Director, Client Success

Redwood Logistics•Chicago, IL

4d•Hybrid

About The Position

As Director, Client Success working within Managed Services (one of our entities), you will be responsible for driving revenue growth and customer retention across a large portfolio of existing customers. You will be a leader of people for the Client Success team. 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. This role usually entails having 1-3 direct reports. In this management capacity, you will help develop and execute strategy for your team of individual contributors while coordinating with senior leaders on overall department and company goals. Your performance will be measured by business retention, contract renewals, continuous improvement, and revenue growth.

Requirements

Industry Depth & Commercial Acumen 8+ years in transportation and logistics with progressive leadership 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, BI tools, Salesforce, and ERP/WMS 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.
Bachelors degree required
Authorized to work in the U.S.
Willingness to travel up to 40%, including occasional international travel.

Responsibilities

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 Lead, mentor, and develop a high-performing Client Success team focused on growth, accountability, and client advocacy.
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.

Benefits

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