Lead Software Engineer (AI-Native) at FreeWill

We’re looking for a Lead Software Engineer (AI-Native) to help us reimagine how software is built at FreeWill.

You will operate as an orchestrator of AI development systems — leveraging tools like Claude Code, Codex, Cursor, and other emerging AI-native toolchains — to rapidly rebuild and evolve our existing products. You will work in a lean, 3-4 person development pod where success is measured by how effectively you:

• Translate product requirements into clear, spec-driven development workflows
• Use AI systems as a force multiplier for speed and quality
• Rapidly ship production-ready systems that improve user outcomes

This role reports into the R&D organization (Senior Engineering Manager) and will partner closely with product and design to deliver high-impact improvements to our existing user experiences. Together with your teammates, you will help define the AI-native playbook for how FreeWill builds software with AI going forward.

The salary range for this role is $190,000 to $210,000 (plus equity and benefits).

Why This Role Is Different

This is a system orchestration engineering role. You are not just writing code — you are:

• Defining how engineering gets done in an AI-first world
• Designing systems that write code with high internal coherence
• Building at 5x traditional speed with lean dev teams

If you’re excited about redefining how software development is done—removing toil, increasing time in the zone, and leveling up our engineering department through mentorship—this role is for you.

Responsibilities

• Lead AI-native software development workflows using tools like Claude Code/Codex/Cursor to generate, iterate on, and ship production code
• Mentor engineers across R&D on AI-native development practices — distill what you learn in your pod 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 → agentic AI-written implementation → automated validation → production rollout
• Build the harness engineering practices — embedding learnings into a clear, repeatable structure for how AI code is developed at FreeWill
• Partner within a small pod to rapidly rebuild and improve existing product flows
• Design systems to proactively manage potential issues with 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 and lessons learned into a repeatable playbook

Required Skills and Experience

• 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 since much of this role involves writing clear specifications, prompts, and documentation

Nice to Have but Not Required

• 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