Head of Operations Strategy & AI Enablement - Remote

Milliman, Inc; Chicago (IL); Remote; USD 190,000 - 313,000; Full time

Benefits offered by this job

Medical, Dental & Vision

401(k) with Match

Discretionary Bonus

Paid PTO

Holidays

Life Insurance

Disability Insurance

FSA

Job summary

Milliman IntelliScript, part of Milliman, Inc., is seeking a Director of Operations Strategy & Enablement to align product, technical, and client-facing teams for maximum efficiency, accuracy, and compliance across the Insurtech portfolio.

You will drive strategic governance, consumer operations, and AI automation, leading high-performing teams and shaping data-driven performance metrics. This role supports remote work with travel to Brookfield, WI as needed and nationwide meetings.

Qualifications

• 10+ years leading operations, enablement or delivery in high-growth B2B software/tech environments.
• Proven track record deploying and governing AI agents, LLMs, or automated tools.
• Deep experience managing workflows and large data environments, improving data quality.
• Strong skill translating complex strategies into scalable execution with data-driven metrics.
• Clear communicator across executive, operations, business, and technical audiences.

Responsibilities

• Strategic Alignment & Operational Governance: translate business goals into actionable roadmaps; establish standardized workflows and cross-functional frameworks.
• Consumer Operations, Data Quality & AI Automation: oversee operations, ensure compliance, expand self-service options; monitor data quality; deploy AI/automation with governance.
• Metrics & Team Leadership: define KPIs and SLAs; lead performance reviews; mentor operations teams.

Skills

Leadership

AI governance

Data management

Strategy & analytics

Communication

Job description

Milliman IntelliScript, part of Milliman, Inc., is seeking a Director of Operations Strategy & Enablement to align product, technical, and client-facing teams for maximum efficiency, accuracy, and compliance across the Insurtech portfolio.

You will drive strategic governance, consumer operations, and AI automation, leading high-performing teams and shaping data-driven performance metrics. This role supports remote work with travel to Brookfield, WI as needed and nationwide meetings.