Senior Product Manager - Connectivity

Reports To: Chief Information Officer

Location: Chicago, IL

Environment: Hybrid

Status: Exempt; Salaried

Purpose of Your Work:

As the Senior Product Manager, Connectivity, you will own the strategic direction and roadmap for how Redwood integrates with carriers, customers, and technology partners across the enterprise. Reporting directly to the CIO, you will lead the evolution of our connectivity capabilities across EDI, APIs, RPA, and modern integration platforms, partnering closely with Engineering, Architecture, Operations, Sales, and Delivery teams to improve how trading partners are onboarded, integrated, monitored, and supported. Today, Redwood's business units connect with trading partners using different tools, workflows, and definitions of success. Your role will be to bring product discipline to this complex, highly cross-functional landscape by establishing baseline metrics, identifying where standardization creates enterprise leverage, and defining a faster, more automated, measurable, and scalable partner onboarding capability. This is a highly visible, ownership role for a product leader who can turn ambiguity into structure, align stakeholders around a clear strategy, and help make connectivity a more reliable and scalable part of Redwood's operating model.

How You Make a Difference Everyday:

• Own the connectivity capability roadmap across EDI, API, RPA, and integration platforms, aligning product investments with the needs of Redwood's managed transportation and brokerage business units
• Lead a structured current-state assessment of how Redwood connects with trading partners today, including connection inventory, tooling, team workflows, and intake processes, and translate findings into a prioritized execution plan
• Own the end-to-end trading partner onboarding experience, streamlining and automating the path from initial engagement to a live, reliable production connection
• Establish where standardized capabilities and operating models create enterprise leverage, and where business-specific workflows should remain differentiated
• Develop the KPI framework for connectivity, establishing baselines and measuring onboarding speed, transaction quality, connector reuse, operational reliability, and support effort
• Partner with Engineering and Architecture to define a platform strategy that enables self-service partner onboarding, including intake, configuration, testing, validation, certification, and controlled promotion to production
• Drive the evolution of Redwood's integration platform by identifying opportunities for self-service onboarding, reusable integration patterns, AI-assisted mapping, automation, and consolidation of duplicative tooling
• Build data-driven business cases for connectivity investments by quantifying opportunities across operational efficiency, cost to serve, reliability, customer experience, and revenue enablement, and communicate recommendations and tradeoffs to executive stakeholders.
• Influence decisions across a highly matrixed organization by aligning cross-functional stakeholders, facilitating productive discussions, and driving alignment around strategic product decisions
• Monitor relevant integration technology trends, vendor capabilities, and emerging standards to keep Redwood's connectivity strategy modern and scalable

You've Got This?
• 7+ years of product management experience leading enterprise software, platform, or technical integration products within logistics, transportation, or supply chain environments, including carrier and customer integrations or TMS ecosystems
• Working knowledge of B2B integration technologies, including EDI (X12/EDIFACT), APIs, data mapping, RPA, and modern integration or iPaaS platforms
• Demonstrated success bringing structure to complex, cross-functional problem spaces by defining product strategy, operating models, success metrics, and scalable processes
• Proven ability to define KPI frameworks, develop data-driven business cases, and secure investment for platform and transformation initiatives
• Exceptional relationship-building, communication, facilitation, and executive presentation skills, with a demonstrated ability to influence technical and business stakeholders without direct authority
• Strategic, analytical, and data-driven mindset, with experience operating effectively in highly matrixed organizations and translating research, operational insights, and business data into actionable product decisions
• Experience with self-service onboarding models, integration automation, or AI-assisted data mapping is a plus
• Bachelor's degree in Computer Science, Information Systems, Business, Engineering, or a related field preferred

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:

$145,000 - 160,000

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.