Director of Revenue Operations

About This Role Careington is a benefit solutions-oriented company. An established leader, we have been a trailblazer in the field of discount health care since 1979. Over the years, our mission has remained the same — to create discount health programs that are marketable to the employer, profitable to the provider and economical for the member. In response to a growing demand for our products and services in recent years, our growth means that we continuously strive to recruit innovators to join our fast-paced, forward-thinking team. About This Role Careington is a benefit solutions-oriented company. An established leader, we have been a trailblazer in the field of discount health care since 1979. Over the years, our mission has remained the same — to create discount health programs that are marketable to the employer, profitable to the provider and economical for the member. In response to a growing demand for our products and services in recent years, our growth means that we continuously strive to recruit innovators to join our fast-paced, forward-thinking team. This role will initially be worked in the office three days per week, two from home. At some point and time in 2027 (Spring to Summer) will revert to five days in the office. The Director of Revenue Operations is a pivotal leadership role responsible for driving operational excellence across the Revenue Operations organization. This position primarily focuses on providing direct leadership to the Revenue Operations team, ensuring high-performing day-to-day operations, maintaining strong SLAs, resolving production issues, and delivering consistent, scalable results. In parallel, the role plays a key part in leading strategic transformation initiatives—including RPA, AI-powered automation, system transformations, process improvements, and technology roadmap execution to support the company’s long-term growth objectives. This role requires deep end-to-end Revenue Operations expertise across all functional areas. The Director develops and articulates a clear vision for the function, optimizes processes and resources, manages budgets and performance metrics, and fosters strong cross-functional collaboration. As a trusted technical and strategic partner, the Director drives continuous improvement while ensuring operational stability and alignment with broader business priorities. EXPECTED WORK AND PERFORMANCE Provide direct operational leadership to the RevOps organization by overseeing and closely coordinating with operational team managers and front-line teams. This includes ensuring day-to-day operational success, maintaining high SLAs (93-99%), resolving production issues, delivering consistent results for clients and internal stakeholders, and driving overall team performance and accountability. Build, lead, coach, and develop high-performing RevOps teams (including operations, agent administration, and support functions) through effective talent management, performance evaluations, training programs, recruitment support and succession planning. Develop, implement and execute operational strategies and transformation programs that align with Careington’s mission, business objectives and long-term growth priorities, with emphasis on RPA, AI-powered automation, digital systems modernization, process redesign and technology roadmap execution. Lead end-to-end system transformations, IT enhancements, technology roadmap development and the delivery of a portfolio of strategic and tactical projects, including compliance initiatives (SOC II, PCI, SSAE/SOC audits) and process optimisation efforts to improve efficiency, quality and scalability. Establish, monitor and analyse key performance metrics, KPIs, budgets, financial reports, QA and profitability data to drive data-informed decisions, cost optimisation and continuous operational improvement. Champion cross-functional collaboration and build strong, trust-based relationships with internal teams, senior leadership, external partners, vendors and stakeholders to drive alignment, remove barriers and ensure successful operational and project outcomes. Drive change management through influence, model breakthrough thinking, proactive problem-solving and a “roll-up-the-sleeves” approach to support adoption of new processes and technologies while maintaining operational stability. Examine operational costs, workflows and systems to identify and implement opportunities for cost reduction, process streamlining and efficiency gains without compromising quality or execution. Review regular auditing reports, operational data and compliance requirements to elevate quality standards and ensure adherence to policies, procedures and regulatory standards. Facilitate the establishment of departmental goals related to production output, process efficiencies, transformation outcomes and enterprise-wide programme growth. Provide escalation support for complex issues, contribute to high-visibility initiatives (e.g. annual reporting, department reorganisation) and act as a technical consultant on both operational and strategic matters. Ensure accountability for operational components of SSAE and SOC audits, risk management and other compliance activities while promoting a culture of innovation and operational excellence. Qualifications Required Bachelor’s degree in Business Administration, Information Systems, Operations Management or a related field. 10+ years of progressive Operations experience, including leadership in process improvement, technology transformation or project execution. Strong end-to-end RevOps knowledge and experience across core areas (e.g. member operations, IR, commissions, billing, AR, commissions, reporting and agent administration) with the ability to step in and provide operational leadership and backup as needed. Advanced proficiency in Microsoft Suite, including Excel, PowerPoint and Word. Preferred 8+ years of experience as a Technical Business Analyst, Project Manager or in RPA/AI/digital transformation roles. Demonstrated success leading RPA, AI, automation, enterprise system implementations or large-scale transformation programmes. Experience with compliance initiatives (SOC II, PCI, SSAE/SOC), technology roadmap development, budgeting and cross-functional project management. Skills Collaborative professional with a drive for results, decisiveness and passion for winning coupled with compassion and a thoughtfully assertive approach. Unquestioned integrity and strong ethical decision-making. Proven ability to design and implement operational strategies, department initiatives and transformation programmes with measurable impact. Analytically oriented with demonstrated success in making timely, effective, principle-based decisions using data and metrics. Highly effective verbal and written communication skills including the ability to articulate vision, explain complex concepts, influence stakeholders and provide clear direction. High level of enthusiasm for building successful teams, big-picture/strategic thinking and a personal sense of urgency with the capacity to overcome obstacles. Strong strategic thinking, analytical skills and proactive problem-solving with expertise in change management and continuous improvement. Ability to prioritise multiple responsibilities/projects while maintaining focus on long-term goals and operational efficiency. Proven ability to develop internal and external relationships especially cross-functionally and with senior leadership. Experience interacting with high-level clients, partners and stakeholders. Strong team player and corporate-focused doer with a “roll-up-the-sleeves” attitude and comfort operating by influence rather than control. Self-motivated, service- and people-oriented with creativity, resourcefulness, accessibility and responsiveness. Positive attitude with a sense of urgency and passion for driving meaningful change, innovation and organisational success. Equal Opportunity Employer This employer is required to notify all applicants of their rights pursuant to federal employment laws. 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