Chief of Staff

Schoolhouse

13d•$179,000 - $196,000•Remote

About The Position

Schoolhouse is seeking a Chief of Staff to help achieve its ambitious 2028 vision by launching key systems, projects, and partnerships. This is a generalist role operating at the center of a fast-growing nonprofit, offering exposure to education leaders and partners. The Chief of Staff will report to the President, taking 0-to-1 bets from idea to early traction, representing Schoolhouse to stakeholders, and managing the organization's operating rhythm. The role involves strategic projects, external relations, and business operations, with the flexibility to evolve as the organization grows. The position requires availability to work in a US timezone.

Requirements

At least 5+ years in a Chief of Staff, operating, or strategy role (founder/early operator at a high-growth startup, or consulting/banking/strategy with hands-on operating experience).
Proven experience taking something from 0 to 1 (a new program, product, or partnership).
Ability to thrive in high ambiguity, turning vague problems into plans, momentum, and results.
Experience in external, high-stakes settings, operating closely with executives.
High-polish writing and speaking skills for credible representation to funders, partners, and the team.
High-output capability across both breadth and depth, with the ability to context-switch effectively.
Exceptional communication skills and ability to build trusted relationships internally and externally.
Sound judgment regarding people and priorities, with discretion to handle sensitive situations.
Strong ownership mentality, filling gaps, asking for help when needed, and following through independently.
Availability to work in a US timezone.

Nice To Haves

Experience with fundraising, development, or board and donor relations.
Experience in education, ed-tech, or another mission-driven organization.

Responsibilities

Lead high-impact, 0-to-1 strategic projects that advance the 2028 vision, such as fundraising or growth strategy.
Run validation experiments, analyze results, and make recommendations for scaling, pivoting, or cutting initiatives.
Serve as a trusted liaison for high-stakes partners, donors, and stakeholders, articulating goals and vision clearly.
Assess how new partners or projects fit the ecosystem and resourcing, providing recommendations for cultivation and securing relationships.
Manage the operating rhythm of the organization and ensure follow-through on decisions to achieve outcomes.
Support critical work across HR, legal, and finance.
Drive people operations, including hiring processes and biannual team retreats.