Employment Type: Contractor
Location: Remote – US
Rate: $100/hr

Dragonfly Editorial is a creative agency that helps companies around the world with content strategy, copywriting, editing, and design.

We’re looking for a skilled Medicaid proposal writer with advanced AI capabilities to support a client engagement. In this freelance role, you’ll work alongside a client’s proposal team during active bid cycles, helping accelerate content development and quality through expert use of AI tools. You’re not just a writer who dabbles in AI — you’re someone who lives at the intersection of deep healthcare knowledge and cutting-edge technology, comfortable building prompts, QCing AI output, and solving whatever the proposal process throws your way.

What you’ll do:

• Partner directly with proposal writers during active bid cycles to accelerate content development using AI tools, including Microsoft Copilot, Visible Thread, and other platforms
• Craft, refine, and document robust prompts for use cases ranging from first-draft development to proof point extraction and competitor analysis
• Pull from baseline content libraries and past proposals to support writers in producing high-quality responses faster, particularly for clinical sections and complex Medicaid scenarios
• Critically evaluate AI-generated output for accuracy, terminology, and quality before returning it to the proposal team
• Contribute to the development of AI best practices, training materials, and prompt libraries as the client team builds out its framework

Our ideal candidate has:

• Deep, hands-on Medicaid knowledge. You know the language, terminology, and nuance, and can apply that expertise to evaluate and improve AI-generated proposal content.
• Advanced AI proficiency. You’re well beyond the basics; you’re skilled in prompt engineering and context window engineering, have crafted your own AI agents, and are comfortable working in most AI tools.
• Proficiency with Microsoft Copilot and familiarity with Visible Thread. You know how to use these tools for content research and analysis.
• Proposal writing background. You can move quickly, adapt to new tools and workflows, and thrive in a fast-paced, bid-driven environment.
• A jack-of-all-trades mindset. You’re comfortable tackling ambiguous problems, building new frameworks as you go, and supporting a team that’s actively growing its AI capabilities.