Transportation Supervisor

Job Description

Job Description

Transportation Supervisor

Location: Albany, NY

Schedule: Monday–Friday | 11:30 AM – 9:00 PM

Position Summary

The Transportation Supervisor is responsible for leading the daily transportation operation by ensuring routes are properly planned, drivers are prepared, and deliveries are executed safely, efficiently, and in accordance with Sidekick's service standards.

This position provides leadership to the driver team through coaching, training, accountability, and operational oversight while partnering closely with Dispatch, Warehouse, and Customer Research to deliver an exceptional customer experience.

The Transportation Supervisor owns route planning, driver performance, transportation readiness, safety, and service recovery. Success in this role requires strong leadership, sound operational judgment, excellent communication skills, and a passion for developing people.

Essential Duties & Responsibilities

Transportation Planning & Route Readiness

• Plan and optimize daily delivery routes.
• Ensure routes are fully staffed each day.
• Partner with Dispatch to ensure routes are assigned and ready for on-time departure.
• Review route plans and adjust staffing or routing based on operational needs.
• Ensure equipment, freight, and drivers are prepared before routes depart.
• Develop staffing plans for vacations, call-outs, and peak delivery periods.

Driver Leadership

• Recruit, interview, onboard, and train professional delivery drivers.
• Coach drivers on safety, customer service, productivity, and Sidekick service standards.
• Review driver performance and provide regular coaching and feedback.
• Review Motive safety events and provide timely coaching.
• Complete performance evaluations and administer corrective action when appropriate.
• Foster a culture of accountability, professionalism, and continuous improvement.
• Conduct field observations and ride-alongs as operational needs require.

Transportation Operations

• Monitor transportation performance throughout the day.
• Respond to transportation-related escalations and driver issues.
• Lead service recovery efforts for transportation-related delivery failures.
• Partner with Dispatch, Warehouse, and Customer Research to resolve operational issues quickly and effectively.
• Ensure customer commitments are met while balancing operational efficiency.

Safety & Compliance

• Ensure compliance with DOT, FMCSA, state regulations, and company policies.
• Monitor Hours of Service compliance.
• Investigate accidents, incidents, and safety concerns.
• Maintain transportation records, inspections, and required documentation.
• Reinforce Sidekick's safety culture through coaching and accountability.

Fleet & Administrative Responsibilities

• Coordinate preventative maintenance and vehicle repairs.
• Monitor vehicle readiness and equipment availability.
• Maintain equipment logs, registrations, and toll account administration.
• Review and approve driver timecards.
• Review transportation reports and operational metrics.
• Support continuous improvement initiatives that improve safety, service, and efficiency.

Qualifications

• Minimum 3 years of transportation, logistics, fleet, or delivery operations leadership experience.
• Experience supervising and developing drivers.
• Strong route planning and operational decision-making skills.
• Working knowledge of DOT, FMCSA, and Hours of Service regulations.
• Experience coaching employee performance and leading teams.
• Strong communication, organizational, and problem-solving skills.
• Ability to thrive in a fast-paced, customer-focused environment.
• Experience with routing software, telematics, or transportation management systems preferred.
• Experience with Motive, DispatchTrack, or similar platforms is a plus.
• Proficiency with Microsoft Office and Google Workspace.

What Success Looks Like

Successful Transportation Supervisors:

• Build efficient routes that support exceptional customer service.
• Develop safe, engaged, and accountable drivers.
• Coach performance through consistent leadership and feedback.
• Identify transportation risks before they impact customers.
• Respond calmly and effectively during service disruptions.
• Build a culture where safety, ownership, and accountability drive daily decisions.

Measures of Success

• Routes depart on time.
• Routes are fully staffed.
• Driver coaching is completed consistently.
• Driver performance improves over time.
• Transportation-related service failures are minimized.
• Safety goals are achieved.
• Customer complaints related to transportation decrease.
• Drivers consistently meet Sidekick's service standards.
• Tomorrow's routes are fully prepared before the end of each shift.

Why Join Sidekick?

At Sidekick Delivery, you'll have the opportunity to build and lead a high-performing transportation team in a growing company where your leadership makes a direct impact on our customers, our employees, and our continued success. We're building a culture centered on ownership, accountability, safety, and exceptional service—and we're looking for leaders who want to help shape what's next.

Sidekick Delivery is a fast-growing logistics company specializing in next-day wine and spirits delivery for top restaurants, retailers, and distributors across California and New York. We combine precision, professionalism, and a customer-first mindset to deliver exceptional service in a high-touch industry.

Company Description

Sidekick Delivery is a fast-growing logistics company specializing in next-day wine and spirits delivery for top restaurants, retailers, and distributors across California and New York. We combine precision, professionalism, and a customer-first mindset to deliver exceptional service in a high-touch industry.