Flexport Is Changing Freight Operations With AI
Clerical tasks are automated; operators focus on exceptions and compliance
Flexport has spent the past several years integrating automation and AI directly into freight execution workflows. The company has described its focus on operational tasks such as pickup scheduling, terminal coordination, customs documentation, and shipment milestone updates. This work sits between booking and delivery and is repeated across shipments and partners.
Between 2023 and 2025, Flexport released multiple products that extended beyond shipment visibility and pricing into execution. Product releases and technical updates describe automation embedded into booking flows, customs review, and operational follow-up, with humans retained for exceptions and regulatory judgment.
Those product decisions coincided with broader organizational changes. Flexport carried out workforce reductions in 2023 and 2024 and raised additional capital tied to platform development, while increasing the cadence of AI-related product launches.
Automation Enters the Freight Workflow
Flexport’s Control Tower links shipment visibility with operational workflows. Product documentation describes a system that connects orders, bookings, customs milestones, and fulfillment events in a single interface, with automated status updates and exception flags generated as shipments move.
Pricing and booking are integrated through tools such as Rate Explorer. Flexport’s public rate portal allows users to retrieve prices and move directly into booking across transportation modes, with the company advertising coverage across hundreds of thousands of routes.
Operational automation also extends into coordination tasks historically handled manually. Flexport’s product materials describe automation for routine pickup scheduling, appointment confirmations, and milestone updates, reducing reliance on repeated phone calls and manual confirmation logging.
Flexport does not publish metrics on the proportion of shipments handled through automated workflows or the autonomy level of these systems. Public documentation indicates that human operators remain responsible for negotiations, partner coordination, and irregular scenarios such as congestion or rollovers.
The company has argued that execution automation depends on system integration. Flexport’s engineering and product posts emphasize unified infrastructure over layered add-ons, citing tighter feedback loops between booking, customs, and fulfillment systems.
Supervised Automation in Daily Freight Work
Flexport describes human-in-the-loop design as an operational principle rather than a governance add-on. Automated systems handle repetitive and rules-based work, while humans review outcomes and intervene in cases involving ambiguity, liability, or regulatory interpretation.
Customs processing is the most developed example. In June 2025, Flexport launched a Tariff Simulator that provides real-time duty and landed-cost calculations across more than 195 countries, allowing scenario modeling by classification, value, origin, and entry date.
In January 2026, Flexport released a Tariff Refund Calculator designed to estimate potential refunds tied to pending legal rulings affecting import duties. The tool was positioned as a follow-on to the tariff modeling system.
Product materials state that automation increases the share of customs entries reviewed compared with manual spot checks, with human review retained for complex or unclear cases. Customs errors can result in shipment holds, fines, or penalties, making oversight mandatory.
Milestone management follows a similar model. Automated systems generate shipment updates and flag anomalies as cargo moves through terminals, carriers, and customs, allowing operators to focus on flagged events rather than continuous monitoring.
Third-party vendor activity provides additional evidence of agent-based automation in use. In 2025, Reuters reported that HappyRobot, an AI-agent vendor focused on freight communications, served more than 70 enterprise customers and listed Flexport among them, citing a tenfold revenue increase.
Flexport leadership has publicly encouraged internal AI adoption. In interviews, CEO Ryan Petersen has described using generative tools to ingest and process large datasets, including freight contracts, more quickly, while retaining human oversight and customer access to operations teams.
Legal disputes underscore the value placed on execution tooling. In 2025, Flexport filed lawsuits alleging former employees removed internal documents and source code before founding a competing freight software company, citing trade secret and copyright claims.
Taken together, these documented developments show how Flexport has embedded automation into booking, customs, and milestone workflows while retaining human oversight for regulated and irregular cases. Product releases and reporting establish the direction of development, even as questions remain about scale and consistency across regions.