System Administrator

The 20; Portland (OR); On-site; USD 65,000 - 80,000; Full time

Benefits offered by this job

401(k) matching up to 4%

Certification reimbursement

Advancement opportunities

Collaborative culture and teamwork

Job summary

The 20 LLC is seeking a System Administrator in Portland, Oregon to maintain and optimize our IT infrastructure across internal and client environments. You’ll work with a collaborative team to ensure system reliability, implement upgrades, and support desks while traveling to client sites as needed.

Ideal candidates have strong AD/Azure AD, Microsoft 365, virtualization (VMware/Hyper-V), networking, and security knowledge, plus scripting skills and a proactive problem-solving mindset.

Qualifications

• Associate or Bachelor's degree in Computer Science, IT, System Administration, or related field.
• 4-6 years IT administration experience.
• IT certifications in Microsoft or related fields are a plus.
• Working knowledge of virtualization, VMware, Hyper-V, or equivalent.
• Strong knowledge of systems, networking software, hardware, and networking protocols.
• Experience with scripting and automation tools.
• Proven track record of developing and implementing IT strategy and plans.
• Strong knowledge of implementing and effectively developing helpdesk and IT operations best practices, including security, storage, data protection, and disaster recovery protocols.
• Annual salary range: $65,000 - $80,000.
• Competitive 401(k) participation with up to 4% contribution match.
• Certification reimbursement to support your continued development.
• Meaningful opportunities for advancement within a growing organization.
• A culture built on drive, accountability, collaboration, and excellence.

Responsibilities

• Maintain, configure, and operate computer systems, network servers, workstations, and networking equipment.
• Install and upgrade computer components and software.
• Troubleshoot hardware and software errors by running diagnostics, documenting problems and resolutions, prioritizing problems, and assessing impact of issues.
• Provide documentation and technical specifications to Project Team and Manager for planning/implementing of new or upgrades to IT infrastructure (hardware or software).
• Lead desktop and helpdesk support efforts, making sure all desktop applications, workstations, and related equipment problems are resolved in a timely manner with limited disruptions.
• Travel onsite to client locations as necessary to provide hands-on technical support, troubleshoot issues, and implement solutions to ensure continuity of services.

Skills

Active Directory / Azure AD

Microsoft 365 Administration

VMware / Hyper-V

Firewall management

Networking fundamentals

Scripting / automation

Education

Associate or Bachelor's degree in Computer Science / IT / System Administration

Tools

IT Glue

Kaseya BMS

Kaseya VSA

Job description

The 20 LLC is a nationwide Managed Service Provider (MSP) and MSP growth platform that partners with both general businesses and IT service companies across the country to deliver world‑class technology solutions and support. We are passionate about fostering a collaborative, innovative environment where our team members and clients can thrive.

We’re looking for a System Administrator who thrives on solving complex challenges while working side‑by‑side with talented teammates. In this role, you’ll ensure our systems run seamlessly, support both internal teams and client environments, and contribute to an IT culture built on trust, collaboration, and a shared drive for excellence. This position offers the opportunity to make a tangible impact through your expertise while working in an environment that values initiative, innovation, and teamwork.

Responsibilities include but not limited to:

• Responsible for the maintenance, configuration, and reliable operation of computer systems, network servers, workstations and networking equipment.
• Install and upgrade computer components and software.
• Troubleshoot hardware and software errors by running diagnostics, documenting problems and resolutions, prioritizing problems, and assessing impact of issues.
• Provide documentation and technical specifications to Project Team and Manager for planning/implementing of new or upgrades to IT infrastructure (hardware or software)
• Lead desktop and helpdesk support efforts, making sure all desktop applications, workstations, and related equipment problems are resolved in a timely manner with limited disruptions.
• Travel onsite to client locations as necessary to provide hands‑on technical support, troubleshoot issues, and implement solutions to ensure continuity of services.

Skills & Experience required:

• Active Directory and Azure AD
• Microsoft 365 administration, including Exchange, SharePoint, OneDrive, and Teams Online
• Virtualization technologies, including VMware and Hyper‑V
• Firewall management and troubleshooting
• Knowledge and experience with complex networking environments
• Deep understanding of Active Directory, Group Policy, and file sharing

Recommended knowledge, skills, and competencies:

• Experience with all modern operating systems
• Experience with documentation platforms such as IT Glue
• Experience with Kaseya BMS and VSA

Qualifications for System Administrator

• Associate or Bachelor's degree in Computer Science, Information Technology, System Administration, or a closely related field, or equivalent experience required
• 4-6 years of IT administration experience
• System administration and IT certifications in Microsoft, or other network related fields are a plus
• Working knowledge of virtualization, VMWare, Hyper‑V, or equivalent
• Strong knowledge of systems and networking software, hardware, and networking protocols
• Experience with scripting and automation tools
• A proven track record of developing and implementing IT strategy and plans
• Strong knowledge of implementing and effectively developing helpdesk and IT operations best practices, including expert knowledge of security, storage, data protection, and disaster recovery protocols
• Annual Salary range: $65,000 - $80,000
• Competitive 401(k) participation with up to 4% contribution match
• Certification reimbursement to support your continued development
• Meaningful opportunities for advancement within a growing organization
• A culture built on drive, accountability, collaboration, and excellence

Physical Demands:

The physical demands below describe the essential job functions needed to complete this job.

• Consistent hand and finger dexterity necessary to operate computer equipment
• Consistently required to sit, stand, walk, talk, hear, and see
• Routine use of hands to type
• Occasional need to stoop, kneel, crouch, twist, crawl, reach, and stretch
• Consistent vision abilities required; close vision, depth perception, and ability to focus
• May require travel dependent on company needs.
• Occasional need to lift and/or move up to 30 pounds

The statements contained in this job description are intended to describe the general nature and level of work being performed by associates assigned to the job. They are not intended to be interpreted as an exhaustive list of all responsibilities, duties, and skills required of the individual(s) holding this position.