Senior Director of Service Delivery

Reports To: Vice President of Service Delivery

Location: Chicago, IL

Environment: Hybrid

Status: Exempt; Salaried

Purpose of Your Work:

As a Senior Director of Service Delivery, working within Managed Services (one of our entities), you will be responsible for leading a team of Service Delivery leaders focused on delivering exceptional customer experience, operational excellence, and strategic value across Redwood's Managed Services customer portfolio.

This role is accountable for ensuring service delivery teams consistently execute against customer commitments while driving standardization, scalability, and continuous improvement throughout the organization. You will provide strategic leadership within execution teams and drive cross-functional collaboration. Working closely with Customers, Carrier Management and Client Solutions, you will ensure customer needs are translated into effective service strategies that deliver measurable business outcomes.

The ideal candidate thrives in a dynamic, fast-paced environment and possesses exceptional leadership, communication, and problem-solving skills. They have a proven ability to build high-performing teams, develop future leaders, and cultivate strong executive-level customer relationships. This individual is highly analytical, embraces data-driven decision making, and champions continuous improvement through operational excellence, technology adoption, and process innovation.

Above all, they will embody the vision, strategy, and culture for the Service Delivery department while ensuring Redwood remains a trusted, value-driven partner for its customers.

How You Make a Difference Everyday:

• Lead and develop a team of Service Delivery leaders responsible for delivering exceptional service across multiple customer accounts
• Own the overall delivery strategy for assigned customer portfolios, ensuring alignment with customer expectations and company objectives
• Establish and maintain executive-level customer relationships, serving as the primary escalation point for strategic service issues
• Participate in Quarterly Business Reviews (QBRs), Executive Business Reviews (EBRs), and ongoing governance meetings with key customer stakeholders
• Develop customer success strategies that improve retention, satisfaction, and long-term growth opportunities
• Partner with any and all necessary Redwood teams to ensure seamless delivery of services across the customer lifecycle
• Drive a culture of customer advocacy by proactively identifying risks, opportunities, and service enhancements before they impact the customer experience
• Own the integrity, accuracy, and governance of operational and customer data across systems, ensuring data quality standards are consistently maintained
• Develop processes and controls that improve data integrity, reporting accuracy, and overall visibility into customer performance
• Utilize data analytics and business intelligence tools to identify trends, measure service performance, and provide actionable insights to internal stakeholders and customers
• Establish meaningful service delivery KPIs, scorecards, and performance dashboards to measure operational performance and customer outcomes
• Lead continuous improvement initiatives by identifying process inefficiencies and implementing scalable solutions that improve quality, productivity, customer satisfaction, and profitability
• Coach, mentor, and develop leaders through regular one-on-one meetings, performance reviews, succession planning, and professional development initiatives
• Foster a culture of accountability, collaboration, innovation, and continuous learning throughout the organization
• Monitor team performance against departmental objectives and implement corrective actions when necessary
• Review customer profitability and operational performance, making recommendations that improve efficiency while maintaining service excellence
• Collaborate with Product and Technology teams to prioritize system enhancements, automation opportunities, and digital transformation initiatives that improve customer experience
• Evaluate customer processes and recommend technology, reporting, or workflow improvements that increase value for both Redwood and the customer
• Support new customer implementations, transitions, and strategic initiatives by ensuring operational readiness and successful service adoption
• Manage executive-level customer escalations through timely communication, root cause analysis, and sustainable corrective action plans
• Monitor contractual service level agreements (SLAs), ensuring commitments are consistently achieved and exceeded whenever possible
• Travel as needed to customer locations for executive business reviews, strategic planning sessions, implementations, and relationship development
• Occasionally provide executive support during critical customer situations outside of standard business hours when required

You've Got This?

• High School diploma required
• BA/BA required, MBA preferred
• Minimum of 10+ years of experience in Transportation / Logistics industry, and a minimum of 5 years in leadership role with direct reports
• Minimum of 6 years of experience with Infios or other Transportation Management Systems Ability to travel up to 20% for customer meetings & training
• Prove track record of problem solving and critical thinking
• Basic understanding of creating and maintaining reporting in tools such as excel and business intelligence dashboards
• Full understanding of transportation modes (small parcel, TL, LTL, partial, flatbed, intermodal) and market trends
• In-depth understanding of building and maintaining carrier and customer relationships
• History of proven customer service and communication skills

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 hybrid 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:

$150,000 - $190,000

This position is eligible to earn an annual incentive 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.