About this role

The Senior Director, Benefit Operations is a key enterprise leader responsible for delivering the operational excellence, integrity, and innovation that power Prescryptive’s pharmacy benefit services. This role owns the strategy, systems, and teams that ensure every claim is accurate, every process meets all operational and regulatory requirements, and every operational function scales effectively as the company grows.

This leader is accountable for all elements of plan administration, oversight of accuracy plan design builds, formulary operations, drug lists, pharmacy networks operations, and other plan-designated details, claims adjudication, operational program governance, and regulatory compliance — balancing near-term execution with long-term transformation. Oversight includes the accuracy of plan configuration and claim data across adjudication platforms, eligibility, accumulators, formulary structures, and data exchange with TPAs, network partners, and other third parties.

The Senior Director, Benefit Operations provides enterprise oversight of all claims operations and adjudication systems, ensuring data integrity and regulatory execution across platforms and processes. They strengthen core operations today while leading multi-year transformation, leveraging AI and automation to improve quality, efficiency, and team performance.

The Senior Director, Benefit Operations also partners closely with Finance, Clinical, Commercial, and Product leaders to align operational delivery with Prescryptive’s strategic growth and service goals. This role ensures operational excellence translates directly into member experience, cost efficiency, and compliance integrity across the enterprise.

As part of an early-stage company, this leader operates with both strategic range and tactical agility — able to zoom out to design scalable systems and zoom in when needed to solve complex operational challenges firsthand. Every Prescryptive leader models this hands-on, solutions-oriented approach.

What you will do

Key Accountabilities

• Enterprise Operations Leadership: Own and evolve the operating model for plan administration, claims adjudication, operational program governance, and regulatory execution.

• Regulatory and Audit Readiness: Maintain flawless operational regulatory compliance with PBM, state, and federal requirements in partnership with Enterprise Compliance and Legal.

• Vendor and Partner Performance: Optimize vendor ecosystem performance through clear SLAs, accountability, and cost management.

• Transformation and Automation: Drive operational modernization and intelligent automation to enhance accuracy, efficiency, and scalability.

• People and Team Development: Build capability, bench strength, and a culture of accountability and continuous improvement.

Principal Duties, Responsibilities, Performance Expectations (Essential Functions):

• Own and evolve the operating model for plan administration, oversight of accuracy plan design builds, formulary operations, drug lists, pharmacy networks operations, and other plan-designated details, claims adjudication, program governance, and regulatory execution.

• Provide executive oversight and accountability for all claims systems and adjudication processes managed by directors and managers, ensuring data integrity, accuracy, and operational regulatory compliance across all tiers.

• Ensure end-to-end claims integrity and plan accuracy: adjudication platform performance, plan configuration accuracy, eligibility management, accumulator integrity, formulary structures, and data exchange with TPAs and other third parties.

• Oversee formulary operations, plan design builds, pharmacy network operations, drug lists, and other plan-designated details to ensure accuracy, compliance, and alignment with benefit requirements and partner expectations.

• Lead enterprise audit readiness with zero major findings; ensure timely, accurate responses to operational audits and regulator inquiries.

• Partner with Enterprise Compliance and Legal to interpret new regulatory guidance and operationalize it effectively within systems and processes.

• Sponsor complex migrations and implementations (platform, data, vendor) with on-time, in-scope delivery and measurable business outcomes.

• Oversee the vendor ecosystem, setting SLAs, driving accountability, and optimizing cost and value across all contracts.

• Define and execute a multi-year operational strategy with clear cost, quality, and service targets; report progress through executive-ready dashboards.

• Identify single points of failure and build bench strength, succession plans, and cross-training to reduce risk.

• Develop, maintain, and enforce Standard Operating Procedures (SOPs), QA programs, training curricula, and policies that ensure compliant, consistent operations across teams and partners.

• Leverage AI and intelligent automation to streamline workflows, reduce manual effort, and elevate accuracy and speed across functions.

• Establish and own core KPIs: first-pass adjudication accuracy, plan design accuracy, rework/adjustment rates, audit findings, cycle time, cost-to-serve, and stakeholder satisfaction.

• Lead cross-functional initiatives with Clinical, Technology, Product, Finance, and Compliance to resolve root causes and improve outcomes.

What you will bring

• Proven success providing strategic leadership in dynamic, high-growth environments with evolving priorities.

• Track record aligning cost, compliance, and member experience to deliver measurable operational improvements.

• Proven people leadership, including multi-level team supervision, management of a remote workforce, success developing others, and a practice of proactive performance management.

• Expertise managing vendor ecosystems and leading complex negotiations to drive performance and value.

• Executive presence with exceptional communication skills for internal leadership, clients, and industry partners.

• History of leading continuous-improvement programs that enhance efficiency, quality, and risk mitigation.

• Deep understanding of PBM operations and claim adjudication platforms (e.g., Rx adjudication systems, eligibility, accumulators, data exchange).

• Ability to interpret and apply regulatory guidance, including ERISA, federal statutes, and state-based requirements.

• Proficiency with Microsoft Word, Excel, PowerPoint, and Teams for reporting and collaboration.

• Strong written and verbal communication skills with the ability to engage diverse audiences at all levels.

• Experience leading AI-enabled automation or workflow initiatives that demonstrably improved quality, cost, or compliance is required.

• Bachelor’s degree in healthcare, business, or related field.

• 10+ years PBM/health plan operations leadership.

Ideally you will also have

• Master’s degree

• Prior experience managing large-scale transformation programs.

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

• Stock options

Prescryptive is committed to fair pay practices. The projected annual salary for this position is $175,000 to $240,000. 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.