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

Why work for DreamHost?

We help people own their digital presence. It's not just wishful thinking. It's our noble cause — an idea that drives everything we do.
When you put your dreams online—your words, your photos, your creations—you shouldn't have to worry about your service provider mining that data for marketing purposes. Those are your dreams — not ours! DreamHost's open platform gives you the power to share your data and the freedom to control how it's used.

Working for DreamHost you can be a steward of your own career. We invest in our people, we promote from within the organization when possible and we offer extensive training to aid in your success. In this role, we offer competitive salary, health, vision, and dental insurance, as well as a company-issued laptop, 401k, opportunities for growth, and much much more! We are proud to be a US employer with a fantastic culture and the ability to offer so much to our employees.

Benefits Offered

• 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

Overview

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

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the role.

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.

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.

Compensation

• $70,000-$90,000 / yearly

**DreamHost provides equal employment opportunities to all team members and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.**