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 Roles

Family Experience & Operations, Senior Associate

The Opportunity

We’re hiring a Family Experience & Operations Senior Associate to ensure families navigating ESA programs feel supported, seen, and empowered — while also improving the systems that make that support scalable and effective.

This role is ideal for someone who thrives at the intersection of family-facing support, systems thinking, and operational efficiency. You’ll respond directly to families, manage communication campaigns, refine our Intercom workflows and knowledge systems, and collaborate cross-functionally to improve how we support families across multiple states.

Key Responsibilities

💬 Family Support & Engagement (40%)

  • Respond to parent inquiries via email and phone with empathy, clarity, and confidence.

  • Track recurring themes and unmet needs from families to inform broader improvements.

  • Support peak seasonal periods (e.g., onboarding new families, tuition deadlines, documentation campaigns).

🛠️ Program Operations & Communication (25%)

  • Manage recurring outreach and communication campaigns (welcome emails, missing documentation reminders, tuition disbursement updates) in MailChimp.

  • Draft and QA help content and guidance to ensure accuracy and accessibility.

  • Coordinate with state partners or vendors (e.g., ClassWallet, FACTS) to clarify or relay family-facing guidance.

⚙️ CX Systems & Knowledge Management (25%)

  • Maintain and refine Intercom workflows, macros, and triage logic to ensure families get timely, personalized support.

  • Manage internal knowledge systems (e.g., Airtable dashboards, SOPs, help center content).

  • Collaborate with data and product teams to streamline intake, automate FAQs, and make backend improvements visible to families.

📊 Continuous Improvement & Insights (10%)

  • Monitor support trends and system usage to identify breakdowns or new needs.

  • Recommend improvements to internal processes that enhance family experience.

  • Contribute to our learning culture by documenting insights and surfacing patterns across states or family types.

Who You Are

  • You bring 3+ years of experience supporting customers or communities,

  • You’re fluent in tools like Intercom, Airtable, Google Workspace, and comfortable learning new systems.

  • You have deep empathy and experience supporting low-income families, especially in navigating complex programs or decisions.

  • You’re a systems thinker — someone who doesn’t just solve problems, but improves the process for the next person.

  • You’re highly organized, self-directed, and thrive in fast-paced, mission-driven environments.

Nice to Haves

  • Experience with education savings accounts (ESAs), microgrants, or other direct-to-family programs.

  • Bilingual in Spanish or other high-need languages.

  • Experience configuring support systems or workflows in Intercom, Zendesk, or similar platforms.

Compensation & Benefits

  • Salary range: $70,000 – 85,000, depending on mastery and experience of required competencies

  • Fully remote team with flexible hours

  • Comprehensive health benefits and unlimited paid time off

  • Professional development opportunities, growth pathways and wellness funds

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

  • Paid benefits also 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 or professional development annually

TO APPLY