Director, AI-Driven Ops Strategy & Enablement (Remote)

Milliman, Inc; Town of Brookfield (WI); Remote; USD 165,000 - 313,000; Full time

Benefits offered by this job

Medical-Dental-Vision

401k plan

Discretionary bonus

Paid time off

Parental leave

Life Insurance

Disability

Job summary

Milliman IntelliScript in Brookfield, WI, is seeking a Director of Operations Strategy & Enablement to align product, technical, and client-facing teams for scalable, compliant delivery across our Insurtech portfolio.

You will lead strategic governance, optimize data quality and AI automation, set KPI-driven oversight, and mentor high-performance teams in a fast-growing B2B software environment. This role offers remote-friendly work with travel to Brookfield as needed.

Qualifications

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

Responsibilities

• Translate business goals into actionable technical and operational roadmaps.
• Establish standardized workflows, playbooks, and cross-functional frameworks linking client and consumer delivery across all teams
• Identify bottlenecks, eliminate redundancies, and ensure team readiness on client and consumer delivery.
• Direct consumer operations functions, ensuring high service standards, compliance, and expanded self-service options.
• Improve data quality through continuous monitoring and feedback loops.
• Evaluate and deploy AI agents and intelligent automation to streamline routine workflows, improve routing, and scale team capacity.
• Define and track KPIs, SLAs, and process health metrics; lead regular performance reviews with leadership.
• Mentor and manage high-performing Operations teams, fostering a data-driven, accountable culture.

Skills

Leadership

AI & Automation

Operations & Data

Strategy & Analytics

Communication

Job description

Milliman IntelliScript in Brookfield, WI, is seeking a Director of Operations Strategy & Enablement to align product, technical, and client-facing teams for scalable, compliant delivery across our Insurtech portfolio.

You will lead strategic governance, optimize data quality and AI automation, set KPI-driven oversight, and mentor high-performance teams in a fast-growing B2B software environment. This role offers remote-friendly work with travel to Brookfield as needed.