Level 2 Engineer, Legal Vertical

Sikich is a professional services firm seeking a Level 2 Engineer specializing in the legal industry to join their Managed Services team. The role involves providing remote support and management for legal clients, focusing on end user support, server administration, and legal-specific IT needs.

Responsibilities:

• Serve as the escalation point for associate-level engineers, taking ownership of end user, server, and infrastructure issues through to resolution
• Triage and troubleshoot incidents and service requests across a mixed SMB client base, with particular attention to legal client issues that carry elevated urgency due to court deadlines, filing windows, or time-sensitive billing cycles
• Support legal document workflows including redlining, track changes, document comparison, PDF editing, and metadata management, understanding that failures in these workflows often carry immediate business impact for legal clients
• Work with Level 3 engineers to escalate complex issues and build exposure to more advanced concepts
• Assist junior team members with training and day-to-day technical questions
• Handle first call resolution for routine end user requests as needed
• Track time and document technical effort accurately in the PSA
• Serve as the team's subject matter resource for legal industry client environments and workflows
• Develop and maintain working knowledge of IT tools common in law firms, including practice management, document management, billing, and legal research platforms, and how they connect to the underlying infrastructure the team supports
• Understand the business context behind legal IT priorities: court deadlines, matter confidentiality, billing cycle pressures, and considerations around client data handling and retention
• Apply that context when triaging incidents, recognizing when a routine issue is actually high-impact for a legal client
• Own the creation and ongoing maintenance of team runbooks specific to legal client environments, covering common platforms, recurring issue patterns, escalation triggers, and client context
• Document legal industry IT concepts in plain language so generalist engineers can quickly understand why certain issues carry higher urgency
• Collaborate with team leads to ensure legal client context is reflected in onboarding materials and ticket handling guidance
• Contribute to continuous improvement of service delivery processes with a focus on legal vertical consistency

Requirements:

• 3+ years of experience in a managed services or IT support environment, with at least 2 years at an L2 or escalation support capacity
• Prior experience supporting law firm clients or working in a legal IT role, whether internal or at another MSP
• Familiarity with legal practice and document management platforms such as Clio, MyCase, Filevine, iManage, NetDocuments, Worldox, Time Matters, or ProLaw
• Hands-on experience with legal document tooling including Adobe Acrobat, Litera or similar document comparison and metadata management platforms, and PDF workflows common in legal environments
• Solid general systems administration skills: Windows 10/11, Server 2016/2022, Active Directory, and Microsoft 365
• Hands-on experience with Microsoft Azure and Microsoft 365 administration, including Azure AD (Microsoft Entra ID), Intune, Defender for Business, and Microsoft 365 security and compliance features
• Active experience with at least one RMM platform such as ConnectWise Automate, NinjaRMM, Auvik, LogicMonitor, or equivalent. Comfort using RMM tooling for alerting, remote sessions, scripting, and basic automation is required
• Good network and connectivity troubleshooting fundamentals including DNS, VPN, and basic firewall concepts
• Strong written communication skills. This role owns documentation and runbooks that others depend on
• Experience with PSA toolsets such as ConnectWise Manage
• Exposure to endpoint security and cybersecurity tooling used in MSP environments, such as SentinelOne, Huntress, ThreatLocker, or similar platforms
• Familiarity with legal industry compliance and data handling considerations, such as state bar ethics rules around client data and legal hold concepts
• Experience supporting small to mid-size professional services firms in a multi-client MSP environment
• Microsoft 365, CompTIA Network+, CompTIA Security+, or equivalent certifications. Cisco certifications are a plus