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

OUTSCHOOL.ORG

Business Development & Marketing Senior Associate

Full Time Role · Remote (U.S.) · $70,000-$95,000

About Outschool.org

Since 2020, Outschool.org has supported hundreds of thousands of families to afford, access and actualize education resources previously out of their reach. Today, Outschool.org builds family navigation tools that help parents find and pay for the education of their dreams. Our state-contracted tools and services currently operate in Arkansas, South Carolina, and Texas.

As the number of policies that provide families with access to public funds to purchase educational resources increase, we’re looking to expand from a handful of state contracts to nationwide infrastructure capable of supporting families across the country.

About the role

We’re hiring a senior associate to help drive business development and marketing execution as we pursue new state contracts, operationalize our sales process, and roll out a rebrand. You’ll work directly with the CEO and a small, equity-minded team on proposals, government RFPs, family-facing email campaigns, pitch decks and one-sheets, and serve as the operational glue that keeps a growing new-business pipeline moving.

This role is ideal for someone who has sold or supported selling technology or services into state or local governments — you’ll bring real fluency in scoping, budgeting, and writing proposals that speak to existing and prospective partners.

What you’ll do

Support new business development. Source and qualify RFP opportunities, support partnership and relationship development, t, and help advance proposals from first call through contract signature.
Operationalize our sales process. Manage the CRM, pipeline hygiene, and follow-up cadences that turn a CEO-led effort into a repeatable and sustainable motion.
Prepare decks, one-sheets, and proposal materials. Craft polished, on-brand assets — we care a lot about visual quality and verbal design.
Scope and price proposals. Partner with leadership to translate program requirements into scopes, budgets, and workstreams.
Run family-facing email campaigns. Own segmentation, copy, and performance for our family audiences across multiple states — with messaging that is culturally responsive, mission-aligned, and optimized for engagement.
Improve SEO for our finder tools and resources. Own content and on-page SEO — keyword research, landing page strategy, resource content that ranks, metadata, and internal linking. Partner with engineering and outside consultants on the technical SEO needed to make our multi-state finder tools discoverable.
Coordinate meetings and travel. Keep the CEO and team moving — scheduling, logistics, prep docs, follow-ups.
Support key sales and brand initiatives including the rebrand rollout. Help implement new brand assets across collateral, web properties, templates, and outbound communications.

Who you are

Proven track record in business development, growth, or marketing — ideally with at least 3 years of some of that at a tech-enabled services company, SaaS vendor, or govtech firm selling into government, K–12, or regulated institutional buyers. We’re flexible on level and years; we’ll size scope and rate to the right person.
Experience scoping and budgeting SaaS or tech-enablement engagements. You know what a credible $500K proposal looks like, and what a $3M one requires.
Strong writing and visual sensibility. You can draft a compelling executive summary, polish a deck, and sweat the details on a one-sheet.
Intentional, capable user of AI tools. You use Claude, ChatGPT, or similar thoughtfully — not as a gimmick, but to do better work and scale your output. You bring a continuous learning mindset and stay current as the tools evolve.
Working knowledge of SEO. Comfortable with keyword research, on-page optimization, and content strategy; able to brief technical SEO work even if you don’t execute it yourself.
Operator mindset. You’re not above scheduling a meeting, redlining a contract addendum, coordinating travel, or chasing down a signature. We’re a nimble org that requires range.
Organized, proactive, self-directing. You’ll be given context and trusted to run.

Nice to have

Familiarity with K–12 state procurement.
Experience with HubSpot or similar CRMs, email platforms (Constant Contact, Mailchimp, etc.), and Canva / Gamma / Google Slides.
Experience with programmatic SEO or location-based / multi-state content strategy.
Government proposal writing experience.
Existing relationships in state or choice policy networks.
Understanding of issues related to educational equity and economic access.

Logistics

Hours: Exempt, 40 hours a week
Rate: $70,000-$95,000 depending on experience
Location: Remote (U.S.), with occasional travel for key meetings
Preference will be given to NYC-based candidates who are available for occasional in-person collaboration.

HOW TO APPLY

Complete our interest form.

Outschool.org is an independent nonprofit fiscally sponsored by the Edward Charles Foundation, and is separate from Outschool.com, an online class marketplace. Outschool.org is an equal opportunity employer and is committed to building a diverse, inclusive team that reflects the communities we serve.

Senior Software Engineer, Data Architecture

Contract or Contract to hire · Remote (U.S.) · 6 month min. contract

About Outschool.org

The Work

We’re looking for a product engineer with focused expertise in PostgreSQL schema design, complex data modeling, and relational database architecture to help build scalable backend tools that serve families, education providers, and state agencies as they navigate learning opportunities enabled by innovations such as Education Savings Accounts (ESAs) and other direct-to-family funding programs.

Because our products and services interface directly with public and private infrastructure, you will lead backend integrations across highly configurable, state and program specific workflows. Success in this role will require a candidate who embraces the design challenges native to working on interoperable data systems that reach across both legacy government systems and partner business systems, while collaborating closely on the product interfaces end users touch every day.

In this 6 month contract period, daily work will involve partnering with our other senior engineer and product director on these workstreams:

1. Flagship finder product interoperability. Our flagship product helps parents in ESA eligible states assess educational service and product offerings available to them with their program dollars — from tutors to ju-jitsu classes, or even private school tuition — to make choices that best fit their child’s needs. We offer this service as a delivery partner via private and public-sector partnerships with clients like state departments of education, and the wallet platforms that administer scholarship funds to parents. As our data architecture focused engineer, you’ll help architect improved cross-entity data integration and handling with those partners. This includes owning complex identity management architecture, and puzzles like how best to verify credentials against shifting state criteria.

2. AI-powered compliance tool. An early stage tool to help parents submit reimbursement requests, evaluates them for eligibility against state policy, and helps program administrators review them efficiently. You'd help shape this architecture from the ground up, working with our product team on a staged scope, and ship it.

3. Canonical postgres engine & ETL. Drive our overarching migration from an Airtable-centric data layer to a highly optimized, production Postgres database. Improve our Python ETL pipelines that ingest weekly state data across multiple regions.

Beyond these areas, you’ll weigh in on architecture across the stack and support our product portfolio as needed to support our rapidly evolving and exciting work!

Skills & Experience

Must-haves:

6+ years of engineering experience with deep relational database depth. You've designed production schemas from scratch, written non-trivial server-side logic, and shipped data-heavy features. You speak fluently about indexes, constraints, migrations, schema evolution, and the architectural trade-offs among different relational models. High proficiency with PostgreSQL is strongly preferred.
Multi-Tenant SaaS Architecture Expertise. Proven experience designing schemas, data isolation layers, and access patterns for systems serving multiple distinct enterprise clients or state agencies.
Shipped LLM features in production. You've built and maintained a user-facing feature that uses LLM APIs (Anthropic, OpenAI, Gemini, or similar) and have opinions on structured output, eval design, prompt iteration, latency/cost tradeoffs, and where AI helps vs. hurts.

Strongly preferred

Client Services & Tech Delivery Comfort. Experience working in product-as-a-service, government tech, or professional services engineering for external clients. You understand that success means delivering robust software that balances the ultimate goal of best serving end users with the need to satisfy complex external compliance and client requirements.
Polyglot Fluency (Python, JS/TS, SvelteKit). Our stack today uses Python for data pipelines, JavaScript/TypeScript in our SvelteKit frontend, and Node sync scripts. SvelteKit experience is a bonus, but we prioritize engineers who can confidently adapt to new languages with minimal friction.

Also valuable

Experience with classification/categorization tasks at scale.
Background in edtech, govtech, or public-interest technology.
Familiarity with Airtable APIs, GitHub Actions, or other low-friction automation tooling.

How you work

We're a small product engineering team with real traction and a wide surface area. That shapes who thrives here:

You're energized by ambiguity and don't need a perfectly defined ticket to make progress.
You enjoy structuring real-world complexity. You don’t expect pristine upstream data, and are energized by the challenge of designing highly structured, elegant internal systems that seamlessly ingest and standardize unpredictable data from external partners.
You communicate technical trade-offs exceptionally well. You can confidently evaluate system feasibility, surface the right architectural questions, and push back constructively when you think a product decision compromises data integrity.
You're excited to pair closely with another senior engineer. You’ll share ownership, code reviews, and design decisions.
You develop thoughtfully with AI. You use tools like Claude Code for speed where they excel, and know exactly when to step in yourself.
You care about building tools that serve families. You care about making a real impact on K–12 education, and you're up for the pragmatism that comes with shipping production software to state agencies and tens of thousands of users.

How we work together:

We ship good enough over perfect — but we care about doing it right, not just fast. That balance is something we actively talk about and recalibrate continuously.
We keep things playful. The work matters, and the families we serve matter, but the team takes itself less seriously than the work.
Async-first, with meaningful live connection time. Slack for day-to-day comms, Linear for issue tracking — and we make space for the fun stuff and the hard stuff live.
We value transparency. No black boxes here — we actively bring the full team's perspectives into big decisions, and we give and ask for feedback often.

Stack

Frontend: SvelteKit (migration from vanilla JS underway), planned design system work
Backend / Data: Python ETL pipelines, Node.js sync scripts, Airtable as a current data layer, migrating toward Postgres/Supabase
AI: TBD API (Anthropic, Gemini, OpenAI) for production features (in active development)
Infrastructure: GitHub Actions for CI/CD and pipeline orchestration, Vercel for new product deployments
Tooling: Linear, GitHub, Slack, Claude / Claude Code

How to apply

Applications go through a short form. We’ll ask for:

A resume or LinkedIn — whichever you keep current.
A short note (a paragraph or two is fine) telling us about one production LLM feature you've shipped — what it did, what was tricky, what you'd do differently.
A few sentences on a data architecture decision you made that you’re proud of that shows off your design thinking skills in complex PostgreSQL schema or multi-tenant architecture design.
Optional: a link to a project, repo, or piece of writing that shows how you think.

We'll get back to every applicant within two weeks. The process from there is a 30-minute intro call, a 45-minute technical conversation, a paid technical exercise (small, scoped, real), and a final round with the team.

We particularly encourage applications from candidates whose backgrounds are underrepresented in tech.