Highway Deputy Chief Administrative Officer; Administrator VIII

Position Summary

The Deputy Chief Administrative Officer assists the Chief Administrative Officer in directing, coordinating, and administering the policies, programs, and operations of the Highway Division. This position supports the development and implementation of division-wide strategies, policies, and procedures that ensure effective management of administrative, financial, and operational functions.

The Deputy CAO plays a central role in organizing and overseeing portfolios, programs, and cross-functional initiatives to ensure alignment with divisional goals and statutory and regulatory requirements. In partnership with the Chief Administrative Officer, the Deputy CAO supports performance oversight, process improvement, and legislative and policy implementation activities to strengthen accountability, operational efficiency, and service delivery.

The position is also responsible for analyzing and interpreting financial and operational data to support strategic planning and decision-making. This includes assessing budgetary and programmatic needs, coordinating with section and program heads, and preparing reports, metrics, and analytical materials to support executive leadership, policy development, and resource allocation.

• Provide strategic financial and operational leadership for the Highway Division by aligning operating budgets, Capital Investment Plan (CIP) expenditures, and funding sources with divisional priorities, statutory requirements, and long-term program objectives. Conduct in-depth financial analysis and forecasting to identify trends, risks, and opportunities and to support executive-level decision-making and policy development.
• Establish and maintain financial oversight, performance measures, and reporting systems that ensure the effective, efficient, and transparent use of public resources, promote accountability and compliance, and support sound financial management across the Division.
• Serve as a principal advisor to the Chief Administrative Officer and Highway Administrator, supporting strategic planning, business process modernization, and major initiatives by setting priorities, allocating resources, and providing oversight of complex and sensitive projects.
• Lead the prioritization and execution of cross-divisional initiatives by ensuring appropriate staffing, training, tools, and technology are in place, and by monitoring progress, risks, and outcomes through regular reporting to senior leadership.
• Act as a liaison among the CAO, Highway Administrator, and other MassDOT, ensuring the Division’s needs and priorities are fully represented.
• Support continuous improvement and the Highway PMO by advancing best practices, strengthening project delivery capabilities, and ensuring the availability of appropriate technical, procurement, and consulting resources to support projects from planning through implementation.
• Maintain strong working relationships with internal and external stakeholders, including government agencies, consultants, and professional organizations, and perform other related duties as assigned by the CAO and Highway Administrator.
• Oversee the alignment of operating budgets and Capital Investment Plan (CIP) expenditures with divisional priorities, program objectives, and statutory requirements; evaluate trade-offs, funding constraints, and investment impacts to ensure resources are deployed in support of strategic outcomes.
• Conduct in-depth analysis of Highway Division revenues, operating expenditures, and funding sources to identify trends, risks, and opportunities; develop forecasts and financial models that inform executive decision-making, long-range planning, and policy direction.
• Ensure the effective, efficient, and transparent use of public resources by establishing financial oversight practices, performance measures, and reporting mechanisms that promote accountability, compliance, and sound financial management across the Highway Division.

• Demonstrated experience leading or executing enterprise-level operational, financial, or administrative transformation initiatives within a large, complex…