Truckload Operations Manager

An asset-based flatbed trucking company (fleet currently ~80-100 trucks, expanding beyond 100) seeks a Truckload Operations Manager in Caledonia, WI (onsite).

Territory: Eastern Wisconsin & Northern Illinois.

Full-Time, Direct Hire.

Compensation: $80,000-$95,000 base salary.

Position Summary: Lead the day-to-day operations of an asset-based flatbed fleet with continued expansion planned. Responsible for overseeing dispatch, load planning, driver management, customer service, fleet utilization, compliance, profitability, and operational performance. The ideal candidate is a hands-on operations leader with experience managing flatbed trucking operations within an asset-based carrier and a proven ability to build processes that support sustainable growth.

Key Responsibilities:

- Lead daily operations of an asset-based flatbed fleet and support continued fleet growth

- Oversee transportation operations from load acceptance through final delivery and customer follow-up

- Manage and develop dispatch personnel; provide operational leadership and accountability

- Plan and assign freight based on equipment availability, driver hours, customer requirements, and profitability

- Monitor key operational metrics (fleet utilization, revenue per truck/mile, empty miles, on-time performance, operating margins)

- Identify inefficiencies and implement corrective actions

- Coordinate with drivers on dispatch instructions, route changes, equipment issues, and load securement

- Ensure compliance with DOT regulations, Hours of Service, and safety standards

- Utilize Samsara and TMS to monitor fleet activity, compliance, and driver performance

- Respond to service disruptions, breakdowns, weather delays, and operational challenges

- Support driver recruiting, onboarding, performance management, and retention

- Partner with sales and pricing teams to evaluate new business opportunities

Requirements:

- Minimum 5 years of transportation, trucking, logistics, dispatch, or fleet management experience

- Previous management experience within an asset-based trucking company

- Direct experience managing flatbed, open-deck, specialized, or similar truckload operations

- Working knowledge of DOT regulations, HOS, weight laws, and transportation safety standards

- Experience monitoring fleet profitability and operational KPIs

- Proven leadership managing dispatch teams and professional drivers

- Experience using TMS, ELD platforms, and fleet management technology

- Proficiency with Microsoft Excel and Office

- Ability to work onsite in Caledonia, WI

Preferred: Experience managing fleets of 50+ trucks; leading operations through growth; Samsara; flatbed load securement and open-deck freight; company drivers and owner-operators; operating budgets and P&L Bachelor's in Transportation, Logistics, Supply Chain, or Business.