ABOUT THE ROLE:
The Vice President, PBM Underwriting owns how Rightway prices and renews pharmacy benefits business. You'll lead the underwriting team that turns client data, market conditions, and contract terms into pricing that's competitive, accurate, and sustainable, for both new business and renewals. You'll partner closely with Sales, Finance, Pharmacy, and Client Success to win the right clients and keep them. This is a senior leadership role with real influence on growth.
WHAT YOU’LL DO:
- Lead underwriting for new business, RFPs, and renewals
- Set underwriting guidelines, approval thresholds, and risk tolerances, and decide when to push back, price for risk, or walk away
- Analyze claims and plan data to identify cost drivers, assess risk, and forecast financial performance
- Work with Legal, Finance, and Sales on contract terms and guarantees that protect margin while keeping offers competitive
- Monitor performance across our book of business against pricing assumptions, and use what you learn to sharpen future pricing and renewal strategy
- Partner with the cost of goods, pharmacy network, and rebate teams so pricing reflects real net costs and contract economics
- Advocate for Rightway’s pricing models clearly to clients, brokers, consultants, and executive leadership
- Build, coach, and develop a high-performing team, and set clear standards for rigor, speed, and documentation
- Report on pricing performance, win/loss trends, renewal outcomes, and risk exposure to the executive team
- Other duties as assigned
WHO YOU ARE:
- 10+ years of experience in PBM underwriting, pharmacy pricing, healthcare analytics, or actuarial work, including 5+ years leading teams
- Deep knowledge of PBM economics, including rebates, pharmacy network pricing, drug acquisition costs, fee structures, and guarantee design
- Strong financial modeling skills and comfort working with large claims datasets (SQL, Excel, and BI tools)
- A track record pricing complex, large-employer or consultant-led deals
- Sound judgment under uncertainty, with the confidence to make and defend a call
- Clear communication, in writing and in the room, with technical and non-technical audiences
- Bachelor's degree in finance, actuarial science, economics, pharmacy, or a related field
EXTRA CREDIT:
- Actuarial credential (ASA, FSA, or MAAA)
- Experience at a PBM, health plan, consultancy, or pharmacy-focused analytics firm
- Experience with pass-through or fully transparent pricing models
- Experience building underwriting tools or automating pricing workflows
COMPENSATION: $210,000 - $250,000 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 $300mm from investors including Khosla Ventures, Thrive Capital, Francisco Partners, 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.
Skills Required
- 10+ years of experience in PBM underwriting, pharmacy pricing, healthcare analytics, or actuarial work
- 5+ years of experience leading teams
- Deep knowledge of PBM economics, including rebates, pharmacy network pricing, drug acquisition costs, fee structures, and guarantee design
- Strong financial modeling skills and experience with large claims datasets using SQL, Excel, and BI tools
- Track record pricing complex, large-employer or consultant-led deals
- Sound judgment under uncertainty and ability to make and defend pricing decisions
- Clear written and verbal communication with technical and non-technical audiences
- Bachelor's degree in finance, actuarial science, economics, pharmacy, or a related field
- Actuarial credential such as ASA, FSA, or MAAA
- Experience at a PBM, health plan, consultancy, or pharmacy-focused analytics firm
- Experience with pass-through or fully transparent pricing models
- Experience building underwriting tools or automating pricing workflows
Rightway Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Rightway and has not been reviewed or approved by Rightway.
-
Healthcare Strength — Core coverage includes full medical, dental, and vision insurance with an HSA option, alongside additional health and wellness resources. These offerings present a comprehensive baseline of healthcare support.
-
Leave & Time Off Breadth — Time off is positioned as ample, with PTO, paid sick days, holidays, and parental leave noted across employer materials. This breadth supports rest, recovery, and family needs.
-
Wellbeing & Lifestyle Benefits — Perks span hybrid work, commuter benefits, in-office meals/snacks, wellness initiatives, ERGs, home-office stipends, and learning/development programs. These elements enhance everyday experience beyond core pay and insurance.
Rightway Insights
What We Do
Our care navigation and pharmacy benefits management solutions are delivered through a consumer-centric app that pairs every member with a live, clinician-led care team. By combining expert, human guidance with intuitive technology, Rightway drives members towards the best care and medication at the best price while eliminating wasteful and preventable spend.
Why Work With Us
Rightway is a company of real humans helping real humans. Join a team that's creating a better healthcare experience for all. Nothing is more important to us than the health and happiness of our members — and our employees.
Gallery
