Sr. Director, Stop Loss (Health Insurance)

Location: Chicago, Illinois, United States; flex employees are expected to work in the office at least three days per week.

Base pay: $133,400–$247,700 annually, plus eligibility for an annual incentive bonus.

Company

hirify.global is a health insurance organization offering employee development programs and a comprehensive benefits package.

What you will do

• Define the long-term vision, strategic direction, and roadmap for stop loss products.
• Serve as Product Owner and lead product development, enhancement, implementation, and ongoing performance management.
• Develop strategies to increase product revenue, customer acquisition, engagement, and retention.
• Coordinate stop loss initiatives across IT, Operations, Sales, Account Management, Marketing, and other corporate functions.
• Use data, competitive analysis, and market insights to guide product design and strategic partnerships.
• Oversee budgets, resource allocation, business cases, cost-benefit analysis, and ROI delivery.

Requirements

• Bachelor’s degree in business or Health Administration and 10 years of experience in healthcare, health insurance, or strategic consulting, or 14 years of relevant experience.
• At least 5 years of management experience and 5 years of stop loss experience.
• Experience with enterprise-wide project coordination, project management, facilitation, presentations, and leadership.
• Knowledge of field sales operations and business strategies in the insurance industry.
• Experience leading and mentoring staff and working with senior management across multiple departments.
• Strong analytical, organizational, communication, business case, risk analysis, and implementation skills.

Nice to have

• Experience managing complex products through the full product development lifecycle.
• Ability to move abstract concepts and early product ideas through development into successful product solutions.
• Experience analyzing market trends, competitive landscapes, and product performance.
• Ability to prepare executive-level documents and presentations and manage multiple priorities in parallel.

Culture & Benefits

• Curated professional development plans and opportunities for career growth.
• Health and wellness benefits, 401(k) savings plan, pension plan, paid time off, and paid parental leave.
• Disability insurance, supplemental life insurance, employee assistance program, and paid holidays.
• Tuition reimbursement and additional incentive programs.
• Hybrid flexibility with a minimum of three office days per week for flex employees.