Vice President, Truckload Operations

Role: Vice President, Truckload Operations

Location: South Barrington, IL (60010) or Tampa, FL
Base Salary: $150,000
Bonus: Performance-based, tied to branch growth
Benefits: 401(k), paid time off, medical and dental insurance

Company Overview

We are a fast-growing transportation and logistics provider headquartered in South Barrington, Illinois, with additional remote operations in Tampa, Florida. The business employs 30+ staff in the Northwest Chicago suburbs, supported by a growing remote team.

The company has delivered strong year-over-year revenue growth and is coming off its best performance to date, generating approximately $44M in annual revenue. With a fully staffed 24/7 in-office operations model, we provide high-touch service and real-time communication on every load.

We are firmly in growth mode, with a strategic objective to expand our freight offerings and scale the business to $100M+ in revenue over the next 3–5 years.

Position Summary

We are seeking a Vice President of Truckload Operations to lead and scale our truckload brokerage division. This is a senior leadership role for a commercially driven, results-oriented operator with deep North American truckload experience.

The successful candidate will be responsible for growing the existing freight portfolio, strengthening carrier networks, and building a high-performing operations team, while working closely with sales leadership to deliver exceptional service and margin performance.

Key Responsibilities

• Lead and manage the truckload brokerage operation, overseeing a team of approximately six direct reports
• Manage and grow an existing freight portfolio across current and new lanes
• Negotiate competitive and sustainable rates with customers and carriers/drivers
• Build, expand, and maintain a reliable carrier base to support current and future freight demand
• Partner closely with sales representatives to ensure consistent, high-level customer service
• Recruit, hire, train, and develop operations talent to support division growth
• Provide hands-on leadership, guidance, and day-to-day operational problem-solving
• Drive performance, accountability, and continuous improvement across the team

Leadership Scope

In this role, you will lead a team of customer and carrier account managers, driving increased wallet share within existing accounts, delegating new opportunities, and providing operational oversight to ensure service excellence. The environment is collaborative, fast-paced, and performance-driven, with a strong emphasis on internal development and accountability.

Experience & Qualifications

• Minimum 5+ years of progressive experience in truckload brokerage or transportation operations
• Experience in non-asset-based and asset-based environments preferred
• Strong knowledge of North American truckload transportation, including dry van and flatbed
• Proven ability to develop and maintain long-term customer and carrier relationships
• Demonstrated leadership presence with the ability to motivate, manage, and scale teams
• Results-driven mindset with strong commercial and market awareness
• Excellent problem-solving skills and ability to respond quickly to service or capacity challenges
• Strong written and verbal communication skills, including report writing and executive-level presentations
• Ability to effectively present information and respond to questions from leadership, customers, and internal teams

Job Type: Full-time

Pay: $110,000.00 - $150,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off

Application Question(s):

• would you be able to provide examples of you managing a freight portfolio and negotiating rates?
• Would you be able to provide examples of when you built a carrier base and also when you negotiated with carriers?
• Would you be able to provide examples of when you Hired, trained & pushed the operations team as well as leading account managers?
• Would you be able to provide examples of when you worked closely with sales representatives?
• Would you be able to provide examples of when you had to respond quickly to service issues?
• Do you have Dry van & flatbed experience?
• Do you have Asset and non-asset based experience?
• Do you have experience in writing reports and presenting information?

Work Location: In person