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.
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.
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. Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast

featuring Anthony Sottile, FreeWills VP of Partner Success on either

Spotify

or

Apple

.

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. 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).
Defining how engineering gets done in an AI-first world
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.
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
Continuously refine workflows for spec-driven development, agentic engineering, and AI-driven QA, documenting patterns and lessons learned into a repeatable playbook
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., 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
~ Strong written communication skills since much of this role involves writing clear specifications, prompts, and documentation

Background in experimentation, A/B testing, or conversion optimization
Experience with AI Security best practices
Recruiter Phone Screen (30 minutes)
Super day 1: AI-Native Build Exercise (1 hour)
Communications & Values and Open Conversation (2 separate interviews; 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
~ Flexible Paid Time Off policy. Flexible hours
~ Company stock options
~Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)
~ Short-term and long-term disability insurance
~ Life and AD&D insurance
~ Free One Medical membership
~ Regular (virtual) team events
~$250 monthly co-working budget which can be used for local co-working spaces and your home wifi bill
~$300 annual budget to outfit your home office or cover utility bills
~$1,000 referral bonuses for growing our FreeWill community
~$Claude (AI Assistant) company/team account

AI Policy
We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.
Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.
If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.
AI use by FreeWill:

Our hiring process may include the use of AI- assisted tools for interview transcription, evaluation, or fraud detection. This processing is conducted in compliance with applicable Data Protection, AI Governance, and Labor Laws.
EEOC & Diversity Statement
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. We also can’t sponsor working visas, so all applicants will need to have work authorization in their respective country.
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.