Executive Assistant to Chief of Staff Growth Track (12-18 months)

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About the Opportunity The organization is seeking an agile, execution-focused professional for the role of Executive Assistant to Chief of Staff Growth Track (12-18 months). Serving within the Office of the CEO, this role acts as the central execution partner to executive leadership, driving operational efficiency, calendar management, project tracking, hiring workflows, and organizational accountability.

This role is structured with a defined advancement pathway: successful performance and compounding trust transition this position from executive operational support into a Chief of Staff capacity over a 12-to-18-month timeframe.

Role Details

  • Role Title: Executive Assistant to Chief of Staff Growth Track (12-18 months)
  • Employment Type: Full time
  • Location: United States (Remote, with strong working overlap during Eastern Standard Time hours)

Key Responsibilities

  • Calendar and Schedule Management: Protect executive focus blocks, batch meetings, enforce daily and weekly priorities, and ensure calendar allocation directly reflects organizational goals.
  • Operational Communication and Follow-Up: Direct internal follow-up mechanisms across messaging and email channels, tracking deliverables, action item owners, and deadlines to maintain operational momentum.
  • Organizational Project Management: Manage and standardize the company operating system across tools such as Asana, Trello, or Notion, establishing clear milestones, project owners, and definitions of completion across departments.
  • Hiring Operations: Coordinate end-to-end recruitment logistics for key company roles, managing candidate pipelines, scheduling, scorecards, assignments, reference checks, and candidate communications.
  • Content Workflow Tracking: Oversee production and scheduling cadences across video, email, and social publication channels, tracking deliverables and approvals to guarantee deadlines are met.
  • Financial and Operational Metrics: Collect and evaluate monthly profit and loss statements, monitor KPI dashboards, track operational expenses, audit payroll data, and provide recommendations on compensation adjustments and operational efficiency.
  • Special Initiatives: Lead operational and administrative projects supporting executive bandwidth, including expense audits, vendor cancellations or renegotiations, and facilities coordination.
  • AI Implementation: Apply AI tools to streamline day-to-day administrative and operational workflows, sharing practical guidance with department leaders on incorporating AI into their operational processes.

Career Progression and Onboarding

  • Weeks 1–4 (Context and Integration): Shadow executive meetings and communications, assimilate decision-making principles, and assume direct ownership of scheduling, documentation, and action items.
  • Days 30–60 (Systems Ownership): Take full ownership of the organizational follow-up cadence, conduct structured weekly planning sessions, and lead hiring operations and key cross-functional tasks.
  • Days 60–90 (Executive Operator Cadence): Run recurring reporting rhythms, coordinate operational prep for executive meetings, and independently direct core operational initiatives.
  • Months 3–18 (Chief of Staff Track): Transition into high-level organizational leverage based on performance, including strategic planning rhythms, decision memos, cross-functional problem solving, and steering major company initiatives.

Required Qualifications

  • Demonstrated experience in executive operational support, executive assistance, or project management.
  • Proven track record of managing executive calendars, meeting schedules, and multi-channel internal communications.
  • Strong proficiency with project management platforms such as Trello, Asana, or Notion, alongside tools like Google Workspace, Slack, Zoom, and Loom.
  • Practical experience coordinating recruitment processes or managing candidate pipelines.
  • Direct working familiarity with AI tools (such as ChatGPT) to automate tasks, synthesize information, and optimize workflows.
  • Absolute discretion and reliability when handling highly confidential organizational, financial, and payroll information.
  • Exceptional written and verbal communication abilities, with the skill to deliver precise reports and hold cross-functional team members accountable.
  • Availability to work remotely within the United States while maintaining strong working overlap with Eastern Standard Time (EST) business hours.

Preferred Qualifications

  • Professional proficiency in Spanish (conversational or fluent).
  • Prior experience working within a fast-growing education, software, or digital media environment.

Compensation

  • Mid-Level Executive Operations: $60,000 - $100,000 base salary, plus performance bonus.
  • Senior Operator: $120,000 - $170,000 base salary, plus performance bonus.
  • Actual compensation offers correspond to candidate experience, seniority, and demonstrated capabilities.
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