Director, Operations Strategy & Enablement - IntelliScript (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

What We Do

Milliman IntelliScript is a group of a few hundred experts in fields ranging from actuarial science to information technology to clinical practice. Together, we develop and deploy category-defining, data-driven, software-as-a-service (SaaS) products for a broad spectrum of insurance, health IT and life sciences clients. We are a business unit within Milliman, Inc., a respected consultancy with offices around the world.

Candidates who have their pick of jobs are drawn to IntelliScript's entrepreneurial and collaborative culture of innovation, excellence, exceptional customer service, balance, and transparency. Every single person has a voice in our company, and we challenge each other to push the outer limits of our full, diverse potential. And, we've shown sustained growth that ensures you'll have room to grow your skillset, responsibilities, and career.

Our team is smart, down-to-earth, and ready to listen to your best ideas. We reward excellence and offer competitive compensation and benefits. Visit our LinkedIn page for a closer look at our company, and learn more about our cultural values here.

Milliman invests in skills training and career development and gives all employees access to a variety of learning and mentoring opportunities. Our growing number of Milliman Employee Resource Groups (ERGs) are employee-led communities that influence policy decisions, develop future leaders, and amplify the voices of their constituents. We encourage our employees to give back to their varied professions, including leadership in professional organizations. Please visit our website to learn more about Milliman's commitments to our people, diversity and inclusion, social impact, and sustainability.

What this position entails

The Director, Operations Strategy & Enablement is a key member of our Operations leadership team, driving Operations strategy, delivery, cross-functional alignment, and process frameworks at Milliman IntelliScript. Intersecting technical execution, consumer operations, and data governance, this role aligns product, technical, and client-facing teams to ensure maximum efficiency, accuracy, and compliance across our Insurtech portfolio.

What you will be doing

Strategic Alignment & Operational Governance

• Partner with leadership to 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

Consumer Operations, Data Quality & AI Automation

• 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.
• Establish AI governance, prompt standards, and risk controls for operational deployments.

Metrics & Team Leadership

• 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.

What we need

• Leadership & Experience: 10+ years leading operations, business enablement, or delivery in high-growth B2B software or tech environments.
• AI & Automation: Proven track record deploying and governing AI agents, LLMs, or automated tools to solve operational challenges.
• Operations & Data: Deep experience managing workflows and high-volume data environments, interpreting large data sets, and improving data quality.
• Strategy & Analytics: Strong skill in translating complex strategies into scalable execution, managing capacity models, and using data-driven metrics.
• Communication: Clear communicator across executive, operations, business, and technical audiences.

Wish List

• Familiarity with HIPAA or FCRA regulations
• Applied knowledge of generative AI, prompt engineering, and operational automation.
• Strong understanding of SaaS models, technical product lifecycles, and consumer operations.
• Hands‑on problem solver with a track record of data-driven decision-making.

Location

The expected application deadline for this job is January 31, 2027. This position is open to remote work. Applicants must be willing to travel to the Milliman office in Brookfield, WI as needed and travel nationwide for meetings, conferences, and team events.

Compensation

The overall range for this role is $165,100 - $313,145. For candidates residing in:

• Alaska, California, Connecticut, Illinois, Maryland, Massachusetts, New Jersey, New York City, Pennsylvania, Virginia, Washington, or the District of Columbia the range is $189,865 - $313,145.
• All other locations the range is $165,100 - $272,300.

A combination of factors will be considered, including, but not limited to, education, relevant work experience, qualifications, skills, certifications, etc.

Individual(s) must be legally authorized to work in the United States without the need for immigration support or sponsorship from Milliman now or in the future.

Milliman Benefits

We offer a comprehensive benefits package designed to support employees' health, financial security, and well-being. Benefits include:

• Medical, Dental and Vision - Coverage for employees, dependents, and domestic partners
• Employee Assistance Program (EAP) - Confidential support for personal and work-related challenges
• 401(k) Plan - Includes a company matching program and profit-sharing contributions
• Discretionary Bonus Program - Recognizing employee contributions
• Flexible Spending Accounts (FSA) - Pre-tax savings for dependent care, transportation, and eligible medical expenses
• Paid Time Off (PTO) - Begins accruing on the first day of work. Full-time employees accrue 15 days per year, and employees working less than full-time accrue PTO on a prorated basis
• Holidays - A minimum of 10 paid holidays per year
• Family Building Benefits - Includes adoption and fertility assistance
• Paid Parental Leave - Up to 11 weeks of paid leave for employees who meet eligibility criteriaLife Insurance & AD&D - 100% of premiums covered by Milliman
• Short-Term and Long-Term Disability - Fully paid by Milliman

Equal Opportunity

All qualified applicants will receive consideration for employment, without regard to race, color, religion, sex, sexual orientation, national origin, disability, or status as a protected veteran.

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