Lead Software Engineer, AI-Native - FreeWill

About FreeWill

FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $15B in gift commitments for nonprofits since we were founded in 2017. Our products make things easier for donors who want to change the world and for nonprofits doing heroic work around the planet. We partner with nonprofits of all sizes to diversify fundraising across individual and institutional giving, from legacy gifts and tax-smart donations to foundation, corporate, and government grants.

About the Role

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.

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

Responsibilities

• 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, distilling 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 harness engineering practices, embedding learnings into a clear, repeatable structure for AI code development
• 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 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 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 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

Benefits & Perks

• Work from home flexibility with flexible hours
• Flexible Paid Time Off policy (recommended minimum of 3 weeks annually)
• Competitive salary plus company stock options
• 401(k) plan
• Medical, Dental, and Vision coverage (select single coverage plans 100% employer paid; subsidized family coverage)
• Short-term & long-term disability, Life, and AD&D insurance
• Free One Medical membership
• Paid parental leave for all parents
• $250 monthly co-working and home wifi budget
• $300 annual home office outfit or utility budget
• $800 annual professional development budget
• $1,000 employee referral bonus
• Claude (AI Assistant) company/team account
• Regular virtual team events and commuter benefits