Director of LTL Services

Reports To: Executive Vice President of Supply Chain Services

Location: Anywhere in U.S. (Chicago, IL preferred)

Environment: Remote; must be willing to travel to Chicago HQ twice per month (to start)

Work Schedule:

This position is full-time and remote Monday through Friday from 8:00 AM to 5:00 PM with an hour break, but flexibility is available based on coverage.

Who We Are:

Recognized by Gartner in their Modern 4PL Market Guide, Redwood Logistics is at the forefront of industry innovation. Our cutting-edge supply chain technology pairs with the expertise of our brilliant minds to empower logistics execution across North America and Mexico.

Leveraging a comprehensive range of services, data-centric network solutions, and a seamlessly integrated platform, we have established our prominence as a key player in the mid-market segment within the freight tech industry.

Whether you’re just starting your career or are an established professional looking for your next opportunity, Redwood inspires innovation across teams to provide transformative solutions for our customers.

Purpose of Your Work:

As Director of LTL Services working within Redwood Supply Chain Solutions, Managed Services (one of our entities), you will be responsible for oversight and optimization of our LTL Operations, managing a spend of $400M.

This role requires a strategic leader with over 10 years of experience in LTL transportation, coupled with a deep understanding of LTL dynamics, carrier management, cost analysis, and service optimization. As Director of LTL Services, you will drive initiatives that enhance service performance, reduce costs, and build strong carrier partnerships to support the growth and success of our logistics network.

How You Make a Difference Everyday:

• Strategic Leadership: Develop and execute LTL strategy to optimize service levels, improve cost efficiency, and support the company's broader logistics and transportation objectives.

• Carrier Relationship Management: Establish and maintain strong partnerships with key LTL carriers. Negotiate contracts, resolve disputes, and manage service agreements to maximize value and ensure service quality.

• Operational Optimization: Identify areas for improvement in current LTL processes, including routing, consolidation, and scheduling. Implement best practices to drive operational efficiency and streamline workflows.

• Cost Management: Oversee the $400M LTL spend, ensuring costs are managed effectively through strategic sourcing, rate negotiation, and optimization initiatives.

• Data Analysis and Reporting: Utilize data to measure performance, identify trends, and make data-driven decisions. Develop and present reports to senior management on LTL performance, cost savings, and service improvements.

• Team Development: Lead and mentor a team of LTL specialists, providing guidance and support to achieve departmental goals and foster professional growth.

• Compliance and Risk Management: Ensure compliance with all regulatory and safety requirements related to LTL transportation. Proactively manage risks associated with service disruptions or non-compliance.

• Cross-Functional Collaboration: Work closely with internal teams, including operations, finance, and IT, to support integrated logistics solutions and ensure alignment across functions.

You’ve Got This?

• Bachelor’s degree in logistics, supply chain management, business, or a related field

• 10+ years of experience in LTL transportation, with at least 5 years in a leadership role.

• Proven experience managing large-scale LTL spend, ideally at or above $100M

• Strong knowledge of LTL carrier networks, pricing models, regulations, and market dynamics.

• Demonstrated ability to analyze complex data, develop actionable insights, and implement strategic initiatives.

• Excellent negotiation, communication, and interpersonal skills.

• Proficiency in transportation management systems (TMS) and other relevant software.

Preferred Skills:

• Experience in 3PL or 4PL environments.

• Strong project management skills with the ability to lead cross-functional teams.

• Knowledge of emerging technologies and innovations in LTL transportation.

What We Offer:

• Access to experts and resources for your Learning & Development journey
• Opportunity for internal mobility
• Employee referral bonus program
• Employee Resource Groups (ERGs)
• Annual fundraising and volunteer events to give back to communities
• Paid time off, floating holidays, time off to volunteer and rollover
• Paid parental leave
• Medical, dental, vision and 401k plans (with match)
• Flexible spending account, mass transit and dependent care plans available
• Health savings account, with a annual company contribution for plan participants
• Short-term and long-term disability; life insurance policies subsidized by company
• Additional benefits including pet insurance, accident care, access to legal advice and more

Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.