Delivery Systems Administrator - Arkansas, US (Remote) (Project Management)

DreamHost helps people own their digital presence through an open platform and a strong focus on user data control. The Delivery Systems Administrator will administer and continuously improve the systems that support organizational delivery, with a focus on ClickUp, workflow automation, AI enablement, reporting, and scalable operational processes.

Responsibilities:

• Serve as the primary administrator and technical expert for the organization's delivery platform, with deep expertise in ClickUp
• Design, configure, and maintain platform architecture, including hierarchy, custom fields, templates, dashboards, forms, permissions, views, and relationships
• Maintain platform governance, documentation, standards, and overall system health
• Partner with the Head of Delivery to implement platform enhancements that support the organization's delivery operating model
• Evaluate new platform capabilities and recommend improvements that increase usability, scalability, and organizational effectiveness
• Design, implement, and maintain workflow automations that reduce manual effort and improve consistency
• Build and maintain AI Agents, Skills, and AI-assisted workflows
• Identify opportunities to simplify operational processes through automation and intelligent workflows
• Develop and maintain integrations between ClickUp and other business systems as needed
• Research emerging AI and automation capabilities and recommend practical applications for the organization
• Build executive dashboards and operational reporting that provide meaningful visibility into delivery performance
• Maintain accurate, consistent, and well-governed operational data that supports reporting and decision-making
• Translate operational requirements into scalable platform configurations and workflow improvements
• Partner with Delivery Leads and business stakeholders to improve delivery workflows, reporting, and system adoption
• Continuously identify opportunities to improve organizational execution through better tooling, automation, and operational practices

Requirements:

• Requirements

• Extensive experience administering ClickUp in a medium or large organization.
• Expert knowledge of ClickUp architecture, including hierarchy, dashboards, automations, custom fields, permissions, templates, forms, relationships, and reporting.
• Experience designing workflow automations, AI Agents, Skills, and system integrations.
• Strong systems thinking with the ability to design scalable operational workflows and improve business processes.
• Experience developing executive dashboards and using operational data to drive decision-making.
• Excellent organizational, analytical, and documentation skills.
• Ability to translate business requirements into scalable technical solutions while managing multiple priorities independently

• Preferred

• Experience supporting Delivery, PMO, Product Operations, Business Operations, or Program Management organizations.
• Experience integrating ClickUp with third-party platforms using APIs or automation tools.
• Familiarity with Agile software development and portfolio management.
• Experience with SQL, scripting, business intelligence platforms, or advanced reporting tools.
• Experience implementing AI-enabled operational processes