Technical Support Engineer

Cascade IT Services is hiring an onsite Technical Support Engineer in Bend, OR. This role is built for people who like clear communication, end-to-end resolution, and documented fixes that improve the next ticket. You will work with a team that values timely updates, accurate time logging, and practical problem-solving using modern tools including NinjaOne, Microsoft 365, Huntress, and AI tools like Claude to move faster.

What you will do

• Answer new support tickets and phone calls, keeping each open ticket moving until the issue is resolved and the customer confirms it works.
• Provide remote, end-to-end fixes by connecting to customer computers through NinjaOne, including use of Command Prompt, PowerShell, and screenshots for records.
• Set up new computers and users, installing security and management tools, joining devices to Microsoft 365, and applying standard settings.
• Manage Microsoft 365 and Google Workspace accounts, including new staff, departures, licenses, passwords, and multi-factor sign-in.
• Respond to security alerts from Huntress (for example, unusual sign-ins or disabled antivirus) using the playbook and escalating quickly when needed.
• Handle compromised accounts and devices: lock accounts, revoke sessions, reset passwords and multi-factor sign-in, check mailbox rules, and clean up computers after isolation.
• Troubleshoot printers and scanners, including network printers, shared printers, and drivers.
• Diagnose network problems at the desk, including WiFi, switch ports and PoE, IP addressing, mapped drives, and network storage, and determine whether the issue is the internet provider, office network, or the computer.
• Fix email delivery problems such as bounces and sending limits, including how SPF, DKIM, and DMARC impact delivery.
• Support OneDrive, SharePoint, and Teams, covering file sync, sharing permissions, and call quality.
• Restore lost email and files from Microsoft 365 backups.
• Keep computers patched and healthy, diagnose hardware problems on Windows laptops and Surfaces, and support macOS.
• Coordinate with outside vendors (internet providers, phone providers, and software vendors) and know where ownership ends and theirs begins.
• Run recurring checks including device health, license counts against what customers pay for, and email security reports.
• Document outcomes clearly in the ticket, and turn repeated fixes into knowledge base articles.

What we need

• At least 2 years of help desk or support work.
• Strong troubleshooting for Windows 10 and Windows 11, including performance, hardware, and printing.
• Solid macOS support experience, including setup, troubleshooting, and Microsoft 365 on a Mac.
• Hands-on Microsoft 365 administration: Exchange Online, Entra ID, OneDrive, SharePoint, Teams, and licensing.
• Google Workspace administration experience: users, groups, email, Drive sharing, and security settings.
• Device management experience enrolling and managing Windows, Mac, and mobile devices using Intune or a similar tool, including Autopilot, compliance policies, and app deployment.
• Working knowledge of networking: IP addressing, DHCP, DNS, VLANs, WiFi, switches, and firewalls.
• Experience responding to security incidents involving compromised accounts and malware, not just reviewing alerts.
• Experience with a remote management tool such as NinjaOne, Datto, or ConnectWise.
• Clear written and spoken English.

Tools you will use

NinjaOne, PowerShell, Command Prompt, Huntress, Microsoft 365, Microsoft Exchange Online, Entra ID, OneDrive, SharePoint, Teams, Google Workspace, Intune, Autopilot, DHCP, DNS, VLANs, Datto, ConnectWise, SPF, DKIM, DMARC, Windows 10, Windows 11, macOS, and Microsoft 365 backups.

Benefits and schedule

• Paid time off
• Retirement plan

Full time, Monday to Friday, about 8:00 to 17:00 Pacific.

• Company laptop provided
• Two month evaluation period for both sides, with a pay review at the end
• Certification exams are paid for
• AI tools such as Claude are used every day to work faster
• Work Location: In person

Compensation

USD 25 per hourly. Expected hours: 40.0 per week. Two month evaluation period applies.

Nice to have

• PowerShell or Bash scripting to automate routine fixes and checks
• Additional security tools (Huntress or others), Bitdefender
• Active Directory and Windows Server
• UniFi or Cisco networking
• Email authentication experience: SPF, DKIM, DMARC
• Microsoft 365 backup tools
• HIPAA experience with healthcare or dental offices
• Experience with phones and tablets
• CompTIA, Microsoft, or Cisco certifications

What good looks like here

• Customers do not have to chase updates, and ticket updates happen before the end of the day.
• Tickets close only after the customer confirms it works.
• Remote sessions do not end mid-fix without communicating what was completed and what comes next.
• Findings are captured in the ticket for both customers and the internal team.
• Time is logged accurately on each ticket because it may be used for billing.
• Team chat availability during Pacific business hours.
• If stuck for more than about 30 minutes, escalation to the team.

How to apply

Apply with your resume and a short note describing one support problem you solved that you are proud of, including how you explained the fix to the customer.

Shortlisted applicants complete a practical test (about 60 to 90 minutes) including a live remote session on a staged problem, a compromised account scenario, and a written reply to a customer.