Upsolve

Upsolve, a nonprofit offering free bankruptcy-filing tools for low-income Americans, found that the filing process was too complex for many users to complete unassisted. Last year 56,000 people started the app but didn't finish — not because they were ineligible, but because they got stuck without enough in-the-moment help. Users in acute financial crisis often lacked the time or emotional bandwidth to dig through a help center or wait for support.

In 2025, Upsolve's product team, led by Chief Product Officer Claire Robinson, built an AI Paralegal embedded directly into the filing application. Unlike a generic chatbot, it is context-aware — it sees where a user is in the filing flow and helps troubleshoot the exact error or question on that screen. It uses retrieval-augmented generation to draw on eight years of expert-written support content, surfacing real-time guidance while human paralegals focus on complex cases and quality review.

In February 2026, Upsolve crossed $1 billion in debt erased for 21,000 families since the organization's founding. The AI Paralegal helped the team scale responsibly, more than doubling the number of low-income families helped annually, while reducing user drop-off and improving accuracy in the filing process.

• Embedding a context-aware AI assistant directly in a complex, high-stakes workflow (rather than a generic help-center chatbot) can meaningfully cut user drop-off.
• Grounding the assistant in retrieval-augmented generation over years of accumulated expert support content lets it give accurate, in-context answers without replacing human review.
• AI-driven efficiency gains let a small nonprofit team scale service volume (families helped annually more than doubled) without proportionally growing headcount.