Contract Senior Software Engineer
Employment Type: Contract/Hourly compensation | Location: Remote
ABOUT EDUCATIONSUPERHIGHWAY
EducationSuperHighway, the national non-profit that connected 99.7% of American students to high-speed internet and 5 million low-income households to affordable broadband, is now launching its 3.0 mission: ending America’s K-12 reading crisis by funding literacy tutoring scholarships for first graders who are reading below grade level.
Beginning in 2027, the Federal Scholarship Tax Credit (FSTC, §25F) creates a new mechanism for employers to offer education philanthropy as a workplace benefit. ESH is building the infrastructure that makes this real, connecting employers, employees, and payroll systems into a seamless giving experience, and tracking every payroll deduction through to the scholarship granting organization that receives it.
ABOUT THE ROLE
You will join ESH's small engineering team on this product, working directly with the engineer who designed the platform, stepping into an active build ahead of the January 1, 2027 launch. The platform's core architecture is already in motion: a mix of automated and manually-supported payroll provider integrations, a multi-tenant giving architecture that supports multiple downstream recipients per employer, a money movement and reconciliation layer built on a bank-sponsored payments provider, employer single sign-on, compliance checks against the IRS list of eligible scholarship granting organizations, and a growing set of live and in-progress employer implementations. You will help extend the integration layer, building on the existing architecture, and share ownership of the wider codebase, then carry that work through to launch and beyond.
You will make real architecture decisions, work on third-party integrations, and build the platform that brings this benefit to life for employers and employees nationwide. This engagement starts as a contract role with a strong path to full-time conversion for the right person.
WHAT WE ARE LOOKING FOR
REQUIRED
- 7+ years of full-stack engineering experience building production web applications
- Early-stage startup experience, comfort with ambiguity, and experience building from 0 to 1 or picking up and extending an early-stage system alongside a small team
- Demonstrated use of AI coding tools such as Cursor, GitHub Copilot, Codex or Claude as a regular part of your development workflow, including planning, code generation, debugging, and refactoring
- Mature judgment about AI outputs: knowing when to trust, when to correct, and when to set the tools aside
- Strong third-party API integration experience, particularly OAuth flows and structured data write-back, ideally with payroll, HRIS, or other vendor APIs that are limited or inconsistent
- Experience modeling relational data for complex, multi-step, multi-tenant stateful workflows
- Proven ability to build and maintain reliable background job pipelines with named queue technology and operational visibility
- Secure handling of PII and financial data
- Comfort deploying and monitoring a production service (a dedicated DevOps/security engineer will support deeper infrastructure work)
- Clear communication and sound judgment in early-stage, ambiguous environments, including the ability to read into and build on an existing codebase quickly
HIGHLY VALUED
- Experience integrating with payroll or HRIS platforms directly or through an integration aggregator such as Finch, including UKG, Rippling, ADP, Dayforce, Workday, or similar
- Background in HR tech, benefits, workplace giving, or fintech
- Familiarity with payroll deduction mechanics or year-end tax document and compliance-driven document delivery workflows
- Experience designing a provider-agnostic abstraction layer for third-party integrations
- Experience with payments or financial data flows, such as ACH, ledgering, or reconciliation, where money must be tracked accurately and audited
- Experience with…