Service Desk Technician - Tier 2

**This position is based in Southern Maryland and will require travel to our White Plains, MD office 1-2 times a week, and sporadic travel may be required around the DMV area to local clients as the need arises.

Job Summary
We are seeking a Tier 2 Service Desk Technician to join our growing team.

This position is responsible for providing day-to-day support for end users across Microsoft 365, Entra ID, Windows 11, endpoint management platforms, and business applications. The ideal candidate is comfortable handling both Tier 1 and Tier 2 support requests while independently managing tickets from intake through resolution.

This is a hands-on support role focused on troubleshooting, customer service, and technical problem solving. The successful candidate will have experience supporting Microsoft cloud environments, user identity and access management, endpoint devices, and common business applications within an MSP or enterprise environment.

The ideal candidate enjoys working directly with users, investigating complex issues, documenting solutions, and delivering a high-quality support experience.

Duties

Microsoft Entra ID & Identity Management

• Provision, modify, and disable user accounts
• Manage Microsoft 365 licensing and group memberships
• Troubleshoot user access issues across Microsoft 365 services
• Support MFA enrollment and authentication troubleshooting
• Investigate Conditional Access policy impacts and sign-in failures
• Troubleshoot security groups, Microsoft 365 groups, and role assignments
• Support onboarding and offboarding processes

Microsoft 365 Administration & Support

• Troubleshoot Exchange Online mail flow and mailbox issues
• Manage shared mailboxes, distribution groups, and permissions
• Support Outlook desktop and Outlook Web Access
• Troubleshoot Teams meetings, calling, chat, and collaboration issues
• Support SharePoint Online and OneDrive access, sync, and permissions issues
• Assist with Microsoft Defender and security-related investigations
• Resolve licensing, provisioning, and application access issues

Windows 11 Endpoint Support

• Diagnose and resolve operating system issues
• Troubleshoot application crashes, performance issues, and profile problems
• Support printers, peripherals, and workstation hardware
• Perform software installations and updates
• Troubleshoot networking, VPN, and connectivity issues
• Support endpoint security and patch management activities

RMM & Endpoint Management

• Utilize RMM tools to monitor and support managed devices
• Deploy software and updates using RMM platforms
• Investigate monitoring alerts and perform remediation
• Support remote troubleshooting sessions
• Assist with endpoint automation and scripting initiatives

Apple Device Support

• Troubleshoot macOS operating system issues
• Support iPhone and iPad users
• Assist with Apple Business Manager enrolled devices
• Support Microsoft 365 applications on Apple platforms

Customer Support & Service Delivery

• Manage support requests through a ticketing system
• Maintain accurate ticket documentation and time entries
• Communicate effectively with users throughout the troubleshooting process
• Contribute to internal knowledge base documentation
• Follow established operational procedures and security standards
• Deliver excellent customer service while maintaining productivity goals
• Manage Microsoft 365 licensing and group memberships
• Troubleshoot user access issues across Microsoft 365 services
• Support MFA enrollment and authentication troubleshooting
• Investigate Conditional Access policy impacts and sign-in failures
• Troubleshoot security groups, Microsoft 365 groups, and role assignments
• Support onboarding and offboarding processes

Required Qualifications

Experience

• 3+ years of IT support experience
• 2+ years supporting Microsoft 365 environments
• Strong Microsoft Entra ID experience
• Strong Windows 10 and Windows 11 troubleshooting experience
• Experience supporting remote users and distributed environments
• Experience using RMM or endpoint management platforms
• Experience working within a ticketing system
• Excellent customer service and communication skills
• Ability to independently manage and prioritize multiple tasks

Technical Skills

• Microsoft 365 Administration
• Microsoft Entra ID Administration
• Exchange Online
• Microsoft Teams
• SharePoint Online
• OneDrive for Business
• Multi-Factor Authentication (MFA)
• Conditional Access troubleshooting
• Windows 10/11 administration and support
• Active Directory fundamentals
• DNS fundamentals
• TCP/IP networking fundamentals
• Basic PowerShell knowledge

Preferred Qualifications

• Previous MSP experience strongly preferred
• Experience supporting multiple client environments simultaneously
• Experience with Microsoft Intune
• Experience with Microsoft Defender products
• Experience with NinjaOne, ConnectWise, ScreenConnect, or similar platforms
• Experience supporting Microsoft GCC or GCC High environments
• Experience supporting macOS and iOS devices
• Security+, Microsoft certifications, or equivalent industry certifications
• Familiarity with NIST 800-171, CMMC, or compliance-driven environments

What Success Looks Like

• Consistently resolves support requests with minimal supervision
• Maintains excellent customer satisfaction
• Produces thorough ticket documentation
• Demonstrates strong troubleshooting methodology
• Identifies recurring issues and contributes to long-term solutions
• Effectively manages workload and priorities in a fast-paced MSP environment
• Collaborates well with team members and clients

Why Join inDirect IT

• Work with modern Microsoft cloud technologies
• Support organizations operating in regulated and security-focused industries
• Gain exposure to Microsoft 365, Azure, cybersecurity, compliance, and managed services
• Collaborate with a highly technical team focused on continuous improvement
• Hybrid remote work environment
• Flexible schedule
• Opportunity to grow into senior technical, engineering, security, or management roles as the company expands

Pay: $65,000.00 - $85,000.00 per year

Benefits:

• 401(k)
• Flexible schedule
• Health insurance
• Paid time off
• Retirement plan
• Vision insurance

Work Location: Hybrid remote in White Plains, MD 20695