Lead Software Engineer, AI-Native at Freewill

ABOUT US FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $13B 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. In the last 8 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 [Upgrade to PRO to see link] and Best Practice Institute [Upgrade to PRO to see link] and in 2025, we were named as one of Forbes' Best Startup Employers [Upgrade to PRO to see link] and the 2025 Most Loved Workplaces® for Diversity [Upgrade to PRO to see link] you can also check us out on Glassdoor [Upgrade to PRO to see link] Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast [Upgrade to PRO to see link] featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify [Upgrade to PRO to see link] Apple [Upgrade to PRO to see link] 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, two-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 (Director of Engineering) and will partner closely with product and design to deliver high-impact improvements to our existing user experiences. Together with your pod partner and our AI engineering lead who is helping to scale our AI initiative, 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 two-person 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 (one other engineer + AI agents) to rapidly rebuild and improve existing product flows - Design systems that are robust, testable, and maintainable, even when generated via AI tools—applying adversarial verification techniques to surface edge cases and failure modes—to proactively manage potential issues with code comprehension and technical debt. - 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 AI-assisted coding tools (e.g., Cursor, Copilot, Codex, Claude Code) in real development workflows - 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—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 - Familiarity with LLM behavior, evaluation, and prompt iteration techniques (chain-of-thought, few-shot examples, agentic loops) - Experience working in small, high-leverage teams (2–4 engineers) - Background in experimentation, A/B testing, or conversion optimization - Experience in the nonprofit technology or fundraising space HIRING PROCESS - Recruiter Phone Screen (30 minutes) - Take-Home Spec-driven Exercise (1 hour; on your own time) - Hiring Manager Interview (45 minutes) - Super Days: 2 separate final interviews with FreeWill Team members (45 minutes -1 hour) - Offer (contingent on positive references) Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing about any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4-6 weeks. AI POLICY Given the AI-native focus of this role, our standard AI policy does not apply to technical assessments. You are encouraged to use AI tools during take-home exercises and live coding challenges. We want to see how you work with AI as a collaborator. However, during phone screens, video interviews, and any conversational evaluation, we ask that your responses reflect your own knowledge and thinking in real time. Please do not use AI tools to generate or feed answers during these conversations. The goal of these stages is to understand how you communicate, reason through problems, and engage with our team directly. BENEFITS AND PERKS In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits: - 💻 Work from home with Regular (virtual) team events - 🏝️ Flexible hours and Flexible Paid Time Off policy. We trust staff to manage their own schedules and take the time off you need to be your best, as long as your work is on track. We recommend staff take a minimum of three weeks annually - 💵 Competitive salary + Company stock options - 💊 Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage) plus 401k - 💚 Short-term and long-term disability insurance along with Life and AD&D insurance - 👶 Paid parental leave for all parents - 🦾 $300 annual budget to outfit your home office or cover utility bills - 🌱 $1,000 annual professional development budget - 🚗 Commuter benefits and $250 monthly co-working budget which can be used for local co-working spaces and your home wifi bill FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We are a remote-first company with employees in the US, Brazil, Canada, and Pakistan! In the US, we are able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US. Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!