Key Responsibilities and Required Skills for Delivery Supervisor

🎯 Role Definition

The Delivery Supervisor is a hands-on operations leader who manages daily delivery and dispatch activities, supervises drivers and delivery associates, enforces safety and regulatory compliance, and continuously improves last-mile and middle-mile performance. This role blends people management, route and load planning, customer-facing communication, and operational analytics to ensure timely, accurate, and cost-effective deliveries while maintaining high standards of safety and service.

📈 Career Progression

Typical Career Path

Entry Point From:

Delivery Driver / Route Driver
Logistics Coordinator / Dispatch Agent
Warehouse Lead / Shipping & Receiving Associate

Advancement To:

Operations Manager / Distribution Manager
Regional Delivery Manager / Area Operations Manager
Director of Transportation / Head of Last-Mile

Lateral Moves:

Fleet Manager
Customer Success / Client Services Manager
Inventory or Warehouse Operations Manager

Core Responsibilities

Primary Functions

Supervise and lead daily delivery operations, including dispatching, route assignments, scheduling, and load planning to meet on-time delivery targets and SLA commitments across assigned territories.
Manage, coach, and develop a team of drivers and delivery associates — recruiting, onboarding, providing ongoing training, conducting performance reviews, and executing progressive discipline when necessary.
Monitor delivery KPIs (on-time delivery rate, on‑time departures, delivery per hour, cost per delivery, fuel consumption, first‑time delivery success) and implement corrective action plans to drive measurable improvement.
Create and optimize route plans using TMS/GPS data and manual adjustments to minimize mileage, reduce fuel spend, and improve delivery density and SLA compliance.
Coordinate closely with warehouse and fulfillment teams to ensure accurate order picking, staging, proper manifests, correct labeling, and timely load-out for scheduled routes.
Verify vehicle readiness by overseeing pre-trip inspections, maintenance scheduling, compliance with maintenance logs, and coordination with fleet maintenance providers to ensure vehicle safety and reliability.
Ensure full compliance with DOT regulations, Hours of Service (HOS) rules, driver qualification files, drug and alcohol testing policies, and any regional transport regulations.
Manage customer communications for delivery windows, ETA updates, exception handling, and escalations; act as primary escalation point to resolve delivery-related issues and manage customer expectations.
Oversee proof-of-delivery processes (POD), signature capture, electronic confirmations, and any documentation required for billing and claims.
Investigate delivery incidents, accidents, cargo claims and losses; conduct root-cause analysis, prepare incident reports, and implement corrective and preventive actions.
Control operating expenses for the delivery function by managing driver labor, overtime, fuel consumption, route efficiency, and subcontractor usage; prepare and present budget variance reports.
Supervise relationships with third‑party carriers, subcontracted drivers, and temporary drivers; negotiate service agreements, monitor performance, and ensure compliance with company standards.
Enforce safety programs and standards including driver safety training, defensive driving initiatives, vehicle loading/unloading safety, and PPE usage; lead safety huddles and toolbox talks.
Maintain accurate operational records including daily manifests, driver logs, maintenance records, vehicle inspections, and accident/incident files to support audits and compliance reviews.
Use data-driven decision making to produce daily, weekly, and monthly operational reports and dashboards for senior leadership — including trend analysis and action recommendations.
Lead continuous improvement initiatives (Lean, Kaizen, 5S) to reduce errors, streamline processes, improve throughput, and increase delivery capacity without proportionally increasing costs.
Plan and scale resources for peak seasons (holiday surges, promotional events) by forecasting demand, hiring temporary staff, and establishing contingency plans to maintain service levels.
Implement and maintain loss-prevention and cargo security procedures to minimize shrinkage and theft; coordinate with loss prevention and legal teams when necessary.
Ensure accurate billing support by validating delivery documentation, signatures, times, and special instructions required for invoicing and chargeback resolution.
Train drivers and supervisors on technology platforms (mobile apps, handheld scanners, telematics) and drive adoption of digital workflow tools to improve accuracy and visibility.
Collaborate cross-functionally with Sales, Customer Service, Warehouse, Procurement, and IT to align service levels, priorities, and operational changes impacting delivery performance.
Act as on-call supervisor for critical delivery incidents and outage events, directing operational response, customer communications, and rapid remediation.

Secondary Functions

Support ad-hoc operational analytics requests; provide data extracts and contextual insights to inform leadership decisions and customer reporting.
Assist with periodic audits and compliance assessments (safety audits, regulatory inspections, customer audits) and manage corrective action tracking until closure.
Contribute to the development and maintenance of standard operating procedures (SOPs), driver manuals, and training curricula that reflect best practices.
Participate in pilot projects for new routing software, telematics solutions, or automation tools and provide operational feedback to product/IT teams.
Coordinate with HR on workforce planning, shift scheduling, payroll anomalies related to delivery operations and driver timekeeping.
Help manage vendor onboarding for leased vehicles, temporary staffing providers, and maintenance contractors, ensuring SLAs and compliance documentation are in place.
Facilitate regular operational reviews and cross-functional meetings to communicate performance trends, resource constraints, and process improvement plans.
Serve as deputy to the Transportation/Operations Manager during absences and support strategic initiatives as assigned.

Required Skills & Competencies

Hard Skills (Technical)

Route optimization and last-mile planning using TMS, route-planning software, or routing modules in transportation management systems.
Fleet management and vehicle maintenance oversight, including preventative maintenance scheduling and record keeping.
Knowledge of DOT regulations, Hours-of-Service (HOS), driver qualification files, and regulatory compliance requirements.
Experience with GPS/telemetry systems, telematics platforms, and real-time tracking tools to monitor driver behavior and route adherence.
Operating proficiency with warehouse systems (WMS), barcode scanning, handheld devices, and electronic proof-of-delivery (ePOD) solutions.
Strong Excel and data-analysis skills (pivot tables, v-lookups, basic formulas) for reporting and KPI tracking.
KPI-driven reporting and dashboard creation; ability to translate operational metrics into action plans.
Experience managing subcontractors and third-party carriers, including contract performance monitoring and cost control.
Knowledge of safety management systems, incident investigation, and root cause analysis methodologies.
Basic budgeting and cost-control experience for labor, fuel, maintenance and subcontracted services.

Soft Skills

Leadership and people management: hiring, coaching, motivating and developing delivery teams under high-pressure conditions.
Excellent verbal and written communication for driver briefings, customer updates, and cross-functional coordination.
Problem-solving and decisive judgment when managing service disruptions, accidents, or high-priority escalations.
Customer-focused mindset with strong interpersonal skills to manage expectations and recover service failures.
Time management and prioritization to balance daily operations, reporting, and continuous improvement work.
Conflict resolution and disciplinary skills to handle driver performance and behavioral issues.
Adaptability and resilience in a fast-paced, changing logistics environment (peak seasons, route changes, staffing variability).
Attention to detail for accurate documentation, POD handling, and regulatory compliance.
Coaching and training skills to develop driver safety and service competencies.
Analytical thinking to review route and performance data and to implement process improvements.

Education & Experience

Educational Background

Minimum Education:

High school diploma or equivalent.

Preferred Education:

Associate's or Bachelor's degree in Logistics, Supply Chain Management, Business Administration, or related field preferred.

Relevant Fields of Study:

Logistics and Supply Chain Management
Business Administration / Operations Management
Transportation Management
Industrial Engineering / Operations Research

Experience Requirements

Typical Experience Range:

2–5 years of progressive experience in delivery operations, dispatch, or route supervision; typically at least 1–2 years in a supervisory role.

Preferred:

3–7 years of combined delivery and supervisory experience in last‑mile, distribution, courier, or freight operations; experience with TMS/WMS systems and driving published KPIs to targets.

Certifications & Requirements (if applicable):

Valid driver's license; Commercial Driver’s License (CDL) may be required depending on fleet composition.
DOT medical certification, drug and alcohol screening compliance where applicable.
Forklift certification and basic first aid/CPR certifications are a plus.
Experience with Lean/Six Sigma or continuous improvement training is desirable.