Executive Assistant (Windsor)

We are seeking an experienced and highly resourceful Executive Assistant to provide dedicated support to multiple C-suite executives in a remote-first environment. This role requires exceptional organizational discipline, strong judgment, and the ability to seamlessly manage competing priorities across a distributed team.

Key Responsibilities:

• Manage complex, high-volume calendaring across multiple executives, time zones, and shifting priorities
• Oversee and prioritize multiple executive inboxes, ensuring timely, accurate, and thoughtful communication
• Prepare, submit, and reconcile expense reports with precision and attention to detail
• Coordinate internal and external meetings, including agendas, materials, and follow-ups
• Anticipate scheduling conflicts, operational gaps, and executive needs proactively resolving issues before they arise
• Serve as a trusted partner and gatekeeper to leadership, maintaining confidentiality and professionalism
• Collaborate cross-functionally with internal teams and external stakeholders in a fully remote environment
• Supporting and managing content for Town Halls, major meetings and significant communications
• Support ad hoc projects and operational initiatives as needed

Qualifications:

• 3+ years of direct Executive Assistant experience supporting senior executives (C-suite experience strongly preferred)
• Proven ability to manage multiple stakeholders and priorities simultaneously
• Exceptional attention to detail and organizational skills
• Strong critical thinking, problem-solving ability, and sound judgment
• High level of proactivity, adaptability and composure in rapid-changing environments
• Excellent written and verbal communication skills
• Self-directed and highly reliable in a remote work setting
• Flexibility to support executives across Central and/or Eastern Time zones, with availability outside standard hours as the norm

What Success Looks Like:

• Calendars are proactively managed and calls are prioritized effectively
• Executives are consistently prepared and aware of upcoming critical items on their calendars
• Competing priorities are managed seamlessly without escalation
• Communication is clear, proactive, and aligned across stakeholders
• You operate as a trusted extension of the leadership team