Director of Client Success

Director of Client Success

Reports To: Senior Director of Client Success

Location: Chicago, IL (Preferred), open to remote (within the U.S.)

Environment: Remote or 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 Director, Client Success working within Managed Services (one of our entities), you will be responsible for driving revenue growth, value realization, strategic relationship development, and customer retention across a large portfolio of existing customers.

This is a hybrid sales and operations role that requires the ability to identify and help close new sales opportunities, as well as acting as the internal and external champion for clients – understanding the complete technological, operational, and procurement scope and strategies.

Your performance will be measured by business retention, contract renewals, continuous improvement, and revenue growth.

How You Make a Difference Everyday:

Strategic Revenue Leadership

• Own the value realization and growth strategy for a large portfolio of strategic, enterprise transportation clients
• Develop multi-year account growth roadmaps aligned to customer supply chain strategy, cost optimization goals, and service objectives.
• Identify opportunities across mode expansion, cross-border, managed transportation, and technology enablement.

Executive Relationship Ownership

• Serve as the commercial owner for assigned accounts, building trusted C-suite relationships.
• Lead structured quarterly and annual executive business reviews focused on ROI, optimization strategy, and forward-looking innovation.
• Act as a strategic advisor on network design, carrier strategy, procurement events, and transportation technology.

Growth & Retention Accountability

• Own gross profit expansion, contract renewals, and revenue retention targets.
• Proactively mitigate churn risk through predictive performance monitoring and stakeholder mapping.
• Lead pricing strategy discussions, contractual renegotiations, and value-based upsell initiatives.

Operational & Analytical Excellence

• Translate transportation data (mode mix, cost-to-serve, service KPIs, claims, accessorial trends) into actionable executive insights.
• Champion continuous improvement initiatives including routing guide optimization, mode shifts, and automation opportunities.
• Leverage TMS, BI platforms, and CRM tools to drive data-backed decision making and storytelling.

Cross-Functional Leadership

• Partner closely with Sales, Operations, Procurement, Carrier Management, and Finance to deliver seamless execution.
• Serve as the internal voice of the customer, influencing product development and process innovation.

Market & Industry Expertise

• Stay ahead of freight market dynamics, capacity shifts, pricing trends, and regulatory impacts.
• Guide customers through market cycles with proactive strategy rather than reactive reporting.

You’ve Got This?

Industry Depth & Commercial Acumen

• 8+ years in transportation and logistics with progressive growth across sales, account management, managed transportation, or solution design.

• Demonstrated success managing enterprise accounts ($100M+ Freight Spend or $10M+ Gross Profit portfolios preferred).

• Strong understanding of all transportation modes including LTL, TL, intermodal, international, parcel, and cross-border freight.

Revenue & Growth Mindset

• Proven track record driving margin expansion, contract renewals, and net revenue growth.

• Experience leading executive-level negotiations and complex pricing conversations.

• Ability to quantify and communicate ROI in transportation cost savings, service improvements, and working capital optimization.

Executive Presence

• Highly polished communicator comfortable influencing stakeholders from warehouse managers to C-suite executives.

• Exceptional storytelling skills using data visualization tools (Tableau, Power BI, etc.).

• Confident facilitator of high-stakes QBRs and renewal conversations.

Analytical & Technical Fluency

• Advanced working knowledge of TMS platforms (strong preference towards experience with Oracle OTM or Infios/MercuryGate), BI tools, Salesforce, and ERP/WMS/Supply Chain Tech integrations.

• Strong command of KPIs including cost-per-mile, mode optimization, routing guide compliance, tender acceptance, OTIF, claims ratio, and accessorial leakage.

• Ability to interpret contract language and translate into operational execution and profitability management.

Leadership & Influence

• Experience building, coaching, and retaining high-performing teams.

• Skilled at navigating matrixed organizations and influencing without direct authority.

• High accountability, ownership mentality, and bias toward action.

Additional Requirements

• Bachelor’s degree required

• Authorized to work in the U.S.

• Willingness to travel up to 40%, including occasional international travel.

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:

$100,000 - $140,000

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.

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.