Director Of Delivery Jobs
Director Of Delivery jobs are open across technology, consulting, healthcare, and financial services, from mid-level program leads to senior and VP-level roles, with specializations in agile delivery, digital transformation, and managed services. Find a role that fits from the openings below and apply directly.
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Senior Director of Service Delivery
Reports To: Vice President of Service Delivery
Location: Chicago, IL
Environment: 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 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.
Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.
Senior Director of Service Delivery
Reports To: Vice President of Service Delivery
Location: Chicago, IL
Environment: 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 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.
Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.
Director Of Delivery Jobs by Experience Level
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Find Director Of Delivery JobsDirector Of Delivery Job Market
Who's Hiring
Top Industries Hiring
- Construction & Real Estate
- Consulting & Professional Services
- Energy
- Manufacturing
- Law & Legal Services
What Employers Look For
The qualifications that appear most often in director of delivery jobs.
- 7 or more years of program or delivery management experience in a technology or services environment
- Demonstrated experience leading cross-functional teams through complex, multi-workstream engagements
- Proficiency with agile delivery frameworks such as Scrum, SAFe, or Kanban
- Experience managing client relationships, stakeholder expectations, and executive-level reporting
- Familiarity with project management tools such as Jira, Asana, or Microsoft Project
- PMP, PgMP, or SAFe certification preferred by a significant share of employers
Tips for Your Director Of Delivery Job Search
Quantify delivery outcomes on your resume
Director of delivery roles demand proof of scale, not just responsibility. Replace vague ownership statements with specific outcomes: programs completed on schedule, teams coordinated, or delivery cycles shortened. Hiring managers filter heavily on measurable execution history.
Tailor your resume to the delivery model
Agile, waterfall, and hybrid delivery orgs each look for different fluency signals. Check the job description for methodology language and mirror it in your resume. A candidate who speaks the same delivery framework as the team moves faster through screening.
Target companies mid-transformation not post-transformation
Director of delivery roles open most often when organizations are scaling new programs or restructuring delivery functions. Prioritize openings at companies that recently secured funding, launched a platform, or announced a major operational change.
Apply early to roles that fit
Migrate Mate lists director of delivery openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Prepare a delivery case study for interviews
Most director of delivery interviews include a scenario or case question about a derailed program or a missed milestone. Prepare one detailed example of a delivery problem you diagnosed and corrected, with a clear explanation of the decision points and result.
Negotiate scope before you negotiate compensation
In director of delivery offers, the reporting structure and portfolio scope vary significantly across employers. Before accepting or countering on pay, clarify which teams, vendors, and programs you own. Scope misalignment is the most common source of early dissatisfaction in these roles.
Director Of Delivery Jobs: Frequently Asked Questions
Which companies are hiring the most director of deliverys?
The companies hiring the most director of deliverys right now include Kennedy/Jenks Consultants, WSP in the U.S., and Redwood Logistics, with the largest share of openings in California, Texas, and Massachusetts, based on current listings on Migrate Mate as of September 2026. Demand is strongest at technology consultancies, enterprise software companies, and large managed services providers.
How many director of delivery jobs are remote?
About 76% of director of delivery openings are fully remote or hybrid as of September 2026, reflecting the coordination-heavy but location-flexible nature of most delivery leadership roles. Sub-areas with the highest remote share include digital product delivery, cloud transformation programs, and SaaS implementation teams, where client and team interactions are conducted primarily through digital tools.
How do you become a director of delivery?
Most directors of delivery move up through program or project management roles, building experience leading multi-team engagements before stepping into delivery leadership. Earning a formal certification such as PMP or PgMP signals methodology fluency. Building a record of on-time, on-budget program execution is more important than any single credential. Transitioning from a senior program manager or delivery manager role with direct reports is the most common path.
Can you get hired as a director of delivery without much experience?
It is uncommon but possible to move into a director of delivery role without deep senior management experience if you can demonstrate ownership of a complex, cross-functional program with measurable outcomes. Smaller companies and startups are more likely to promote from within or hire candidates with strong execution records over candidates with long titles. Framing your experience around accountability for delivery results, not just task coordination, makes the strongest case.
What does the director of delivery interview process look like?
The typical process starts with a recruiter screen focused on delivery methodology and team scale, followed by a hiring manager conversation about a specific program or transformation you led. Later rounds usually include a panel with cross-functional stakeholders and a case exercise or presentation on how you would approach a delivery challenge. References are checked carefully, often with direct questions about how you managed scope changes or stakeholder conflict.
Where can I find and apply to director of delivery jobs?
You can find and apply to director of delivery jobs on Migrate Mate, which lists current openings from across the United States. Find roles that match your background and apply directly to each listing from the page.
See All 56 Director Of Delivery Jobs
Find roles that match your experience and apply in just a few clicks.
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