Director, Strategic Sales (TMS, WMS & SaaS Focused)

Redwood Logistics LLC; United States; On-site; USD 90,000 - 171,000; Full time

Benefits offered by this job

Learning & Development

Internal mobility

Employee referral bonus program

Employee Resource Groups (ERGs)

Paid time off & holidays

Paid parental leave

Medical, dental, vision & 401k with "

Transit & dependent care benefits

Job summary

Redwood Logistics LLC is seeking a Director of Strategic Sales (TMS, WMS & SaaS Focused) to lead high-impact initiatives across North America and Mexico. You will drive targeted platform services sales, build pipelines, and coordinate with cross-functional teams to maximize customer value.

You will deliver strategic selling across multiple service offerings, manage complex RFPs, and mentor a growing sales organization while traveling up to 50% to meet clients and close deals.

Qualifications

• At least 10 years of sales experience focused on TMS, WMS, and related supply chain services.
• Minimum 5 years in strategic selling across multiple service offerings.
• 3–5 years delivering or managing supply chain technology solutions.
• Proficient with TMS/WMS software and able to articulate ROI drivers.
• Strong negotiation, communication, analysis, and networking at all levels.
• Demonstrated leadership and adaptability to evolving business needs.

Responsibilities

• Promote and sell Redwood’s Platform Services including TMS, WMS, RedwoodConnect and partner SaaS solutions.
• Build a self-driven pipeline focused on goal-oriented sales and new logo growth.
• Conduct sales calls to current and potential customers across the full product set.
• Manage RFPs through the entire sales cycle with stakeholders.
• Consult with customers to offer technology solutions addressing supply chain challenges.
• Develop customer-facing presentations across Redwood service lines.
• Transition customer solutions from sales to delivery teams.
• Maintain Salesforce for pipeline and forecasting.

Skills

TMS/WMS sales

Strategic selling

Supply chain tech

TMS/WMS proficiency

Negotiation

Communication

Networking

Leadership

Job description

Current job opportunities are posted here as they become available.

Director, Strategic Sales(TMS, WMS & SaaS Focused)

Director, Strategic Sales (TMS, WMS & SaaS Focused)

Reports To: Vice President, Innovate Sales

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 Director, Strategic Sales (TMS, WMS & SaaS Focused) within Redwood Innovate (one of our entities), you will be responsible for achieving sales targets to meet planned objectives and develop strategic sales strategies to align with company goals. A key function of the position is to promote the overall Redwood Platform Services offerings and sponsor the growth of self-driven strategic sales opportunities, while maintaining high customer satisfaction.

How You Make a Difference Everyday:

• Promote and sell Redwood’s Platform Services including TMS, WMS, RedwoodConnect and partner SaaS solutions
• Build a self-driven and qualified pipeline focused on goal-oriented sales and new logo growth
• Conduct sales calls to current and potential customers, focusing on Redwood’s Platform Services and cross sales opportunities
• Effectively manage technology and transportation RFP’s throughout the entire sales cycle, communicating both internally and externally with key stakeholders
• Consult with customers to offer various technology solutions that will solve current supply chain challenges while enabling future scale
• Understand customer requirements and scope to qualify potential opportunities while articulating relevant value drivers within the organization
• Identify potential customer roadblocks to selecting and implementing a technology solution, and work internally and externally to solve the potential challenges
• Develop and present customer facing presentations across all Redwood service lines, primarily in Platform Services
• Collect requirements for, manage, and operate customer facing technology demonstrations
• Effectively transition customer solutions from the sales cycle to the appropriate delivery teams
• Participate in QBR’s and continuous improvement feedback loops with the customer to drive organic growth within the current book of business
• Work effectively across the Redwood BU’s to enable clients to maximize value from the Redwood offerings
• Recommend sales strategies for improvements based on TMS, WMS, and SaaS market research and competitor analysis
• Maintain strategic customer and Redwood partner relationships
• Report on personal and/or department activity as requested
• Maintain and effectively utilize Salesforce to manage opportunities, provide pipeline movements, and provide accurate forecasting
• Perform other related duties as assigned
• Build and develop self-generated pipeline via networking, partnerships and relationships

You’ve Got This?

• Minimum 10 years demonstrated sales experience focused on TMS, WMS, Supply Chain Integrations, and/or Supply Chain Consulting
• Minimum 5 years experience in strategic selling into multiple service offerings
• Minimum 3-5 years experience delivering or managing supply chain technology solutions
• Proficient with Transportation Management and/or Warehouse Management software capabilities; ability to articulate value and ROI drivers to prospective customers
• Strong understanding of application and partner integration approaches
• Strong negotiation, communication, analysis, and networking skills from C-level to end user
• Strong leadership skills
• Flexibility to quickly adapt to business need and/or industry changes
• Strategic thinker
• Travel up to 50%

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 Monday through Friday, with normal business hours from 8:00 AM to 5:00 PM. As an exempt position, some work will be required outside of normal business hours.

Compensation Range:

$90,000 - $170,500

This position is eligible to earn monthly, and 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 LOGISTICS
1765 N. Elston Ave., Suite 216,Chicago,IL,60642
P:844-467-3396
E:[e-mail]