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

Chief of Rail Commercial & Business Development

San Carlos, California

Job ID: 149643
Job Status: Full-time

Caltrain is seeking to recruit a Chief of Rail Commercial & Business Development. This position reports to the Caltrain Executive Director and will ensure the overall commercial health of the railroad by directing Caltrain activities in the following areas: Financial Planning, Reporting & Budget, Contracts, Procurement, Commercial Real Estate, Funding & Fare Programs, and Partnerships & New Business. This position will integrate the entire contracts, finance, budgets, and grants teams in the implementation of business strategies. In connection with the broad ranging responsibilities, this position will serve as a key strategic advisor to the Executive Director and will have responsibility for the structure, communication, and execution of key strategic initiatives for the Joint Powers Board Caltrain.

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.

Examples of Essential Functions:

  • Define Caltrain’s business and financial strategies and oversee all business and financial efforts related to the agency.

  • Develop a long-term fiscally sustainable operating plan, including operational cost containment and efficiency recommendations.

  • Develop strategic business plans to deliver the operating and capital plans, including how best to meet any revenue requirements, projected liabilities, and contractual requirements.

  • Identify, quantify, and measure risk for Caltrain in the implementation of its operating and capital plans and the development of appropriate risk management strategies.

  • Focus resources on strategic initiatives to achieve revenue growth.

  • Identify commercially and financially beneficial arrangements to support organization, including grants and funding strategy as well as monetization of railroad assets.

  • Drive accountability and communication across the agency to effectively manage budgets, contracts, financial liabilities, grants, and public funding.

Examples of Essential Duties:
  • Manage and provide direction to Caltrain Director of Budgets and Financial Analysis, and Director of Grants and Funds Management.

  • Guide the development of the annual operating and capital budgets for Caltrain.

  • Guide the development of a long-term Operating Plan for Caltrain.

  • Participate and help guide the development and implementation of Caltrain’s Capital Plan, including State of Good Repair, Grade Separation, and key capital initiatives.

  • Develop a strategy for Caltrain’s fare system to support and implement the agency’s updated financial and business models, including leading a Caltrain Fares Strategy Task Force with participation from key senior staff from Rail Operations and Maintenance, Finance, Fares Program, and Communications.

  • Oversee implementation for Caltrain’s fares through programs such as Clipper and Go Pass, including introduction of standardized quality assurance and measures to ensure the total fares and revenue system is optimized.

  • Address first- and last-mile needs in support of ridership growth by analyzing a menu of different actions related to parking, publicly operated feeder services, private employer buses, bicycles, pedestrian access, and agreements with mobility companies.

  • Identify additional new revenue streams including but not limited to advertising opportunities, sale of fiber capacity, net metering, and sponsorship opportunities.

  • Provide leadership for contract administration across all rail-related contracts.

  • Oversee funding and grant identification, application, tracking and compliance.

  • Establish, maintain, and report on the Caltrain risk register, including associated business continuity planning activity.

  • Perform all job duties and responsibilities in a safe manner to protect oneself, 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, or closely related field. Master’s degree preferred.

  • Minimum of nine (9) years of progressive commercial experience including financial and capital planning, business plan development, proforma analysis, debt and capital markets, contract negotiations, risk analysis, marketing, budgeting, or equivalent level of relevant experience.

  • Five (5) years supervisory experience

Preferred Qualifications:
  • Demonstrated experience and track record in a comparable executive leadership role, supporting the development and execution of operating and capital plans.

  • Public sector experience is highly desirable.

  • Business team leadership, externally with key stakeholders and internally with support staff including shared services.

  • Executive presence, confidence, communication skills, influence skills and superior negotiation skills.

  • Must possess effective oral and written communication skills.

  • Rail products, services, industry knowledge and technical expertise is highly desirable.

  • Demonstrated ability to lead and manage through changing business conditions, including an evolving operating environment.

  • Proven ability to engage and navigate organizational complexities, with the ability to understand key business drivers, strategies, competing priorities, and an organizational “political map.”

  • Ability to quickly grasp complex technical and business concepts and express them in clear language. Demonstrated ability to actively listen to all stakeholders. Excellent written and verbal skills including presentation skills.

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

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Transit Job Listing - Chief of Rail Commercial & Business Development