Forward Deployed Engineer at loadsmart – Chicago | Jobyssey

ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!

We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.

With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.

We're looking for an independent, pro-active thinker, technically sharp Forward Deployed Engineer to join our team. We're looking for someone who's as comfortable writing production code as they are sitting in a room with an operations stakeholder who doesn’t care about architecture but focuses on what works for the business.

This role sits at the front line of Loadsmart's AI-driven automation work. You'll take AI agents and workflows - built on our brokerage, dock scheduling, and shipper platforms and make them actually work in production: for a specific team, a specific workflow, and a specific set of real-world edge cases. You'll build the integrations, tune the AI behavior, and ship working software fast, then feed what you learn back into the platform so it doesn't have to be rebuilt from scratch next time.

LOCATION: US Remote with travel up to 50% to client engagements and Loadsmart's Chicago office.

TEAM: R&D

Job Type: Exempt

WHAT YOU GET TO DO:

Shadow client teams and their day-to-day operations to see workflows firsthand, then run structured discovery to identify and prioritize the pain points worth solving.
Design the right solution for each prioritized pain point - whether that's an automation, an AI agent, a system integration, or a combination - and scope it before building.
Build and integrate that solution against real systems, including transportation management systems (TMS), warehouse management systems (WMS), and enterprise resource planning (ERP) platforms.
Prototype and ship working automation - such as automated check calls and shipment tracking, carrier qualification and onboarding flows, and voice or chat-based agents - prioritizing action and execution speed to deliver value.
Tune prompts, agent behavior, and voice or transcription models based on real production data and edge cases - and keep refining after launch, since agent behavior surfaces new edge cases as real usage grows.
Identify security, compliance, and infrastructure requirements early in each project, and work with the right internal stakeholders to resolve them before they become blockers.
Feed what you learn back to product and supporting engineering teams, turning recurring patterns into reusable platform capabilities rather than one-off fixes.

REQUIRED QUALIFICATIONS:

5+ years of full-stack engineering experience, with strong proficiency in Python and TypeScript, including supporting libraries and frameworks that leverage fast prototyping.
Hands-on experience designing and implementing automated workflows and AI-driven solutions to optimize business processes.
Proven experience building and maintaining APIs and integrations with third-party or enterprise systems.
Demonstrated ability to work directly with non-technical stakeholders — translating operational needs into technical solutions, and clearly explaining technical trade-offs and progress, both in writing and in conversation.
Comfortable being the person in the room when things don't go as planned — able to debug, re-scope, or improvise a solution in front of a customer rather than escalating and waiting.
A track record of shipping working software quickly in ambiguous, fast-changing environments.

NICE TO HAVE QUALIFICATIONS:

Experience with voice or transcription-based systems, especially in operational or logistics contexts.
Familiarity with freight, transportation, or supply chain systems (TMS, WMS, or ERP platforms).
Experience working in a growth-stage or startup environment where the platform underneath your work is still being built.
Exposure to agent orchestration frameworks or evaluation/monitoring tooling for LLM-based systems.
Prior experience in a role that required both building software and owning a customer relationship.

WORKING AT LOADSMART:

• Competitive base salaries - we believe in rewarding top talent

• Extremely competitive Equity package - become a shareholder in our company!

• Loadie Time Off - PTO and sick days without a limit

• Comprehensive Medical, Dental, and Vision insurance plans

• 401k Match

*Applicants must be currently authorized to work in the United States on a full-time basis. Loadsmart will not sponsor applicants for work visas.

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.

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