Role Description We’re looking for a proactive, detail-oriented Executive Assistant to support both our CEO and COO. This is a high-trust role that sits at the center of the company’s leadership operations. You’ll manage competing priorities across two executives, keep information flowing across a distributed team, and help ensure leadership can focus on the decisions that matter most. This is an ideal fit for someone who thrives in fast-paced startup environments, is comfortable with ambiguity, and takes pride in being the person who makes everything run smoothly behind the scenes.

Key Responsibilities

• Calendar & Schedule Management
• Manage complex, shifting calendars for both the CEO and COO, proactively resolving conflicts and protecting focus time.
• Serve as the gatekeeper for executive time, using sound judgment to prioritize meeting requests, scheduling inquiries, and ad-hoc asks.
• Coordinate across time zones (US, Canada, Latin America) to schedule internal and external meetings.
• Meeting Preparation
• Prepare agendas, supporting documents, and briefing materials for leadership meetings, board meetings, and investor calls.
• Vendor Coordination & Procurement
• Serve as the primary point of contact for our IT vendor and other operational vendors.
• Research new vendors and tools as needed, preparing recommendations with pricing and capability comparisons.
• Travel Coordination & Expense Management
• Plan and book travel for leadership, including flights, accommodations, and detailed itineraries for offsites, conferences, and investor meetings.
• Tracking and processing expense reports and managing budgets for the executive or department.
• Recruiting & People Operations Support
• Assist with onboarding logistics for new hires as the team grows.
• Project Coordination
• Assisting with special projects, research, and data compilation as needed by the executive.
• Event Planning
• Coordinating company events, offsites, conferences, and team-building activities.
• General Operations & Organization
• Maintain and improve shared systems, documentation, and SOPs that keep the leadership function organized.
• Take on ad-hoc projects as they arise, the nature of a startup means no two weeks look the same.

Qualifications

• 2+ years of experience in an executive assistant or senior administrative role, ideally supporting C-suite or founder-level executives.
• Demonstrated experience in a remote-first environment, working across distributed teams and time zones.
• Fluent English proficiency (C1+ level) both written and verbal.
• Exceptional organizational skills with a strong attention to detail and the ability to manage multiple competing priorities.
• Proficiency with Google Workspace (Calendar, Gmail, Docs, Sheets), AI tools, scheduling tools.
• High degree of discretion and integrity in handling confidential information.
• Proactive, solutions-oriented mindset – you anticipate needs rather than wait to be told.
• Willingness to work Pacific Time (PST) hours to support CEO.

Preferred Qualifications

• Experience at a startup or high-growth company (Series A–C stage).
• Familiarity with ATS platforms (Ashby preferred, but Greenhouse, Lever, etc. are fine).
• Comfort with health tech, telehealth, or DTC consumer health businesses.
• Experience supporting multiple executives simultaneously with competing demands.

Benefits

• Up to $1,500 USD/month.
• Fully remote.
• Direct exposure to startup leadership at a fast-growing health tech company.
• Opportunity to grow the role as the company scales.

Interview Process

• Please refrain from messaging or emailing people directly; if you are interested, apply directly, your application will be reviewed by a human.
• Application & Criteria Questionnaire: When submitting your application and resume, tell us why you want to join Maximus and take your time with the questions. The Criteria Questionnaire will be sent to you automatically and is mandatory.
• Take home assignment (45min): Take home assignment to show us your prioritization, proactivity, and writing skills. Submit your take home directly to the Recruiting Lead via email.
• Chat with Recruiting Lead (30min): Chat with the Recruiting Lead to dive more into your background and fit for the role/company.
• Chat with COO (30min).
• Chat with CEO (30min).

Equal Opportunity Employer Maximus is an equal opportunity employer, which not only includes standard protected categories, but the additional freedom from discrimination against your free speech and beliefs, as long as they are aligned with company values. We celebrate intellectual diversity. Note: We utilize AI note-taking technology during our interview sessions to ensure we capture all answers and details accurately. Candidates are also encouraged to use AI note-takers for their own records if they wish.