About the Role

Rightway is looking for a Director of PBM Contracting to lead the drafting, negotiation, and management of pharmacy benefit management (PBM) agreements across our client  relationships. In this role, you will partner closely with sales, client success, underwriting, finance, clinical, operations, and legal to structure commercial terms, financial guarantees, and service commitments that protect Rightway while delivering on our promise to clients and members. You will own the contract lifecycle end to end—from initial term sheets and RFP responses through redlines, execution, and post-signature amendments—and serve as a key voice shaping how Rightway structures financial, commercial, and operational commitments across our book of business.

WHAT YOU’LL DO:

• Lead negotiation and drafting of PBM services agreements, amendments, and statements of work with health plans, self-funded employer groups, consultants, and other PBM clients, from bid, initial draft through execution
• Structure and negotiate key financial and clinical terms, including financial guarantees, pricing conditions, reservation of rights, and performance guarantees
• Manage the full contract lifecycle, including redlines, tracked-changes review, exhibit updates, post-execution addenda, and renewal negotiations
• Partner with legal, finance, underwriting, client success, clinical, and operations stakeholders to align contract terms with regulatory requirements, financial models, and operational capabilities
• Serve as a key point of contact for  client-side legal and procurement teams throughout negotiations, keeping deals moving toward signature
• Serve as subject matter expert, reviewing and responding to RFP and RFI requirements related to PBM contracting
• Maintain and evolve contract templates, playbooks, and standard clause libraries to improve consistency and turnaround time across the contracting team
• Track key contract obligations and deadlines, and identify and escalate risk areas to leadership

Who You Are

• 7+ years of experience in contracting, commercial legal, or contract management roles, with direct experience negotiating PBM, health plan, or other healthcare services agreements
• Experience working within a Contract Lifecycle Management tool as well as managing document workflows involving tracked changes, redlines, and multi-party review across legal, finance, and clinical stakeholders
• Strong working knowledge of PBM economics and contract structures, including  financial guarantees, pricing methodologies, performance guarantees, and audit rights
• Excellent drafting and negotiation skills, with the ability to translate complex commercial and regulatory concepts into clear contract language and communicate to key client-side stakeholders including consultants
• Proven organizational skills with ability to manage multiple, concurrent negotiations under deadline pressure while maintaining accuracy and attention to detail
• Strong cross-functional collaborator, comfortable partnering with finance, underwriting, client success, clinical, operations, sales, and legal to reach commercially sound outcomes
• Sound judgment in identifying and escalating legal, financial, and regulatory risk, with a solutions-oriented approach to resolving open issues
• Bachelor’s degree required; JD, MBA, or other advanced degree a plus

EXTRA CREDIT:

• JD or paralegal backgroundFamiliarity with ERISA, state pharmacy benefit regulations, or public-sector procurement and contracting requirements
• Experience building or maintaining contract playbooks, clause libraries, or negotiation training materials for a growing team
• Experience using Artificial Intelligence tools in drafting and negotiating contracts

COMPENSATION:  $148,000 - $160,000 annually, in addition to bonus and equity

Compensation offered will be determined by geographic location, experience, and qualifications.