Technical Operations Associate

About the Role

Caravan Supply Chain is a growing freight brokerage seeking a Technical Operations Associate to support internal technology, automation, and IT infrastructure. This role offers significant room for growth into systems, automation, and solutions engineering. Prior logistics industry experience is not required; technical aptitude, adaptability, and a willingness to learn are valued.

Key Responsibilities

• Troubleshoot employee hardware, software, VPN, remote-access, and account issues.
• Administer and support SaaS platforms and internal business systems.
• Provide technical and operational support for Transportation Management Systems (TMS), including troubleshooting, user assistance, and workflow improvements.
• Administer and maintain existing automations.
• Maintain technical documentation and SOPs.
• Assist with data and transportation-system workflows.
• Work with APIs, scripts, logs, and integrations as experience grows.
• Identify repetitive processes that can be automated.
• Support and develop AI-assisted and agentic workflows.

Requirements & Tech Stack

• Strong technical curiosity and problem-solving ability.
• Ability to independently research unfamiliar technical problems.
• Basic familiarity with scripting, APIs, Git, databases, networking, or system administration.
• Interest in automation and AI-enabled software development.
• Reliable communication and documentation habits.
• Desire to grow into increasingly technical ownership.
• Experience with AI architecture, agentic workflows, coding agents, agent harnesses, MCP/tool integrations, Claude Code, Codex, Cursor, or similar systems is a strong plus. Candidates who can use AI agents effectively are particularly valued.

Qualifications

• Familiarity with Transportation Management Systems (TMS), freight brokerage operations, or logistics software is a plus, but not required.
• Training will be provided.
• A degree is not required.
• Relevant experience includes personal projects, GitHub repositories, homelabs, automations, AI experiments, and self-directed technical work.

Schedule & Compensation

• Part-time: 25–30 hours/week.
• Schedule: Weekday business hours, starting at 8:00 AM.
• Onsite availability in downtown Chicago is required.
• Starting Compensation: $25/hour, depending on experience and technical aptitude.
• Potential for full-time opportunities based on performance, mutual fit, and business needs.