Executive Assistant to Chief of Staff – Growth Track
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Job Description
Executive Operations assistant protecting an education and software CEO’s time through calendar, accountability, hiring, and project management. Performance-based path to Chief of Staff.
Responsibilities:
- Own and optimize the CEO’s calendar, protecting deep-work blocks and aligning schedules with company goals
- Run internal follow-ups, action items, reminders, escalations, and communications across Slack, WhatsApp, and email
- Build and manage the company operating system using Trello, Asana, Notion, or similar tools
- Track project owners, deadlines, next actions, and definitions of done
- Hold leaders and teams accountable for deliverables and reporting cadence
- Run end-to-end hiring operations, including pipeline management, scheduling, scorecards, assignments, Loom reviews, and references
- Oversee content operations for YouTube, Instagram, and email without creating content
- Track weekly content output, deadlines, approvals, and delivery
- Collect monthly P&L data, KPI dashboards, and weekly reports
- Analyze profit and loss statements and payroll, and provide recommendations on raises, compensation structures, inefficiencies, and staffing
- Execute personal and local projects supporting business performance, such as managing a home studio build-out
- Advise department leaders on practical AI use in their daily responsibilities
- Complete scheduling, meeting notes, and action-item tasks during onboarding
- Progress from execution and systems ownership into Chief of Staff-style planning, cross-functional problem-solving, and high-priority initiative management
Requirements:
- Highly organized and extremely self-accountable
- Strong project management skills; experience with Trello, Asana, or similar tools
- Exceptional attention to detail
- Strong writing and communication skills, including detailed reports and clear, direct updates
- Ability to make good decisions independently and anticipate needs
- Ability to hold people accountable and handle tough conversations
- Discretion, trustworthiness, and comfort with high confidentiality and sensitive information
- Comfort with high access and high expectations
- Experience or fluency using AI tools in daily workflows; at minimum, ChatGPT instead of Google
- Familiarity with Google Workspace, Slack, Trello/Asana, Calendly, Zoom, and Loom
- Spanish preferred but not required
- Strong overlap with EST working hours
- Must complete a required 5-minute camera-on Loom video submission
- Must complete the final assignment involving a Google document and embedded YouTube videos
Benefits:
- Performance bonus
- High-speed CEO training and full context into CEO decision-making
- Growth track to Chief of Staff over 12–18 months, performance-based
- Remote work with strong overlap with EST working hours
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