Director, Underwriting

Prescryptive Health, Inc. • Wyoming, MI

1d • $175,000 - $225,000

About The Position

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 The Director of Underwriting is a senior underwriting leader responsible for driving disciplined pricing and risk evaluation across Prescryptive’s offerings to its business customers. This role partners with the VP, Finance and the Senior Director of Underwriting to ensure new business and renewal pricing decisions are financially sound, competitive, and aligned with Prescryptive’s transparent model. The Director leads complex deal work, supports renewal margin stability, and contributes to drug trend and pricing guardrail discussions. Prescryptive operates in a nimble environment with tight timelines and evolving priorities. This role requires strong analytical precision, comfort with reprioritization, and the ability to deliver rigorous underwriting analysis at speed. AI-enabled tools are expected to be used to accelerate modeling, benchmark prior deals, ingest historical underwriting work, and simplify go-forward workflows. Success is measured by accurate pricing execution, disciplined renewal management, strong cross-functional partnership, and consistent underwriting rigor under pressure.

Requirements

• 6+ years of PBM underwriting or pharmacy pricing experience
• Experience pricing employer groups in self-funded environments
• Experience modeling specialty utilization, rebate impact, and guarantee structures
• Demonstrated experience supporting both new business and renewals
• Strong Excel modeling skills with complex scenario capability
• Demonstrated commercial judgment in pricing decisions
• Ability to independently structure pricing within defined guardrails
• Demonstrated ability to manage multiple concurrent deals with shifting priorities
• Demonstrated ability to operate effectively in fast-paced, high-accountability environments
• Comfort using AI-enabled tools to accelerate modeling, ingest prior underwriting work, and improve analytical efficiency
• Bachelor's degree in business, economics, math or other analytics discipline

Nice To Haves

• 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
• Early-stage or scaling company experience
• Demonstrated use of AI to streamline financial modeling and analytical workflows
• MBA degree

Responsibilities

• Accurate and disciplined pricing for complex opportunities
• Renewal margin stability and risk assessment
• Financial model integrity
• Clear communication of pricing implications
• Consistent application of underwriting guardrails
• Reliable execution under compressed timelines
• Effective use of AI to improve speed and analytical quality
• Lead underwriting for specific strategic or non-standard employer opportunities
• Evaluate utilization assumptions, specialty exposure, rebates, guarantees, and administrative fee structures
• Structure pricing within defined guardrails
• Clearly communicate financial trade-offs and risk considerations
• Use AI tools to benchmark assumptions against prior comparable work and surface potential risk indicators
• Conduct renewal analyses and pricing recommendations
• Identify trend shifts and margin risk
• Recommend adjustments based on claims performance and market conditions
• Use AI to synthesize historical claims data and highlight anomalies or emerging patterns
• Build and maintain underwriting models
• Refine pricing assumptions using historical performance data
• Improve underwriting tool scalability and workflow efficiency
• Leverage AI to automate repetitive modeling steps, ingest prior deal documentation, and reduce cycle time
• Ensure clarity and defensibility in documentation
• Contribute to drug trend and specialty risk discussions
• Participate in underwriting governance conversations
• Collaborate closely with Senior Director and VP, Finance to ensure pricing consistency
• Manage multiple concurrent deals with shifting timelines
• Deliver accurate work within tight turnaround expectations
• Maintain underwriting rigor in fast-moving commercial situations

Benefits

• Flexible time off, including 12 paid holidays
• 401k match plus 100% employer paid medical, dental, and vision premiums
• Company contribution to Health Savings Account, if enrolled in high deductible health plan
• Stock options

What This Job Offers

• Job Type: Full-time
• Career Level: Director