Top Tech Jobs & Startup Jobs in Chicago, IL

Owns end-to-end delivery of client integrations involving purchase orders, bookings, shipping notifications, milestones, and invoices. Gathers requirements, designs solutions, leads testing and user acceptance, supports deployment and adoption, troubleshoots integration issues, and recommends improvements. The role collaborates across Sales, Account Management, Operations, Solutions Engineering, Product, and customers while supporting pre-sales integration requests and maintaining operational procedures.

Own complex Flexport.org partner accounts serving nonprofits, NGOs, and mission-driven organizations. Lead RFPs, renewals, business reviews, account growth, retention, and cross-functional solutions across ocean, air, trucking, and customs. Act as a strategic supply chain partner, identify expansion opportunities, mentor teammates, improve processes with AI-enabled tools, and navigate regulated humanitarian logistics environments.

The Enterprise Account Executive will acquire and grow customer accounts by selling Flexport’s supply chain and fulfillment solutions. Responsibilities include prospecting, conducting discovery, developing tailored solutions, closing new and expansion business, leading client business reviews, coordinating onboarding, and collaborating with operations teams across ocean, air, trucking, and customs. The role requires strong relationship-building, consultative selling, structured sales execution, and experience in logistics or supply chain industries.

Drive Control Tower pipeline, award conversion, and revenue growth across Flexport’s Central region. Partner with Account Executives on consultative sales, solution design, customer presentations, technology demonstrations, ROI business cases, pricing, and margin protection. Translate contracts into operational SOPs and ensure awarded shipping volume converts into customer attainment. The role requires supply chain expertise, quota-carrying sales experience, and travel of up to 25% across the Midwest and South.

An 18-month rotational program across gateway operations, customs, and sales/account management. Participants manage live shipment and client work while developing global trade expertise, AI and low-code automation skills, SQL proficiency, reporting capabilities, and Lean process improvement experience. The program includes certifications, mentorship, performance evaluations, and a capstone project solving a real business problem. Graduates primarily move into account management, with potential paths into automation engineering, consulting, sales engineering, operations, sales, or customs.

Lead and develop Flexport’s mid-market sales team in Chicago. Responsibilities include hiring, coaching, setting quotas, monitoring performance metrics, improving consultative sales processes, driving revenue growth, and executing go-to-market strategies. The role partners with senior leadership and offers a 50/50 base salary and uncapped bonus compensation model.

Lead and grow a Trade Advisory team providing customs and trade compliance advice. Oversee client portfolios, develop service offerings, ensure regulatory compliance, mentor associates, and drive operational and revenue goals.

Manage and execute post-entry filings (PSC, protests), monitor liquidation statuses, maintain trackers, run analytics and reporting, coordinate automation and ACE portal access, interface with CBP and clients, manage deadlines, invoices, SOPs, and support Trade Advisory operations.

As a Global Operations Specialist, you will manage the shipment lifecycle for ocean and air freight, ensure data integrity, and maintain communication with partners to minimize delays in transit.

The Global Operations Associate will manage customer supply chains, ensure shipment quality, handle client issues, and coordinate logistics within a regional network.