Tier 2 Technician, IT Managed Services
LetterNine | Independence, OH (onsite/hybrid) | Starting at $60,000 | Full-time
We're an 11-person, security-first MSP in Independence supporting small and mid-size businesses across the Cleveland metro (and a growing Charlotte client base). Our pitch to clients is local experts, no offshore call centers, no scripts. Our pitch to techs is the same: real problems, real ownership, no ticket mill. We're hiring a Tier 2 Technician to own escalations from our Tier 1 team: the AD/GPO problems, the Exchange messes, the "network is slow" tickets that take actual troubleshooting.
You will not spend your days resetting passwords. We have a Tier 1 team and a dispatch structure for that. Tier 2 here means the interesting work: the tickets that need diagnosis, not scripts.
What you'll actually do
- Own escalated tickets from Tier 1 through resolution in ConnectWise
- Troubleshoot and administer Windows Server, Active Directory, and Group Policy across multiple client environments
- Manage Microsoft 365, Exchange Online, Entra ID, and Intune issues beyond basic user administration
- Work network problems: VLANs, VPN, DNS, DHCP, and WatchGuard firewall troubleshooting
- Support Azure workloads and Synology NAS deployments
- Document your fixes so the next tech can use them; our knowledge base is a working tool here, not a graveyard
- Escalate to our Tier 3 engineers when needed, and learn from them when you do
What we're looking for
- 2+ years in an MSP, or 3+ years in internal IT with multi-site or multi-environment exposure
- Comfortable being the escalation point: you can take a ticket Tier 1 couldn't crack and run it to ground
- Real AD and Group Policy experience (not just unlocking accounts)
- Working knowledge of M365 administration and Exchange troubleshooting
- Networking fundamentals you can apply under pressure
- You write things down. Documentation is not optional here, and it's part of how we judge good work.
Nice to have: ConnectWise experience, WatchGuard or other firewall administration, any security services exposure, relevant certs (we care more about what you can do).
How hiring works here
- Short phone screen with our Service Desk Team Lead (30 minutes)
- Conversation with our COO (45 minutes)
- Paid working interview: 2 to 4 hours, about $200, working three sanitized real-world scenario tickets (AD/GPO, M365/Exchange, network/firewall). You see how we work, we see how you work. No trick questions, no whiteboard algorithms.
- Offer decision within a week of the working interview
Structure and growth
You'll report to our Service Desk Team Lead and join a service desk of two other Tier 2 techs, a Tier 1 team, and two Tier 3 escalation engineers. The escalation path is real and short: strong Tier 2s here grow into Tier 3 engineering work (projects, security services, client infrastructure design), not into a bigger ticket queue.
Compensation and benefits
- $60,000 to $78,000 based on experience
- Health, dental, and vision insurance
- 401(k)
- Paid time off
- Onsite in Independence with hybrid flexibility once you're up to speed
Location
Independence, OH (I-77 and I-480, easy reach from most of the Cleveland metro). No relocation required or expected; this is a local role.
Pay: From $60,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Paid time off
Application Question(s):
- Briefly describe a Group Policy issue you personally diagnosed and fixed.
Ability to Commute:
- Independence, OH 44131 (Required)
Work Location: In person
