Jobs › Health Care Service Corporation

Sr. Director, Stop Loss

Health Care Service Corporation · Chicago, IL · $133,400–$247,700 a year · Full time

Posted Oct 2, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a product roadmap you built. How did you decide what to build first?

What they are checking: Whether they have real product strategy experience and a clear way of prioritizing.

Tell me about a time you defined business requirements for a new product or enhancement.

What they are checking: Whether they can turn strategy into requirements that operations and IT can build.

Tell me about a time a product initiative missed its deadline. What did you do?

What they are checking: Whether they own delivery problems and get projects back on track.

What would you do

Sales wants more competitive stop loss pricing to hit targets, but profitability is under pressure. How do you handle it?

What they are checking: Whether they balance growth and profitability and bring both sides to a clear decision.

How would you coordinate stop loss activities across underwriting, actuarial, claims and sales?

What they are checking: Whether they can lead across corporate areas they do not directly manage.

About the work

Explain how specific and aggregate stop loss work for a self-funded employer.

What they are checking: Whether they know the product mechanics deeply enough to lead its strategy.

Stop loss loss ratios are rising across the block. How do you figure out why and what to do?

What they are checking: Whether they can diagnose performance through large claims, specialty drugs, pricing and mix.

How do high-cost specialty drugs and gene therapies change how you design and price stop loss products?

What they are checking: Whether they understand the trends that are reshaping stop loss risk.

How do you compare HCSC's stop loss offering against competitors?

What they are checking: Whether they think about competitive positioning in terms of contract terms, service and price.

What is a laser in stop loss, and when would you use one?

What they are checking: Whether they know common contract features and the risk trade-offs they create.

Practice this interview out loud.

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The full job description

As published by Health Care Service Corporation.

At HCSC, our employees are the cornerstone of our business and the foundation to our success. We empower employees with curated development plans that foster growth and promote rewarding, fulfilling careers. Join HCSC and be part of a purpose-driven company that will invest in your professional development. Job Summary This position is responsible for providing overall strategic leadership over the performance, management and development of enhancements to Stop Loss; assuming role of Product Strategist for Stop Loss, ensuring Stop Loss meets company profitability and operational requirements, supporting Sales and Account Management in achieving stop loss targets, managing performance of Stop Loss with input from other stakeholders, coordinating all Stop Loss activities across corporate areas to ensure performance meets targets and development and implementation initiatives meet assigned deadlines. This person is also responsible for developing, in collaboration with others, the vision and future roadmap for all stop loss related product activities including defining business requirements, leading product development, implementing and sustaining the strategic product roadmap, competitive positioning and product design for both existing and next-generation product offerings. Job Responsibilities: • Develop, in collaboration with others, the long-term stop loss product vision and strategic direction • Develops and manages the stop loss product roadmap and prioritization process • Develops and implements strategies that significantly increase product revenue • Responsible for deploying strategies to improve customer acquisition, engagement, and retention • Serves as Product Owner for Stop Loss Product • Partners and engages with IT and Operations for end-to-end success • Leverages data to influence and shape product design decisions • Operates with a high level of autonomy to drive results • Partners with Marketing Teams on Go to Market plan for Stop Loss Product • Assess strategic partnerships and opportunities that advance the priorities of the stop loss product • Responsible for achieving strong ROI in applicable markets. Required Job Qualifications: • Bachelor’s Degree in business or Health Administration AND 10 years’ experience in health care, health insurance, or strategic consulting environment OR 14 years’ experience in health care, health insurance, or strategic consulting environment • 5 years management experience. • 5 years of stop loss related experience • Enterprise-wide project coordination, project management, facilitation, presentation, and leadership experience. • Knowledge of field sales operations and business strategies in the insurance industry. • Experience leading and mentoring staff. • Clear and concise verbal and written communication skills. • Experience interacting successfully with senior management and staff across multiple departments. • Organizational skills, including ability to prioritize tasks. • Creativity and innovation, risk analysis, analytical rigor, and implementation expertise. • Business acumen and project/process integration skills. • 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 Qualifications: • Proven track record of managing complex products through product development lifecycle • Excellent interpersonal and leadership skills with demonstrated ability to build effective working relationships with individuals and groups at all levels. • Demonstrated ability to communicate effectively both orally and in writing, including formal presentations and the facilitation of group planning sessions. • Ability to work within cross-functional teams. • Ability to write executive level documents and make executive level presentations. • Demonstrated excellent attention to detail including proven ability to manage multiple projects and priorities in parallel. • Demonstrated ability to dive deep in understanding the product, business, and market trends (including the competitive landscape). • Demonstrated ability to move abstract concepts and early product ideas through product development phases to deliver effective and successful product solutions with strong ROI #LI-TR1 INJLF Are you being referred to one of our roles? If so, ask your connection at HCSC about our Employee Referral process! Pay Transparency Statement: At Health Care Service Corporation, you will be part of an organization committed to offering meaningful benefits to our employees to support their life outside of work. From health and wellness benefits, 401(k) savings plan, pension plan, paid time off, paid parental leave, disability insurance, supplemental life insurance, employee assistance program, paid holidays, tuition reimbursement, plus other incentives, we offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting https://careers.hcsc.com/totalrewards . 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. Flex employees are expected to be in the office a minimum of three days a week. Management will have discretion to modify an employee's weekly schedule for exigent circumstances. 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. We are a drug-free and smoke-free workplace. Employment may be contingent upon successful completion of drug screening in accordance with applicable law. Base Pay Range $133,400.00 - $247,700.00 Exact compensation may vary based on skills, experience, and location.

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