Senior AI Engineer (Automation)

Senior AI Engineer (Automation)

Reports To: Principal AI Engineer

Location: Remote (within the U.S.)

Environment: Remote

Status: Exempt, Salaried

Who We Are:

Recognized by Gartner in their Modern 4PL Market Guide, Redwood Logistics is at the forefront of industry innovation. Our cutting-edge supply chain technology pairs with the expertise of our brilliant minds to empower logistics execution across North America and Mexico.

Leveraging a comprehensive range of services, data-centric network solutions, and a seamlessly integrated platform, we have established our prominence as a key player in the mid-market segment within the freight tech industry.

Whether you’re just starting your career or are an established professional looking for your next opportunity, Redwood inspires innovation across teams to provide transformative solutions for our customers.

Purpose of Your Work:

Redwood Logistics is seeking a Senior AI Engineer to design, build, and deploy intelligent automation systems that transform how we operate. This role sits at the intersection of AI engineering, software development, and operational process design, and is responsible for turning high-volume, repetitive, or complex logistics workflows into reliable, AI-powered systems.

You will work with large language models, agentic frameworks, and workflow orchestration tools to automate processes across freight brokerage, carrier management, document handling, customer communication, and operational exception management. This is a hands-on engineering role: you will ship production systems, not prototypes.

The ideal candidate is a strong software engineer who has gone deep on applied LLM and AI systems someone who can architect a multi-agent pipeline in the morning and debug a production issue in the afternoon. You thrive in ambiguity, move fast, and care deeply about whether your systems actually work in the real world.

How You Make a Difference Everyday:

• Design and build agentic AI systems using LLM-based orchestration frameworks (LangChain or similar) to automate complex, multi-step logistics workflows.

• Develop prompt engineering strategies, tool-use architectures, and retrieval-augmented generation (RAG) pipelines that enable reliable, context-aware AI behavior in production.

• Architect multi-agent systems where specialized agents collaborate on routing, validation, enrichment, communication, and exception handling across a freight operations workflow.

• Build robust agent monitoring, observability, and fallback mechanisms to ensure AI systems perform reliably at scale and degrade gracefully when they don't.

• Identify and prioritize high-ROI automation opportunities across freight operations carrier onboarding, load tendering, document extraction, invoice reconciliation, exception triage, and customer status updates.

• Partner with Operations, Brokerage, and Customer Success teams to understand workflows deeply, validate automation logic, and measure real-world impact.

• Build AI-powered document processing pipelines for freight-relevant documents: bills of lading, rate confirmations, carrier invoices, proof of delivery, and compliance documents.

• Develop extraction, classification, and validation systems that handle variability in document formats, quality, and completeness.

• Implement guardrails, output validation, and confidence scoring to prevent incorrect AI actions from propagating through downstream systems.

You’ve Got This?

• 2+ years of experience building and deploying LLM-powered applications: RAG pipelines, agentic systems, or structured output extraction.

• Deep understanding of prompt engineering, context management, tool use, and the failure modes of LLM-based systems.

• 4+ Years of experience integrating AI/ML systems with real-world APIs, databases, and event-driven architectures.

• Strong problem-solving instinct: able to decompose a complex operational workflow into an automatable system with clear inputs, outputs, and failure paths.

• Proficient in leveraging Azure or AWS to deploy scalable machine learning algorithms into production

• MS or PhD in Computer Science, Data Science, Applied Mathematics, Physics, or equivalent work experience.

• Ability to communicate with technical and non-technical stakeholders is a plus

• Three years of experience in supply chain, logistics, transportation, or a similar space is a plus.

What We Offer:

• Access to experts and resources for your Learning & Development journey
• Opportunity for internal mobility
• Employee referral bonus program
• Employee Resource Groups (ERGs)
• Annual fundraising and volunteer events to give back to communities
• Paid time off, floating holidays, time off to volunteer and rollover
• Paid parental leave
• Medical, dental, vision and 401k plans (with match)
• Flexible spending account, mass transit and dependent care plans available
• Health savings account, with a annual company contribution for plan participants
• Short-term and long-term disability; life insurance policies subsidized by company
• Additional benefits including pet insurance, accident care, access to legal advice and more

Work Schedule:

This position is full-time and remote Monday through Friday from 8:00 AM to 5:00 PM with an hour break, but flexibility is available based on coverage.

Compensation Range:

Salary Range:

$120,000 - $180,000

This position is eligible to earn annual incentives based on individual and company performance.

The estimated pay range reflects an anticipated range for this position. The actual base salary offered will depend on a variety of factors, including the qualifications of the individual applicant for the position, years of relevant experience, specific and unique skills, level of education attained, certifications or other professional licenses held, and the geographical location in which the applicant lives and/or which they will be performing the job.

Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.