Rightway

Lead pharmacy teams delivering service across phone, chat, and email, and partner with product and engineering teams to improve workflows and member outcomes. | Requires at least seven years in contact center, pharmacy, or healthcare operations, including managing managers; pharmacy, PBM, or healthcare-services experience is preferred. | ABOUT THE ROLE: Rightway's care team supports members, providers, and pharmacies across phone, chat, email, and other digital channels. This Director will lead that team, made up of pharmacy technicians and pharmacists, and will own service delivery across every channel. The ideal candidate pairs strong people leadership with an operational mindset, and is comfortable partnering with product and technical teams to build the tools their team relies on every day. This is a highly visible role that shapes how members experience pharmacy support at Rightway. WHAT YOU’LL DO: Lead and develop a team across telephony, email, chat, and other digital channels, working through managers and team leads. Build and coach a bench of people managers, holding them accountable to consistent service standards and to Rightway's management expectations. Set team structure and staffing plans in partnership with functional and People leadership, including hiring, workload distribution, and channel coverage. Own operational performance across every channel, setting goals for quality, speed, and member satisfaction, and holding the team accountable to them. Continuously evolve workflows and processes to maximize speed, consistency, and ease for both members and staff. Establish and monitor the metrics that matter, including volume, resolution rates, quality scores, and member satisfaction, and translate them into action plans. Collaborate with clinical leadership to implement member specific medication optimization and site of service strategies that improve clinical appropriateness and drive cost savings. Partner with product and engineering teams to define requirements for the tools the care team relies on, including the chat platform, call tracking system, and AI assisted workflows. Represent the voice of the care team in roadmap discussions, prioritizing improvements with the greatest operational impact. Pilot new technology and workflows with the team, measuring impact before scaling company wide. Lead the team through organizational growth and evolving ways of working, with clear communication and training plans that support a seamless omnichannel experience. Anticipate the impact of change on the team and build thoughtful plans that keep the member experience consistent as the team grows and evolves. Act as a steward of company culture and values while introducing new ways of working. WHO YOU ARE: 7 or more years of experience in contact center, pharmacy operations, or healthcare services operations, including several years managing managers or leading multi team organizations. Proven experience leading frontline teams of 20 or more people through periods of growth and technology adoption. Strong operational and analytical mindset, comfortable setting goals, reading dashboards, and translating data into action. Experience partnering directly with product and engineering teams to influence a roadmap. Excellent communicator who can represent the team's needs to senior leadership and translate company strategy into day to day priorities for the team. Pharmacy, PBM, or healthcare services background strongly preferred. COMPENSATION: $155,000 - $190,000 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.

Lead and mature the GRC function by overseeing audits, risk management, AI governance, team priorities, control libraries, and compliance with security and privacy frameworks. | Requires 5–10 years of experience, a relevant certification such as CISSP, CISA, or CISM, and demonstrated leadership of SOC 2 and HITRUST certifications. | ABOUT THE ROLE: Join Rightway as a Security GRC Manager, a role that owns and matures our GRC function. You will enhance our policies and procedures, streamline workflows, mature our risk management program, own our integrated SOC 2 + HITRUST attestation as we scale, and lead the GRC team. WHAT YOU’LL DO: Team Leadership: Lead and mentor a small GRC team, setting priorities, reviewing work, and growing the function alongside the business. Control Library Development: Own and evolve our unified control library, maintaining mappings across SOC 2, SOC 1, and the latest HITRUST version, and addressing gaps or inefficiencies as the organization and framework requirements change. Audit Ownership: In partnership with Engineering, IT, People, and Finance, lead the audit program for control requirements and evidence production, proactively in anticipation of SOC 1, SOC 2/HITRUST, and customer audits. Data Privacy and Protection: Partner with Legal as a key stakeholder in the Data Privacy program, including HIPAA/HITECH, BAAs, data privacy and protection impact assessments, incident/breach analysis, and data handling requirements. AI Governance: Own and mature the AI governance program modeled after ISO/IEC 42001, including the AI risk register, Statement of Applicability, and AI risk assessments for internal use cases. Respond to customer and partner AI governance questionnaires, and maintain alignment to emerging requirements such as the Colorado Automated Decision-Making Technology Act (ADMTA). Contract security and privacy review: Review and negotiate security, privacy, data protection, incident notification, audit rights, AI, and related language in customer and vendor agreements. Control Monitoring: Monitor, measure, and report on control effectiveness for security and compliance in Drata, maintaining continuous control monitoring and evidence collection, and adjusting strategy and implementation as needed. Policy Enhancement: Collaborate cross-functionally to improve policies and related procedures, boosting operational efficiency, control maturity, security, and compliance Business Continuity Planning: Lead business continuity planning and testing, with a focus on a Business Impact Analysis (BIA) informed program. Third Party Risk Management: Revamp and execute a flexible yet thorough Third Party Risk Management (TPRM) program, keeping a keen eye on data security and technical risk, not just compliance. Risk Management: Own the security risk management program, participating in preparation, discussion, tracking (risk register), and remediation of enterprise risks within your sphere of influence, in addition to annual risk assessments activities. Training Programs Development: Engage with organizational stakeholders to develop and implement effective security and compliance training programs. Customer Trust: Own and maintain the customer assurance program, including the security questionnaire and RFP response process, trust center content, and the tooling that supports timely, accurate responses for the Proposal Unit and prospective clients. WHO YOU ARE: 5-10 years of related work experience. Maintains a certification relevant to the role (e.g, CISSP, CISA, CISM). Personally led SOC2 with HITRUST CSF certification in a high growth environment and understands how to mature controls consistent with organizational maturity and capacity. Familiarity with AI governance frameworks (e.g., ISO/IEC 42001) and the risk considerations of AI systems that process sensitive data. Experience leading or mentoring GRC analysts, with the ability to set priorities, review work, and grow the function alongside the business. A deep understanding of risk assessment methodology, HIPAA, and HITECH, including the practical distinction between covered entity and business associate obligations. Comfortable negotiating and redlining BAAs and conducting four-factor breach risk assessments alongside Privacy and legal. Passionate advocate for governance, risk, and compliance, believing that these are not merely check box activities, but vital tools that significantly improve security posture and protect the organization. Possess an intermediate to advanced understanding of the Software Development Life Cycle and of IT and security tooling (Jamf, CrowdStrike, Arctic Wolf, Wiz, Serval, Knowbe4, Drata) as it relates to controls (e.g. AWS, Okta, JIRA, GIT/GITHUB). Ability to perform qualitative and quantitative risk assessment. EXTRA CREDIT: Experience with joint SOC 2/HITRUST attestations. A blend of deep, technical and compliance knowledge and experience. COMPENSATION: $144,000 - $175,000 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.

Lead architecture and delivery of software systems while mentoring engineers and collaborating with product and design teams. | 5+ years professional experience with strong JavaScript/TypeScript and backend framework proficiency, comfortable owning complex systems with a product-minded approach. | ABOUT THE ROLE: We’re hiring Senior Software Engineers to work on Rightway’s products across web, mobile, and backend systems. Our backend platform spans multiple technologies, with newer services built using React, Node, NestJS, and TypeScript, alongside existing services implemented in Ruby on Rails. Senior engineers at Rightway are expected to bring strong technical ownership, contribute to system design, and help teams deliver reliable, high quality software. We're an AI-native engineering team that uses AI tooling daily in our development workflow and expects our senior engineers to lead adoption, establish best practices, and help the team get better at working with these tools. WHAT YOU’LL DO: Lead the architecture and delivery across the Rails backend and React frontend Build the integrations that connect our service to our Node.js/NestJS PBM platform Mentor mid-level and junior engineers through pairing and code review discussions Set testing and code-quality standards for your area, and raise risks early Collaborate closely with product and design partners to deliver thoughtful solutions Participate in architectural discussions and help guide technical decisions Write clean, maintainable, and well tested code Review code and provide technical guidance to teammates Help improve reliability, performance, and developer experience WHO YOU ARE: 5+ years of professional experience building production software Strong experience with JavaScript or TypeScript and React Solid backend experience with Ruby on Rails, Node, or similar frameworks Experience working with APIs using GraphQL or REST Interest in working across multiple backend technologies Comfortable owning complex systems and improving them over time Collaborative, pragmatic, and product minded EXTRA CREDIT: Experience with Ruby and Rails Experience building backend services with Node, NestJS, and TypeScript Experience with Protobuf and or gRPC Familiarity with healthcare systems or regulated environments Experience handling sensitive data and privacy considerations Startup or fast paced product experience Experience leading AI-assisted development workflows and establishing team standards around AI tooling COMPENSATION: $160,000 - $195,000 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.