Deputy Director of Operating Rules Systems Integration (Boston)

The Deputy Director of Operating Rules Systems and Integration provides strategic leadership and enterprise oversight for the Authority's operating rules systems, documentation governance, and cross-functional integration. Acting with delegated authority from the Senior Director, this position directs the development, implementation, maintenance, governance, and continuous improvement of enterprise operating rules management systems, digital and physical documentation. The Deputy Director ensures Authority-wide standards for operating rules governance, document management, and systems integration; directs complex cross-functional initiatives; and ensures operating rules are effectively developed, maintained, communicated, and integrated across Operations. The position is accountable for maintaining the integrity, accessibility, consistency, and regulatory compliance of the Authority's operating rules framework while supporting long-term modernization and organizational readiness.

• Direct the strategic planning, governance, and continuous improvement of the Authority's operating rule systems and enterprise documentation framework to support long-term organizational objectives.
• Direct the lifecycle management of operating rules, bulletins, special instructions, and associated documentation to ensure consistency, accuracy, version control, and regulatory compliance.
• Serve as the executive owner of the Authority's digital rule management systems, digital rule architecture, publication processes, and controlled document management across ORC-managed platforms.
• Represent the Authority with executive leadership, regulatory agencies, and external stakeholders on matters involving operating rule governance, documentation systems, and operational modernization initiatives.
• Serve as the system owner for Comply365 operating rules and compliance libraries, overseeing digital rule management, document structure, publication standards, and user accessibility.
• Lead the modernization of operating rule systems through the implementation of digital rulebooks, connected documentation, interactive authoring, automation, and enhanced document accessibility.
• Exercise delegated authority on behalf of the Senior Director to establish enterprise standards, approve documentation governance practices, and resolve complex cross-functional issues related to operating rule systems and implementation.
• Direct the integration of operating rule changes across Operations, Safety, Training, Quality, Information Technology, and other departments to ensure operational readiness and consistent implementation.
• Be accountable for the integrity, accessibility, governance, and enterprise implementation of the Authority's operating rules management framework.
• Serve as the department's principal authority for operating rule documentation structure, publication standards, and rule integration workflows.
• Lead the development and implementation of enterprise documentation governance standards and operating rule management practices.
• Make operational and administrative decisions regarding operating rule governance, documentation standards, publication practices, and system enhancements that impact multiple operating departments.
• Evaluate existing operating rules and supporting documentation and recommend revisions that improve clarity, usability, operational effectiveness, and regulatory alignment.
• Represent ORC on cross-functional committees, implementation teams, executive initiatives, and regulatory projects related to operating rule systems and documentation governance.
• Develop performance measures and reporting to evaluate the effectiveness of operating rule governance, communications, documentation practices, and implementation activities.
• Ensure operating rule systems, documentation, and governance practices remain aligned with applicable regulatory requirements, industry standards, and Authority policies ensuring organizational consistency and operational effectiveness.
• Provide functional leadership and operational direction to Operating Rules Compliance Examiners and cross-functional implementation teams, establishing priorities, assigning work, monitoring progress, and ensuring consistent execution of departmental objectives.
• Direct the work of consultants, contractors, and other external resources supporting operating rule modernization, documentation governance, digital systems, and enterprise integration initiatives.
• Direct the planning, prioritization, and execution of department-wide initiatives involving multiple internal and external stakeholders.
• Monitor budgets, contracts, and technology resources supporting operating rule systems and documentation modernization initiatives
• Develop organizational staffing plans, recommend resource needs, and establish operational structures necessary to support the continued growth and modernization of the Operating Rules & Compliance Department.
• Recommend staffing levels, organizational changes, and resource allocations necessary to achieve departmental objectives.
• Perform other duties and special projects as assigned.

• Indirectly oversee and supervise a team of rules compliance examiners.
• Directly supervise intern and contractor support functions until expansion of team.
• Directly supervise business administrator/analyst role upon team expansion.

• Bachelor's degree from an accredited institution in transportation, administration, or another related field.
• Five (5) + years of experience in transit compliance, rule administration, or operations, preferably in transit or safety-sensitive industries.
• Two (2) years supervisory/lead experience.
• Strong knowledge of operating rules, procedures, and compliance practices within a transit operation.
• Strong analytical, organizational, and project coordination skills.
• Strategic leadership and influence.
• Project coordination and cross-functional collaboration.
• Clear communication and stakeholder engagement.
• Continuous improvement and analytical mindset.
• Excellent written and verbal communication skills.
• Familiarity with FTA/FTA, DOT, and Massachusetts regulations.

• 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 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.

• Field experience in transportation craft.
• Experience managing digital document systems (Comply365 or similar).
• Experience leading enterprise-wide operational governance, documentation management, or regulatory compliance programs.
• Digital document management & system administration (Comply365).
• Experience developing and implementing enterprise documentation governance, controlled document management, or digital content management systems.
• Experience representing an organization before executive leadership, governing bodies, or regulatory agencies.
• Experience providing functional leadership over cross-functional teams, project resources, consultants, or matrixed staff in support of enterprise initiatives.
• Regulatory alignment and compliance.
• Rulebook Restructure & Governance.

Job Conditions:

• Ability to effectively read, comprehend, communicate, and respond to instructions, orders, signs, notices, inquiries, etc. in English.
• Be at least eighteen (18) years of age, except if participating in an approved high school internship / co-op program.
• Ability to commute to assigned work locations in the Boston, MA metro area, as required by the role.
• Ability to provide internal and external customers with courteous and professional experiences.
• Ability to work effectively, independently, and as part of a diverse workforce team (or supervise, if required).
• Ability to uphold the rights and interests of the MBTA while building and maintaining effective relationships with employees and co-workers.
• Ability to adhere to rules, regulations, collective bargaining agreements (if applicable), and policies of the MBTA, including the EEO, anti-discrimination, anti-harassment, and anti-retaliat]]>