Executive Assistant

Apree Health (parent company of Castlight Health and Vera Whole Health) is a healthcare company focused on improving access, experience, and outcomes. The Executive Assistant in the Office of the CEO partners closely with the CEO and supports the broader executive team to strengthen alignment, manage priorities, and enable high-impact leadership execution.

• Coordinate and manage the CEO’s calendar, inbox, and scheduling with a prioritization-first mindset
• Assess urgency and importance across meetings, requests, and commitments; flag tradeoffs and recommend focus areas
• Prepare agendas and materials for leadership meetings; track follow-ups and action items
• Coordinate internal and external meetings, travel, and logistics across time zones
• Anticipate needs and prepare context, materials, and follow-ups to keep executives operating at a high level
• Partner with senior leaders to coordinate schedules, planning cycles, and sensitive communications
• Provide communications support, ad hoc project coordination, and initiative support requiring discretion and strong follow-through
• Adapt quickly to evolving priorities and shifting business needs
• Plan and execute key company and leadership events, including offsites and Sales Kickoffs
• Support special initiatives, transformation efforts, and ad hoc projects as assigned
• Conduct basic research, organize data, and assist with presentation development
• Anticipate upcoming needs tied to business cycles, growth initiatives, or organizational change
• Strengthen executive operating rhythm and cross-functional coordination

• 5+ years of experience supporting a CEO or senior executive in a complex, fast-paced organization (experience supporting multiple executives preferred)
• Ability to manage priorities and assess urgency (judgment, not just execution)
• Comfort working across time zones and adapting to a fast-changing environment
• Advanced proficiency with Microsoft Office (Outlook, Word, PowerPoint, Excel)
• Comfort with collaboration tools (Teams, Zoom, SharePoint)
• Exceptional organization and disciplined follow-through
• Clear and concise communication skills
• High level of discretion and reliability with sensitive information
• Ability to operate independently and anticipate needs
• Familiarity with board support and executive governance processes

• Remote (East Coast)
• Flexibility required, including availability outside standard business hours when needed
• Compensation range: $32.21 to $48.32 per hour