Director, PBM Contracting

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. CYBERSECURITY AWARENESS NOTICE In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the @ rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment. ABOUT RIGHTWAY: Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them. Since its founding in 2017, Rightway has raised over $200mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global. We’re headquartered in New York City, with satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs. HOW WE LIVE OUR VALUES TO OUR TEAMMATES: We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our core values: 1) We are human, first Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding. 2) We redefine what is possible We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems. 3) We debate then commit We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team. 4) We cultivate grit Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity. 5) We seek to delight Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success. Rightway is proud to be an Equal Opportunity Employer that believes in the strength of diverse thought, beliefs, backgrounds, and education. We foster an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis protected by applicable law. All employment decisions are based on merit, qualifications, need, and performance.