Supervisor, Care Team (Weekends/2nd Shift)

TRAINING HOURS: First four weeks 9:00am-5:30pm EST M-F.

SHIFT OPTIONS:

12:30pm-9:00pm EST Tuesday-Saturday

OR

12:30pm-9:00pm EST Sunday-Thursday

OR

12:30pm-9:00pm EST Saturday & Sunday with two weekdays off.

ABOUT THE ROLE:

The Supervisor, Care Team provides day-to-day leadership and oversight of front-line Pharmacy Technicians and Leads, ensuring the delivery of high-quality support to our members, pharmacies, and providers — whether they reach us by phone, chat, or email. This role is critical to maintaining service level performance, coaching team members, monitoring attendance and resolving escalated issues in real time. You will work closely with the Managers, Sr. Managers and cross-functional teams to uphold operational standards and foster a collaborative team culture.

WHAT YOU’LL DO:

• Provide day-to-day supervision and support for Pharmacy Technicians and Leads as their direct supervisor, including managing timecards, monitoring schedules, tracking attendance, and overseeing individual performance.
• Partner with the Workforce Management team to adjust staffing and queue assignments for your channel, maintaining service level performance and optimizing team productivity.
• Help implement and refine Care Team workflows to meet department standards, client expectations, and service guarantees.
• Foster a positive team culture by conducting regular structured feedback conversations, coaching team members, reinforcing development goals, and promoting collaboration.
• Monitor individual and team performance metrics, identifying trends and supporting action plans to improve outcomes.
• Participate in quality monitoring initiatives and NPS survey programs that promote first-contact resolution and reduce repeat member outreach.
• Assist with onboarding new clients by preparing frontline teams and coordinating across internal stakeholders to ensure readiness.
• Proactively monitor call or chat activity to identify emerging issues, escalating or supporting resolution as needed, including member escalations.
• Help maintain knowledge base materials, standard operating procedures, and training documentation shared across channels.
• Demonstrate a working understanding of PBM workflows, including pharmacy claims processing and industry terminology.
• Participate in special projects as determined by management, utilizing your expertise and skills to drive business outcomes.
• Support cross-training efforts, helping your team build skills across both phone and chat.
• Uphold compliance with regulatory and privacy requirements, including HIPAA, across all member interactions.

WHO YOU ARE:

• Bachelor's degree preferred or equivalent work experience.
• Nationally Certified Pharmacy Technician (preferred); state licensure or registration required where applicable by law.
• 3+ years of experience in a healthcare contact center, retail pharmacy, PBM, or pharmacy operations setting, with a strong understanding of pharmacy-related customer service.
• Experience as a people leader, having previously led teams of pharmacy technicians (preferred).
• Proven ability to coach, motivate, and support frontline team members in a high-volume, service-driven environment.
• Comfortable balancing team performance metrics with individual development and engagement.
• Strong problem-solving skills, with the ability to think quickly and resolve member or provider issues in real time.
• Skilled at using data to identify trends, support team improvements, and drive operational efficiency.
• Excellent verbal and written communication skills, with confidence handling escalations and communicating across teams.
• Detail-oriented, highly organized, and able to manage multiple priorities in a fast-paced setting.
• Familiarity with pharmacy claims, PBM systems, and HIPAA/privacy requirements preferred.

COMPENSATION: $65,000 - $75,000 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.