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About This Role
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 the2025 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 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
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. 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!
Compensation Range: $190K - $210K
Salary Context
This $190K-$210K range is above the median for AI Software Engineer roles in our dataset (median: $192K across 198 roles with salary data).
Role Details
About This Role
AI Software Engineers build the applications and systems that AI models run inside. They own the API layers, data pipelines, frontend integrations, and infrastructure that turn a model into a product users interact with. Every AI company needs engineers who can build the software around the AI.
The challenge is building reliable systems around inherently unreliable components. Models are probabilistic. They'll give different answers to the same question. They hallucinate. They're slow. They're expensive. Your job is to build an application layer that handles all of this gracefully while delivering a product that users trust and enjoy.
Across the 9,079 AI roles we're tracking, AI Software Engineer positions make up 5% of the market. At freewill, this role fits into their broader AI and engineering organization.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
What the Work Looks Like
A typical week includes: building API endpoints that serve model inference with caching and fallback logic, designing the data pipeline that feeds context to a RAG system, implementing streaming responses in the frontend, debugging a race condition in the async inference pipeline, and optimizing database queries for the vector search layer. It's full-stack engineering with AI at the center.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
Skills Required
Full-stack engineering skills with AI integration experience. Python and TypeScript are the most common requirements. You'll need to understand API design, database architecture, and how to build reliable systems around probabilistic outputs. Experience with streaming, async processing, and caching patterns is increasingly important as real-time AI applications proliferate.
Knowledge of vector databases, embedding APIs, and LLM integration patterns (function calling, structured outputs, retry logic) differentiates AI software engineers from general software engineers. Understanding cost optimization (caching strategies, model routing, batched inference) is valuable since inference costs can dominate application economics.
Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
Compensation Benchmarks
AI Software Engineer roles pay a median of $220,000 based on 1,601 positions with disclosed compensation. Senior-level AI roles across all categories have a median of $229,300. This role's midpoint ($200K) sits 9% below the category median. Disclosed range: $190K to $210K.
Across all AI roles, the market median is $213,000. Top-quartile compensation starts at $263,911. The 90th percentile reaches $318,400. For comparison, the highest-paying categories include AI Safety ($256,000) and Research Engineer ($252,000). By seniority level: Entry: $111,000; Mid: $193,200; Senior: $229,300; Director: $272,300; VP: $235,830.
freewill AI Hiring
freewill has 1 open AI role right now. They're hiring across AI Software Engineer. Based in US. Compensation range: $210K - $210K.
Location Context
AI roles in Austin pay a median of $209,100 across 306 tracked positions.
Career Path
Common paths into AI Software Engineer roles include Software Engineer, Full-Stack Developer, Backend Engineer.
From here, career progression typically leads toward Staff Engineer, AI Architect, Engineering Manager.
If you're a software engineer, you're already 80% there. Learn the AI integration patterns: RAG, streaming inference, function calling, structured outputs. Build a project that demonstrates you can wrap an AI model in a production-quality application with proper error handling, caching, and user experience. That's the portfolio piece that gets you hired.
What to Expect in Interviews
Technical screens look like standard software engineering interviews with an AI twist. Expect system design questions about building reliable applications around probabilistic models: handling streaming responses, implementing retry logic for API failures, and designing caching strategies for LLM outputs. Coding rounds test standard algorithms plus practical integration patterns like async processing and rate limiting.
When evaluating opportunities: Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
AI Hiring Overview
The AI job market has 9,079 open positions tracked in our dataset. By seniority: 106 entry-level, 4,384 mid-level, 3,343 senior, and 1,246 leadership roles (Director, VP, C-Level). Remote roles make up 6% of the market (531 positions). The remaining 8,478 roles require on-site or hybrid attendance.
The market median for AI roles is $213,000. Top-quartile compensation starts at $263,911. The 90th percentile reaches $318,400. Highest-paying categories: AI Safety ($256,000 median, 66 roles); Research Engineer ($252,000 median, 457 roles); AI Engineering Manager ($251,622 median, 55 roles).
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
The AI Job Market Today
The AI job market spans 9,079 open positions across 16 role categories. The largest categories by volume: AI/ML Engineer (6,862), AI Product Manager (453), AI Software Engineer (451). These three account for the majority of open positions, though smaller categories often have higher per-role compensation because of specialized skill requirements.
The seniority mix tells a story about where AI teams are in their maturity. Entry-level roles (106) are outnumbered by mid-level (4,384) and senior (3,343) positions, reflecting that most companies are past the 'build a team from scratch' phase and need experienced engineers who can ship production systems. Leadership roles (Director, VP, C-Level) total 1,246 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 6% of all AI roles (531 positions), with 8,478 requiring on-site or hybrid attendance. The remote share has stabilized after the post-pandemic correction. Senior and specialized roles (Research Scientist, ML Architect) are more likely to be remote-eligible than entry-level positions, partly because experienced hires have more negotiating power and partly because these roles require less hands-on mentorship.
AI compensation is structured in clear tiers. The market median sits at $213,000. Top-quartile roles start at $263,911, and the 90th percentile reaches $318,400. These figures include base salary with disclosed compensation. Total compensation (including equity, bonuses, and sign-on) runs 20-40% higher at companies that offer those components.
Category matters for compensation. AI Safety roles lead at $256,000 median, while Prompt Engineer roles sit at $141,440. The spread between highest and lowest-paying categories reflects the premium on specialized technical skills versus broader analytical roles.
The most in-demand skills across all AI postings: Python (1,649 postings), Aws (898 postings), Azure (723 postings), Rag (671 postings), Gcp (536 postings), Pytorch (434 postings), Claude (410 postings), Kubernetes (406 postings). Python dominates, appearing in the vast majority of role descriptions regardless of category. Cloud platform experience (AWS, GCP, Azure) is the second most common requirement. The newer entrants to the top skills list (RAG, vector databases, LLM APIs) reflect the shift from traditional ML toward generative AI applications.
Frequently Asked Questions
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