Lead Software Engineer, AI-Native

FreeWill

2d•$190,000 - $210,000•Remote

About The Position

FreeWill is seeking a Lead Software Engineer (AI-Native) to help reimagine software development. This role involves operating as an orchestrator of AI development systems, leveraging tools like Claude Code, Codex, and Cursor to rapidly rebuild and evolve existing products. The engineer will work in a lean, 3-4 person development pod, focusing on translating product requirements into AI-driven development workflows, using AI as a force multiplier for speed and quality, and shipping production-ready systems. This role reports to the R&D organization (Senior Engineering Manager) and collaborates with product and design teams. The position is key in defining FreeWill's AI-native software development playbook. The salary range for this role is $190,000 to $210,000, plus equity and benefits. This is a system orchestration engineering role focused on defining how engineering is done in an AI-first world, designing systems that write code with high internal coherence, and building at an accelerated pace with lean teams.

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

Nice To Haves

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

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