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Contract Senior Software Engineer
Employment Type: Contract/Hourly compensation | Location: Remote
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.
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.
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
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 single sign-on and identity provider integrations (OIDC, SAML, Okta)
Experience integrating with Salesforce or another CRM
Build on the existing API-first full-stack platform connecting employers, employees, and payroll systems, and extend it toward launch, working alongside the existing engineer
Work with the existing engineer on integrations with payroll and HRIS providers (today primarily through the Finch aggregator, starting with ADP Workforce Now, with Dayforce, Workday, and UKG next), including both automated data sync and write-back and manually-supported implementation paths, with a roadmap to bring more providers under automation over time
Build direct integrations for providers an aggregator cannot reach, starting with Rippling using custom objects, workflows, or file-based paths as needed. Handle assisted provider connections, where requests are applied by a person within about two business days, by treating a pending deduction as possibly already applied
Maintain and extend a provider-agnostic integration layer so adding new payroll providers does not require rebuilding the core platform
Build and refine employee-facing enrollment flows and employer-facing campaign and dashboard tooling, supporting multiple employers and multiple downstream giving recipients on a shared, multi-tenant platform, including employer single sign-on (OIDC, SAML 2.0, or an email-code fallback), a check against the IRS list of eligible scholarship granting organizations when a designation is made and at every deduction, and capture of the employee's state at payment
Design reliable background job pipelines with status tracking, retry logic, dead-letter handling, and error visibility, particularly for payroll deduction sync, including webhook ingestion and drift detection between payroll systems and the platform
Support money movement and reconciliation by building to the procedures set by ESH's finance team and working with a payments and ledgering provider such as Modern Treasury, matching payroll deduction files and ACH remittances to enrollments and keeping an audit trail
Build compliance-aware document workflows, including year-end acknowledgement generation and delivery for donations to ESH (other scholarship granting organizations issue their own receipts from donor data the platform passes to them), with delivery status tracking and failure recovery
Handle sensitive employee and financial data with appropriate security practices, including data minimization by design (for example, retaining only what is needed until an employee enrolls, and hashing identifiers such as email addresses)
Make sound architecture decisions under ambiguity, balancing speed with long-term extensibility, and document decisions clearly for a small, fast-moving team
Engineering is a small team: the engineer who designed the platform, a part-time front-end contractor, and a part-time DevOps and security engineer being added ahead of launch.
