About the Role

We are looking for a skilled, curious, and organized contractor to support our growing client work. You will conduct discovery sessions with nonprofit staff, help build and deliver training materials, and support clients in organizing their data for better AI outcomes. This is hands-on, client-facing work that requires both technical fluency and strong communication skills.

This is a per-project contract role, starting at approximately 15 to 20 hours per month with the potential to grow over time.

What You'll Do

Discovery and Workflow Analysis

• Meet with nonprofit staff across roles and functions to understand their day-to-day workflows

• Identify risks, friction points, root causes, and opportunities for improvement through active listening and structured inquiry

• Assess the underlying data workflows and infrastructures that shape what AI can realistically do for each organization

• Translate findings into a clear use case matrix that maps workflows to potential AI applications

Training Development and Delivery

• Research current capabilities, limitations, and risks across major AI platforms (Claude, ChatGPT, Google Gemini, Microsoft Copilot, and emerging agent tools)

• Build and maintain training materials tailored to each client's use cases and comfort level

• Deliver training sessions to non-technical audiences, explaining complex topics in plain, approachable language

• Help clients understand data privacy considerations specific to nonprofits, including how AI tools handle sensitive information and what that means legally and operationally

Data Governance Support

• Work with clients to organize, tag, and structure their data in support of a broader data roadmap

• Execute roadmap milestones with appropriate oversight from Grapevine and partner organizations

• Work with clients to understand and select expert vendors

• Maintain a clear understanding of each client's trajectory and flag issues or opportunities as they arise

What We're Looking For

Qualities

• A genuine listener who makes people feel heard, especially non-technical staff who are still finding their footing with AI

• Clear, patient communicator who can translate technical concepts for audiences ranging from Executive Directors to program staff

• Organized and self-directed, with a strong instinct for what "done" looks like and a commitment to meeting it

• Intellectually curious and willing to explore new tools, even without a complete roadmap

Skills and Experience

• Demonstrated hands-on experience with AI tools -- not just using them, but experimenting with how they work, testing agents, and building or iterating on workflows

• Solid understanding of how large language models function, including concepts like training and inference, retrieval augmented generation (RAG), prompting, memory, and agentic behavior

• Familiarity with data privacy considerations for nonprofits, including how AI providers handle data use and retention and what constitutes third-party disclosure

• Ability to assess a client's data infrastructure and spot foundational gaps that would expose organizations to risk or undermine AI adoption

• Experience working with or for nonprofits is a strong plus

• Comfort producing polished, finished deliverables with limited direction

Engagement Details

• Type: Independent contractor, hourly rate

• Commitment: Approximately 15 to 20 hours per month to start, with potential to grow over time

• Location: Remote. Candidates must be based in a continental US time zone