Outside Sales Executive

Direct Drive Logistics; Milwaukee (WI); On-site; USD 80,000 - 500,000; Full time

Benefits offered by this job

401(k)

401(k) matching

Cell phone reimbursement

Flexible spending account

Health insurance

Health savings account

Life insurance

Paid time off

Paid training

Vision insurance

Job summary

Direct Drive Logistics in Milwaukee, WI seeks an Outside Sales Executive to grow B2B freight and logistics accounts. You will prospect, meet clients in person, present tailored transportation solutions, and manage a sales pipeline.

You will negotiate rates, collaborate with operations, and monitor market trends to sharpen sales strategies. A bachelor’s in business is preferred but not required; this is an on-site role with local travel.

Qualifications

• B2B sales experience in freight/logistics preferred.
• On-site Milwaukee, WI with travel.
• Strong pipeline management required.

Responsibilities

• Prospect and qualify leads; schedule meetings; present customized transportation solutions.
• Negotiate rates and service agreements with clients.
• Manage sales pipeline and CRM activities; track progress and close opportunities.
• Collaborate with operations and customer service teams to ensure smooth execution of shipments.
• Monitor market trends and competitor offerings to adjust sales strategies.

Skills

Sales

Lead generation

Communication

Customer service

Team leadership

CRM

Office software

Time management

Driver’s license

Travel willingness

B2B sales

Education

Bachelor’s degree in business or related field

Tools

CRM systems

Office software

Job description

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.

Role Description

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.

Qualifications

• 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.

Job Type: Full-time

Pay: $80,000.00 - $500,000.00 per year

• 401(k)
• 401(k) matching
• Cell phone reimbursement
• Flexible spending account
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Paid training
• Vision insurance

Experience:

• B2B sales: 3 years (Required)
• 3PL: 1 years (Required)

Work Location: In person and customer meetings