Job Description

Senior Software Engineer

Reports To: Lead Software Engineer

Location: Chicago, IL/Remote

Environment: Hybrid/Remote

Status: Exempt

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.

Position Description:

As a Senior Software Engineer with Redwood Logistics, you will play a central role in designing and building the next generation of AI-enabled products that power our brokerage and managed services platforms. This role focuses on scalable feature development, AI integration, and platform evolution. You will collaborate closely with Redwood's AI Product team to deliver intelligent systems, agentic workflows, and data-driven automation capabilities that redefine digital logistics operations.

Responsibilities:

• Lead the design and development of new platform capabilities across Redwood's technology ecosystem.
• Partner with the AI Product and Data Science teams to integrate predictive, generative, and agentic models directly into product workflows.
• Architect scalable, high-performance systems leveraging microservices, APIs, and event-driven patterns to support AI-enabled decisioning and automation.
• Own full-stack development across .NET Core, C#, and modern JavaScript frameworks (React preferred), ensuring maintainable, production-grade solutions.
• Guide technical design reviews, ensuring solutions align with Redwood's long-term architectural direction and platform modernization roadmap.
• Collaborate with cloud and infrastructure teams to optimize performance, reliability, and scalability within Azure and containerized environments.
• Implement automated testing, CI/CD pipelines, and observability frameworks to support rapid, high-quality releases.
• Mentor engineers in advanced coding practices, architectural thinking, and AI integration techniques.
• Contribute to the definition of Redwood's AI platform architecture, shaping reusable service patterns, data orchestration flows, and model-serving frameworks.
• Stay current with emerging AI frameworks, developer tooling, and best practices, driving innovation and continuous improvement.

Qualifications:

• Bachelor's Degree in Computer Science or equivalent professional experience.
• 5+ years of professional experience in software engineering, with a focus on scalable, distributed, or data-intensive systems.
• Proven experience building and deploying cloud-native applications using .NET Core, C#, and modern JavaScript/TypeScript frameworks (React, Angular, or Vue).
• Strong understanding of AI/ML integration patterns, APIs, and data pipelines, with practical experience collaborating with data science or ML engineering teams.
• Expertise in Azure cloud services, including container orchestration (AKS), serverless computing, and event-driven design.
• Experience developing RESTful and GraphQL APIs with attention to performance, resilience, and data integrity.
• Solid understanding of CI/CD pipelines, test automation, and secure deployment workflows.
• Strong command of relational and non-relational databases (SQL, Cosmos DB, Postgres, or Snowflake preferred).
• Excellent communication and collaboration skills, with the ability to work cross-functionally across engineering, product, and AI teams.
• Experience developing agentic or AI-driven applications, leveraging LLMs or orchestration frameworks.
• Familiarity with event streaming (Kafka, Event Hubs) and data pipeline orchestration tools (Airflow, Data Factory).
• Preferred experience in logistics, brokerage, or supply chain technology.
• Knowledge of domain-driven design and service mesh architectures.
• Proven success in influencing platform-level design and scaling AI capabilities into production applications.

Rewards:

• Culture of unlimited growth with new positions and departments created regularly to support our growing customer base
• Paid parental leave policies
• Medical, dental, vision and 401k plans (with match)
• Flexible-spending, mass transit and dependent care plans
• Health savings account, with company contribution
• Short-term, long-term and life insurance policies subsidized by company
• Cell phone discounts; reduced fees for health and fitness clubs
• Additional benefits including pet insurance, accident care and more
• Competitive referral bonus program
• Competitive PTO plans, with extra floating holiday and time off to volunteer
• Fundraising and volunteer opportunities to give back to our local, national and international communities

Work Schedule:

This position is full-time and hybrid or 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:

$130,000 - $150,000

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.

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