Level 2 Engineer, Legal Vertical

Level 2, Legal Industry Specialist (US - Remote)

What to expect when you join Sikich

Team members at Sikich have a lot in common while also being part of a rich and varied group of contributors, creating a distinct and thriving culture. Chief among our commonalities is a desire for growth and a shared unity of purpose in our professional lives. We believe that through different perspectives, challenging the status quo and rewarding action, we accelerate innovation and drive growth - for our clients, for ourselves and for our communities.

The professional services landscape continues to evolve. For Sikich, this means we have an opportunity to further cement our leadership position in this industry and continue to grow our organization in increasingly exciting ways. This growth is meaningful for every team member at our company because larger companies simply see more interesting client opportunities and can attract impressively talented individuals like you. Through a dedicated focus on key business priorities and intentionally creating a rewarding employee experience, Sikich has developed into a highly regarded provider of professional services and a sought-after employer of choice.

Do you want to work with other skilled practitioners and serve clients in a way that makes a difference? Are you seeking a supportive environment backed by a deep and extensive set of skillsets? Are you ready to make an impact and be acknowledged for your contributions? If you answered yes to these questions, we see a mutually beneficial and gratifying relationship on the horizon!

Are you ready to grow with us?

Position Summary

Sikich LLC is seeking a Support Engineer - Managed Services | Legal Industry Specialist join our Managed Services team. This is a Level 2 support role with a defined specialty focus on legal industry clients. The role is generalist in scope, covering end user support, server administration, and common SMB infrastructure, with added subject matter ownership around law firm environments and the tools attorneys and legal staff depend on daily.

As a Level 2 engineer, you will serve as a key escalation point for Level 1 engineers, providing remote support and management of end users, servers, and day-to-day IT needs across a mix of small and mid-size clients, with a concentration on regional and solo law firm accounts. You will apply your understanding of how law firms operate, what platforms they rely on, and why certain issues carry outsized urgency to both the ticket queue and the runbooks and documentation that help the broader team support legal clients more effectively.

What will you do in this role?

Technical Support

• 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.

Legal Industry Specialization

• 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.

Knowledge Transfer and Documentation

• 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.

What do you need to succeed in this role?

Required

• 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.

Preferred

• 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.

Shift

• Preferred: 8:00 AM to 5:00 PM Central, Monday through Friday.
• Participation in 24/7 on-call rotation required.

In compliance with this state's pay transparency laws, the base compensation range for this role is $71,139.25 - $116,104.63 - $161,070.00. This is not a guarantee of compensation or salary, as final offer amount may vary based on several factors including but not limited to experience and geographic location. Compensation ranges for roles in our Government Services pillar are determined by contract with the specific government agency Sikich is servicing.

In addition, specific skills/experience required are as follows: .....

• Servant Leader - You are hyper focused on engaging employees, fostering their development, and building a positive culture.
• Solutions Focused - You see opportunities in every business problem and can develop, articulate, and implement solutions.
• Collaboration - You are a relationship builder across all levels of the organization and across all business units.
• Instills Trust - You do what you say, and you follow through on commitments, you act with integrity, you are consistent and are perceived as credible.
• Impact & Influence Thinking - You gain support for ideas, proposals, and solutions, and get others to act, with or without formal authority, to advance initiatives/objectives.

About Sikich

Sikich offers the public and private sectors a varied platform of professional services across consulting, technology and compliance. Highly specialized and hands-on teams deliver integrated solutions rooted in deep industry experience. Our approach is strategically and thoughtfully designed to help our clients, teams, and communities accelerate success.

Sikich Total Rewards

Our team members enjoy expansive benefits ranging from competitive compensation and insurance options to wellness programs and a flexible time off policy, to name only a few. Sikich also takes pride in prioritizing team members' health, total wellbeing and time spent with family, friends and in the pursuit of personal goals, hobbies, and endeavors.

Some examples of our many benefits:

• Sikich maintains a Flexible Time Off (FTO) Policy. We encourage every full-time employee, as your role permits, to utilize paid time off (personal time, mental/physical health care, vacation, sick leave, etc.). Waiting for time off to accrue is common at other companies. At Sikich, you do not have to wait for this benefit to kick in. FTO is activated on your first day with our organization.
• Sikich will also recognize paid holidays during the year and strives to permit employees to have time off the last week of the calendar year when client and project work permits.
• Sikich offers a comprehensive wellness program to engage, challenge and empower team members to take responsibility for their wellbeing. Activities can be tracked through our wellness provider to obtain gift cards and other rewards.

We also offer:

• Flexible work arrangements
• Health, dental, vision, life, and accident/death/disability insurance options
• HSA employer contribution
• Nine (9) paid holidays annually.
• A robust paid Parental Bonding Leave program covering birth, adoption, and foster children.
• 401(k) with employer contributions
• CPA bonus with four (4) paid exam days & four (4) paid study days.
• Tuition reimbursement
• Generous employee referral bonus program
• Client referral bonus program
• Pet insurance
• FORCE - Sikich community volunteer program enabling each team member to use up to four hours of paid time annually to volunteer and make a difference in their local communities.

Want to learn more? Visit our Careers website or Glassdoor profile.

Sikich is an Equal Opportunity Employer M/F/D/V

Sikich practices in an alternative practice structure in accordance with the AICPA Professional Code of Conduct and applicable law, regulations, and professional standards. Sikich CPA LLC is a licensed CPA firm that provides audit and attest services to its clients, and Sikich LLC and its subsidiaries provide tax and business advisory services to its clients. Sikich CPA LLC has a contractual arrangement with Sikich LLC under which Sikich LLC supports Sikich CPA LLC's performance of its professional services. Sikich LLC and its subsidiaries are not licensed CPA firms.

"Sikich" is the brand name under which Sikich CPA LLC and Sikich LLC provide professional services. The entities under the Sikich brand are independently owned and are not liable for the services provided by any other entity providing services under the Sikich brand. The use of the terms "our company", "we" and "us" and other similar terms denote the alternative practice structure of Sikich CPA LLC and Sikich LLC.

[RG1]Good network and connectivity troubleshooting fundamentals, including Routing basics, site-to-site and client VPNs, and basic firewall rules and log review.

[JS2]I think we can cover this in an interview. It allows us to Hold these questions back and ask live to see what they know