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Grant Writing Subject Matter Expert (6 Month Contract Role, EST Hours) at FreeWill . Location Information: United States. We build technology that empowers both donors and fundraisers to make the most meaningful donations of their lives.. Serve as the definitive "ground truth" for what constitutes excellent versus poor grant writing, providing the reference standard for AI models.. Review AI-generated grant content and assess quality.. Create and maintain an annotated library of evaluated AI outputs.. 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.. Establish clear standards for output quality and structured guidelines for grant writing best practices.. Document best practices across different grant types.. Drive improvement in key performance metrics.. Partner with leadership to align AI training priorities with broader product strategy.. 7+ years of hands-on grant writing and proposal development experience for US nonprofits.. Experience evaluating or awarding grant proposals.. Deep understanding of grant proposal success factors such as narrative structure, funder alignment, evidence presentation.. 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).. Strong ability to critique others' grant writing and provide actionable feedback.. Experience identifying patterns across large content sets and developing classification frameworks or taxonomies.. Comfort with qualitative analysis methodologies.. Excellent written communication skills.. Ability to create clear, structured documentation of standards, processes, evaluation criteria, and insights.. Comfort presenting findings to both technical and non-technical stakeholders.. Self-directed and comfortable with ambiguity in an early-stage environment.. Passionate about nonprofit mission and impact.. Competitive salary. Remote work