ClickUp Systems Architect and Automation Engineer

ClickUp Systems Architect & Automation Engineer
Remote | Paid Project First | Long-Term or Full-Time Potential
We are a U.S.-based trucking company building a scalable operations system around ClickUp.
We need a senior specialist who can understand business processes, design the ClickUp architecture, build working workflows, connect external platforms through APIs and automation tools, and document the complete system.
This is not a normal Project Manager or basic ClickUp administrator position.
Main objective
Build ClickUp as the company’s central work-management, coordination, documentation, and automation layer.
Specialized platforms such as DataTruck, Fleetio, Samsara, Netradyne, RingCentral, and QuickBooks may remain the authoritative systems for their specific data. ClickUp should receive the operational information employees need, trigger the correct work, track responsibility, and send updates between systems.
Responsibilities
Business-process discovery
Review existing workflows across Dispatch, Safety, Fleet, Recruiting, HR, Accounting, and management.
Identify manual work, duplicate entry, missing ownership, weak handoffs, and disconnected systems.
Decide what should be automated and what should remain a controlled human decision.
Define which platform owns each type of data.
ClickUp architecture
Design Spaces, Folders, Lists, task types, statuses, Custom Fields, relationships, permissions, views, Forms, templates, Docs, dashboards, and reporting.
Create a scalable structure that remains understandable as the company grows.
Design role-based permission models.
Prevent duplicate records and conflicting sources of information.
Establish naming, documentation, version-control, and change-management standards.
Workflow and dashboard development
Build workflows for departments and recurring business processes.
Create task templates, intake Forms, recurring processes, reminders, dependencies, and escalation logic.
Build operational and management dashboards.
Connect SOPs and training materials to real tasks and responsibilities.
Integrations and automation
Build and maintain integrations between ClickUp and systems such as:
DataTruck
Fleetio
RingCentral
Google Workspace, Gmail, and Drive
Samsara
Netradyne
Jotform
Recruiting and driver-application systems
Other trucking platforms
Use:
ClickUp native automations
ClickUp API
Webhooks
n8n
Make
Zapier
Python or JavaScript when appropriate
AWS or middleware services when necessary
AI agents and skills
Design practical ClickUp AI agents and reusable skills.
Connect agents to approved company knowledge, SOPs, tasks, messages, and documents.
Build workflows that summarize calls or messages, identify the related employee, driver, load, or task, and create the correct follow-up.
Add controls so AI-generated actions can be reviewed when human approval is required.
Document agent instructions, sources, limitations, and escalation rules.
Reliability and documentation
Build monitoring for failed integrations and automations.
Prevent silent failures, duplicate task creation, and incorrect field updates.
Maintain technical documentation, system diagrams, data maps, credential ownership, change logs, and recovery procedures.
Test changes before production deployment.
Train the Technical Systems Administrator and ClickUp Coordinator to operate and maintain completed workflows.
Initial paid project
The engagement begins with a small paid project.
The candidate will be asked to:
Review one real company process.
Identify current problems and data sources.
Design the ClickUp structure.
Define statuses, fields, relationships, permissions, views, and dashboards.
Define integrations and automation logic.
Build a working prototype.
Document the design and explain how it should be maintained.
Successful work may lead to a larger project, fractional cooperation, or a full-time position.
Must-have experience
Building advanced ClickUp systems from scratch
ClickUp workspace and permission architecture
Custom Fields, relationships, Forms, templates, dashboards, and automations
ClickUp API and webhooks
n8n, Make, Zapier, or equivalent platforms
REST APIs, JSON, authentication, and data mapping
Business-process and SaaS integration design
Automation testing, monitoring, and error handling
Technical documentation and system handoff
Ability to communicate with a non-technical business owner
Strong advantages
AI agents, LLM workflows, RAG, or knowledge-connected assistants
RingCentral call or message automation
Google Workspace integrations
Python or JavaScript
Transportation, trucking, logistics, fleet, safety, or dispatch systems
Experience designing systems for small or medium-sized businesses