Technical Operations Associate

Technical Operations Associate

Caravan Supply Chain — Chicago, IL

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.

Apply

Send your resume and a short introduction (e.g., cover letter). If you have a GitHub profile, personal projects, code samples, automations, AI agents, homelab work, or anything else you have built, we encourage you to share links or examples of your work.

Submit your application to [email protected].

Website: caravansupplychain.com