Chief of Staff Medicare Answers Now Cleveland, OH Job Details Full-time From $85,000 a year 22 hours ago Benefits Health insurance 401(k) Paid time off 401(k) matching Professional development assistance Flexible schedule Life insurance Qualifications Executive administrative support Research Project management Task prioritization Meeting facilitation Portfolio management Critical thinking Full Job Description I'm looking for a Chief of Staff who can help me manage a very full professional portfolio without becoming another layer of management. I own Medicare Answers Now, a national insurance agency with 17 employees, and my work extends well beyond the company. I also lead Trusted Healthcare Alliance, produce national industry events, serve in industry leadership roles, speak across the country and work extensively in healthcare policy and advocacy. There are a lot of moving pieces. I need someone who can see the whole board. What You'll Do Keep CEO priorities, commitments and strategic initiatives moving Turn meetings and ideas into owners, deadlines and action Prepare me for important meetings and decisions Research issues and bring me conclusions, options and recommendations Track follow-through so I don't have to Coordinate priorities across multiple organizations and initiatives Manage CEO-level special projects Identify problems, conflicts and missed dependencies early Help determine what needs my attention and what doesn't Work closely with our COO and leadership team without stepping into their operational responsibilities Push back when you think I'm wrong or trying to do too much What I'm Looking For You are smart, resourceful and exceptionally organized, but organization alone isn't enough. You need excellent judgment. You anticipate. You ask good questions. You connect dots. You can take an objective without being given every step. When something goes wrong, your instinct is to understand it and find a solution. You also know when something is important enough to bring to me. We're looking for: 7+ years of progressive professional experience Experience working directly with senior executives, founders or organizational leaders Exceptional written and verbal communication Strong critical thinking and problem-solving skills Excellent judgment and discretion Demonstrated project and priority management Confidence interacting with senior executives and external stakeholders Comfort with ambiguity and changing priorities Strong technology skills, including AI and modern productivity tools Chief of Staff experience is preferred but not required. Healthcare or insurance experience is helpful, but I care more about how you think. This is not an Executive Assistant position. Administrative support, calendar management and travel logistics are separate from this role. The Bottom Line I don't need someone to follow me around taking notes. I need someone who can hear what we're trying to accomplish, understand the moving pieces, make sure the right people are moving them forward and tell me when something needs my attention. If you're the kind of person who naturally thinks three steps ahead, I want to talk to you.

Pay:

From $85,000.00 per year

Benefits:

401(k) 401(k) matching Flexible schedule Health insurance Life insurance Paid time off Professional development assistance Application Question(s): Tell me about a time you had to coordinate multiple priorities across different teams or organizations without having direct authority over everyone involved. What was your role and how did you keep the work moving?

Experience:

Project management: 2 years (Preferred) reporting to the

CEO:

5 years (Required) Willingness to travel: 25% (Required)

Work Location:

Hybrid remote in Cleveland, OH 44134