Careers at Outschool.org

About Outschool.org

Outschool.org is a nonprofit organization committed to ensuring all families — especially those from historically underserved communities — can access and make the most of education funding programs like Education Savings Accounts (ESAs), microgrants, and other direct-to-family funding initiatives. Through tools, resources, and personalized support, we help families navigate their educational options with confidence.

Since 2021, we’ve supported tens of thousands of families and partnered with over 40 community organizations and multiple state agencies to deploy more than $100M in education funding directly to families.

You may recognize our for-profit sister organization, Outschool.com. Our work in the education sector is often aligned and complimentary but we operate independently.

What It’s Like to Work at Outschool.org

  • We honor rest and real life. Our generous pay and unlimited time off reflect a belief that rest fuels the work. Most folks take 6+ weeks off each year, no guilt attached.

  • We trust each other deeply. You'll have room to lead, explore, and stretch without micromanagement. Self-direction is the norm, not the exception.

  • We show up with open hands. Titles and hierarchy matter less than presence, thoughtfulness, and the willingness to do what needs doing. Everyone rolls up their sleeves.

  • We build for belonging. Our work is rooted in care for BIPOC families and communities navigating systems not designed for them. That means humility, listening, and evolving — always.

  • We’re here for the swirl. If you need a roadmap with mile markers, this isn’t your place. The work shapeshifts. That’s the point. We learn as we go, and we love that.

  • Our culture is warm, messy, and human. We laugh a lot. We drop the occasional f-bomb. We’re more “voice notes and gifs” than memos and protocols.

  • Play is part of the practice. Our retreats aren’t strategy marathons — they’re about fun, food, movement, connection, and playing full out together.

  • Curiosity is sacred. We ask good questions, follow hunches, and know that creativity blooms when rules take a back seat.

  • You’ll thrive here if... you’re values-rooted, flexible, collaborative, and excited to co-create something that’s never been done before.

  • You probably won’t love it if... you crave predictability, prefer formality, or feel safest with lots of structure and clearly drawn lines.

OPEN POSITIONS

Senior Project Manager/Project Director

Full-Time | Remote | Outschool.org

About Outschool.org

Outschool.org is a nonprofit organization committed to ensuring all families — especially those from historically underserved communities — can access and make the most of education funding programs like Education Savings Accounts (ESAs), microgrants, and other direct-to-family funding initiatives. Through tools, resources, and personalized support, we help families navigate their educational options with confidence.

Since 2021, we’ve supported tens of thousands of families and partnered with over 40 community organizations and multiple state agencies to deploy more than $100M in education funding directly to families.

The Opportunity

We’re hiring a Senior Project Manager (or Project Director) to lead and strengthen how Outschool.org delivers projects that help families access and use ESA funds effectively — and to improve the internal systems that make that delivery scalable, consistent, and high quality.

This role sits at the intersection of program delivery, partner management, and internal operations. You’ll support a portfolio of client-facing projects (including state, vendor, funder and community partnerships) while also driving improvements to the internal tools, workflows, and reporting systems that power those projects across teams.

It’s ideal for a leader who thrives in a fast-moving, collaborative environment — someone who can balance external relationship management with internal systems thinking to help our organization scale impact confidently and sustainably.

Key Responsibilities

Project Leadership & Delivery (35%)

  • Lead multiple concurrent projects — including ESA contracts and grant-funded initiatives —  projects from kickoff through completion.

  • Define scope, deliverables, and success metrics in collaboration with internal and external stakeholders.

  • Develop project plans, track milestones, and ensure timely, high-quality execution.

  • Manage stakeholder communications, project documentation, and reporting.

  • Anticipate and mitigate risks; ensure projects stay aligned with mission and partner expectations.

  • Managing contractor resources to deliver projects. 

Internal Operations & Systems (30%)

  • Design and maintain internal project management systems, templates, and workflows that improve consistency and visibility across teams.

  • Support implementation of tools such as Airtable, Asana, or similar systems for tracking deliverables, deadlines, and dependencies.

  • Collaborate with team leads to align resourcing and ensure efficient handoffs between functions.

  • Identify and implement process improvements that make it easier to launch and manage new state or partner projects.

  • Develop dashboards and reporting structures that provide real-time visibility into progress and performance.

Partner & Client Management (20%)

  • Serve as a key operational liaison for state  point for state agencies, vendors, philanthropic funders or other external partners.

  • Build strong, trust-based relationships grounded in transparency and shared outcomes.

  • Translate partner needs into actionable plans for internal teams.

  • Facilitate regular updates, meetings, and retrospectives to ensure continuous alignment.

Learning, Reporting & Continuous Improvement (15%)

  • Synthesize insights across projects to surface cross-state trends, risks, and opportunities.

  • Manage operational reporting and funder compliance, ensuring consistent data and accountability across contracts and grants.

  • Contribute to reports and case studies for funders, partners, and internal learning.

  • Document and share best practices to strengthen project operations organization-wide.

  • Support a culture of reflection, improvement, and intentional learning across the team.

Who You Are

  • You bring 7+ years of experience in project management or program leadership, ideally within education, government, or social impact settings.

  • You’re equally comfortable leading complex external projects and building the systems that make them run smoothly internally.

  • You’re a structured, strategic operator who loves turning ambiguity into clarity and frameworks.

  • You have a track record of delivering complex, multi-stakeholder projects on time and with high partner satisfaction.

  • You’re highly organized, detail-oriented, and collaborative, with strong communication and facilitation skills.

  • You’re motivated by educational equity and the opportunity to make public funding more accessible and effective for families.

Nice to Haves

  • Familiarity with Education Savings Accounts (ESAs) or similar family-directed funding programs.

  • Familiarity with custom web development and design solutions. 

  • Familiarity with marketing, either digital or grassroots efforts.

  • Experience with sales operations.

  • Experience with government partnerships, procurement, or grant-funded project delivery.

  • Comfort working in tools like Airtable, Asana, Google Workspace, Slack, and CRM or data dashboards.

  • Experience managing remote, cross-functional resources.

Compensation & Benefits

  • Salary range: $100,000-$130,000, depending on mastery and experience of required competencies

  • Fully remote team with flexible hours

  • Comprehensive health benefits 

  • Unlimited paid time off

  • 2 x 2 week organization-wide breaks each summer and winter 

  • Professional development opportunities, growth pathways, and wellness funds

  • A mission-aligned, values-driven team working to transform educational access

  • Paid benefits include:

    • up to $500 USD for work-from-home supplies when you join Outschool.org, then $100 annually; 

    • up to $500 USD annually for classes on Outschool.com;

    • up to $200 USD annually for DEI learning materials; 

    • up to $2,500 USD for wellness and/or professional development annually

Application will be open until Dec 1st at 12:00 PST. APPLY HERE.

Family ESA Customer Support + Event Coordinator - Multiple Roles

Organization: Outschool.org
Compensation: $25–$35/hour (contract hourly)
Location: Remote, U.S.-based only. Preference will be given to candidates who live in or near Texas. 

Outschool.org is seeking compassionate, detail-oriented Family Customer Support AND Event Coordinator Contractors to help families navigate Education Savings Account (ESA) and other education funding programs. Contractors will provide timely, accurate, and empathetic support via email, phone, and chat, helping families access, understand, and use public funds to support their children’s learning. Additionally, for those interested, there are opportunities to coordinate and help host ESA learning events in different locations within Texas. You can apply if you are interested in either role or both.

This role is ideal for individuals who are skilled communicators, comfortable working remotely, and motivated by educational equity. You’ll handle family inquiries, troubleshoot common issues, and document insights to improve our support systems. 

We’re looking for contractors based in the U.S. who can work flexibly across time zones, especially during peak family support periods. Compensation ranges from $25–$35/hour, depending on experience and availability.


Application will remain open until filled. APPLY HERE.