Job Description

About Les Olson IT

Les Olson IT is one of the fastest-growing and most capable technology service providers in the West. We do I.T. the LOC Way—through talent, passion, and compassion—driving continual growth and a strong market position by delivering superior service.

Unlike most technology companies, Les Olson IT has been in business for over 70 years. We are a family-owned and family-operated company, a tradition that began at the Olson family dinner table and continues today. From those beginnings, we have grown to more than 320 employees across nine locations in two states.

Les Olson Company strives every day to elevate people, whether it's our clients, our team members, or members of the local community.

• We seek to elevate our clients by delivering cutting-edge IT strategy, security, solutions, and support. Each of our team members recognizes that they have a direct impact on the success of the local businesses we serve every day.
• We seek to elevate every team member's career, firmly believing that customer success cannot happen without employee success. We do this by working with each employee to design a fulfilling career path that grows and evolves as they do.
• We seek to elevate our local community members by rewarding our employees for volunteering at local charities and participating in our ongoing food drives.

Our work environment promotes both growth and balance. We encourage and support our employees in building meaningful, fulfilling paths, both professionally and personally. Les Olson Company offers competitive salaries, continuing education, generous benefits, and a fun, collaborative work environment. At the end of the day, it is the people that matter most to us!

What You’ll Do

In this senior-level role, you will:

• Manage and maintain essential customer IT operations—servers, security tools, operating systems, backups, applications, and devices.
• Design, deploy, and troubleshoot Windows Server 2012/2016/2019/2022 environments.
• Administer and support Microsoft 365, Google Workspace, and other cloud email solutions.
• Configure and manage VMware and Hyper-V virtual environments, including VMs, storage, compute, and memory.
• Design, configure, and troubleshoot Active Directory forests, domains, and advanced Group Policies.
• Provide expert-level troubleshooting for DNS, DHCP, File, Print, Web, and Domain Controller services.
• Configure and optimize Azure AD, cloud resources, and virtual environments.
• Diagnose advanced issues with TCP/IP, DNS, DHCP, and coach junior engineers.
• Design and configure RAID, server hardware, and storage solutions (SAN/NAS).
• Serve as Tier 3 escalation, leading root‑cause analysis and resolution for complex incidents.
• Manage large, high-impact IT projects independently.
• Participate in an on-call rotation and respond to service requests across phone, chat, email, and ticketing systems.
• Maintain strong communication and exceptional customer satisfaction.

What You Bring

• 8+ years in Information Technology with strong System Administration experience.
• Excellent communication skills and a collaborative, team-first mindset.
• Strong customer-facing experience.

Certifications (or willingness to obtain within 1 year)

• CompTIA Security+, Server+ (or equivalents)
• VMware VCXD
• Microsoft 365 Expert Administrator (MS‑102)
• Cloud certification: AWS, Azure, or Google Cloud Architect

Technical Expertise

• Expert knowledge of Windows Server and Active Directory (OUs, Users, Groups, GPOs, FSMO roles).
• Extensive hands-on experience with VMware or Hyper-V.
• Strong hardware/software RAID skills.
• Advanced troubleshooting aligned to the OSI model.
• Expert knowledge of:
• • Microsoft 365
  • Google Workspace
  • Azure AD
  • Azure or AWS virtual environments
  • LAN/WAN, VLAN, VPN
  • Backup systems (Datto, Veeam, StorageCraft)
  • SAN/NAS storage
  • Endpoint security solutions
• Advanced PowerShell skills
• Advanced knowledge of Linux or Apple iOS
• Valid driver’s license & reliable transportation

Leadership & Strategic Support

• Serve as the technical team lead for Systems Administration operations, providing guidance, mentorship, and oversight to junior and mid-level engineers.
• Act as a trusted partner to the IT Director in developing IT standards, operational processes, infrastructure strategy, and technology roadmaps.
• Assist the IT Director with workload prioritization, resource planning, project coordination, and service delivery objectives.
• Lead technical discussions, architecture reviews, and infrastructure improvement initiatives.
• Review and approve technical solutions, change requests, and system designs to ensure alignment with organizational standards and best practices.
• Coordinate team activities, provide escalation support, and ensure timely resolution of critical business-impacting incidents.
• Facilitate knowledge-sharing sessions, documentation standards, and ongoing technical training for IT staff.
• Monitor team performance metrics and identify opportunities for operational efficiencies and service improvements.
• Serve as acting IT Director during absences, managing day-to-day infrastructure operations and technical decision-making.
• Collaborate with executive leadership, vendors, and business stakeholders to support organizational technology goals.

Leadership Experience

• 2+ years of technical leadership, team lead, or supervisory experience in a Systems Administration, Infrastructure, or Managed Services environment.
• Proven ability to mentor, coach, and develop technical staff while fostering a collaborative, high-performing team culture.
• Experience leading infrastructure projects, coordinating cross-functional teams, and managing competing priorities.
• Strong organizational, planning, and decision-making skills with the ability to balance strategic initiatives and operational responsibilities.

Benefits

• Paid Time Off
• Sick Days
• Paid Holidays
• 401k match + Pension
• Work-life Balance
• Full Medical, Dental & Vision + HSA
• Life Insurance
• Local Volunteer Opportunities