Remote Finance Executive Assistant Jobs in Silver Spring, MD

Job Title: Executive Project Manager

Industry: Healthcare / Managed Care / Value-Based Care

Location (city, state): 100% Remote

Assignment Type: Contract-to-Hire

Pay: $35–$38/hour

Work Schedule: Full-time, 40+ hours/week; schedule requires flexibility and availability to support executive needs. Overtime eligible.

Benefits: This position is eligible for medical, dental, vision, and 401(k).

About The Company:

A growing, physician-led healthcare organization providing value-based, home and virtual care to patients with complex chronic conditions. Through coordinated clinical services and technology, the organization works to improve patient outcomes and reduce unnecessary hospital and ER utilization.

About The Department:

The department supports a national C-suite leadership team across the country, including the CEO, CFO, and CAO/CPO. This role will work closely with senior executives in a fast-paced, highly collaborative environment, providing high-level project management, operational, and executive support across multiple locations.

Job Description:

Seeking an adaptable and highly organized Executive Project Manager to support the CEO and senior leadership team in executing strategic priorities, growth initiatives, and enterprise-wide projects. This is a hands-on role for someone who can move quickly, manage multiple high-priority initiatives, and operate effectively in an environment where priorities can shift and processes may not always be fully defined.

The ideal candidate brings a combination of project management, executive support, business operations, presentation development, and strategic execution. Healthcare experience is preferred but not required; candidates from consulting, strategy & operations, business operations, or high-growth startup environments are encouraged to apply.

Key Responsibilities:

Project & Executive Operations

• Manage enterprise-wide strategic projects and organizational initiatives
• Coordinate executive action plans, implementation activities, timelines, and deliverables
• Maintain project plans, dashboards, status reports, and escalation items
• Coordinate cross-functional workstreams across clinical, finance, IT, sales, and operations
• Support new client contract implementation and go-live activities
• Maintain SOPs, policies, agreements, templates, and other key organizational documentation

Sales & Business Development Support

• Support proposal development and client/prospect information requests
• Develop executive sales decks, capabilities presentations, implementation charts, flowcharts, and client-facing materials
• Coordinate business development follow-up and implementation milestones
• Support client and prospective client meetings

Presentation Development

• Develop executive-level presentations for client meetings, Board Meetings, Investor Meetings, and strategic planning sessions
• Transform complex information and data into clear, visually compelling presentations
• Create presentation materials, infographics, leave-behinds, and executive documentation

Analytics & Reporting

• Develop executive dashboards and reports related to program performance, member outcomes, contract compliance, business development, and event effectiveness
• Monitor KPIs and identify trends, gaps, and areas requiring executive attention
• Support ad-hoc reporting and data analysis for executive leadership, finance, and sales

Conference & Event Management

• Lead planning and execution for industry conferences and client events
• Coordinate venues, registration, speakers, sponsorships, materials, logistics, and post-event reporting
• Support provider events, community outreach programs, and leadership conferences

Administrative Operations

• Support the Chief Administrative Officer with action-item tracking and executive deliverables
• Coordinate with external legal and actuarial partners
• Track contracts, MOUs, licensing, and insurance documentation
• Support leadership meetings, agendas, materials, and follow-up
• Maintain document, presentation, proposal, and template libraries
• Support implementation and go-live coordination for new client contracts

Qualifications:

• Minimum 5 years of project management experience
• Minimum 3 years supporting executive leadership
• Experience in Executive Project Management, Strategy & Operations, Consulting, Business Operations, Healthcare Operations, or a high-growth/startup environment
• Strong executive presence and communication skills
• Comfortable supporting sales/business development, client meetings, presentations, and follow-up
• Advanced PowerPoint, Excel, and Word skills
• Strong Microsoft 365 and Teams experience
• Comfortable with AI and technology productivity tools and able to learn new technology quickly
• Experience with Salesforce, HubSpot, Monday.com, Smartsheet, Power BI, or Tableau preferred
• Adobe Creative Cloud or Canva experience preferred
• Healthcare, managed care, or value-based care experience preferred but not required
• Experience with dashboards/analytics and conference or event management preferred
• Bachelor’s degree in Business Administration, Healthcare Administration, Organizational Leadership, or related field required

Additional Details:

This is a high-visibility, fast-moving role supporting the CEO and C-suite leadership team. The successful candidate must be comfortable operating with urgency, juggling multiple competing priorities, and executing without needing extensive structure or direction. Strong PowerPoint skills are particularly important, and candidates will complete a 30-minute PowerPoint exercise as part of the interview process.

The interview process is entirely virtual and includes:

1. 30-minute meeting with leadership
2. Panel interview with the Chief Administrative Officer and panel
3. 30-minute PowerPoint exercise within 24 hours of the panel interview
4. Final meeting with the CEO

Perks:

• 100% remote opportunity
• Direct exposure to CEO and C-suite leadership
• High-visibility strategic projects
• Opportunity to work across strategy, operations, sales, analytics, and business development
• Contract-to-hire with $95,000–$100,000 salary potential upon conversion
• Opportunity to join a growing healthcare organization at an exciting stage of growth

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.