Senior Executive Assistant

I’m looking for an experienced Executive Assistant who is organized, resourceful, a strong communicator and enjoys being part of a fast-moving environment.

I own Medicare Answers Now, a national insurance agency with 15 employees, but my work extends well beyond the company. I lead a national healthcare organization, serve in industry leadership roles, speak across the country, participate in national events, and work extensively in healthcare policy and advocacy.

There is always something interesting going on, and I’m looking for someone who can become a trusted partner in keeping the day-to-day details organized and moving.

What You’ll Do

• Manage my calendar, meetings and scheduling across multiple organizations
• Coordinate travel, itineraries, speaking engagements and conferences
• Help prepare for meetings and make sure materials and information are ready
• Draft routine emails and correspondence
• Track deadlines, requests and follow-up
• Maintain files, contacts and executive information
• Coordinate with our team, executives, event organizers, vendors and industry partners
• Handle expenses and other executive administrative responsibilities
• Help identify scheduling conflicts or missing details before they create problems
• Handle occasional personal scheduling and logistics

Communication Is a Big Part of This Job

I cannot do my job effectively without good communication, and I need an Executive Assistant who is comfortable communicating with me even when I’m busy.

That means reminding me when I’m running behind, interrupting me when I need to move to the next meeting, following up when I’ve forgotten something, and telling me when you need an answer from me to keep something moving. If something changes or you’re concerned about a deadline, I need to know.

You are not bothering me by doing those things. That is part of the job.

At the same time, I don’t expect you to read my mind or know everything. Ask questions when you need context. Tell me when something doesn’t make sense. If you think there’s a better way to handle something, say so.

I want an EA who communicates with me, not someone who quietly works around me.

What I’m Looking For

• 5+ years of Executive Assistant or senior-level administrative experience
• Experience supporting a CEO, founder, executive or other senior leader
• Excellent written and verbal communication
• Strong organization and attention to detail
• Good judgment and discretion
• Ability to anticipate needs and think ahead
• Strong problem-solving skills
• Experience managing calendars and travel
• Confidence communicating with executives and external partners
• Ability to manage changing priorities without losing track of details
• Strong technology skills, including AI and modern productivity tools
• Reliable follow-through
• Enough confidence to respectfully interrupt, remind and redirect me when necessary
• A sense of humor and the ability to roll with the occasional curveball

Healthcare or insurance experience is helpful but not required.

How We Work

This is a high-trust position with a lot of autonomy, but autonomy doesn’t mean silence.

I’ll give you context and the outcome I’m trying to achieve. Sometimes I’ll know exactly what I want. Other times, we’ll figure out the best approach together.

I appreciate initiative, and I also want you to ask when you’re unsure rather than guess. Mistakes happen. Communicate, fix them, learn from them and move forward.

I want this person to become someone I can rely on, bounce things off of and trust with the details while I’m focused on the bigger picture.

Compensation & Benefits

Compensation is competitive and based on experience and demonstrated capability.

Benefits include medical coverage, 401(k), $50,000 employer-provided life insurance, two weeks vacation, two weeks sick time, paid company holidays, Thanksgiving week off, the week between Christmas and New Year’s off, and flextime.

The Bottom Line

I’m looking for someone who enjoys making things work, communicates well and takes pride in being dependable.

You’ll have a front-row seat to a growing business and a lot of interesting work happening across healthcare, advocacy, education and events. No two weeks will look exactly alike.

If you’re organized, confident enough to speak up and know that sometimes the best way to support a busy executive is to say, “Amanda, you have to go,” I’d love to hear from you.

Pay: From $55,000.00 per year

Bene…