IT Helpdesk Technician

About Roberts Resorts & Communities

This company operates nationally and is growing by the day. At Roberts Resorts & Communities, we're on a mission to build community and fulfilling dreams. Through our core values of resourcefulness, integrity, passion, and epic customer service, we're dedicated to making a difference in the lives of 30,000 people. If you're passionate about creating meaningful impact, thrive in a culture of integrity, and are committed to delivering exceptional service, we invite you to join us in turning visions into reality and shaping a brighter future together.

Position Summary

The Help Desk Technician provides day-to-day technical support to our multi-location environment (approximately 25 locations) and end users, ensuring timely issue resolution and an exceptional customer experience. This role is responsible for logging, prioritizing, and tracking help desk requests, troubleshooting technical issues, and collaborating with IT team members to support ongoing operations. This is a fast-paced environment where being able to think and adapt to changes is important.  

Performance Objectives

• Provide Tier 1 support; triage, resolve, and escalate when needed.
• Creates and updates user access and accounts for cloud-based identities including Microsoft 365, Adobe, Google Workspace and Apple Business Manager operations where applicable.
• Displays superior documentation skills using industry standards ticketing system best practices.
• Utilizes effective troubleshooting skills to diagnose, repair, maintain, and upgrade hardware and software.
•  Reduces repeat issues by performing effective troubleshooting, documenting fixes, and applying root-cause remediation (not just temporary workarounds).
• May be required to travel (may include overnight stay) to various Roberts Resorts and Communities locations to perform various duties (<10%).
• Participate in a weekly on-call rotation to provide after-hours support, ensuring timely response to critical incidents, system outages, and service disruptions.
• Trains and guides end-users on the use of systems and applications, as appropriate.
• Continuously expand technical knowledge, including Level 2 support tasks and PC troubleshooting
• Collaborate with senior help desk staff to learn and apply new support procedures
• Maintains regular and consistent in-person attendance.

Core Technology Stack:

• Microsoft 365 (primary stack)
• Google Workspace
• Apple Business Manager
• Adobe
• Rent Manager (Accounting) (Hosted RDP Environment as well as a Web Portal) 
• Newbook (Reservations)

Key Competencies: Preferred

1. Demonstrated understanding of Tier 1 support concepts, including troubleshooting methodology, root-cause analysis, change control, and escalation.
2. Familiarity with device lifecycle workflows.
3. Experience supporting Microsoft RDP in a hosted VM environment.

Education & Experience:

• High School diploma or equivalent (G.E.D.) prior to being hired;
• 1–2 years of experience with Microsoft Office (Outlook, Excel, Word, PowerPoint, Access)
• Experience supporting remote users
• Strong foundational PC troubleshooting skills
• Experience troubleshooting network configuration issues
• Strong communication, problem-solving, and customer service skills

Preferred

• Associate’s degree in Computer Science, Computer Information Systems, or related field. 
• 2+ years of experience in an IT Help Desk or technical support environment
• Industry Certifications: CompTIA, Microsoft, Cisco, LPI, etc.
• Experience supporting or working with retail and restaurant POS systems is a plus

Benefits and Perks

We believe in taking care of our team so they can thrive both at work and in life. As a full-time employee, you’ll enjoy a comprehensive benefits package designed to support your health, growth, and lifestyle, including:

• Medical, Dental, and Vision coverage for you and your dependents
• Employer-paid life insurance for peace of mind
• A full menu of voluntary coverages — STD, LTD, Accidental, Critical Illness, Hospital Indemnity, Pet Insurance, and Legal Service Plans
• 80 hours of PTO plus 11 paid holidays to recharge and refresh
• 401(k) with a 3% company match to invest in your future
• The chance to be part of an inclusive, supportive community where your contributions matter

Commitment to Diversity

Roberts Resorts & Communities stands firm in our commitment to Equal Employment Opportunity. We believe in a workplace free from discrimination based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, or any other protected characteristic. Diversity is our strength. We foster an inclusive environment where authenticity is valued, and everyone feels a sense of belonging. We empower individuals to reach their full potential and contribute their best. Join us in creating a workplace where diversity is celebrated, voices are heard, and excellence thrives.