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.

Key Accountabilities

• 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

What You Will Own

• Complex Deal Execution
• 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

Renewal Pricing and Margin Support

• 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

Modeling and Process Improvement

• 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

Strategic Contribution

• 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

Operating Agility

• Manage multiple concurrent deals with shifting timelines
• Deliver accurate work within tight turnaround expectations
• Maintain underwriting rigor in fast-moving commercial situations

Required Experience and Capabilities

• 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

Preferred Experience

• 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

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 paid medical, dental, and vision premiums
• Company contribution to Health Savings Account, if enrolled in high deductible health plan
• Stock options

Prescryptive is committed to fair pay practices. The projected annual salary for this position is $175,000 - $225,000. When preparing an offer, we consider the candidates resume, experience, interview feedback, 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, national origin, veteran status or any other basis covered by appropriate law. All employment is decided on the basis of qualifications, merit, and business need.