About Us

Milestone Advisors is a Salt Lake City-based firm that simplifies tax, accounting, and IT so businesses can operate with confidence and clarity. We act like an extension of our clients’ teams, delivering proactive, root-cause solutions that help companies scale without outgrowing their systems. With a collaborative, hands-on approach and fast, human-centered support, Milestone offers professionals opportunities to solve complex problems and build long-term client relationships.

About the Role

Milestone Advisor’s Technology division is growing! We’re looking for a Level 2 Engineer who loves solving problems, building repeatable processes, and delivering top-tier customer experience. This role is ideal for someone with a few years of MSP experience supporting multiple small business customers (or similar experience in a smaller, fast-moving IT environment).

This is not a behind-the-scenes role. As a Level 2 Engineer at Milestone, you are the face of IT for our clients. You’ll work directly with business owners, office managers, and end users across multiple organizations, often as their primary point of contact for technical issues. That means you need to be comfortable jumping between different client environments, adjusting your communication style to your audience, and building the kind of trust that makes clients feel like you’re part of their team, not just a vendor on the other end of a ticket. Customer service is our key differentiator. We’re a customer service company that happens to do IT.

You’ll handle escalations, support core Microsoft and Windows environments, strengthen client networks, and help coach and level up our Level 1 technicians by creating clear SOPs and documentation they can follow.

What’s in it for you

• Medical, Dental, and Vision benefits package

• 401(k) with company match

• Growth runway in a team that values ownership, initiative, and learning

• A supportive culture to allow you to live a fulfilling, happy, and impactful life

Key Responsibilities

• Provide Tier 2 support and escalation for client and internal IT issues, troubleshooting through root cause resolution

• Administer and support Microsoft 365 environments (including identity and access management)

• Manage and support Entra ID/Azure administration tasks (access, roles, policies, device/user management as applicable)

• Administer Windows desktop environments (builds, performance, troubleshooting, security best practices)

• Administer Windows Server environments (roles, services, patching, troubleshooting, maintenance)

• Use PowerShell to streamline administration, reporting, and repeatable tasks

• Support and troubleshoot networking: DHCP, DNS, VLANs, VPNs, switches, routers, and access points

• Maintain excellent ticket hygiene and documentation in the ticketing system

• Create and maintain process documentation / SOPs (we create a lot of process docs)

• Train, mentor, and coach our Level 1 technicians; build SOPs and runbooks that help L1 solve more issues independently

• Partner closely with the IT Manager and work cross-functionally with leadership as needed

Required Experience / Skills

• High level of customer service with strong communication (you can explain technical topics clearly and calmly)

• Experience supporting multiple users and environments (MSP preferred; smaller org IT experience also highly valued)

• Hands-on experience with:

  • Microsoft 365 Administration

  • Entra ID / Azure administration

  • Windows Desktop Administration

  • Windows Server Administration

  • PowerShell

  • Networking fundamentals and practical troubleshooting (DHCP/DNS/VLAN/VPN/switching/routing/APs)

  • Documentation platforms/tools (any type; clarity and consistency matter most)

Education / Certifications

• College degree is preferred, but not required with applicable certifications and relative real-world experience

Nice to Have

• Autotask PSA (or similar ticketing system)

• Datto RMM (or similar RMM tool)

• Backup & Disaster Recovery tools/platforms

• Rewst (or similar automation platform)

• Light software development experience (e.g., Python, JavaScript, C#, or similar) to help automate repetitive tasks and improve workflows

• Linux server administration

• Ubiquiti networking experience

• Practical experience using AI tools to improve support quality, documentation, or automation