability to run competing priorities without dropping details.
• Professional presence and etiquette; front door to the executive team.
• Advanced Microsoft 365, video conferencing, expense and travel platforms.
• On-site work in Mequon, WI.

Responsibilities

• Own the CEO’s calendar end to end and prioritize requests.
• Screen inbox and draft responses for CEO.
• Coordinate calendars across ELT for meetings and offsites.
• Prepare agendas, pre-reads and briefing materials for meetings.
• Coordinate travel (domestic and international) and offsites.
• Manage office logistics and vendor relationships; support HR/IT onboarding.

Skills

Executive support

Microsoft 365

Discretion with confidential info

Written communication

Prioritization & judgment

Professional presence

Tools

NetSuite

HubSpot

SharePoint

Smartsheet

Job description

Ever wondered what it’s like to be the right hand to a CEO at a company scaling fast under new ownership? Here’s your shot.

About Dr. Comfort

Dr. Comfort is the leading brand in therapeutic footwear for people living with diabetes. We design and manufacture shoes, diabetic socks, compression products and custom orthotic insertsincluding 3D-printed orthotics produced in our own lab in Mequon. Our products are dispensed through podiatrists, orthotic and prosthetic clinics, the VA, DME providers and direct to consumers nationwide.

We are a private equity backed company of roughly 220 employees on a multi-year growth plan. That means real investment, real pace, and a leadership team that is building infrastructure as it goes. It also means your work is visible and it matters.

The Role

The CEO and the executive leadership team are looking for an Executive Assistant who takes ownership of the administrative details so they can stay on the business. The right person anticipates what is coming, protects calendars with judgment rather than a rulebook, and becomes the person the leadership team goes to first because they always know where things stand.

You will support the CEO primarily, with defined support to the rest of the ELT finance, operations, sales, marketing and product and you will keep the HQ office running for the people who work in it.

What You’ll Do

Calendar and time

• 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

Communication

• 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

Meetings and board support

• 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

Travel and events

• 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

Office and administration

• 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

What We’re Looking For

Required

• 5+ years supporting a C-level executive
• Demonstrated discretion with confidential information
• Exceptional written communication
• Strong judgment about priority and urgency, and the confidence to say no on the CEO’s behalf
• Proven ability to run competing priorities for multiple executives without dropping details
• Professional presence and etiquette; this role is the front door to the executive team
• Advanced Microsoft 365 (Outlook, Word, Excel, PowerPoint, Teams), video conferencing, and expense and travel platforms
• Comfort with ambiguity and shifting priorities in a company that does not have deep administrative infrastructure
• Able to work on-site in Mequon, WI, with occasional early, late, or event hours

Preferred

• Experience supporting leadership in a private equity–backed or carve-out environment
• Familiarity with board governance processes and board material preparation
• Familiarity with ERP and purchasing systems (NetSuite), HubSpot, SharePoint, Smartsheet or similar
• Event planning experience: trade shows, sales meetings, offsites
• Administrative certification such as CAP (Certified Administrative Professional)

• Reports to: Chief Executive Officer
• Type: Full-time, exempt
• Schedule: Monday–Friday, core business hours, with flexibility around travel, board meetings, and company events
• Travel: Minimal -occasional local events and company meetings
• Compensation: $60,000–$70,000 base, plus annual bonus
• Benefits: Medical, dental and vision; 401(k); paid time off and holidays