Freight Engineer Jobs in Chicago, IL (NOW HIRING)

Why p44LSP.ai? 

At project44, we believe in better - and p44LSP.ai is what better looks like for the logistics service provider market. 

For years, project44 focused on global shippers as our core customer. That focus worked. Our Shipper business is a category leader growing 20% year-over-year. That strength is what makes the next chapter possible. 

Shippers and LSPs are fundamentally different businesses. Shippers buy logistics software to support their core operations. Logistics Service Providers - freight forwarders, brokers, and 3PLs - sell logistics as their product. Their software is their competitive edge. They buy fast, build on APIs and agents, and reward teams that ship in weeks, not quarters. 

This is why we created p44LSP.ai: a dedicated, AI-native division built to serve the LSP market with the focus, speed, and resources it deserves. It's the scope and ownership of an AI startup, backed by the infrastructure of a $124M business - 259K carriers, billions of shipment outcomes, agents in production, and direct access to project44's data graph, carrier network, and enterprise relationships. 

This is a small, hand-picked team operating across Chicago, San Francisco, Bangalore, and the EU. Flat org. Forward-deployed engineering. AI coding tools across the workflow. Agents as the product surface. Customers who pilot in weeks and tell you what they think directly. 

The LSP market is moving fast. AI agent startups are growing 300%+ year-over-year, and seven of eight sell to LSPs. We have the data position, the platform, the customers, and now the team. We're hiring the engineers who will build it with us. 

AI at LSP44

Every LSP44 team member is expected to be an intelligent, hands-on user of AI - and for Product, that bar is even higher: the products you're defining are AI agents. We don't expect everyone to be a data scientist, but we do expect everyone to identify where AI adds value, direct it effectively, evaluate its outputs critically, and govern it responsibly, in your own workflow and in the products you build.

The Role 

Most engineers build for customers. FDEs build with them. You'll be embedded directly with high-value LSP accounts - owning integration architecture, customizing agent workflows, and serving as the ground truth between how LSPs actually operate and how our product team thinks they do. Your job is to transform logistics from a reactive service into a programmable network - replacing manual workflows with autonomous agent-to-agent coordination. What you learn in the field shapes the roadmap. You ship in weeks, not quarters.

What You'll Work On 

• Own end-to-end integration for dedicated LSP accounts - configure bi-directional webhooks and event-driven pipelines so AI agents can read, act, and write data into customer TMS, WMS, and ERP systems instantly
• Unify disparate customer data into a single actionable signal - driving dynamic interoperability across core business systems
• Customize interfaces and agent logic to fit existing LSP workflows across freight procurement, load tendering, and exception handling - reducing time-to-value and making adoption feel natural
• Feed the right context to agents and debug decisions when they go wrong - tracing failures back to the specific data point, prompt, or tool use that caused them
• Build event-driven pipelines (Kafka/PubSub) that carry agent intent at the scale of millions of logistics events per day
• Serve as the ground truth - we can't build a world-class product in a silo. Your field observations directly inform what gets on the roadmap and when

What We're Looking For 

Qualifications 

• 5+ years in software engineering, solutions engineering, or technical implementation in a customer-facing role
• Mastery of API-first design and bi-directional webhook configuration
• Experience with event-driven architecture and stream processing (Kafka, PubSub, or similar)
• Hands-on integration experience with TMS, WMS, or ERP systems
• Strong debugging skills across distributed, agent-driven workflows
• Deep domain knowledge in logistics - freight procurement, load tendering, carrier management, and exception handling. LSP customers don't trust engineers who don't understand their world. You need to speak their language to earn the right to change how they work.

Nice to Have 

• Experience with agentic AI systems - context feeding, prompt engineering, tool invocation, stateful agents
• Prior experience in a forward-deployed or field engineering role
• Containerization and orchestration (Docker, Kubernetes)

How You Work 

• You take ownership of outcomes, not just deliverables
• You bring back what you see in the field and use it to make the product better
• You move fast, iterate in the open, and don't wait for perfect conditions
• You can translate technical complexity to both engineers and LSP operators without losing either audience

Work Authorization: Candidates must be authorised to work in the US without current or future employer-sponsored visa support.

In-office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site, in our beautiful headquarters 3 days a week. Together, we're building something extraordinary-learn, grow, and thrive in our fast-paced, transformative environment.
We continually evaluate our pay ranges to reflect skills, experience, and market conditions. The base salary offered will be determined by assessing a candidate's experience and skills relative to the scope and responsibilities of the position, as well as the specific geographic location where the job will be performed. Base salary is one component of project44's total compensation package, which also includes stock options for all EOR and project44-employed team members, bonus or commission eligibility depending on role, and a benefits package tailored to your country of employment. Specific benefits package offerings vary by country and may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs. The base salary range for this position is USD130,000 - USD190,000

Diversity & Inclusion 

At project44, we're designing the future of how the world moves. As we work to deliver a truly world-class product, we're intentionally building teams that reflect the unique communities we serve. We're focused on creating a company where all team members can bring their authentic selves to work every day. 

project44 is an equal opportunity employer. If you share our values and passion for the future of logistics, we'd love to review your application. Even if you don't meet 100% of the requirements, please consider applying - studies show you can still be a strong candidate at 50%. 

For any accommodation needed during the hiring process, please email recruiting@project44.com.