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

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 improvements and maintain accurate account documentation within Salesforce, Confluence, SharePoint, and other internal systems.

Thought Leadership

• Promote Oracle product adoption and Redwood innovations through customer communications, educational content, and industry best practices.
• Develop creative engagement strategies that strengthen customer relationships and drive long-term success.

You've Got This?

• Bachelor's Degree required, preferably in Supply Chain Management, Business, Information Systems, Logistics, Engineering, or related field.
• 5+ years of experience in a customer-facing role within the transportation/logistics industry
• 2+ years of experience working with Oracle Transportation Management (OTM) and/or Oracle Global Trade Management (GTM) - highly desired
• Strong understanding of transportation operations, logistics, supply chain execution, and transportation technology
• Demonstrated experience leading executive customer relationships
• Experience facilitating Customer Business Reviews and strategic planning sessions
• Strong organizational and project management abilities with the ability to manage multiple strategic accounts simultaneously
• Ability to effectively multitask and prioritize responsibilities and lead by example
• Ability to travel up to 50% for customer meetings and training
• Proven track record of successful problem-solving and critical thinking
• Intermediate understanding of creating and maintaining reporting, including using MicrosoftOffice products (Outlook, Excel, Word, and Power Point)
• History of proven customer service as well as written and verbal communication skills

Tools You Will Use:

• Zendesk
• Confluence
• MS Office Word, Excel, SharePoint and PowerPoint
• Tableau
• Salesforce
• Chargebee

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

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.

Compensation Range:

Salary Range:

$100,000 - $125,000

This position is eligible to earn annual incentives based on individual and company performance.

The estimated pay range reflects an anticipated range for this position. The actual base salary offered will depend on a variety of factors, including the qualifications of the individual applicant for the position, years of relevant experience, specific and unique skills, level of education attained, certifications or other professional licenses held, and the geographical location in which the applicant lives and/or which they will be performing the job.