Transit Systems 2023-05-23 2023-06-27

Chief of Staff, Rail

San Carlos, California

Job ID: 149641
Job Status: Full-time

Caltrain is seeking to recruit a Chief of Staff, Rail. The Chief of Staff reports to the Executive Director, Caltrain and to the Peninsula Corridor Joint Powers Board (Caltrain). The chief of staff is the next level executive, assuming a complex role of support to the executive director, executive leadership, rail administrative departments and staff. This role will provide direction and communication of the strategic direction of the Executive Director. The chief of staff is responsible for coordinating key policy and strategic issues facing the agency, understanding issues from multiple perspectives, and working collaboratively with stakeholders to ensure positive interaction between Caltrain and the communities it serves. The Chief of Staff is the direct support to the Executive Director on comprehensive planning, finance, budgeting and administering of Caltrain functions, programs, and activities.

About Caltrain:
Caltrain is the commuter rail system serving San Francisco, San Mateo and Santa Clara counties that spans 77 miles and is governed by the Peninsula Corridor Joint Powers Board (PCJPB), which consists of agencies from the three Caltrain counties. Each member agency has three representatives on a nine-member Board of Directors. The member agencies are the City and County of San Francisco, SamTrans and the Santa Clara Valley Transportation Authority. Caltrain operates a fleet of 29 locomotives and 123 passenger cars. The average weekday ridership for Caltrain is over 60,000 passengers.

Founded in 1992, Caltrain provides commuter rail service along the San Francisco Peninsula, through the South Bay to San Jose and Gilroy. It is owned and operated by the Peninsula Corridor Joint Powers Board, which is comprised of nine representatives from San Francisco, San Mateo and Santa Clara counties. Caltrain’s vision is to provide a safe, reliable, sustainable modern rail system that meets the growing mobility needs of the San Francisco Bay Area region.

Essential Functions:

  • Serve as the executive in the absence of the Executive Director, assume full responsibility and authority for Caltrain. Lead in communicating the vision, mission, and values of the organization through responsible and effective leadership.

  • Responsible for the establishment of goals and objective based on KPI’s of the Executive Director and the PCJBP. Disseminate the strategic vision to executive leadership, departments, staff and contracted agencies.

  • Direct oversight of the Executive Team, Rail Administration, Government & Community Affairs, Strategy & Policy, Rail HR Liaison, contracting agencies and administrative staff. Hire, mentor and take appropriate corrective and/or disciplinary action.

  • Ensure EEO policies and procedures are followed.

  • Coordinate staff training and professional development. Monitor and evaluate employee performance.

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

Examples of Essential Duties:
  • Lead multi-divisional initiatives on behalf of the Executive Director, Caltrain that include developing and implementing solutions to issues that have District wide impact.

  • Responds to a variety of issues, handles sensitive negotiations with little or no precedence; requiring expedient and diplomatic action; involving coordination with other agencies, the private sector and/or the general public.

  • Work closely with senior management to ensure that Caltrain provides world-class service while advancing equity and inclusion; health and safety; workforce development.

  • Serves as liaison between the agency and other external agencies, building consensus to accomplish agency goals; prepares and revises requests for information on behalf of the agency for various governmental offices and oversight agencies.

  • Represents Caltrain and the Executive Director as designated in meetings, as a committee member, and before community and business groups.

  • Oversees and coordinates the preparation for Caltrain Board of Directors and Board Committee meetings and works with all departments and agencies in the preparation of reports, presentations, and other materials going to the Caltrain Board.

  • Assists the Executive Director, Caltrain in formulating policy recommendations for the Board of Directors and attends Board and Committee meetings.

  • Provides strategic direction and leadership on strategic communications, brand management, and partnership and engagement efforts aligned with the overall vision and strategic goals for Caltrain.

  • Evaluate job performance of staff which also includes the professional development of staff through the identification of on-the-job and other professional development opportunities.

  • Perform all job duties and responsibilities in a safe manner to protect yourself, fellow employees and the public from injury or harm. Promote safety awareness and follow safety procedures in an effort to reduce or eliminate accidents.

  • Perform other duties as assigned.

Minimum Qualifications:
Sufficient experience, training and/or education to demonstrate the knowledge and ability to successfully perform the essential functions of the position. In lieu of a degree, work-related experience that demonstrates the skills and experience necessary to perform this role will be accepted.

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, civil engineering, or related field.

  • Nine (9) years of senior level management and leadership experience operating within a complex multicultural and diverse environment.

  • Five years public agency or commuter rail transit experience.

  • Four (4) years supervisory experience

Learn More/Apply
To obtain more information or to submit a resume and cover letter, please contact Gregg Moser, Principal at K&A, at

When applying, mention you saw this listing on

Transit Job Listing - Chief of Staff, Rail