Weekend Transportation Jobs in Kettering, MD (NOW HIRING)

The United Planning Organization (UPO) is the designated Community Action Agency for Washington, District of Columbia, and has served the residents of the District since 1962. Our Vision for the future is “UPO’s Washington: A city of thriving communities and self-sufficient residents”; our Mission is “Uniting People with Opportunities.”

All qualified applicants are encouraged to apply for this position or any other position currently advertised on our website. Please visit us at www.upo.org to view all of our vacancies and to learn more about our company and services.

POSITION: TRANSPORTATION AND LOGISTICS MANAGER

PROGRAM/DIVISION: Shelter Hotline Program/

Community Health Division

BULLETIN No: 0242026

SALARY RANGE: $53,000-$58,000 per year Commensurate with experience

OPENING DATE: April 22, 2026

CLOSING DATE: Open until filled

FIRST SOURCE: N/A

JOB SUMMARY:

Lead and oversee daily transportation operations and staff for the Shelter Hotline. Enforce policies and procedures governing scheduled and on-demand transportation and outreach services for individuals experiencing homelessness in the District of Columbia. Responsible for training and supervising staff and serving as the primary liaison among government agencies, service providers, customers, city officials, and internal personnel.

MAJOR DUTIES:

Oversee day-to-day shift operations and staff performance. Utilize fleet management systems to monitor vehicles and generate operational reports. Develop daily staffing plans and assign duties to drivers and dispatchers. Review routes and schedules to ensure adequate coverage and address service gaps. Verify shift reports for accuracy and completeness. Review repair requests and prepare work orders as needed. Manage driver and dispatcher performance to ensure productivity, efficiency, and quality service. Supervise scheduled and on-demand transportation services. Document and report vehicle accidents, incidents, and safety concerns. Serve as a liaison with government agencies, community partners, service providers, and city officials. Conduct regular field observations to ensure compliance and service standards. Plan, evaluate, and adjust daily operations, including route development and modifications.

Analyze transportation challenges and implement corrective solutions. Recommend operational improvements to enhance customer service and outreach effectiveness. Ensure compliance with daily driver check-in and check‑out procedures. Coordinate daily with city shelters to maintain accurate bed availability information. Monitor staff performance and conduct quality assurance reviews to ensure compliance with contracts and policies. Track and document time and attendance, including leave usage. Monitor attendance patterns, tardiness, and overtime utilization. Lead regular pre-shift briefings with drivers and dispatchers. Supervise staff through coaching, training, performance evaluations, and disciplinary actions as appropriate. Perform other related duties as assigned.

MINIMUM QUALIFICATIONS:

Candidate must have the qualifications listed in this section to be considered for the position. High school diploma or GED. Two years of experience operating a 24- passenger vehicle. Must possess a current CDL driver’s license with an A or B class license with passenger endorsement, air brakes, DOT passenger safety protocol, emergency procedures and 2 years of CDL driving experience. Current five (5) year driving record cannot exceed more than two points. Must be able to work a varied schedule, including nights, holidays and weekends, and drive during all types of weather. Must have comprehensive geographic knowledge of Washington, DC to effectively navigate the streets and neighborhoods. Must be able to work sensitively and effectively with individuals of diverse educational, socio-economic and cultural backgrounds.

Ability to effectively use or learn to use Microsoft Office programs (specifically, Outlook and Word) and use electronic time-keeping programs. Possess effective organizational and professional communication skills, both written and verbal. Ability to read, write, in order to submit written reports as required. Possess the abilities to work well under extreme pressure. Ability to work effectively both independently and in team environments.

DESIRED QUALIFICATIONS:

First-Aid & CPR certification. Experience working with homeless population.

OTHER REQUIREMENTS:

In the event that an offer is extended, the candidate will be required to successfully complete a criminal background check and/or FBI fingerprinting, as well as pre-employment drug screening, as applicable for the position.

EMPLOYMENT TYPE:

Full Time/Regular (37.5) Hour Workweek (Shift Hours: 3:45pm -12:00am)

POSITION ELIGIBLE

FOR TELEWORK: o YES (possibly and temporarily due to COVID-19, x NO

and based on UPO Telework Policy, position duties & program requirements)

Competitive Benefits:

To be considered for this position:

Submit your resume and driving record online.

UPO is an Equal Opportunity Employer