Delivery Specialist II (Lead Delivery Supervisor)

Position Overview

Ready Set Fun Entertainment is seeking an experienced and highly dependable Delivery Specialist II to serve in a leadership role within our operations team. This position performs all duties of a Delivery Specialist while also overseeing delivery crews, ensuring safety compliance, maintaining equipment standards, and upholding company service excellence.

The Delivery Specialist II acts as the on-site team lead during deliveries and pickups, ensuring efficient operations, proper setup procedures, and a high-quality customer experience.

Primary Responsibilities

Leadership & Supervision

  • Lead and supervise delivery team members during daily routes
  • Assign tasks and ensure team efficiency during loading, setup, and breakdown
  • Train new Delivery Specialists on safety standards, setup procedures, and company expectations
  • Monitor crew performance and provide coaching as needed
  • Ensure all team members follow proper safety protocols and company policies
  • Serve as the primary on-site decision maker during deliveries

Delivery & Setup Operations

  • Safely load, transport, and unload bounce houses and event rental equipment
  • Lift, carry, push, or maneuver equipment weighing 100+ pounds (team lifting required when appropriate)
  • Perform advanced setup of inflatables, ensuring proper anchoring (stakes, sandbags, or alternative secure methods)
  • Evaluate setup areas for slope, hazards, overhead obstructions, and weather-related risks
  • Ensure all electrical connections, blowers, and extension cords are safely installed and protected
  • Provide customers with clear safety instructions and operational guidance

Inspection & Quality Control

  • Conduct detailed equipment inspections at both delivery and pickup
  • Identify wear, damage, or safety concerns before and after events
  • Complete condition reports and document damages with photos when necessary
  • Ensure equipment is cleaned, sanitized, and properly packed for return
  • Verify all inventory is accounted for before leaving job sites

Logistics & Operational Oversight

  • Review daily route schedules and confirm accurate order fulfillment
  • Confirm proper load sequencing to maximize route efficiency
  • Maintain cleanliness and organization of company vehicles and trailers
  • Assist in maintaining warehouse organization and equipment tracking
  • Communicate with management regarding delays, issues, or customer concerns
  • Assist in scheduling adjustments when weather or logistical issues arise

Customer Experience

  • Represent Ready Set Fun Entertainment with professionalism at all times
  • Handle customer questions, concerns, or minor complaints on-site
  • Escalate major issues to management appropriately
  • Ensure each event location is left clean and orderly

Qualifications

  • Ability to lift and maneuver 100+ pounds repeatedly
  • Valid driver’s license with clean driving record
  • Proven reliability and strong attendance record
  • Previous experience with bounce house or event rental setup preferred
  • Experience driving trucks and trailers preferred
  • Demonstrated leadership ability
  • Strong problem-solving skills
  • Excellent time management and organizational skills
  • Strong communication and customer service skills
  • Ability to work weekends, evenings, and in varying weather conditions

Physical Requirements

  • Frequent lifting, bending, kneeling, pushing, and pulling
  • Standing and walking for extended periods
  • Working outdoors in heat, cold, or light rain
  • Ability to safely operate hand trucks, dollies, and basic tools

What Sets This Role Apart

  • Leadership-level responsibility
  • Oversight of crew safety and performance
  • Higher level of accountability for equipment condition and customer satisfaction
  • Opportunity for advancement into Operations Manager or Route Manager