Entry Level It Help Desk Jobs in Bend, OR (NOW HIRING)

Join Our Team at R-2 Contractors!
Since 2009, R-2 Contractors has been a trusted leader in Civil & Underground construction, specializing in power infrastructure projects nationwide. From renewable energy to major utility work, we deliver expert excavation, grading, trenching, and foundation services that keep communities connected and moving forward.
What truly sets us apart is our culture. At R-2, we're a team of people who are hungry to take on challenging projects, humble enough to learn, grow, and collaborate, and smart in how we plan, build, and solve problems. We believe in showing up for each other, doing things the right way, and owning every aspect of our work.
If you take pride in precision, thrive in tough conditions, and live by "Pride, Grit, & Own It!," you'll fit right in! We're building more than infrastructure-we're building a team that pushes limits and stands behind every job we do.
Position: Information Technology Senior Technician
Status: Full-Time
Pay Scale: $28 - $34 DOE
Work Location: On-site - Prineville, OR office
Work Schedule: Monday through Friday from 7:00 AM to 4:00 PM
R-2 Contractors is currently seeking an Information Technology Senior Technician to support daily technical operations and maintain operational stability across all company locations. This position serves as the primary frontline contact for user issues, resolving hardware and software tickets to minimize workforce downtime. Beyond reactive troubleshooting, the Senior Technician handles Tier 2 escalations, coordinates daily tickets with the managed service provider (MSP), manages the physical IT inventory lifecycle, and translates technical workflows into repeatable processes to prepare the department for future scaling.
Responsibilities:
- Act as the primary responder for the internal help desk, diagnosing and resolving hardware, software, and peripheral issues for office and remote users.
- Serve as the definitive escalation point for complex technical issues that exceed foundational tier support boundaries before involving senior IT leadership.
- Liaise daily with the external MSP help desk to track open cases, provide local on-site context, and ensure third-party technical support aligns with internal company timelines.
- Design and author technical step-by-step documentation for the IT department, covering critical tasks such as workstation provisioning, mobile device configuration, and account onboarding.
- Create foundational how-to documentation for employees regarding company systems to streamline user adoption and reduce recurring common support tickets.
- Offer hands-on training to employees in systems that the company deploys, keeping up with those systems as they evolve.
- Manage the complete physical lifecycle of IT hardware, including unboxing, asset tagging, and maintaining absolute data accuracy within internal databases.
- Coordinate the preparation, packing, tracking, and shipping of company hardware to various offices and active field personnel.
- Oversee the accuracy of the IT inventory system and perform routine audits to ensure physical field assets match digital records and enforce standards for how assets are tagged and tracked.
- Maintain organized IT storage areas, stage retired equipment for secure disposal, and perform basic component upgrades, such as memory and drive replacements.
- Perform routine data entry and audit tasks within internal systems to ensure records of users, licenses, and assigned assets remain entirely accurate.
- Configure and deploy corporate workstations, tablets, and phones, ensuring all equipment adheres to strict company security and software standards prior to user assignment.
- Travel to active job sites and company offices to conduct physical equipment installations, network hardware resets, and hands-on operational support as needed.
Requirements:
- 5+ years of dedicated experience in an IT help desk, technical support, or field technician environment.
- Deep familiarity with Windows 11 environments, the Microsoft 365 suite, and SharePoint data structures.
- Functional knowledge of configuration platforms - specifically Verizon, Intune, and Apple Business Manager - for securing and deploying remote mobile assets.
- A clear understanding of TCP/IP, DNS, and local wireless hardware to perform on-site network diagnostic tasks.
- Prior exposure to construction-adjacent platforms such as HCSS software (HeavyBid, HeavyJob, Fleet), Samsara, or Bluebeam is highly valued.
- Demonstrated ability to construct clear, logical, and highly detailed technical documentation and standard operating procedures.
- Professional interpersonal skills, with a proven capability to communicate technical solutions to non-technical personnel in a patient and respectful manner.
- Exceptional administrative and logistical tracking skills, ensuring asset management processes are followed precisely without deviation.
- An associate's degree (or higher) in Information Technology, Cybersecurity, or a related discipline is preferred.
- Active industry certifications (such as CompTIA Network+, Security+, Microsoft 365 Certified: Endpoint Administrator, or ITIL Foundation) are highly valued.
Ready to Join Our Team? If you're ready to bring your technical expertise, organization, and problem-solving skills to a growing company, apply today and be part of a team that values quality, accountability, and operational excellence!
*R-2 Contractors is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or protected veteran status

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