Customer Success Director (Oracle Focused)

Customer Success Director (Oracle Focused) Reports To: Vice President of Customer Success Location: Chicago, IL or Remote Environment: Remote 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 a Customer Success Director working within Innovate (one of our entities), you will serve as the executive relationship owner and strategic advisor for a portfolio of Redwood's Oracle Transportation Management (OTM), Global Trade Management (GTM) and RedwoodConnect (RWC) customers. This role partners with customers throughout their implementation journey and long-term adoption lifecycle to maximize business value, accelerate user adoption, ensure successful transitions from implementation to support, and identify opportunities for continued optimization and growth. The ideal candidate combines strong customer relationship management skills with deep Oracle OTM/GTM knowledge and supply chain expertise to become a trusted advisor to executive stakeholders. This individual champions customer outcomes, drives strategic planning, manages renewals, develops growth opportunities, and advocates internally on behalf of customers to ensure long-term success. How You Make a Difference Everyday: Customer Relationship Management Own and manage a portfolio of strategic Oracle OTM/GTM and RedwoodConnect (RWC) customer accounts throughout the customer lifecycle. Build trusted relationships with executive sponsors and key business, transportation, and IT stakeholders. Serve as the primary strategic advisor and customer advocate, aligning customer objectives with Redwood's solutions and long-term partnership strategy. Strategic Customer Success Develop and execute Strategic Account Plans and multi-year customer roadmaps focused on value realization, user adoption, optimization, and supply chain transformation. Advise customers on best practices across Oracle OTM/GTM, RedwoodConnect, Managed Services, AI, and other Redwood solutions. Lead change management, user adoption, and operational readiness efforts throughout implementation and post-go-live. Customer Engagement Lead Customer Business Reviews (CBRs), Steering Committees, roadmap sessions, and executive meetings focused on KPIs, business outcomes, product adoption, and ROI. Support customer advocacy initiatives including reference programs, case studies, webinars, and customer advisory activities. Implementation & Customer Success Partner with Delivery, Sales, and Support teams to ensure successful implementations, seamless transition to support, and ongoing customer success. Monitor customer adoption, identify risks, coordinate issue resolution, and drive continuous optimization following go-live. Customer Health & Growth Proactively manage customer health, support performance, Business-at-Risk (BAR) accounts, and overall customer satisfaction. Own renewal strategy while identifying and developing upsell and cross-sell opportunities across Redwood's portfolio. Build business cases that demonstrate customer value and ROI for expanded services. Internal Leadership & Operational Excellence Act as a customer escalation point and collaborate across Sales, Delivery, Product, and Support to resolve complex issues and improve customer outcomes. Capture customer feedback to influence product improveme…

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