IT Systems Administrator

Dream Resorts and it's subsidiaries Maui Resort Rentals and Beachview Rentals is seeking a detail-oriented and strategic IT Systems Administrator / Contract and Vendor Manager to oversee our IT systems, vendor relationships, and contract lifecycle. This role bridges the gap between technical systems administration and procurement/vendor management, ensuring that our technology stack is cost-effective, secure, well-managed, and scalable. You will work in close collaboration with and under the oversight of our CTO, but this role demands someone who is genuinely comfortable operating autonomously taking ownership of their domain, proactively identifying issues and opportunities, and bringing well-reasoned recommendations to leadership.

Systems Administration

• Administer and maintain core business SaaS applications including Google Workspace, Slack, Asana, Salesforce, DocuSign, 1Password, etc..
• Manage user provisioning, access controls, and security compliance across all systems
• Support employee onboarding and offboarding including account setup, device provisioning, and deprovisioning
• Monitor system performance, uptime, and data integrity
• Maintain IT asset inventory and documentation

Vendor & Contract Management

• Oversee vendor relationships for business applications, hardware (Apple, Unifi, etc.), and IT services (contractors or outside service providers).
• Lead contract negotiations, renewals, procurement, and compliance for all IT-related services and products
• Track license agreements, identify cost optimization opportunities, and ensure vendors meet SLA expectations
• Develop and maintain policies and procedures for IT procurement and vendor management

Employee Support & Enablement

• Serve as the primary point of contact for IT support across enterprise applications and systems
• Create and maintain documentation, training materials, and onboarding resources for staff
• Drive adoption of collaboration and productivity tools across the organization
• Travel occasionally to support team needs across company locations (travel required on an as-needed basis)

Endpoint & Asset Management

• Deploy, secure, and manage employee endpoints (laptops, phones, tablets, etc.).
• Maintain inventory of IT assets and oversee lifecycle management.
• Ensure device compliance with security policies (encryption, patching, MDM, etc.).

Required Qualifications

• 3–5 years of experience in IT systems administration, vendor management, or a closely related IT role
• Hands-on experience with Google Workspace Admin, Salesforce, and cloud-based VoIP systems (e.g., RingCentral)
• Proven track record managing vendor contracts and technology procurement
• Strong understanding of security best practices, access management, and IT compliance
• Excellent organizational skills with the ability to manage multiple systems and priorities simultaneously
• Clear communicator who can translate technical concepts for non-technical stakeholders
• Comfortable working independently in an evolving environment with minimal day-to-day direction

Preferred Qualifications

• ITIL, PMP, or other relevant IT certifications
• Experience supporting a SaaS-heavy, distributed workforce
• Background in endpoint/MDM management

Working Location

This position is preferably based in Orange County, CA (Balboa Peninsula) or Maui, HI with the expectation of being a hybrid role. Some onsite presence will be required. 

You will work with a high degree of autonomy while working with a distributed team across US time zones, mostly between Hawaii and Pacific Time. Our company is growing — processes, tools, and priorities evolve, and we need someone who embraces that. Some travel may be required.

Compensation and Benefits:

• Salary Range $90,000 - $110,000
• 100% employer paid Medical, Dental and Vision premiums
• Employer paid Life & AD&D
• PTO plus 9 Paid Holidays
• 401(k) with 5% match