Head of Strategy & Analytics

Head of Strategy & Analytics @ high-growth healthtech / AI company

Onsite:
Chicago, IL

Think:
Operating system for smarter healthcare decisions, at scale.

Company has raised $100M+ to solve one of the biggest cost problems for employers: helping employees find high-quality care without the complexity. The platform is used by 1,500+ employers and partners, giving HR leaders, CFOs, and benefit consultants a data-driven way to control costs and drive real benefits utilization.

The product works. Now it’s scaling. We’re turning data into direction to 10x a proven platform.

This is the kind of opportunity you rarely get twice.

This is not a narrow role. This is an opportunity for someone who loves building, thrives in ambiguity, and loves to turn data into direction and chaos into clarity.

If you’re a systems thinker who loves blending strategy with data, and you move at the speed of a startup but think like an operator — this role is for you.

• Tackle the company’s toughest strategic questions by turning scattered business, product, and operational data into clear direction and a single source of truth.
• Build the models, frameworks, and dashboards that help us spot problems early, uncover growth levers, and guide high-velocity decision‑making.
• Work directly with the executive team to set priorities, pressure‑test assumptions, and shape how we scale the business.
• Use AI tools and data automation to move faster, break bottlenecks, and deliver insights that drive action.

• You have experience in a senior Strategy, Biz Ops, or Analytics role at a high‑growth company – AND – ideally prior experience in management consulting.
• You are often given the hardest problems to solve (fast).
• You’re fluent in SQL, dashboards (Looker/Tableau/Mode), modeling, forecasting, and AI tools, and use them daily.
• Python is a plus
• You’ve partnered with C‑suite stakeholders, and know how to turn data into decisions.
• You want ownership, accountability, and real impact, not a comfortable job.
• Competitive salary and equity compensation