Commercial Services Manager; Innovate

Reports To:

Vice President, Commercial Services

Location:

Chicago, IL or Remote

Environment:
Flexibility based on location

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.

As a Commercial Services Manager working within our Innovate business, you will be responsible for validating new opportunities for Redwood. This includes conducting opportunity discovery, quantifying opportunity value, costing and pricing, and opportunity negotiation and contract facilitation. Additionally, this role will be responsible for monitoring and managing overall Commercial Services team internal deal flow metrics, and dashboards to ensure optimal deal support and goals are being met.

Your role will directly influence revenue targets and customer conversion rates. You will work directly with our strategic sales team, business leaders and engineering teams to facilitate and solution opportunities for Redwood.

• Spearhead the commercial process for Innovate opportunities, proactively identifying and resolving issues, aligning stakeholders, and driving deals towards timely, successful close.
• Validate all new business opportunities for scope, objective, and clarity.
• Manage timeline, expectations, deadlines, and resources on new opportunities. Escalate when necessary.
• Convey timelines, deliverables, risks, delays, to project team and lead team members.
• Manage multiple opportunities with a project-based delivery model.
• Provide daily management and oversight of all aspects of sales cycle.
• Support the design and overall solution to generating client proposals.
• Coordinate all discussion related to deals, including managing the communication between external sales teams and internal business units.
• Collaborate with internal delivery teams and external sales to develop commercially viable, competitively priced proposals that account for broader affiliate and partner relationships and overall client business context.
• Maintain all project related documentation, including discovery notes, workflows, legal contracts, and sales proposals.
• Evaluate opportunities and generate weekly reporting on the overall health and outlook of the sales pipeline to multiple internal business units.
• Generate month end reporting by pulling data from multiple systems and identify trends over time and areas of opportunity within the business.
• Ad-hoc reporting when necessary.
• Prepare high-impact presentation materials for senior management and company stakeholders to generate insights that inform strategic choices and company directives.
• Provide technical and industry knowledge to contribute to strategy or assist other internal teams.
• Act as a sales‑adjacent subject matter expert, translating client logistics, operational, functional, and technical requirements into actionable recommendations for Innovate products, services, and solution design.
• Partner with legal team to amend and modify commercial language to support deal flow and ensure proper commercial contracting terms.

• Minimum 5‑8 years’ experience implementing, supporting, or operating transportation management systems (TMS) or global trade management systems (GTM), particularly Oracle Transportation Management Cloud or Oracle Global Trade Management.
• Strong verbal and written communication; including interpersonal skills and working closely with other teams, including external clients.
• Strong analytical skills; detail oriented.
• Ability to interpret, design, and deliver projects on time across all levels.
• Ab…