Principal Actuary

About the role

The Principal Actuary will lead the actuarial function for product design, pricing and performance measurement, reporting to the CFO and collaborating with executive, product and data‑science teams. The role owns methodology, risk models and HRA design, influencing pricing, plan design and external stakeholder discussions.

About the company

HealthJoy provides a digital benefits operating system that simplifies healthcare and wellness for employees, using AI‑driven predictive analytics, NLP and machine learning to guide users to affordable, high‑quality care. The fast‑growing startup (300+ staff) has won Inc.’s Fastest Growing Startups and Built In Chicago’s Best Places to Work awards.

Requirements

• ASA or FSA designation (MAAA preferred) with at least 7 years health actuarial experience, preferably on commercial or employer‑sponsored plans
• Deep understanding of self‑funded plan economics, including stop‑loss, lasering and claims forecasting
• Hands‑on experience designing and modeling employer‑funded HRAs, ensuring integration with medical plans, HSA compatibility, ERISA/COBRA requirements and IRS compliance
• Experience forecasting HRA utilization, setting rollover and forfeiture assumptions, and pricing incentive dollars based on member behavior
• Proven ability to build or review program savings studies and critically assess common methodologies
• Strong SQL skills; Python or R experience is a plus
• Track record of standing behind numbers that have been reviewed by outside parties
• Cultural fit: motivated by creating measurement standards up front rather than flashy ROI slides
• Desire for broad ownership, visibility and direct influence on product, pricing and partner decisions
• Preference for working in a high‑growth, senior‑leadership environment reporting directly to the CFO