Senior Software Engineer

EducationSuperHighway is building a platform that connects employers, employees, and payroll systems to support workplace giving for literacy tutoring scholarships. The Senior Software Engineer will extend the platform’s integrations and broader codebase, make architecture decisions, and help carry the product through launch and beyond.

Responsibilities:

• 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

Requirements:

• 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