Forward Deployed Engineer

About the role

Overview

A billion-dollar logistics technology scale-up is hiring a Forward Deployed Engineer to join their team. The role is fully remote across the US, with Chicago preferred, and involves up to 50% travel to client sites and the Chicago office. This is a full-time, permanent position with a base salary of $115,700 to $180,800, a competitive equity package, unlimited PTO, comprehensive medical, dental and vision cover, and a 401k match.

This is the founding Forward Deployed Engineer hire, which means the person who takes this role isn't walking into an established playbook - they're helping write it. Day to day, you'll be embedded with enterprise shipper accounts, shadowing their operations teams, identifying the real bottlenecks in manual freight workflows, and shipping AI-powered automation that actually works in production. You'll work at the intersection of hands-on engineering and direct client engagement, supported by an applied AI engineering squad and a senior logistics partner who owns the broader client relationship. The work is varied and fast-moving: one week you're tuning an LLM agent against live edge cases, the next you're in a room with an ops stakeholder translating a messy manual process into something buildable. If you want to be close to the bleeding edge of applied AI, own your outcomes end to end, and build something that compounds over time, this role has real substance behind that promise.

Key Responsibilities

Shadow client operations teams to observe workflows firsthand, then run structured discovery to identify and prioritise the pain points worth solving

Design the right solution for each prioritised problem, whether that's an automation, an AI agent, a system integration, or a combination, and scope it before building

Build and integrate solutions against real enterprise systems including TMS, WMS, YMS, and ERP platforms

Prototype and ship working automation fast, including automated check calls, shipment tracking, carrier qualification and onboarding flows, and voice or chat-based agents

Tune prompts, agent behaviour, and voice or transcription models based on real production data and edge cases, continuing to refine after launch as real usage surfaces new cases

Identify security, compliance, and infrastructure requirements early, and work with internal stakeholders to resolve them before they become blockers

Feed patterns and learnings back to product and engineering so recurring solutions become reusable platform capabilities, not one-off fixes

Help define and document the FDE operating model as the practice scales

Requirements

Must-haves

5+ years full-stack engineering experience

Strong Python and TypeScript proficiency, including fast-prototyping frameworks

Hands-on experience building and shipping AI-driven automation workflows in production, including prompt design, agent and tool orchestration, and model tuning

Proven track record building and maintaining APIs and integrations with third-party or enterprise systems, including REST and GraphQL

Demonstrated ability to work directly with non-technical stakeholders, translating operational needs into technical plans they trust

Comfortable debugging, re-scoping, or improvising in front of a client when things don't go to plan

Track record of shipping working software quickly in ambiguous, fast-changing environments

Willingness and availability to travel up to 50% across the US

Bias to action and comfort owning outcomes end to end, from discovery through production, without a fully scoped spec

Nice-to-haves

Prior forward-deployed, solutions engineering, or implementation engineering experience

Familiarity with freight, transportation, or supply chain systems and workflows

Experience with voice or transcription-based systems in operational contexts

Exposure to agent orchestration frameworks or LLM evaluation and monitoring tooling

EDI familiarity and experience with enterprise platforms such as SAP, Oracle, Manhattan, or Blue Yonder

Experience in a growth-stage or startup environment where the platform is still being built

Genuine curiosity about logistics and shipper operations

What Success Looks Like

By month 12, you have shipped real AI automation across multiple live client accounts, not just one

You have helped define and document what the FDE role actually looks like at this business, creating a repeatable framework others can build on

Patterns from your client engagements are feeding back into the platform as reusable capabilities, reducing rebuild time on future projects

Client ops stakeholders trust you to translate their messy manual processes into working automation, and internal engineering partners know how to work with you effectively

Team and Culture

You'll be embedded with the applied AI engineering squad as a build partner, with a senior logistics and customer-facing partner owning project scope and the client relationship

This is a high-autonomy, high-visibility mandate: you're expected to operate independently across discovery, build, and deployment

Sales, account management, and customer success teams are part of your working environment on each shipper account

The role is genuinely founding in nature: you're co-creating the process, not executing someone else's

Challenges

There is no established FDE playbook here: you'll be operating in real ambiguity and expected to define the motion as you go, which demands a strong bias to action and comfort with incomplete information

The travel commitment is real: up to 50% of your time will be spent embedded at client sites, which suits some people and doesn't suit others

You'll be context-switching constantly between deep technical work and client-facing communication, often in the same day, which requires genuine range rather than a preference for one or the other

The interview process is thorough: two first-round interviews, two virtual onsites, a conversation with the Head of Talent Acquisition, and a final challenge onsite in Chicago. That's a commitment, and it reflects how seriously the business is treating this founding hire