Director, Underwriting

Who is Prescryptive?

Prescryptive is the healthcare technology company enabling the direct access marketplace for prescription drugs. Our platform aligns incentives so affordability, choice, and patient access become the natural outcome of a functioning system. Learn more about us by following us on LinkedIn or visiting Prescryptive.com.

About this role

As the Director of Underwriting at Prescryptive, you will lead complex underwriting for new and renewing pharmacy benefit business, partnering with Product, Pricing, Sales, and Finance to develop pricing that is financially sound, competitive, and aligned with Prescryptive’s transparent model.

This is a hands-on underwriting role, not an underwriting oversight role. You will work directly on complex deals, independently structure pricing within defined guardrails, and manage competing priorities and tight timelines without sacrificing underwriting rigor.

You will also help advance our underwriting capabilities by bringing forward industry insights and improving how we work, including using automation and AI-enabled tools to accelerate modeling, leverage historical underwriting work, and improve data quality and efficiency.

What you will do

• Execute deal-level underwriting using historical claims, pharmacy network pricing, rebate commitments, and other deal-specific inputs.
• Partner with Product, Pricing, and Sales to optimize deal-specific pricing and identify savings opportunities.
• Manage multiple concurrent deals with shifting timelines while maintaining accuracy and underwriting rigor.
• Coordinate deal-level rebate commitments with aggregators and lead underwriting for complex or non-traditional deal structures.
• Partner with Finance to evaluate deal-level risk and margin sufficiency.
• Analyze client and product profitability and bring forward insights on network economics, manufacturer contracting, specialty trends, and operational cost drivers.
• Improve underwriting tools, processes, and data quality through automation and AI-enabled capabilities while maintaining clear, defensible documentation.

What you will bring (minimum requirements)

• 8+ years of underwriting experience, including substantial hands-on PBM/pharmacy benefit underwriting experience across new business and renewals.
• Recent hands-on experience independently building and evaluating pharmacy benefit pricing for self-funded employer groups. Experience incorporating pharmacy quotes or assumptions into broader health plan or TPA underwriting models does not meet this requirement.
• Deep understanding of PBM economics, including pharmacy network pricing, specialty utilization, rebates, guarantees, and margin drivers.
• Advanced Excel modeling skills, with the ability to independently build, interrogate, and modify complex underwriting models.
• Demonstrated commercial judgment, including the ability to evaluate risk, make pricing recommendations, and independently structure deals within defined guardrails.
• Ability to manage multiple complex deals simultaneously in a fast-paced, high-accountability environment.
• Comfort using AI-enabled tools to improve modeling, analysis, and underwriting efficiency.

Ideally you will also have

• Experience pricing mid-market and large employer groups.
• Exposure to underwriting governance frameworks.
• Experience in transparent or pass-through PBM environments.
• Experience improving underwriting automation or tooling.
• Experience in an early-stage or scaling company.

What we have to offer

• The opportunity to grow alongside an early-stage company shaking up a big, old-fashioned industry.
• Flexible time off, including 12 paid holidays.
• 401k match plus 100% employer-provided medical, dental, and vision premiums.
• Company contribution to Health Savings Account.
• Stock options.

Prescryptive is committed to fair pay practices. The projected annual salary range for this position is $175,000 - $225,000. When preparing an offer, we also consider relevant experience, internal equity, and location.

Prescryptive is an Equal Opportunity Employer. Prescryptive does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability.