Outside Sales Executive

Company Description

Direct Drive Logistics is a global freight shipping provider offering full truckload, less than truckload, temperature-controlled, flatbed, intermodal, international container, and expedited shipping solutions. The company specializes in handling shipments of all sizes and levels of complexity, delivering customized logistics services with a focus on reliability and customer satisfaction. As a TIA-certified GOLD member, Direct Drive Logistics carries primary auto and cargo insurance on its logistics side, reflecting a strong commitment to safety and accountability.

The team treats every shipment with exceptional care, emphasizing quality, dependability, and long-term customer partnerships. Applicants can expect to join a company dedicated to responsive service and continuous improvement in freight solutions.

The Outside Sales Executive is a full-time, on-site role based in Milwaukee, WI responsible for growing new and existing customer accounts for freight and logistics services. In this position, the individual will prospect and qualify leads, schedule in-person and phone meetings, and present customized transportation solutions to potential and current clients. The role involves building and maintaining strong relationships, negotiating rates and service agreements, and collaborating with operations and customer service teams to ensure smooth execution of shipments.

Daily activities include managing a sales pipeline, tracking activities in CRM tools, preparing proposals, and following up to close opportunities and achieve revenue targets. The Outside Sales Executive will also monitor market trends, competitor offerings, and customer feedback to support continuous improvement of sales strategies and service offerings.

• Strong Sales and Lead Generation skills, including prospecting, qualifying opportunities, and managing a structured sales pipeline.
• Excellent Communication and Customer Service skills, with the ability to build trust, handle inquiries, and resolve issues professionally.
• Demonstrated Team Leadership or cross-functional collaboration skills to work effectively with operations, dispatch, and support staff.
• Experience in freight, logistics, transportation, or a related B2B sales environment is highly beneficial.
• Ability to work on-site in Milwaukee, WI, meeting clients face-to-face and representing the company in local and regional markets.
• Proficiency with CRM systems and basic office software (e.g., email, spreadsheets, presentations) to track and report sales activities.
• Strong organizational and time-management skills, with a focus on meeting targets and managing multiple accounts and priorities.
• Valid driver’s license and willingness to travel locally/regionally for client meetings; bachelor’s degree in business or related field preferred but not required.