Executive Director, Actuarial (Chicago)

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Job Summary

The Executive Director, Medicare Part D Actuarial will lead the actuarial function for Medicare Part D products, including Individual MAPD and PDP, with end-to-end accountability for product strategy, pricing, and financial performance. The Executive Director provides actuarial leadership across product strategy, benefit design, formulary and pharmacy network strategies, and is responsible for Medicare Part D bid development and submission, quarterly forecasting, monthly close support, and bid audits. This position reports to the DSVP, Pharmacy Finance and Actuarial and serves as a key strategic partner to senior leaders across Pharmacy, Product, Finance, Compliance, and Operations. The role also acts as the primary actuarial point of contact for external vendors and consultants.

Key Responsibilities

Medicare Part D Product & Pricing Leadership

• Lead actuarial strategy for Individual MAPD and PDP products, ensuring financial sustainability, regulatory compliance, and competitive market positioning.
• Provide actuarial leadership on product strategy and component strategies, including benefits, formulary, rebate, network, and mail, balancing affordability, growth, and margin objectives.
• Partner cross-functionally with Pharmacy, Product, Finance, Compliance, and Operations to align actuarial assumptions with enterprise strategy.

Bid Development & Financial Management

• Oversee end-to-end Medicare Part D bid development and submission, including pricing, assumptions, documentation, and internal governance approvals.
• Lead quarterly forecast updates and support monthly close activities, ensuring accuracy, transparency, and alignment between actuarial projections and financial results.
• Provide actuarial support for annual PBM market checks and negotiations.
• Identify key financial risks and opportunities, proactively communicating insights and recommendations to executive leadership.

Market Intelligence & Strategic Insights

• Lead Medicare Part D market intelligence, including competitor analysis, CMS policy changes, regulatory guidance, and industry trends.
• Translate market insights into actionable recommendations for product design, pricing strategy, and long-term Medicare positioning.

Audit, Governance & Compliance

• Serve as actuarial lead for CMS bid audits, internal audits, and financial audits, ensuring defensibility of assumptions, data integrity, and timely responses.
• Establish and maintain strong actuarial governance, controls, and documentation standards to support regulatory and audit requirements.

Vendor & External Partner Management

• Act as the primary actuarial point of contact for external actuarial vendors and consultants.
• Oversee vendor scope, deliverables, timelines, and quality, ensuring alignment with business objectives and regulatory expectations.
• Leverage external partnerships to enhance modeling sophistication, analytics, and strategic decision-making.

Leadership & Talent Development

• Lead, mentor, and develop a high-performing actuarial team supporting Medicare Part D.
• Foster a culture of accountability, collaboration, and continuous improvement, with a focus on developing future actuarial leaders.
• Set clear priorities, performance expectations, and development plans aligned with organizational goals.

Job Requirements

• Bachelor’s degree in business, Finance, Actuarial Science, Mathematics, Economics, Computer Science or Management Information Systems.
• 10 years of data, transactional application-based knowledge or group health underwriting experience.
• 10 years of management experience, including overseeing two or more departments led by managers.
• Experience in leading one or more major (multi year) group insurance implementation projects.
• Experience in leading one of the following: Actuarial Systems or Applications and systems related teams including testing, building, and writing requirements.
• Experience in quality and auditing and system testing (including creating test scripts).
• Experience planning skills including setting goals at a position appropriate level, long term planning (one year or longer), budget and expense management, creating staffing models for up to two years, establishing department vision.
• Problem solving, negotiation skills, and organizational alignment.
• Clear and concise verbal and written communication skills. Experience presenting to all levels of management including audiences with diverse communication preferences.
• Overseeing the annual budget and allocating resources for various projects and operational needs.
• Translating needs and initiatives into compelling business cases.
• Conducting cost-benefit analyses to justify investments and ensure ROI.

Preferred Job Requirements

• Bachelor’s degree in Actuarial Science, Mathematics, Statistics, Economics, or a related field; advanced degree preferred.
• FSA designation.
• 10+ years of progressive actuarial experience, including significant leadership responsibility in Medicare Part D.
• Deep expertise in Medicare Part D pricing, bid development, forecasting, and regulatory requirements.
• Strong strategic influence, executive presence, and financial acumen.
• Strong understanding of pharmacy benefit economics, including formulary and network strategy impacts.
• Proven experience leading CMS bid audits and financial audits, and partnering with external actuarial firms.
• Demonstrated ability to communicate complex actuarial and financial concepts clearly to senior leaders and non-technical stakeholders.

HCSC Employment Statement

We are an Equal Opportunity Employment employer dedicated to providing a welcoming environment where the unique differences of our employees are respected and valued. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected characteristics.

Base Pay Range

$161,500.00 - $299,700.00

Exact compensation may vary based on skills, experience, and location.

We offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting

The compensation offered will vary depending on your job-related skills, education, knowledge, and experience. This role aligns with an annual incentive bonus plan subject to the terms and the conditions of the plan.