Jobs at Outschool (Now Hiring) — 11 open

The Role

Outschool is on a path to become the leading Education Savings Account (ESA) platform in the country. Over the past few years we built the operations and systems that made that growth possible — entering new funding marketplaces, standing up reimbursement, and serving families across a fast-growing set of state programs. As the public-funding program matures from building new systems to running and scaling them, we’re creating this role to be the connective tissue that keeps it all moving — and continually makes it run better and scale.

The Public Funding Project Lead leads cross-functional execution across Customer Experience, Marketing, Legal, Finance, and Product — turning strategy into coordinated, on-time delivery for launches, new-program onboarding, and reimbursement expansion. Just as importantly, you’ll be our internal expert on the ESA family: the person who lives and breathes the persona and makes sure everything we ship reflects how these families actually navigate their funding. You’ll also lead our push to use AI to work faster and more efficiently, turning manual processes into scalable automations. 

As the program’s work distributes to teams across the company, you’ll be the point person who keeps a multi-team effort aligned, spots risks before they become problems, brings deep ESA expertise to bear on our strategy, and raises the bar on how we execute.

At other companies, this role would be equivalent to a senior position. At Outschool we have decided to take an unconventional approach to titling that aligns with our values and is focused on impact above status. You can learn more about our titling philosophy here.

CORE RESPONSIBILITIES:

• Lead cross-functional execution of public-funding and ESA initiatives across CX, Marketing, Legal, Finance, and Product — translating strategy into coordinated project plans, clear owners, and on-time delivery.
• Build trusted working relationships with the owners in each function — CX, Marketing, Legal, Finance, and Product — well enough to understand their real constraints and broker tradeoffs.
• Act as Outschool’s internal ESA-family expert, bringing the lived persona into product, go-to-market, and support decisions, and pressure-testing our messaging and experience before it reaches families.
• Own the project-management systems and operating cadence for the public-funding program — roadmaps, dependencies, status tracking, and clear decision-making across teams.
• Drive and coordinate AI-enabled efficiency — identify and (with engineering as needed) build automations such as order-fulfillment and invoicing workflows that reduce manual effort and help the program scale.
• Continuously look for ways to improve and scale ESA operations — spotting inefficiencies and bottlenecks, streamlining and automating workflows, and building processes that hold up as volume grows.
• Keep our distributed operating model coordinated: ensure the teams that own individual pieces of public funding stay aligned, and proactively surface and resolve risks.
• Partner with the Partnerships Lead to coordinate the internal execution of partner-driven launches, keeping Product, CX, Legal, and Finance aligned as new partners and programs come online.

DESIRED EXPERIENCE & SKILLS:

• Proven project or program management experience leading cross-functional initiatives to on-time, on-budget delivery.
• A track record of acting as a trusted partner across functions — not just tracking a plan, but building enough credibility with each team that they bring you problems early.
• Comfortable working through disagreement: can surface competing priorities between teams, facilitate toward a decision, and communicate tradeoffs and risks to stakeholders clearly, even without formal authority.
• Strong operational and process orientation, with the ability to turn ambiguous, fast-changing requirements into clear, repeatable workflows.
• A track record of not just running operations but improving them — finding efficiencies and building processes that scale with growth.
• Demonstrated use of AI tools to speed up delivery and improve efficiency.
• Deep understanding of — or the ability to quickly ramp on — the ESA, public-funding, and homeschooling landscape and the families it serves.

OTHER CONSIDERATIONS:

• • Lived experience with ESAs, homeschooling, or education-choice programs
  • Previous EdTech or online-marketplace experience
  • Previous experience in startups, especially in the hypergrowth phase