Chief of Staff

This is a fully remote position, open to applicants in United States.

📋 Description

• Collaborate closely with the CEO and Executive Team to convert vision and goals into actionable strategy, execution, and efficient operations.

• Tackle ambiguous, high-impact challenges and spearhead growth initiatives.

• Provide essential support and staffing to the CEO.

• Design, implement, and refine operating rhythms such as weekly staff meetings, quarterly planning, and annual strategy and goal-setting sessions.

• Ensure the Executive Team remains aligned, accountable, and operates with agility.

• Proactively identify organizational issues and facilitate their resolution.

• Organize and safeguard the CEO's schedule while preparing materials and background information for external meetings.

• Lead strategic initiatives from start to finish, encompassing diagnosis, alignment, execution, and closure.

• Assist in M&A evaluations, philanthropic fundraising, cross-functional strategies, executive offsite planning, and operational enhancements.

• Compose team meeting talking points, investor updates, board materials, and customer follow-ups in the CEO's voice.

• Monitor organizational signals through interactions with product teams and customer calls, providing the CEO with insights and recommended actions.

• Act as a thought partner to executive and senior leaders across go-to-market, finance, product strategy, and talent sectors.

• Challenge leadership perspectives and facilitate alignment across various functions.

• Willingness to travel 15–20% of the time.

⛳️ Requirements

• Ideal candidates will have K-12 education experience or experience in a high-growth technology startup.

• 6+ years of experience in a chief of staff, strategy, operations, management consulting, banking, or a comparable role supporting senior executive leadership.

• Outstanding written and verbal/presentation skills suitable for executive-level communication.

• Capability to write in another person's voice for diverse audiences and simplify complex concepts.

• A genuine interest in how AI and emerging technologies are transforming business and education.

• Proven track record of managing cross-functional initiatives, driving decisions, and achieving results without direct authority.

• Strong analytical and structured thinking capabilities.

• Ability to synthesize intricate information and present it as clear recommendations.

• Experience in designing and managing operating cadences, including leadership syncs, goal/OKR processes, and strategic planning cycles.

• Demonstrated capacity to quickly acclimate to a complex environment and strategically think across multiple functions.

• High level of integrity, discretion, and professionalism when handling sensitive business, team, and strategic information.

• Passionate about enhancing education for every student.

• Strong experience in utilizing and developing AI agents is preferred.

🏝️ Benefits

• Competitive salary along with a performance-based bonus structure.

• Comprehensive health, dental, and vision benefits.

• 401(k) retirement plan with company matching contributions.

• Flexible remote work arrangements.