---
title: 'Forward Deployed Engineer at Loadsmart'
canonical: 'https://feeny.ai/job/forward-deployed-engineer-loadsmart-chicago-b0cbc465zwcv'
type: 'job'
last_seen: '2026-09-10'
---

# Forward Deployed Engineer at Loadsmart

- **Company:** Loadsmart
- **Location:** Chicago, IL
- **Compensation:** $116k–$181k
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-08-21
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.lever.co/loadsmart/152abf3a-d8b3-4289-b746-3c16dbabc703

## Job description

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.

## About Loadsmart

## Company Overview
- **One-liner**: Loadsmart is a digital freight platform that uses AI-powered agents, transportation management software, and brokerage services to help shippers, carriers, and warehouses move freight more efficiently.
- **Entity Type**: Private (Late‑stage venture‑backed)
- **Headquarters**: Chicago, Illinois, USA
- **Founded**: 2014
- **Founders**: Ricardo Salgado, Felipe Capella

## Core Business
- **Industry**: Transportation, Logistics, Supply Chain & Storage (with a strong AI/software component)
- **Target customers**: B2B – enterprise shippers, carriers, and warehouse operators; small to large businesses in retail, manufacturing, consumer goods, etc.
- **Mission / Purpose**: To become “the nexus of moving freight” by combining technology and human expertise to reduce freight spend and increase service levels [loadsmart.com/about](https://loadsmart.com/about/).

## Products & Services
- **ShipperGuide (AI‑native TMS)**: Cloud‑based transportation management system that plans, procures, executes, and settles freight across all modes. AI agents embedded in the TMS handle tendering, tracking, document collection, auditing, and claims. [loadsmart.com/about](https://loadsmart.com/about/)
- **Opendock (Dock, Gate & Yard Management)**: Digitizes freight entry, movement, and exit at facilities. Carrier self‑service scheduling, gate automation, and yard management across 4,500+ warehouses and 230,000+ carriers. The scheduling agent automatically reschedules when a pickup slips. [loadsmart.com/about](https://loadsmart.com/about/)
- **AI Agents (Logistics Automation)**: Six specialized agents that run repetitive freight tasks end‑to‑end (document collection, tracking, retendering, load audits, claims, scheduling). Claimed to auto‑resolve 80%+ of work, with the remainder escalated to human Freight Experts. [loadsmart.com/about](https://loadsmart.com/about/)
- **Freight Brokerage**: Technology‑enabled brokerage backed by 100,000+ vetted carriers. Execution is governed by the user’s routing guide and carrier preferences. [loadsmart.com/about](https://loadsmart.com/about/)
- **Managed Transportation**: End‑to‑end transportation management as a service, combining the Loadsmart platform with dedicated specialists and forward‑deployed engineers. [loadsmart.com/about](https://loadsmart.com/about/)

## Market Standing
- **Valuation / Market Cap**: Not publicly disclosed.
- **Key Metrics**:
  - *Annual Revenue*: USD 250 M (as of latest fiscal year) [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)
  - *Total Funding*: USD 346.4 M (company site) / USD 368.1 M (LinkedIn) – both figures appear in search results; the company site reports $346.4 M. [loadsmart.com/about](https://loadsmart.com/about/)
  - *Headcount*: ~400 employees (LinkedIn reports 392, Built In 495; company site says 400+). [loadsmart.com/careers](https://loadsmart.com/careers/)
  - *Year‑over‑Year Headcount Growth*: +10.2% [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)
- **Notable Investors / Partners**: BlackRock, Maersk Growth, Ports America, TFI International, Chromo Invest, Connor Capital, SoftBank Latin America Fund, CSX Corp. [loadsmart.com/about](https://loadsmart.com/about/)
- **Growth Signals**:
  - Acquired Opendock and Kamion in November 2021.
  - Workforce distributed across 25 countries (United States, Brazil, Philippines, Colombia, El Salvador, etc.).
  - Active job postings up 100% year‑over‑year (14 open roles as of search date). [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)
  - LinkedIn followers: 34,627 (+12% yearly). [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)

## Competitive Advantages
- **AI‑native platform**: AI agents are embedded in both the TMS and dock/yard system, not bolted on, enabling high automation rates (80%+ of repetitive tasks auto‑resolved).
- **Unified data model**: ShipperGuide, Opendock, and the brokerage service share one data set, eliminating data silos.
- **Large carrier network**: 100,000+ vetted carriers for brokerage; 230,000+ carriers connected through Opendock.
- **Strategic backing**: Investors include global logistics players (Maersk, TFI International, Ports America) and financial heavyweights (BlackRock), providing both capital and industry credibility.
- **Proven revenue base**: $250 M in annual revenue demonstrates market traction with enterprise clients.

## Strategic Focus
- **Expanding AI capabilities**: Continuous development of AI agents to handle more freight tasks and compound auto‑resolution rates.
- **Platform integration**: Driving adoption of the full suite (TMS + dock/yard + brokerage) to create stickiness and cross‑sell opportunities.
- **Global scaling**: Maintaining offices in Chicago, New York, and across Latin America while enabling remote work; hiring across engineering, sales, and AI roles globally.
- **Customer success**: Shifting user role from “operating the system” to “supervising results” through automation. [loadsmart.com/about](https://loadsmart.com/about/)

## Why Work Here
- **Culture**: Described as “the nerds of logistics” – a mix of industry veterans, data scientists, and innovative engineers focused on reinventing freight. Emphasis on collaboration, fun, and celebration of achievements. [loadsmart.com/careers](https://loadsmart.com/careers/)
- **Work model**: Hybrid/remote‑first; headquarters in Chicago (West Jackson) with additional offices in Latin America. Most roles open to remote within the US and select countries (Brazil, Philippines, etc.). [jobs.lever.co/loadsmart](https://jobs.lever.co/loadsmart/)
- **Employee ratings**: 3.7/5 on LinkedIn (322 reviews) – Work‑Life 4.0, Compensation 4.0, Culture 3.6, Career 3.5. [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)
- **Growth opportunities**: Rapidly growing (10%+ YoY headcount), recent job posts include senior engineering, AI automation, sales, and director‑level roles.
- **Total rewards**: Formal “Total Rewards” program – details not fully listed but implies competitive compensation and benefits. [loadsmart.com/careers](https://loadsmart.com/careers/)

## Sources
1. [loadsmart.com/about](https://loadsmart.com/about/)
2. [loadsmart.com/careers](https://loadsmart.com/careers/)
3. [jobs.lever.co/loadsmart](https://jobs.lever.co/loadsmart/)
4. [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart)
5. [builtin.com/company/loadsmart](https://builtin.com/company/loadsmart)

## Other roles at Loadsmart

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- [Senior QA Engineer (Remote-Brazil)](https://feeny.ai/job/senior-qa-engineer-remote-brazil-loadsmart-sao-paulo-5r7c9264p8rz) — São Paulo, Brazil
- [Associate Pricing Analyst](https://feeny.ai/job/associate-pricing-analyst-loadsmart-sao-paulo-ajrpymcs7nat) — São Paulo, Brazil
- [Senior Paid Media Manager (Enterprise B2B)](https://feeny.ai/job/senior-paid-media-manager-enterprise-b2b-loadsmart-united-states-jnfbr85fvf9y) — United States
- [Analytics Engineer (Remote - Brazil)](https://feeny.ai/job/analytics-engineer-remote-brazil-loadsmart-florianopolis-cbfcjp0zn9fm) — Florianópolis, Brazil
- [Sales Development Representative- ShipperGuide TMS](https://feeny.ai/job/sales-development-representative-shipperguide-tms-loadsmart-chicago-v0nzxwgef7v0) — Chicago, IL
- [Financial Settlement Representative - LTL](https://feeny.ai/job/financial-settlement-representative-ltl-loadsmart-philippines-nmeyk1xpqxjc) — Philippines
- [Account Manager (Tech Touch/ High Volume)](https://feeny.ai/job/account-manager-tech-touch-high-volume-loadsmart-sao-paulo-dj84ttkmh933) — São Paulo, Brazil
- [Marketing Demand Generation Manager (Brazil)](https://feeny.ai/job/marketing-demand-generation-manager-brazil-loadsmart-sao-paulo-q0jp76jrzvdc) — São Paulo, Brazil
- [Director,  SaaS Sales ShipperGuide](https://feeny.ai/job/director-saas-sales-shipperguide-loadsmart-chicago-e164h0angyvr) — Chicago, IL