Technical Operations Associate

Caravan Supply Chain Inc.; Chicago (IL); On-site; USD 34,000 - 41,000; Part time

Job summary

Caravan Supply Chain Inc. is seeking a Technical Operations Associate for a part-time role in downtown Chicago. The position offers 25–30 hours per week with an 8:00 AM start time during weekday business hours.

Starting wage is $25 per hour, with potential to grow into more senior, full-time opportunities as performance and business needs evolve. This hands-on technical operations role focuses on supporting employee hardware and software, SaaS platforms, and Transportation Management Systems.

Qualifications

• TMS or logistics software familiarity is a plus; training provided.
• Strong problem-solving and independent research ability.
• Basic scripting, APIs, Git, databases, networking, or sysadmin.
• Interest in automation and AI-enabled software development.
• Strong documentation and communication habits.
• Desire to grow into technical ownership.
• Experience with AI architectures, agentic workflows, or related tools is a strong plus.

Responsibilities

• Troubleshoot employee hardware, software, VPN, and accounts.
• Administer and support SaaS platforms and internal systems.
• Support Transportation Management Systems (TMS) and workflows.
• Maintain and improve automation scripts and integrations.
• Maintain technical documentation and SOPs.
• Assist with data and transport-system workflows.
• Work with APIs, scripts, logs, and integrations as experience grows.
• Identify repetitive tasks suitable for automation and AI-assisted workflows.

Skills

Technical troubleshooting

Scripting basics

APIs

Git

Networking basics

Automation interest

AI workflows

Tools

TMS

Job description

Part-time | 25–30 hours/week | Starting $25/hour

Potential path to full-time

About Caravan Supply Chain

Caravan Supply Chain is a rapidly growing freight brokerage providing transportation and logistics solutions across North America. As we expand our operations, we are investing in our internal technology, automation, and IT infrastructure to support continued growth.

We are seeking a Technical Operations Associate to help scale these capabilities, support our employees, and contribute to more efficient, technology-driven workflows.

This is a hands-on technical operations role with significant room to grow into systems, automation, and solutions engineering. Prior logistics industry experience is not required; we value technical aptitude, adaptability, and a willingness to learn.

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

What We’re Looking For

• Familiarity with Transportation Management Systems (TMS), freight brokerage operations, or logistics software is a plus, but not required. Training will be provided.
• 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.

We particularly value candidates who can use AI agents effectively: scope a task, review generated work, investigate failures, and iterate toward a working solution.

A degree is not required. Personal projects, GitHub repositories, homelabs, automations, AI experiments, and self-directed technical work are relevant experience.

Schedule & Compensation

Approximately 25–30 hours per week, with an 8:00 AM start time during weekday business hours.

Onsite availability in downtown Chicago is required to provide hands-on technical support for employees, hardware, and internal systems.

Compensation starts at $25/hour, depending on experience and technical aptitude.

We are open to discussing potential full-time opportunities as the role evolves, based on performance, mutual fit, and business needs.