FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $12B 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 and Best Practice Institute and in 2025, we were named as one of Forbes' Best Startup Employers and the 2025 Most Loved Workplaces® for Diversity; you can also check us out on Glassdoor! 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.

Full-time • Contract (6 Months) • Working in EST Time Zone

About the Role

Grant Assistant is FreeWill’s newest product helping nonprofits win more funding through AI-powered tools. We’re seeking an experienced grant professional to be a Grant Writing Subject Matter Expert (SME). You’ll leverage your deep grants expertise to train, evaluate, and refine our AI models; AI experience is a plus, but not required. 

 

What this role is: You’re teaching AI systems to replicate your grant writing or evaluation expertise. You’ll spend time evaluating AI outputs, labeling what’s excellent versus what needs improvement or is altogether incorrect, annotating why certain approaches work, documenting patterns, and working with clients and engineers to improve model performance. This is a unique opportunity to shape the future of AI-assisted grant writing and scale impact to countless nonprofits, helping them better fund and achieve their missions. 

 

What this role is not: You won’t be writing grants for nonprofit clients, managing a portfolio of partner relationships, or doing traditional grant consulting. 

 

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think that an individual's pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation.

This is a full-time contractor position for 6 months and will have a monthly retainer of $9,000. 

What You’ll Do

As our grants subject matter expert and AI model trainer, your primary responsibility is teaching our AI systems to write grants like an expert. You won't be writing grants for clients—you'll be training AI models to do it. 

Key Responsibilities

AI Model Training & Ground Truth Establishment

• Serve as the definitive "ground truth" for what constitutes excellent versus poor grant writing, providing the reference standard our AI models learn from
• Review AI-generated grant content and assess quality
• Create and maintain an annotated library of evaluated AI outputs 

LLM Judge Development & Calibration

• Provide expert judgment to train and assess performance of evaluation systems in collaboration with engineers 
• Iterate on evaluation approaches based on real-world performance and edge cases

Quality Framework & Standards Definition

• Establish clear standards for output quality and structured guidelines for grant writing best practices 
• Document best practices across different grant types 

Strategic Impact & Measurement

• Drive improvement in key performance metrics
• Partner with leadership to align AI training priorities with broader product strategy

Required Qualifications

Grant Writing Expertise 

• 7+ years of hands-on grant writing and proposal development experience for US nonprofits, with a proven track record of winning competitive applications, or experience evaluating or awarding grant proposals
• Deep understanding of what makes grant proposals succeed: narrative structure, funder alignment, evidence presentation, tone calibration, storytelling techniques
• Experience across multiple funding sources (federal, foundation, corporate) and grant types (program support, capacity building, capital campaigns, research)
• Demonstrated versatility across a wide range of programmatic and thematic areas (such as: health, education, faith-based initiatives, environmental conservation) with the ability to adapt narratives and strategies to each funder’s mission and priorities 

Evaluation & Analytical Skills  

• Strong ability to review others' grant writing and provide specific, actionable critiques 
• Experience identifying patterns across large sets of content and developing classification frameworks or taxonomies
• Comfort learning qualitative analysis methodologies such as open coding, thematic analysis, or systematic evaluation processes
• Skill in translating tacit knowledge into explicit, teachable principles that can be documented and learned

Communication & Documentation 

• Excellent written communication skills: you can articulate why something is good or bad in a way that both humans and AI training systems can learn from
• Ability to create clear, structured documentation of standards, processes, evaluation criteria, and insights
• Comfort presenting findings and recommendations to both technical and non-technical stakeholders

Mindset  

• Self-directed and comfortable with ambiguity in an early-stage environment where your role is pioneering
• Passionate about nonprofit mission and impact, with genuine commitment to scaling expert grant support through technology
• Detail-oriented without losing sight of the bigger picture: you can critique individual outputs while tracking systemic patterns

Hiring Process

The hiring process for this role is as follows:

1. Initial Phone Screen (15 minutes)
2. Hiring Manager interview (30 minutes)
3. Assignment: Grant critique and quality framework exercise (1-2 hours)
4. Live Presentation: Present your quality framework and evaluation approach (1 hour)
5. 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.

 

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 that’s 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!

 

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.