Director, Strategic Sales; Brokerage

Current job opportunities are posted here as they become available.

Reports To:

Vice President – Strategic Solutions

Location:

Carol Stream, IL

Environment: Hybrid (expectations to work onsite 3 days a week as travel schedule permits; up to 50% travel)

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

By combining a full suite of services, a robust freight brokerage supported by data-driven network solutions, and a seamlessly integrated platform, we’ve positioned ourselves as a trusted partner in the supply chain industry for small, mid, and enterprise-sized customers.

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

Purpose of Your Work:

As the Director of Strategic Salesworking within Redwood Multimodal(one of our entities, others include Managed Services and Innovation & Technology),you will be a pivotal force in driving aggressive sales targets, translating strategic vision into tangible revenue and activity objectives, and shaping the future of our market presence.

How You Make a Difference Everyday:

• Join a focused, high-impact sales team where your individual contributions directly drive significant growth and market share within our brokerage business, cultivating a collaborative environment with less internal competition.
• Promote and sell Redwood’s core brokerage services, which primarily focus on Full Truckload, Flatbed, and Refrigerated FTL. Other services include LTL, Partial TL, Hotshot Flatbed, Refrigerated LTL, and Intermodal.
• Actively identify significant cross-selling opportunities across our full-service suite (including Redwood’s innovative technology/TMS, outsourced freight management, distribution, and project management services).
• Utilize your industry experience and network to prospect new clients by leveraging our sales enablement tools (Linked In Sales Navigator, Zoom Info, Salesforce) and SDR support, effectively establishing a robust sales pipeline.
• Quarterback and internally/externally manage brokerage RFPs, contracts, and customer relationships throughout the entire sales cycle, communicating both internally and externally with key stakeholders.
• Develop and present customer-facing presentations on our brokerage capabilities to strategically solve potential customers’ challenges.
• Collaborate with and effectively hand off accounts to Business Development and Operations teams to ensure smooth post-sale transitions and continuous customer success.
• Proactively identify and recommend innovative sales strategies, informed by a deep analysis of brokerage market trends and competitive landscapes.
• Drive growth opportunities within newly landed accounts during their first 12–36 months.
• Leverage internal introductions and a commission structure designed to reward holistic client solutions, maximizing revenue potential by expanding services within existing and new accounts.
• Consult with customers to offer a range of brokerage and logistics solutions that address current supply chain challenges while enabling future scalability.
• Conduct in Quarterly Business Reviews (QBRs) and continuous improvement feedback loops with customers to drive organic growth within the current book of business, in close partnership with operations.

You’ve Got This?

• Minimum 3-5 years demonstrated outside sales experience focused on FTL asset-based or 3PL.
• Significant industry/shipper contacts that you think could find value in Redwood Multimodal offerings.
• Proficient with the ability to articulate value and ROI drivers to prospective customers
• Strong negotiation, communication, analysis, and networking skills from C-level to end user
• Strong leadership skills
• Flexibility to quickly adapt to business needs and/or industry changes
• Strategic thinker

What We Offer:

• Access to experts and resources for your Learning & Development journey
• Opportunity…