ClickUp Systems Architect and Operations Coach (U.S. Business Experience Required)

About the Role

We are a U.S.-based trucking company building a fully systemized, process-driven operation. Our goal is to run the entire company through ClickUp — including dispatch, safety, onboarding, and internal operations.

We are looking for a highly experienced ClickUp Systems Architect who can not only build advanced systems and automations, but also train and coach non-technical employees (dispatchers, drivers, and office staff).

This is not a typical IT role. This is a business systems role focused on usability, efficiency, and real-world operations.

Key Responsibilities

1. ClickUp System Architecture (Primary Responsibility)

• Design and build complete operational workflows inside ClickUp
• Create and maintain:
  • task structures
  • dashboards
  • forms
  • advanced automations
• Build scalable systems for:
  • dispatch operations
  • driver onboarding
  • safety/compliance tracking
  • issue management
• Continuously improve system performance and usability

2. Employee Training & Adoption (Critical)

• Train non-technical employees on how to use systems effectively
• Conduct onboarding sessions (live + recorded)
• Create simple, practical SOPs and training materials
• Identify confusion points and fix systems accordingly
• Ensure high adoption across all departments

3. Automation & AI Implementation

• Build advanced automations within ClickUp (not basic triggers)
• Develop API integrations when needed
• Implement AI tools for:
  • internal knowledge base
  • employee support (“how-to” assistance)
  • process automation

4. Systems Integration

• Connect ClickUp with tools such as:
  • Samsara
  • Fleetio
  • DataTruck
  • Google Workspace
• Ensure smooth data flow and eliminate manual work

5. IT Administration (Secondary)

• Manage user accounts, permissions, and access
• Provide basic troubleshooting and system support

Requirements

• Proven experience building advanced systems in ClickUp (portfolio required)
• Experience working with U.S.-based, non-IT businesses (logistics, transportation, operations, etc.)
• Strong understanding of business operations (not just technical skills)
• Experience training non-technical employees
• Experience with automation tools, APIs, and AI integrations
• Ability to simplify complex systems into easy-to-use workflows

What We Are NOT Looking For

• Pure IT administrators
• Developers without operations experience
• Candidates who only build systems but cannot train people

Success in This Role

• Employees clearly understand and use the system
• Reduction in operational confusion and manual work
• Systems are simple, scalable, and reliable
• High adoption across dispatchers, drivers, and office staff

Compensation

• Based on experience and proven results
• Performance-based bonuses will be introduced after onboarding period

How to Apply

Please include:

1. Examples of ClickUp systems you have built
2. Description of a system you built from scratch
3. Experience training non-technical teams
4. Tools and automations you have implemented

Important: This role requires both technical system-building skills and strong communication/training ability. If you only have one of these, this position is not a fit.