Senior AI Product Manager, Human-in-the-Loop Systems

Vouch Insurance; Chicago (IL); Hybrid; USD 170,000 - 210,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Parental leave

Flexible vacation

Wellness allowance

Technology allowance

Development opportunities

Lunch & Learns

Job summary

Vouch is building an AI-driven insurance advisory platform with a focus on human-in-the-loop decision making. This Chicago-hybrid role sits at the seam between brokers and the learning engine, owning the end-to-end product engagement and ensuring measurable improvements in the system’s performance.

You will partner with AI and software engineers, run pilot programs, and translate feedback into incremental product iterations.

Qualifications

• Shipped AI products in production with real users and feedback loops.
• Able to walk through code you wrote and demonstrate a frontend prototype.
• Experience designing workflows and feedback loops across systems.

Responsibilities

• Sit alongside brokers to observe and define human-in-the-loop interaction patterns.
• Map broker needs to system capabilities and translate into actionable outputs.
• Define asset and recommendation strategies for brokers to act on.
• Build and refine feedback loops with domain experts to improve system outputs.
• Lead pilot users, gather feedback, and drive iterative improvements.
• Collaborate with engineers to instrument the system and measure learning improvements.
• Define north-star, driver, and guardrail metrics tied to unit economics.

Skills

AI product management

Frontend foundation

Systems thinking

Data analysis (SQL/Snowflake)

Communication

Tools

Claude Code

Cursor

Lovable

v0

Replit

Job description

Vouch is building an AI-driven insurance advisory platform with a focus on human-in-the-loop decision making. This Chicago-hybrid role sits at the seam between brokers and the learning engine, owning the end-to-end product engagement and ensuring measurable improvements in the system’s performance.

You will partner with AI and software engineers, run pilot programs, and translate feedback into incremental product iterations.