Drayage Sales Manager

Drayage Sales Manager

Lincoln Park, Chicago, IL (On-Site)

Competitive Base Salary + Performance-Based Compensation

Avenue Logistics is looking for an experienced logistics leader to build, expand, and streamline our drayage and transloading operations.

Built by proven industry leaders, Avenue Logistics is a fast-growing logistics company with an opportunity to significantly expand our capabilities across ports and warehouses.

As a Drayage Sales Manager, you'll take ownership of this growing area of our business—developing the strategy, processes, partnerships, and team needed to create a scalable, best-in-class operation.

This isn't a role focused on maintaining what's already been built. We're looking for someone who understands drayage and can expand Avenue’s drayage offerings, including potential transload and cross-docking solutions when applicable, and is excited about the opportunity to build the infrastructure for our next stage of growth.

You'll work from our open-concept office in Chicago's Lincoln Park neighborhood, collaborating directly with executive leadership, sales, operations, and technology teams.

At Avenue Logistics, our mission is simple: help customers and carriers maximize their transportation needs through clear communication, market expertise, and exceptional service. We invest in our people, promote from within, and reward performance.

What You'll Do

• Own the strategy and day-to-day performance of Avenue's drayage and transloading operations.
• Evaluate current processes and implement scalable workflows that improve efficiency, visibility, and service.
• Expand our network of drayage carriers, cross-dock facilities, warehouses, and strategic partners across key markets.
• Develop standardized processes for quoting, scheduling, container management, transloading, and shipment execution.
• Partner with Customer Sales to develop competitive drayage and transloading solutions for new and existing customers.
• Identify opportunities to expand Avenue's presence across key ports and inland markets.
• Establish and monitor operational KPIs to measure service, efficiency, capacity, and growth.
• Work closely with Avenue's technology team to identify opportunities for automation and improved shipment visibility.
• Develop best practices around port and rail operations, appointment management, free time, demurrage, detention, and accessorials.
• Build, develop, and lead a high-performing team as the division continues to grow.

The Opportunity

This role provides the opportunity to build and shape a growing division within Avenue Logistics.

You'll have the support of an established sales organization, experienced leadership team, proprietary technology, and existing customer relationships—but the opportunity to determine how we scale our drayage and transloading capabilities.

Success in this role means creating an operation that can support significant growth without sacrificing service.

Why Avenue?

• Build and own a growing business line with direct visibility to executive leadership.
• Opportunity to expand an existing operation and create the infrastructure needed to scale it.
• Established customer sales organization capable of driving new drayage and transloading opportunities.
• Best-in-class proprietary technology with opportunities to further automate and streamline operations.
• Ability to develop strategic relationships across ports, rail ramps, carriers, warehouses, and transloading facilities.
• Fast-growing company where you can directly influence how the business evolves.
• Collaborative, entrepreneurial environment where strong ideas can quickly become action.

What You'll Bring

• Significant experience in drayage, transloading, intermodal, or port logistics, ideally within the third-party logistics industry.
• Deep understanding of drayage operations, port and rail processes, and transloading workflows.
• Proven ability to build, improve, or scale transportation operations.
• Strong network and understanding of drayage carriers, warehouses, transloading facilities, and major port and rail markets.
• Experience developing operational processes, SOPs, KPIs, and performance standards.
• Strong commercial mindset with the ability to partner with sales teams on pricing, solutions, and customer growth.
• Experience leading and developing teams.
• Ability to identify operational inefficiencies and turn them into scalable solutions.
• Strong communication, negotiation, and relationship-building skills.
• Entrepreneurial mindset with the ability to operate strategically while staying close to day-to-day execution.

Compensation & Benefits

Compensation

• Competitive Director-level base salary
• Performance-based compensation
• Compensation package designed to reward the growth and success of the division

Benefits

• Medical, Dental & Vision Insurance
• 401(k) retirement plan with generous company match
• Paid Time Off (Vacation, Sick, and Floating Holiday)
• Life Insurance
• Professional development and leadership opportunities

Ready to Build What's Next?

If you've spent your career in drayage and transloading and see opportunities to do it better, faster, and at greater scale, this is an opportunity to put that experience to work.

We're looking for a leader who can take what Avenue has today and build the processes, partnerships, technology, and team that will support where we're going next.

Apply today and help build the future of drayage and transloading at Avenue Logistics.