Lead Software Engineer, AI-Native

About Us

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. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the 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.

In the last 9 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. We were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and the 2025 Most Loved Workplaces® for Diversity by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers .

Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple .

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.

FreeWill has set compensation bands for fairness and transparency. We don’t think that an individual’s pay should be determined by how comfortable they are negotiating, so we like to be up front. 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