Senior Software Engineer

Employment Type: Contract | Potential to Convert to Full-Time 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 to end the reading crisis in America's K-12 schools. Beginning in 2027, the federal Education Freedom Tax Credit 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. This is ESH's first engineering hire for this product. You will make real architecture decisions, own third-party integrations, and build the platform that brings this benefit to life for employers and employees nationwide ahead of the 2027 launch. This engagement starts as a contract role with a strong path to full-time conversion for the right person.

What You Will Do

• Design and build an API-first full-stack platform connecting employers, employees, and payroll systems
• Own integrations with payroll and HRIS providers — authorization flows, data sync, and deduction management
• Build employee-facing enrollment flows and employer-facing campaign and dashboard tooling
• Design reliable background job pipelines with status tracking, retry logic, and error handling
• Handle sensitive employee and financial data with appropriate security practices
• Make sound architecture decisions under ambiguity, balancing speed with long-term extensibility

What We Are Looking For Required

• 7+ years of full-stack engineering experience building production web applications
• Demonstrated use of AI coding tools such as Cursor, GitHub Copilot, 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
• Experience modeling relational data for complex, multi-step stateful workflows
• Proven ability to build reliable background job pipelines with operational visibility
• Secure handling of PII and financial data
• Clear communication and sound judgment in early-stage, ambiguous environments

Highly Valued

• Experience integrating with payroll or HRIS platforms — UKG, Rippling, ADP, Workday, or similar
• Background in HR tech, benefits, workplace giving, or fintech
• Familiarity with payroll deduction mechanics or year-end tax document workflows
• Early-stage startup experience, working with ambiguity, and building from 0 to 1.

Compensation & Benefits EducationSuperHighway offers market-rate compensation competitive with for-profit companies. Specific compensation details will be shared with candidates during the interview process. For candidates who convert to full-time, ESH offers a comprehensive benefits package including:

• Comprehensive health, dental, and vision benefits
• Generous PTO and flexible remote work
• The opportunity to build a team and function from scratch and to help close the K-12 literacy gap in America