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Salary: USD 190,000 - 210,000 / annual
FreeWill is a social-good startup that has partnered with 2,400+ nonprofits and generated $15B in gift commitments since 2017. The company has grown from 5 to 200+ employees and has been recognized as a Most Loved Workplace by Newsweek and Best Practice Institute, as well as one of Forbes' Best Startup Employers in 2026.
You will serve as a Lead Software Engineer focused on AI-native development, operating as an orchestrator of AI development systems within a lean 3-4 person pod. This role reports to the Senior Engineering Manager in the R&D organization and partners closely with product and design teams.
Key responsibilities include:
- Lead AI-native software development workflows using tools like Claude Code, Codex, and Cursor to generate, iterate on, and ship production code
- Mentor engineers across R&D on AI-native development practices and distill learnings into patterns others can adopt
- Translate product requirements into clear technical specs, prompts, and system instructions that guide AI-driven development
- Own end-to-end delivery from spec through agentic AI-written implementation, automated validation, and production rollout
- Build harness engineering practices and embed learnings into a repeatable structure for AI code development at FreeWill
- Partner within the small pod to rapidly rebuild and improve existing product flows
- Design systems to manage code comprehension and technical debt that are robust, testable, and maintainable
- Continuously refine workflows for spec-driven development, agentic engineering, and AI-driven QA, documenting patterns into a repeatable playbook
This is fundamentally a system orchestration engineering role focused on redefining how software development is done in an AI-first world—removing toil, increasing flow time, and leveling up the engineering department through mentorship.
REQUIREMENTS:
- 7+ years of experience as a software engineer with strong experience building and shipping production systems across the full stack
- Experience cultivating a culture of mentorship and knowledge sharing across engineering teams, particularly around AI-native system orchestration best practices
- Experience building development tooling and workflows that bake quality in from the start
- Demonstrated experience using agentic coding tools (e.g., Cursor, Copilot, Codex, Claude Code) in real development workflows
- Familiarity with LLM behavior, evaluation, and prompt iteration techniques (chain-of-thought, few-shot examples, agentic loops)
- Strong ability to write clear technical specifications and break down problems into structured, verifiable units of work
- Experience working in modern web stacks (e.g., React, Node.js, TypeScript, APIs, cloud infrastructure)
- Proven ability to ship quickly with high quality in ambiguous, fast-moving environments
- Strong debugging and systems thinking skills—able to validate, correct, and improve AI-generated outputs for correctness, security, and performance
- Comfort operating with high autonomy and minimal process on small teams while maintaining rigor in outcomes
- Strong written communication skills for writing clear specifications, prompts, and documentation
NICE TO HAVE:
- Experience rebuilding or refactoring existing systems or leading large-scale codebase migrations
- Experience working in small, high-leverage teams (3–4 engineers)
- Background in experimentation, A/B testing, or conversion optimization
- Experience with AI Security best practices
- Experience in the nonprofit technology or fundraising space
