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

Vouch; Chicago (IL); Hybrid; USD 140,000 - 200,000; Full time

Benefits offered by this job

Competitive compensation and equity

Health, dental, and vision insurance

Parental leave

Flexible vacation time

Wellness allowance

Technology allowance

Company-sponsored personal and pro-fes

L&D: Ethena partnerships and Lunch & L

Wellbeing perks and Caregiver Support

Regular performance reviews

Job summary

Vouch is building an AI-powered insurance advisory platform and seeks a founding product partner to bridge humans and software. You will embed in a team of AI and software engineers, owning the seam between brokers and the system, and running a parallel build track to avoid single-threaded engineering.

You will report to the Director of Product, collaborate with leadership, and drive measurable learning through instrumentation and iterative design to improve decision quality and business

Qualifications

• Shipped AI products in production with feedback loops improving the system over time.
• Able to walk through code or artifacts demonstrating hands-on development.
• Systems thinking: design workflows and feedback loops that improve over time.
• Experience defining success criteria for unmeasured problems.
• Strong field research ethos: shadow practitioners and extract actionable insights.
• Experience in regulated or complex professional domains (insurance/fintech/healthcare).
• Clear written communication; able to produce decision logs and architecture discussions.

Responsibilities

• Sit alongside brokers to observe and experiment with human-in-the-loop interactions.
• Ensure the team solves the right problem by aligning broker needs with system output.
• Map broker workflows into tangible assets, advice units, and actionable recommendations.
• Design feedback loops for domain experts to validate and enrich system output.
• Stand up broker-facing solutions by mid-week without blocking on engineering leads.
• Run the learning backlog, form hypotheses, and feed them into the next cycle.
• Build instrumentation to measure system intelligence and performance, and iterate.
• Define north-star and guardrail metrics tied to unit economics and hold the team accountable.

Job description

Vouch is building an AI-powered insurance advisory platform and seeks a founding product partner to bridge humans and software. You will embed in a team of AI and software engineers, owning the seam between brokers and the system, and running a parallel build track to avoid single-threaded engineering.

You will report to the Director of Product, collaborate with leadership, and drive measurable learning through instrumentation and iterative design to improve decision quality and business