(Managed Transportation) Director of Client Success
Redwood Logistics(Managed Transportation) Director of Client Success Reports To: Senior Director of Client Success Location: Chicago, IL (Preferred), open to remote (within the U.S.) Environment: Remote or Hybrid Status: Exempt , Salaried 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, Client Success working within Managed Services (one of our entities), you will be responsible for driving revenue growth, value realization, strategic relationship development, and customer retention across a large portfolio of existing customers. This is a hybrid sales and operations role that requires the ability to identify and help close new sales opportunities, as well as acting as the internal and external champion for clients – understanding the complete technological, operational, and procurement scope and strategies. Your performance will be measured by business retention, contract renewals, continuous improvement, and revenue growth. How You Make a Difference Everyday: Strategic Revenue Leadership Own the value realization and growth strategy for a large portfolio of strategic, enterprise transportation clients Develop multi-year account growth roadmaps aligned to customer supply chain strategy, cost optimization goals, and service objectives. Identify opportunities across mode expansion, cross-border, managed transportation, and technology enablement. Executive Relationship Ownership Serve as the commercial owner for assigned accounts, building trusted C-suite relationships. Lead structured quarterly and annual executive business reviews focused on ROI, optimization strategy, and forward-looking innovation. Act as a strategic advisor on network design, carrier strategy, procurement events, and transportation technology. Growth & Retention Accountability Own gross profit expansion, contract renewals, and revenue retention targets. Proactively mitigate churn risk through predictive performance monitoring and stakeholder mapping. Lead pricing strategy discussions, contractual renegotiations, and value-based upsell initiatives. Operational & Analytical Excellence Translate transportation data (mode mix, cost-to-serve, service KPIs, claims, accessorial trends) into actionable executive insights. Champion continuous improvement initiatives including routing guide optimization, mode shifts, and automation opportunities. Leverage TMS, BI platforms, and CRM tools to drive data-backed decision making and storytelling. Cross-Functional Leadership Partner closely with Sales, Operations, Procurement, Carrier Management, and Finance to deliver seamless execution. Serve as the internal voice of the customer, influencing product development and process innovation. Market & Industry Expertise Stay ahead of freight market dynamics, capacity shifts, pricing trends, and regulatory impacts. Guide customers through market cycles with proactive strategy rather than reactive reporting. You’ve Got This? Industry Depth & Commercial Acumen 8+ years in transportation and logistics with progressive growth across sales, account management, managed transportation, or solution design. Demonstrated success managing enterprise accounts ($100M+ Freight Spend or $10M+ Gross Profit portfolios preferred). Strong understanding of all transportation modes including LTL, TL, intermod…