Product Support Specialist

ABOUT THE ROLE: We are seeking Product Support Specialists to join a newly established Technical Operations team at Rightway. These individuals will own the full lifecycle of client-facing technical work — from pre-launch configuration and file setup through post-launch monitoring and issue resolution. The team sits within the Product organization and serves as the primary technical interface between Rightway's internal systems and the clients, health plans, and vendors that connect to them. WHAT YOU’LL DO: Technical Implementation: Configure Single Sign-On (SSO) integrations for client employer portals — both inbound (employer IdP → Rightway) and outbound (Rightway → third-party vendors) — following established specifications and validating against test cases before go-live. Execute and validate file transformations across eligibility, accumulator, claims, and related file types, working within the Client Implementation Hub (CIH) and escalating to Data Engineering when files fall outside standard formats or tooling coverage. Set up and configure custom provider networks in Rightway's internal systems (including H1 and ClearCost), ensuring accuracy against client-specific specifications. Configure client engagement and wellness programs in third-party platforms (including Iterable), including population targeting, message setup, and QA before activation. Maintain accurate implementation records, configuration logs, and handoff documentation for each client engagement. Operational Support: Serve as the primary point of escalation for registration and eligibility issues, investigating root causes, applying standard resolutions, and coordinating with Data Engineering or Engineering when issues require deeper intervention. Monitor file ingestion pipelines and audit file processing results for completeness and accuracy; triage and resolve discrepancies proactively before they surface as member-facing problems. Manage provider search and drug search accuracy issues — identifying data quality problems, triaging with the relevant internal team, and tracking to resolution. Process & Documentation: Build and maintain standard operating procedures (SOPs) for each implementation and support workflow owned by the Technical Operations team. Identify recurring issue patterns and work with the team lead and Product to drive upstream fixes — either in tooling, configuration defaults, or client-facing documentation. Create and maintain internal knowledge bases, escalation guides, and QA checklists to support onboarding of future team members and ensure consistency across specialists. Cross-Functional Collaboration: Coordinate with Data Engineering on file type ownership, transformation rules, and escalation boundaries as the CIH tooling matures. Partner with Client Success and the Implementation team to align on client timelines, flag configuration blockers early, and ensure handoffs are complete before go-live dates. Surface member and client-impacting product issues to Product Management with clear reproduction steps and supporting documentation. Provide structured feedback to Product on tooling gaps in CIH and internal configuration systems that would reduce manual effort or error rates over time. WHO YOU ARE: Highly organized and process-driven — you build checklists, document your work, and look for patterns in recurring problems. A structured problem-solver who can work through unfamiliar technical issues methodically even without deep engineering background; you know when to escalate and when to push further. Detail-oriented and accurate; configuration errors have downstream member impact and you take that seriously. Clear written communicator — you can document a complex issue, write a handoff note, or draft an escalation path without ambiguity. Adaptable and self-directed in a startup environment; comfortable with evolving tooling, shifting priorities, and building processes that don't yet exist. Preference for candidates with direct experience in Rightway health guide, pharmacy guide, or registration support operations — internal familiarity with Rightway's member experience, system workflows, and client structure is a meaningful advantage. Previous experience in a technical support, client onboarding, or operations role in healthcare or technology is a plus; deep technical credentials (engineering, coding) are not required. EXTRA CREDIT: Opportunity to help build a net-new function at Rightway and define how technical implementation work gets done as the team scales. Exposure to a broad cross-section of Rightway's internal systems, client configurations, and implementation workflows. Career development pathways into Technical Operations leadership, Product Management, or Implementation Management as the team grows. COMPENSATION: $20.00 - $31.00 /hr 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.