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Title: Deputy Chief, Caltrain Planning
Company: Caltrain
Location: San Carlos, California
Job Status: Full-time
Job ID: 138959
The Deputy Chief, Caltrain Planning, reports to the Executive Director, Rail with a dotted line to the Chief of Staff, Rail and is responsible for leading the Caltrain Planning Department and overseeing all Caltrain planning efforts related to long-range, system-wide planning, major integrated project planning, station, and access planning, capital program planning, service and operations planning, and regional planning and policy development.

  • Maintains, advances, and updates Caltrain’s Long Range Service Vision through the development and stewardship of supporting plans and policies related to service development, capital planning, and other policy initiatives.

  • Leads Caltrain planning participation in major regional and state integrated projects and initiatives, including the Downtown Extension, the reimagining of Diridon Station, the development of a new Redwood City Station as well as Caltrain engagement with the California High Speed Rail Authority and the Link21 Program.

  • Leads station improvement planning, station access planning, TOD planning, and other community related planning initiatives and projects along the rail corridor.

  • Oversees capital planning, including responsibility for the development and maintenance of an overall capital improvement plan and the advancement of individual capital projects through the planning stage of project development.

  • Leads the development of key policy initiatives and positions for the railroad including, the advancement of equity policies, fare policy, rea-estate, and TOD related policy. Engages in regional and state policy initiatives and planning efforts as required.

  • Supervise staff. Hire, mentor, and take appropriate corrective and/or disciplinary action. Ensure EEO policies and procedures are followed. Participate in the selection of staff. Coordinate staff training and professional development. Establish performance objectives. Monitor and evaluate employee performance.

  • Provide regional leadership guidance by defining Caltrain’s place in the larger megaregional rail system and working with stakeholders to ensure appropriate representation in regional and state plans while maximizing connectivity to other fixed-guideway and rubber-tired services.

  • Drives strategic cohesion across all planning initiatives and ensures that all planning studies and efforts support the Long-Range Service Vision and the nearer term strategic priorities of the railroad.

  • Support the successful delivery of real estate initiatives needed to deliver enhanced service, increase ridership, enhance revenue opportunities, and support local land use initiatives.

  • Evolves the Caltrain service as it recovers from Covid-19 and prepares to transition to a higher tempo electrified service. Ensures that service plans are financially sustainable, consistent with strategic goals and policy, and responsive to stakeholder needs.

  • Advances implementation of Caltrain’s Equity, Connectivity, Recovery and Growth policy, working within Caltrain Planning and other departments to advance equity initiatives and develop additional equity focused programs and plans.

  • Provide regular reports to the Chief of Staff, Rail, Executive Director, Rail, and the Board of Directors on the progress of planning programs and make recommendations for Board action or response.

  • Represent Caltrain at regulatory, intergovernmental, and private sector meetings. Work closely with community leaders and members, neighborhood councils, businesses, property owners, neighborhood groups, and public/private organizations related to Caltrain planning initiatives, policies, and programs.

  • Represent the agency’s planning program in internal Executive Team meetings, committee and Board meetings, and directly with Board members.

  • Work with Human Resources to develop a succession plan for the agency’s planning staff, including human capital initiatives and workforce retention strategies.

  • Evaluate staff job performance, which also includes the professional development of staff by identifying on-the-job and other professional development opportunities.

  • Perform all job duties and responsibilities safely to protect oneself, fellow employees, and the public from injury or harm. Promote safety awareness and follow safety procedures to reduce or eliminate incidents.

  • Perform other duties as assigned. Supervision: Works under the general supervision of the Executive Director, Rail, and the Chief of Staff, Rail who establishes goals and objectives and evaluates performance.

Minimum Qualifications:
Sufficient education, training, and experience to demonstrate the knowledge and ability to perform the position’s essential functions successfully. Development of the required knowledge and abilities is typically obtained through but not limited to:
  • Bachelor’s degree in business administration, public administration, transportation or urban planning, real estate, or related field.

  • Eight (8) years of professional experience leading and managing planning functions in a large, complex, and highly integrated organization.

  • Four (4) years of management level experience

Preferred Qualifications:
  • Experience with Transit Oriented Development design and planning principles is desirable.

  • Knowledge of federal, state, and local rules and regulations related to planning, construction, and delivery of fixed-guideway services.

  • Must have knowledge of transportation planning and funding.

  • Commuter rail experience is desirable.

  • Experience with policy advocacy, policy research and analysis, and coalition building is desirable.

Ideal Candidate:
The Deputy Chief, Caltrain Planning must be a thoughtful leader who can drive the agency’s vision for expanded, electrified rail service along the peninsula. This position will deliver Caltrain’s modernized service vision by shaping the service, infrastructure, and financial planning functions of the Peninsula Corridor Joint Powers Board (Caltrain). The Deputy Chief, Caltrain Planning must be a dynamic policy problem-solver, able to forge innovative planning, financial, and community partnerships that tackle the complexities of Caltrain’s evolving challenges and opportunities.

For more information or to submit a resume and cover letter, please reach out to Gregg Moser, Principal at K&A, at

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