Psa Jobs in Portland, OR (NOW HIRING)

Varsity, a company under Treeline, is looking for a Client Engineer to handle complex technical issues across both remote and onsite client environments. This is a hybrid role that combines senior-level remote support work with direct, in-person client engagement in the field.

You will pick up escalations from Specialist I, work through root cause on complex problems, and travel to client sites across the city metro area as needed to deploy technology, resolve issues, and build client relationships in person. Beyond technical depth, this role requires someone who is genuinely at ease with people: able to walk into a client environment, read the room quickly, and communicate clearly and professionally whether you are speaking with an executive or an individual end user. Strong independent judgment, a valid driver's license, and the ability to manage ambiguity in both remote and field settings are all essential.

ABOUT US

Varsity is a technology services company operating as part of Treeline. Treeline is building a comprehensive software stack to transform traditional Managed Service Providers into a software-defined model powered by automation and AI.

Together, our work is grounded in the belief that organizations deserve technology partners who combine deep expertise with a genuine commitment to the people they serve. We help clients in the nonprofit, education, and healthcare sectors make strategic technology decisions that create real impact in their communities. Developing and implementing great solutions requires both proven methodology and people who place a high value on delivering exceptional service.

Requirements

DUTIES AND RESPONSIBILITIES

• Escalation Resolution: Receive and resolve tickets escalated from Specialist I, taking full ownership from intake through root-cause resolution and client communication.
• Triage and Scope Assessment: Quickly assess escalated issues to determine whether resolution is achievable remotely or requires an onsite visit, and whether it can be resolved promptly or requires a structured, longer-cycle approach. Communicate scope and timeline clearly to clients and internal stakeholders.
• Onsite Field Support: Travel to client sites across the city metro area as needed to deploy technology, resolve issues that require hands-on work, and maintain strong in-person client relationships.
• Audience Awareness: Calibrate communication and prioritization to the person you are supporting. Managers and executives have different needs and expectations than individual end users, and you will adjust accordingly without being prompted.
• Infrastructure-Layer Troubleshooting: Diagnose and resolve issues at the infrastructure level including M365 tenant configuration, networking, endpoint management at scale, and cross-system dependencies.
• M365 Administration: Manage complex administration tasks across Exchange, SharePoint, Teams, and Entra ID/AAD, including policy configuration, permissions, and cross-tenant issues.
• macOS Support: Provide advanced macOS support across security and system settings, application deployment and management, MDM tools and Apple Business Manager, application syncing and integration with iOS and Apple Cloud, and resolution of complex security and login issues.
• Networking: Troubleshoot DNS, DHCP, VPN, and firewall issues across client environments and coordinate with network vendors when needed.
• AI Platform Support: Support end users and client organizations working with generative AI platforms including Microsoft Copilot, Google Gemini, ChatGPT, and Claude. Apply working knowledge of prompt techniques and the underlying technologies behind these tools to troubleshoot and advise effectively.
• Client Communication: Communicate directly with client contacts and end users on complex issues, setting expectations, explaining technical findings clearly, and maintaining trust through longer resolution cycles.
• Tooling: Work within our PSA and RMM platforms to manage escalated work, maintain accurate records, and support reporting visibility across client accounts.
• Documentation: Produce thorough, reusable documentation on complex resolutions, configurations, and recurring patterns, leaving the environment better than you found it.
• Multi-Client Environment Management: Maintain working knowledge of multiple client environments simultaneously and recognize when an issue in one environment may reflect a pattern elsewhere.

QUALIFICATIONS

To perform this job successfully, a candidate must be able to perform each essential duty satisfactorily and be in possession of the following minimum qualifications:

• 3 to 5 years of experience in IT support, with demonstrated experience resolving escalated or complex issues in a managed services environment.
• Based in either Portland or New York metro area, with a valid driver's license and reliable personal transportation for client site visits.
• Strong hands-on M365 administration: Exchange, SharePoint, Teams, Entra ID/AAD, including policy, permissions, and tenant-level configuration.
• Advanced macOS support experience: security and system settings, application deployment, MDM tools, Apple Business Manager, iOS and Apple Cloud integration, and complex login and security issue resolution.
• Experience troubleshooting networking issues: DNS, DHCP, VPN, and firewall concepts beyond the basics.
• Solid working knowledge of generative AI platforms including Copilot, Gemini, ChatGPT, and Claude, with applied experience in prompt techniques and a clear understanding of the underlying technologies.
• Proficiency with RMM and PSA platforms; willingness to learn our specific tooling quickly.
• Ability to quickly assess whether an issue requires remote or onsite resolution and whether it can be resolved promptly or requires a longer-cycle approach.
• Strong communication skills with demonstrated ability to adapt tone, detail level, and prioritization when supporting individual users, managers, and executives.
• Strong interpersonal skills; able to build rapport with clients quickly and maintain professional, trusted relationships across a variety of personalities and seniority levels.
• Comfortable representing Treeline in person at client sites; presents professionally and communicates with confidence in face-to-face settings.
• Methodical approach to ambiguous problems: diagnose before you fix, document as you go.
• Certifications such as CompTIA Network+, Security+, Microsoft 365 Administrator (MS-102), or equivalent are preferred.
• Experience supporting multi-client MSP environments strongly preferred.

Benefits

WHY WORK WITH US

We are a small, highly effective team that values impactful execution, modern tooling, and minimal bureaucracy. Communication is open, collaboration is genuine, and the work is meaningful. A few other things that define how we operate: 

• We offer a competitive salary, comprehensive benefits package, flexible working conditions, and the chance to be part of a team that takes its work seriously.
• We are an agile organization and we are always improving.
• We believe our people are what make us effective.
• Every individual is responsible for doing their part and supporting the team around them.
• Our benefits are designed to support the health and wellness of employees and their families.
• We are committed to using technology to make a real difference for the organizations we serve.
• We offer 100% Medical/Dental/Vision.

We are an equal opportunity employer and welcome candidates from all backgrounds to apply. If you are an ambitious individual who wants to build a career in the evolving IT managed services landscape, then we would love to hear from you.

Note: Background checks will be performed as a condition of employment.