[Hiring] Lead Software Engineer @FreeWill

Role Description

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. 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 AI Security best practices
• 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 day 1: AI-Native Build Exercise (1 hour)
• Super day 2: Communications & Values and Open Conversation (2 separate interviews; 45 minutes and 30 minutes)
• 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 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.

Benefits

• Work from home
• 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
• Flexible hours
• Competitive salary
• Commuter benefits
• Company stock options
• 401k
• 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
• Paid parental leave for all parents

Perks

• 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
• $800 annual professional development budget
• 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.

For example: 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.

The Recruiter will be able to provide additional guidance during the hiring process if needed. 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. Human oversight and decision making is maintained throughout the hiring process and for all final hiring decisions. 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. 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 their respective country.

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!