Top Tech Jobs & Startup Jobs in Chicago, IL

Manage customer freight execution in a third-party brokerage environment. Responsibilities include quoting, load setup, coverage monitoring, shipment tracking, appointment coordination, customer and carrier service, issue resolution, scorecard reconciliation, receivables follow-up, and maintaining accurate transportation and account records.

Designs, operates, secures, and optimizes Azure and AWS infrastructure, hybrid identity, Windows Server, databases, monitoring, and networks. Manages Entra ID, Sentinel, Terraform infrastructure-as-code, automation, cloud networking, physical network equipment, compliance activities, threat assessments, and business continuity. Provides on-site Chicago support, escalation assistance, documentation, and rotating after-hours production support.

The Senior Accountant supports monthly close, accruals, reconciliations, journal entries, fixed assets, intercompany accounting, and GAAP-compliant reporting. The role assists with FP&A budgeting and forecasting, audits, tax preparation, state and local tax filings, financial analysis, and process improvement. The position requires collaboration with internal teams and external accounting partners while maintaining accurate records and adapting to changing business needs.

Develop and grow assigned freight brokerage customer accounts through data-driven sales strategies, business reviews, expansion planning, cross-selling, pricing negotiation, and coordination with Operations on onboarding, load tendering, tracking, and issue resolution. The role requires customer relationship management, account growth analysis, negotiation, and industry awareness in a fast-paced environment. It is hybrid, based in Chicago, Austin, St. Louis, or Carol Stream, with occasional travel under 20%.

Own strategic relationships with Oracle OTM/GTM and RedwoodConnect customers throughout implementation and ongoing adoption. Develop account plans, lead executive business reviews, manage customer health and renewals, identify expansion opportunities, and drive value realization. Partner with Sales, Delivery, Product, and Support to resolve escalations, improve outcomes, and transition customers successfully to support. Serve as a trusted supply chain technology advisor while advocating for customer needs and promoting product adoption.

Leads strategic client success for enterprise transportation accounts, owning retention, renewals, revenue growth, value realization, and executive relationships. Develops account growth strategies, leads QBRs, negotiates pricing and contracts, identifies upsell opportunities, and translates transportation data into optimization initiatives. Partners cross-functionally with sales, operations, procurement, carrier management, finance, and product teams while coaching high-performing teams and monitoring market trends.

Collects and analyzes product performance, user behavior, market, and competitor data to support product strategy. Creates KPI dashboards and reports, conducts user research, translates findings into feature requirements and workflow diagrams, and collaborates with Product Managers and Engineering leads on prioritization, roadmaps, and product improvements. Communicates actionable insights that guide feature development and technology investment.

Develops and grows Redwood’s private equity channel partner network by recruiting partners, managing agreements, generating referral opportunities, supporting sales cycles, and coordinating transitions to delivery teams. Builds strategic relationships, presents supply chain solutions, manages partner pipelines and performance, facilitates lead flow, analyzes markets and competitors, and drives revenue growth. The role is remote, requires significant private equity contacts and sales experience, and involves travel up to 25%.

Direct strategic sales for TMS, WMS, SaaS, and supply chain technology solutions. Responsibilities include building qualified pipelines, winning new logos, managing RFPs, consulting with customers, conducting technology demonstrations, negotiating solutions, maintaining partner relationships, forecasting in Salesforce, and transitioning sold solutions to delivery teams. The role requires strong supply chain technology expertise, strategic selling experience, and travel up to 50%.

Designs and operates Redwood’s internal engineering platform, including cloud infrastructure, Kubernetes, Terraform, Helm, GitOps, CI/CD, observability, and developer self-service capabilities. The role improves reliability, security, scalability, incident response, operational readiness, and cloud efficiency through automation and cross-functional collaboration with engineering, architecture, security, data, and MLOps teams.