[Hiring] Chief of Staff @Schoolhouse

Role Description

We're looking for a Chief of Staff to take our ambitious 2028 vision and launch the key systems, projects, and partnerships that get us there. This is a rare generalist role for someone who wants to operate at the center of a fast-growing nonprofit that is already the largest free human tutoring organization in the world.

Reporting to the President, you'll take our most important 0-to-1 bets from idea to early traction, represent Schoolhouse to our most important stakeholders, and run the operating rhythm that keeps the organization on track. The work touches nearly every part of the organization and it will evolve as we do.

You'll own three things:

• Strategic projects: Lead high-impact, 0-to-1 projects that advance our 2028 vision like fundraising or growth strategy. Run validation experiments, read the signal honestly, and build the case for whether to scale into a full initiative, pivot the approach, or cut it entirely.
• External relations: Serve as a trusted liaison for high-stakes partners, donors, and stakeholders. Understand and articulate our goals and vision clearly, judge how a new partner or project fits our ecosystem and resourcing, and turn that into recommendations for the relationships we should cultivate and secure.
• Business operations: Run the operating rhythm of the organization and the follow-through that turns decisions into outcomes. Support critical work across HR, legal, and finance, and drive the people operations that keep us healthy, like hiring processes and our biannual team retreats.

Some examples of what this could look like in your first year:

• Design and pilot a suite of new fundraising channels, then write the roadmap that decides which channels we scale and how.
• Run point on a new organizational growth partnership (akin to the College Board) from first conversation through scoping, agreement, and pilot launch.
• Revamp an existing operational workflow, like our term planning or hiring process, into an improved version that the whole team uses.
• Plan two company retreats end to end, from strategic objectives to agenda to logistics.

Qualifications

• At least 5+ years in a Chief of Staff, operating, or strategy role — as a founder / early operator at a high-growth startup or in a consulting / banking / strategy role with hands-on operating experience since.
• You've helped take something from 0 to 1: a new program, product, or partnership.
• You thrive in high ambiguity. You can take a vague, high-stakes problem with no clear owner and turn it into a plan, momentum, and a result.
• You shine in external, high-stakes settings and have operated closely with executives. Your writing and speaking are high-polish, and you can represent Schoolhouse credibly to a funder, a partner, or the whole team.
• You're high-output across both breadth and depth. You context-switch without dropping balls, create clarity amid the noise, and build high-quality things fast.
• You are an exceptional communicator who builds trusted relationships easily — internally across every function, and externally with partners and stakeholders.
• You have sound judgment about people and priorities, and the discretion to handle sensitive situations well.
• You have a strong ownership mentality. You fill gaps, ask for help when you need it, and follow through without being managed.
• You're available to work in a US timezone.

Bonus Points

• You have experience with fundraising, development, or board and donor relations.
• You have experience in education, ed-tech, or another mission-driven organization.

Benefits

• Work with an amazing team. We’ve got folks with backgrounds in education, consulting, astrophysics, startups, and more.
• Fully remote with flexible working hours.
• Meetings are in US Pacific Time mornings.
• Take real time off. We have unlimited PTO & use it. Folks regularly take time off throughout the year.
• Competitive salary and comprehensive benefits.
• Work-from-home stipend. Professional development budget. Health, dental, vision (for US employees).
• Semesterly retreats and monthly regional meetups.
• Make an impact you can see. Check out our community stories page. Watch students help each other learn. See tutors grow into leaders. Your work will help real people learn and grow.

About the Application Process

We might make some adjustments, but our previous interview process has consisted of:

• A 30 minute intro call.
• A 45 minute past project walkthrough with Matt.
• A 45 minute strategy case with the leadership team.
• A 45 minute panel-style discussion with team members across functions.
• Reference calls.

We’re building an inclusive and equitable platform for learners across the world, and it’s important our core team reflects these principles too. We strongly encourage people from underrepresented groups to apply!