Chief of Operations Planning, Scheduling & Strategy

The Chief of Operations Planning, Scheduling & Strategy (OPSS) serves as the MBTA's senior leader for operational planning, service design, scheduling, and performance strategy. The Chief provides vision, direction, and integrative leadership across Planning & Scheduling, Alternative Service Planning, Workforce Modernization, Lean Strategy & Operations Analytics, and Operations Policy, all in support of the MBTA's Operational Modes. The Chief of Operations Planning, Scheduling & Strategy will report to the Deputy Chief Operating Officer. This role ensures that MBTA's operational decisions are grounded in rigorous data analysis, long-range system planning, and continuous improvement principles. The Chief of OPSS drives initiatives that enhance service reliability, optimize resource allocation, strengthen workforce readiness, and embed a culture of operational excellence across the organization. The position requires a strategic thinker who can anticipate systemwide needs and proactively advance solutions in a complex operational environment. The Chief must exercise sound judgment, maintain strict confidentiality, and demonstrate exemplary project management skills—effectively planning, prioritizing, and deploying staff and resources to deliver high-impact results on time and in alignment with MBTA's mission to provide safe, reliable, and equitable transit for all riders. Above all, the Chief of OPSS must continuously collaborate with the operational modes to ensure the delivery of operational and service goals. Lead and integrate the functions of service planning, scheduling, and operational strategy across all modes of transit. Oversee the development and implementation of alternative service models and contingency planning. Drive the MBTA's Operations workforce modernization efforts, including initiatives to ensure that workforce scheduling, planning, and related operations technology tools are providing superior functionality for the organization and MBTA customers Champion Lean methodologies and continuous improvement practices across Operations. Lead the Operations Analytics team to develop actionable insights that inform decision-making and performance improvement. Collaborate with the COO, Deputy COO, and other senior leaders to align planning and strategy with organizational goals. Represent Operations in cross-departmental initiatives, capital planning, and external stakeholder engagements. Ensure integration of service planning with capital projects, maintenance schedules, and customer experience goals. Supervise Directors and Managers across the OPSS portfolio, fostering a culture of accountability, innovation, and collaboration. Prepare and present materials for executive leadership, Board meetings, and public forums. Serve as a key advisor to MBTA leadership on strategic planning, operational readiness, and policy development. Perform all other duties and projects that may be assigned. Supervision Direct supervision of multiple Director-level staff responsible for Planning, Scheduling, Workforce Strategy, Lean Strategy & Analytics, and +60 employees that help facilitate the day-to-day as well as long-term Operations strategy. Bachelor's Degree from an accredited institution. Twelve (12) years' experience in transit operations, planning, or leading strategic initiatives, preferably in a large or highly regulated industry. Seven (7) years of experience managing staff and leading cross-functional teams or enterprise-wide initiatives. Have the ability to work in a fast-paced environment and manage multiple projects simultaneously. Have the ability to think strategically and develop creative solutions. Handle sensitive and confidential information in an appropriate manner. Excellent written and verbal communication skills. Have the ability to work with a diverse range of stakeholders. Proficiency in Microsoft Office Suite. A High School Diploma or GED with an additional seven (7) years of directly related experience substitutes for the bachelor's degree requirement. An Associate's degree from an accredited institution with an additional three (3) years of directly related experience substitutes for the bachelor's degree requirement. A Master's degree in a related subject substitutes for two (2) years of general experience. A nationally recognized certification or statewide/professional certification in a related field substitutes for one year of experience. Preferred Experience and Skills Master's degree in a related field. Experience with Lean, Six Sigma, or other continuous improvement methodologies. Familiarity with transit scheduling software and workforce planning tools.