General Manager, Transportation

San Rafael, California, United States Full-time

Provides executive leadership and management of  Whistlestop’s Transportation Services including new business development, financial management, policy and compliance enforcement, administrative management, human resources, fiscal budgeting, strategic and organizational planning, revenue enhancement, operating efficiency, and interactive engagement with external stakeholders, customers, clients and donors on all matters pertaining to Transportation Services.


1. Take an active role on Whistlestop's senior management team representing the financial and operations planning, and execution needs of the transportation services business.

  • Work closely with CEO, COO and CFO to provide strategic planning, analysis, forecasting and reporting, including analysis and execution of new business models, new program development partnership opportunities, and contract negotiations. 
  • Work with CFO and COO to prepare transportation budgets, and track actuals against monthly targets.
  • Partner with COO on business development efforts in transportation for new accounts and growth in current accounts.
  • Responsible for daily operations as well as implementation of new services and programs.

2. Ensure operational excellence, compliance with legal, regulatory, contractual and best practice requirements for transportation operations, including:

  • Oversee assigned functional area to ensure operational excellence within all transportation service functions.
  • Work with CFO, IT and Project Manager to plan for transportation specific technology infrastructure and system needs.
  • Lead change management, actively helping managers, staff and clients embrace innovation and change.
  • Work with project manager to identify and implement new projects to increase revenues, reduce costs and/or increase operational efficiencies.
  • Responsible for all matters pertaining to client service and engagement including collecting and maintaining customer satisfaction metrics and designing and implementing programs aimed at improving them.
  • Monitor the collection of statistical information for regular reports, which must be accurate and on time. Analyze and report data to the CEO and appropriate agencies as required.
  • Ensure effective management of all aspects of Transportation Services programs including the Marin Access Paratransit program, as well as other transportation services contracts to further Whistlestop’s mission, while being in compliance with ADA, FTA, DOT, HAZMAT and CHP rules and regulations as well as contract specifications.
  • With transportation management team, represent and promote Whistlestop’s interest at all meetings and events with advisory committees, councils, other transit agencies and the general public.
  • Maintain and periodically update comprehensive safety and training, fleet operations policies, practices and procedures in collaboration with the operations management team.

3. Be an inspirational, supportive and motivational manager who can help the transportation team and operations managers reach personal, team and organizational financial & service goals.

  • Manage 5 direct report operations managers with responsibilities for fleet & maintenance, call center, contract services, safety & training and paratransit contracts.
  • Supervise and develop managers by establishing performance goals and accountability, providing training and guidance, modeling appropriate leadership methods and giving continual feedback and coaching.
  • Help operations line managers set and realize operational and professional development goals for themselves and their teams.
  • Provide active leadership with regards to Transportation Services human resource issues including the hiring, training, development, evaluation, retention and, when needed, corrective action and termination of staff.
  • Ensure information is regularly and effectively communicated to members of the Transportation Services team including written communication as well as staff meetings, one-on-one meetings, All Hands Meetings, and safety meetings.

Required Qualifications & Experiences: 

  • Bachelors’ degree in related field or equivalent
  • Experience and comfort with a variety of IT applications
  • Experience launching a new service or divisiion
  • Demonstrated increasing responsibilty in an organization of at least 50 people, with at least 3 direct reports
  • Experience in analyzing and managing against margins including revenue growth, expense reduction through efficiencies, margin analysis
  • Complex project leadership skills with a demonstrated ability to prioritize and set & meet deadlines
  • Highly comfortable with data driven decision making and experience engaging this practice throughout the organization
  • Ability to anticipate, identify and creatively solve problems, follow through on solutions and evaluate periodically
  • Excellent verbal and written communication skills
  • Ability to provide excellent customer service to riders as well as public organizations and contracting agencies, and lead others to do the same
  • Use professional judgment, discretion and respect when dealing with all individuals regardless of position or status
  • Clean driving record; insurable
  • Submit to background check and fingerprinting

Preferred Qualifications & Experiences:

  • 5+ years operations management in the transportation industry (ideally with a fleet of at 50+). Could include responsibility for: call center, scheduling, dispatch, drivers, maintenance, safety & training, IT.
  • IT management experience, ideally adopting new transportation software into organization workflow
  • Knowledge of the American’s with Disabilities Act and how this act applies to public Paratransit service operations
  • Knowledge of FTA drug testing and DMV licensing requirements

 Whistlestop is an Equal Opportunity Employer