Executive Assistant - 19116

We are a team of purpose-driven individuals who find meaning in service. Every one of us is here because we care deeply about people — and we believe our work should uplift, support, and unlock the potential in others.

We’re seeking an Executive Assistant who brings world-class excellence to organization, communication, and execution. The ideal candidate thrives in turning complexity into clarity and chaos into systems. You should be detail-oriented, solutions-driven, and proactive in anticipating needs.

Above all, we are looking for someone who aligns with our core values and brings integrity and care to every interaction.

This is a full-time (40 hrs/week), fully remote role supporting the CEO of Vita High School and the Learner-Driven Education Alliance.

You will act as the operational and communications anchor for the CEO — ensuring that no message, meeting, or priority falls through the cracks. You will own inbox and calendar management, streamline communications, and serve as a trusted liaison between the CEO and both internal and external stakeholders.

This is more than an administrative role. It’s an opportunity to partner closely with a founder driving a national movement in learner-driven education.

• Own and manage the CEO’s email inbox end-to-end: prioritize, organize, and respond
• Maintain a same-day response standard (within 8 hours)
• Draft responses in the CEO’s voice and escalate only when necessary
• Identify and highlight time-sensitive or high-priority messages
• Maintain a consistently organized, near “Inbox Zero” environment

• Manage communications across multiple platforms, including:
  • Email
  • WhatsApp
  • SMS / text messaging (via LeadConnector or similar tools)
  • Slack (if/when adopted)
• Act as the primary communication liaison between the CEO and internal team
• Ensure timely responses and clear communication flow across all channels

• Own and maintain a highly accurate, up-to-date calendar
• Proactively schedule, reschedule, and resolve conflicts
• Coordinate internal meetings and support scheduling with external stakeholders
• Align scheduling with a structured weekly framework (“Perfect Week”)
• Manage scheduling across tools such as Google Calendar and LeadConnector

• Provide day-to-day administrative and operational support
• Exercise sound judgment in prioritization, delegation, and time management
• Proactively identify opportunities to improve efficiency and workflows
• Support the CEO by managing competing priorities and protecting focus time

• Participate in regular check-ins with the CEO (minimum 3x per week)
• Come prepared with updates, priorities, and key items requiring attention
• Ensure strong alignment on ongoing tasks and initiatives

• Highly organized with the ability to manage complex calendars and multiple priorities
• Proactive and solutions-oriented, with a strong sense of ownership
• Strong communicator, comfortable interacting with a range of stakeholders
• Demonstrates discretion, professionalism, and sound judgment
• Comfortable operating in a fast-paced, evolving environment
• Confident in managing upward and providing thoughtful input when needed

• Highly structured, repetitive work with limited variability
• Minimal ownership or decision-making responsibility
• Limited interaction or communication across teams

• Exceptional organizational and time management skills
• Strong calendar management and prioritization capabilities
• High level of discretion and confidentiality
• Excellent written and verbal English communication skills
• Experience with tools such as Gmail, Google Calendar, WhatsApp, and messaging platforms
• Full-time availability (40 hrs/week) with flexibility to align with the CEO’s schedule

• Experience supporting senior executives or founders
• Familiarity with GoHighLevel / LeadConnector
• Experience using AI tools (e.g., ChatGPT, Claude) for drafting communications
• Background in education or mission-driven organizations

• The CEO’s time and focus are consistently protected and optimized
• Communications are handled promptly, clearly, and professionally across all channels
• The calendar operates seamlessly with minimal intervention from the CEO
• Internal stakeholders feel informed, supported, and aligned
• Daily operations run smoothly with clarity and efficiency