[Hiring] Delivery Systems Administrator @DreamHost, LLC

Role Description

The Delivery Systems Administrator is responsible for administering, optimizing, and continuously improving the systems that support organizational delivery. Working directly with the Head of Delivery, this role ensures the organization's delivery platform remains scalable, intuitive, and aligned with the company's delivery operating model.

This role combines deep platform expertise, automation, AI enablement, and systems thinking to improve how work is planned, executed, measured, and reported. The ideal candidate is an expert ClickUp administrator who enjoys building scalable systems, simplifying complex workflows, and enabling teams to work more effectively.

Responsibilities

• Delivery Platform Administration
  • 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.
• Automation & AI
  • 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.
• Operational Enablement
  • 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.

Qualifications

• 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.

Compensation

$70,000-$90,000 / yearly

Benefits

• Full health/vision/dental for the entire family at zero cost to team member.
• 3% Safe Harbor contributed to 401(k) plus up to 1% employer match.
• Opportunities for profit sharing and bonuses.
• Generous time-off (starting at 15 vacation days).
• 11 Paid holidays (Technical Support and Technical Operations use a floating holiday policy).
• Paid sick leave (80 hours accrued).
• Tuition reimbursement (50/50 up to a specific amount).
• Pet Insurance.
• Thrive Pass wellness allowance of $30 per month.
• Udemy online learning courses.
• Disability Insurance.
• Generous maternity/paternity leave.
• Discounted personal travel through corporate booking program Egencia.
• Laid-back atmosphere.
• Fun monthly company events.
• Free web hosting.