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.
Skills Required
- 5+ years of full-stack engineering experience
- Strong proficiency in Python and TypeScript, including supporting libraries and frameworks for rapid prototyping
- Hands-on experience designing and implementing automated workflows and AI-driven business-process solutions
- Experience building and maintaining APIs and integrations with third-party or enterprise systems
- Ability to work directly with nontechnical stakeholders and translate operational needs into technical solutions
- Ability to debug, re-scope, or improvise solutions directly with customers
- Track record of rapidly shipping working software in ambiguous, fast-changing environments
- Experience with voice or transcription-based systems
- Familiarity with freight, transportation, or supply chain systems, including TMS, WMS, or ERP platforms
- Experience in a growth-stage or startup environment
- Exposure to LLM agent orchestration frameworks or evaluation and monitoring tools
- Prior experience combining software development with customer relationship ownership
Loadsmart Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Loadsmart and has not been reviewed or approved by Loadsmart.
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Leave & Time Off Breadth — Unlimited PTO (“Loadie Time Off”) and sick time are described in postings as available without a limit, broadening flexibility for time away. Availability is noted across many U.S. roles, though exact application can vary by position and location.
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Healthcare Strength — Comprehensive medical, dental, and vision coverage is consistently cited in job postings, indicating a solid core health offering. This breadth forms a standard tech-style benefits baseline for U.S. employees.
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Equity Value & Accessibility — Stock options are frequently offered and positioned as competitive alongside base pay and other benefits. This ownership component is presented as a meaningful part of total rewards.
Loadsmart Insights
What We Do
We are industry veterans and data-scientists using innovative technology to fearlessly reinvent the future of freight. As the ‘nerds of logistics’, we seek intelligence in data to solve deep-rooted inefficiencies in the industry. We give shippers, brokers and carriers access to our data connections (linking supply and demand) and suite of award-winning solutions to strike the perfect balance of cost and service. We’re creating a more efficient and environmentally responsible way to move more with less. For more information, please visit: https://loadsmart.com
