Swing Shift Operations Supervisor (Full-Time) - Boston MA

Hallcon • Medford, MA

19h

About The Position

Hallcon is a leading mobility and infrastructure services company providing turnkey transportation solutions to clients across industries— including technology firms, manufacturers, railroads, universities, hospitals, airports, business parks, and public transit agencies.
Our services span commuter and campus shuttles, on-demand and microtransit operations, integrated command centers, electric vehicle (EV) infrastructure, maintenance, analytics, and rider experience optimization.
We are currently seeking an experienced Swing Shift Operations Supervisor to support our expanding commuter and shuttle services across the Boston region.
Schedule Details:
Wednesday through Sunday - 6pm - 2:30am, Monday & Tuesday – off days
The Role
The Swing Shift Operations Supervisor will oversee the day-to-day operations of commuter and shuttle programs, ensuring safe, reliable, and efficient transportation services that exceed client expectations. This position requires strong leadership, problem-solving, and communication skills, as well as familiarity with the transportation landscape and regulatory environment in the greater Boston area.
The ideal candidate will bring at least 3 years of operations or transportation management experience, with a focus on team leadership, safety compliance, and service performance.

Requirements

• Minimum 3 years of experience in transportation operations, fleet management, or dispatch supervision.
• Strong knowledge of the Boston, MA transportation region, including commuter and campus shuttle operations.
• Familiarity with FMCSA and DOT regulations and local transportation compliance standards.
• Strong communication and interpersonal skills with the ability to engage effectively with clients, employees, and riders.
• Proficiency in Microsoft Office Suite and standard reporting tools.
• Ability to work flexible hours, including weekends and holidays, as required.
• Must be at least 21 years of age and authorized to work in the United States.

Nice To Haves

• Experience working with fleet management systems, dispatching software, and route monitoring technology preferred.
• CDL Class B with Airbrake endorsement highly desirable.

Responsibilities

• Supervise daily driver activities and performance to ensure adherence to company policies, schedules, and client service standards.
• Serve as the primary on-site liaison between drivers, dispatchers, and client representatives.
• Monitor route performance, address service interruptions, and take corrective action to maintain on-time reliability and compliance with service level agreements (SLAs).
• Conduct driver audits, including pre-trip inspections, safety checks, and documentation reviews.
• Respond promptly and professionally to client and rider inquiries, ensuring a positive customer experience.
• Prepare operational reports, safety summaries, and performance updates for management review.
• Support workforce planning, training, and onboarding of new drivers and support staff.
• Collaborate with maintenance and dispatch teams to ensure vehicle readiness and service continuity.
• Promote a culture of safety, accountability, and continuous improvement across all operations.

Benefits

• Competitive compensation with medical, dental, vision, 401(k), and paid time off benefits.
• Career development and advancement opportunities within a growing organization.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed