Executive Assistant & Administrative Coordinator
Location: Chicago, IL
Reports to: CEO
About Us:
First Stop Health provides care that people love®?with our convenient, high-quality, and confidential virtual care solutions – Telemedicine, Virtual Mental Health, and Virtual Primary Care. We help our patients save time and money through compassionate care that’s available 24/7 via app, website, or phone.
First Stop Health offers a comprehensive benefits package that includes various health and medical coverage options, dental and vision coverage, disability, and life coverage, making healthcare easily accessible. For those that choose to waive medical coverage a monthly medical waiver allowance will be provided.
First Stop Health offers a remote-first work environment and flexible paid time off, including Summer Fridays. Furthermore, the employer match 401k plan and monthly phone stipend demonstrate the company's commitment to employee financial well-being. The First Stop Health membership benefit is another added perk for employees and provides Virtual Urgent Care, Virtual Mental Health, and Virtual Primary Care from their very first day!
Position Overview
The Executive Assistant & Administrative Coordinator is a key partner to the senior leadership team, providing high-level executive support while overseeing administrative functions that ensure efficiency and organization across the company. Reporting to the CEO, this role serves as a trusted partner, anticipating needs and ensuring that the executive’s time is optimized, priorities are aligned, and key initiatives are executed with efficiency. This role supports a remote senior leadership team located across the country and requires some (likely 1x a week on average) presence in our Chicago office location, as well as occasional travel for leadership meetings and company events.
The ideal candidate is proactive, detail-oriented, and highly organized, with the ability to manage complex schedules, coordinate high-impact projects, and facilitate seamless communication across a distributed executive team.
Key Responsibilities:
Executive Support
- Provide comprehensive administrative and strategic support primarily to the CEO and occasionally to other senior leaders, including calendar management, travel coordination, and expense reporting
- Act as a liaison between senior leadership and internal/external stakeholders, ensuring effective communication and follow-ups
- Manage meeting logistics, including agenda preparation, note-taking, and action item tracking
- Draft, edit, and prepare correspondence, presentations, and reports for executive meetings
- Handle confidential and sensitive information with discretion and professionalism
Administrative & Office Operations
- Oversee administrative functions to ensure smooth office operations on in-office days. This may also include supporting department initiatives, mail distribution, etc. for departments that are not located near the office
- Manage vendor relationships and the primary point of contact for all matters related to the company’s physical office space in Chicago, IL
- Support company-wide initiatives, events, and team engagement activities
- Assist with onboarding coordination for senior hires and key administrative processes
Project Coordination & Special Initiatives
- Assist in coordinating cross-functional projects, tracking deadlines, and ensuring timely execution of key initiatives
- Research and compile data for decision-making and strategic planning
- Identify and implement process improvements to enhance efficiency within the executive team
Travel & Meeting Coordination
- Arrange complex multi-city travel itineraries for senior executives and the Board of Directors
- Plan logistics for offsite Board meetings, leadership meetings, and company events
- Occasionally travel to support offsites and events
Qualifications:
Education:
Bachelor’s degree preferred, or equivalent experience
Experience:
- 5+ years of experience in executive support, administration coordination, or related roles, preferably in a fast-paced environment
- Must be proficient in Microsoft Office and virtual communication platforms (Zoom, Teams, Slack, etc.).
- Must have experience with project management and event planning
Skills:
- Exceptional organizational and multitasking skills
- Strong written and verbal communication
- Ability to anticipate needs and proactively solve problems
- Discretion in handling sensitive information
- Flexibility and adaptability in a dynamic, hybrid work environment
Work Environment & Travel
• Remote First: We are a remote first company. This role does require some in-office presence, on average 1x per week.
• Remote support: Must be comfortable working with a distributed senior leadership team across multiple time zones.
• Travel: Occasional domestic travel required for executive meetings, company events, and leadership offsites.
First Stop Health is committed to diversity, equity, inclusion, and belonging. Research shows that women, people of color and other historically underrepresented groups tend to only apply to jobs in which they meet all the job requirements. Unsure if you check every box? Apply. We would love to consider your unique experiences and how you could make First Stop Health even better.
To learn more about First Stop Health, visit www.fshealth.com and if you require any assistance during the application process or have questions, please don't hesitate to contact our talent acquisition team via email at careers@fshealth.com