Vice President of Service Delivery

Reports To: Executive Vice President of Managed Services

Location: Chicago, IL or Remote (within the U.S.)

Environment: Hybrid/Remote

Status: Exempt, Salaried

Purpose of Your Work:

As a Vice President of Service Delivery working within Managed Services (one of our entities),you will be responsible for the performance, scalability, and evolution of Redwood's Managed Services delivery organization. This role unifies account management, client success, and client logistics around one operating model: delivering reliable execution, measurable customer value, and profitable long-term partnerships. You will shape the service strategy, lead through senior leaders, strengthen enterprise customer relationships, and ensure Redwood's delivery capabilities support growth, retention, innovation, and operational excellence.

How You Make a Difference Everyday:

• Set and execute the enterprise service delivery strategy, operating model, and multi-year roadmap for Redwood Managed Services.
• Lead and develop the Service Delivery leadership team, build organizational capability, and establish succession plans for critical roles.
• Own the customer experience across the lifecycle, from implementation and transition through steady-state operations, renewal, expansion, and strategic transformation.
• Maintain executive-level relationships with strategic customers and serve as the senior sponsor for governance, business reviews, value realization, and critical escalations.
• Establish clear accountability for customer health, retention, contractual SLAs, operational KPIs, savings commitments, service recovery, and customer profitability.
• Partner with the EVP, Managed Services and Commercial leadership to support revenue growth, expansion strategy, pricing, renewals, and the business case for investment.
• Own the financial performance of service delivery, including margin, cost to serve, capacity, productivity, staffing models, and resource allocation.
• Use operational, customer, and financial data to create executive-ready insight, identify leading indicators of risk, and prioritize actions that improve ROI.
• Champion a proactive service model that uses health signals, standardized governance, automation, and root-cause prevention to reduce failure demand and improve reliability.
• Partner with Product and Technology to prioritize TMS, analytics, workflow, and automation capabilities that make service delivery more visible, scalable, and differentiated.
• Lead enterprise continuous improvement across processes, operating rhythms, and customer-facing standards while preserving the flexibility required by complex networks.
• Represent the voice of the customer internally and ensure customer insight informs product strategy, commercial decisions, carrier partnerships, and operational priorities.
• Ensure operational readiness for new business, implementations, transitions, network changes, and major customer initiatives.
• Build a culture of accountability, transparency, customer ownership, collaboration, and continuous learning across the Managed Services organization.

You've Got This?

• Bachelor's degree in business, supply chain, operations management, or a related field; MBA preferred.
• 15 or more years of experience in transportation, logistics, managed transportation, 3PL, or 4PL services, including significant executive leadership of client-facing and operational organizations.
• Demonstrated success leading large, complex, multi-site or multi-modal transportation programs and enterprise customer portfolios.
• Executive presence with the ability to influence C-suite customers, board-level stakeholders, commercial leaders, and cross-functional partners.
• Strong commercial and financial acumen, including experience with P&L or operating budget accountability, margin, pricing, savings validation, cost to serve, and growth strategy.
• Deep understanding of transportation operations, TMS platforms, carrier management, freight audit and pay, analytics, service-level governance, and customer value measurement.
• Proven ability to design and scale operating models, lead transformation, standardize execution, and drive accountability through influence in a matrixed environment.
• A builder of people and organizations who develops leaders, strengthens culture, and creates an environment where high performance is sustainable.
• Exceptional communication, negotiation, problem-solving, and presentation skills, with the judgment to lead effectively through ambiguity and high-pressure situations.
• Ability to travel up to 30% for executive customer meetings, strategic planning, implementations, and relationship development.

Scope and Operating Expectations:

This role is highly visible internally and externally and requires regular engagement with customers, senior leaders, and cross-functional teams. The VP is expected to be accessible during material customer situations and major implementation milestones, including occasional support outside standard business hours when business continuity requires it.

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/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:

$190,000 - $215,000

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.