IT Support Technician Cascade IT Services, Bend, Oregon. Full time, based in Bend or Central Oregon. About us Cascade IT Services is a managed service provider in Bend, Oregon. We look after the computers, email, networks and security for small businesses across Central Oregon, from dental offices and accounting firms to nonprofits. Our customers are business owners, not IT people, and they count on us to explain things plainly and fix them properly. We are a small, growing team. The role You will be the first person our customers reach when something breaks. You will work the support queue every day alongside our engineer, visit customer offices around Central Oregon when a problem needs hands on help, fix what you can yourself, and hand off cleanly when something needs him. You report to the owner. What you will do

• Answer new support tickets and phone calls, and keep every open ticket moving until it is resolved and the customer has confirmed it.
• Connect remotely to customer computers through NinjaOne and fix problems end to end, including command prompt, PowerShell and screenshots for the record.
• Set up new computers and users: install our security and management tools, join them to Microsoft 365, and apply the 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, such as unusual sign ins or disabled antivirus, following our playbook and escalating quickly when it matters.
• Handle compromised accounts and devices: lock the account, revoke sessions, reset passwords and multi factor sign in, check for malicious mailbox rules, and clean up a computer after it has been isolated.
• Troubleshoot printers and scanners, including network printers, shared printers and drivers.
• Diagnose network problems at the desk: wifi, switch ports and PoE, IP addressing, mapped drives and network storage, and whether a problem is the internet provider, the office network or the computer.
• Fix email delivery problems such as bounces and sending limits, and understand how SPF, DKIM and DMARC affect them.
• Support OneDrive, SharePoint and Teams, including file sync, sharing permissions and call quality.
• Restore lost email and files from Microsoft 365 backups.
• Keep computers patched and healthy, and diagnose hardware problems on Windows laptops, Surfaces and Macs.
• Work with outside vendors (internet providers, phone providers, software vendors) and know where our responsibility ends and theirs begins.
• Run the recurring checks: device health, license counts against what customers pay for, and email security reports.
• Write it down. Every ticket gets clear public notes, and anything you solve twice becomes a knowledge base article. What good looks like here
• Customers never have to chase us. If you are waiting on them, you tell them; if they are waiting on you, they hear from you the same day.
• Every ticket gets an update before the end of the day, even if the update is "still working on it."
• A ticket closes because the customer confirmed it works, not because it went quiet.
• Remote sessions never end partway through a fix without telling the customer what is done and what comes next.
• Findings go in the ticket where the customer and the team can see them, not in a private note or a chat message.
• Time is logged accurately on every ticket, because for many of our customers it is what we bill.
• You are reachable in the team chat during Pacific business hours.
• When you are stuck for more than about 30 minutes, you ask. What we are looking for
• At least 2 years of help desk or support work. MSP experience, or supporting several client companies, is preferred.
• Strong Windows 10 and 11 troubleshooting, including performance, hardware and printing problems.
• Solid macOS support experience, including setup, troubleshooting, and Microsoft 365 on a Mac.
• Hands on Microsoft 365 administration: Exchange Online, Entra ID, OneDrive, SharePoint and Teams, plus licensing.
• Hands on Google Workspace administration: users, groups, email, Drive sharing and security settings.
• Device management experience: enrolling and managing Windows, Mac and mobile devices through 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 such as compromised accounts and malware, not only reading alerts.
• Experience with a remote management tool such as NinjaOne, Datto or ConnectWise.
• Clear, friendly written and spoken English.

Much of this job is explaining things to people who are not technical.

Nice to have:

scripting in PowerShell or Bash to automate routine fixes and checks, Huntress or another security tool, Bitdefender, Active Directory and Windows Server, UniFi or Cisco networking, email authentication (SPF, DKIM, DMARC), Microsoft 365 backup tools, HIPAA experience with healthcare or dental offices, phones and tablets, and any CompTIA, Microsoft or Cisco certification. Schedule and benefits

• 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.
• We pay for certification exams, and we use AI tools such as Claude every day to work faster.

How to apply Apply here with your resume and a short note describing one support problem you solved that you are proud of, and how you explained the fix to the customer. Shortlisted applicants do a practical test of about 60 to 90 minutes with our engineer: a live remote session on a staged problem, a compromised account scenario, and a written reply to a customer.

Pay:

From $25.00 per hour Expected hours: 40.0 per week

Benefits:

Paid time off Retirement plan

Work Location:

In person