Help Desk Lead

About the role

LawToolBox is a LegalTech SaaS company pioneering AI for legal, creating a secure, connected command center for law firms, corporate legal departments, and government agencies. We bring AI to where attorneys work, helping them think through strategic next steps so their clients get better outcomes. As our Help Desk Manager, you own the entire support operation—end to end, start to finish. This is a senior individual contributor role, meaning you don’t manage a team, but you absolutely manage the function: the processes, the standards, the tooling, the knowledge infrastructure, and the customer experience at every touchpoint.

You’ll work directly with a demanding and sophisticated client base—attorneys, paralegals, legal operations professionals, IT administrators, and Microsoft Partners supporting law firms across the country. These are not casual users. They operate in high-stakes environments where deadlines are hard, downtime is costly, and they expect expert-level support delivered with professionalism and speed.

Responsibilities

• Own the Help Desk Function End to End: Design and continuously improve how support operates—ticket workflows, escalation paths, response standards, SLA targets, and quality benchmarks. Identify issues, fix them, and build systems to prevent recurrence.
• Senior-Level Technical Support: Handle complex Tier 2 and Tier 3 support issues across the full LawToolBox and Microsoft 365 stack—SharePoint, Teams, Exchange, Entra ID, OneDrive, and the integrations between them. Resolve escalations and provide Engineering with the context they need to move fast.
• Microsoft 365 & Integration Expertise: Serve as the internal and external authority on Microsoft 365 as it relates to LawToolBox. Diagnose tenant configuration issues, permissions problems, sync failures, Exchange routing, Teams channel behavior, and SharePoint permission inheritance across diverse client environments.
• Client Relationship Management: Support a sophisticated mix of clients—attorneys, legal professionals, IT staff, and Microsoft Partners. Adapt communication style fluidly, represent LawToolBox with professionalism, and treat every interaction as an opportunity to strengthen the relationship.
• Cache, Browser & Client-Side Diagnostics: Diagnose and resolve client-side issues—browser cache conflicts, cookie and session problems, extension interference, and compatibility issues across Chrome, Edge, and Safari. Document patterns and build repeatable resolution guides.
• Knowledge Base Ownership: Own the help center as a strategic asset. Write and maintain support documentation for end users, IT admins, and Microsoft Partners. Identify gaps from ticket trends and close them proactively.
• Ticket Operations & Trend Reporting: Maintain a clean, well-prioritized queue and track key metrics: volume by category, resolution time, escalation rate, recurring issues, and customer satisfaction. Report to Customer Success and leadership, surface product issues to Engineering and Product, and use data to raise support quality.
• Onboarding & Implementation Support: Partner with Customer Success during client onboarding to ensure proper configuration in the Microsoft environment—correct permissions, integrations, and a seamless first experience with LawToolBox.

Requirements

• 5+ years in a technical support or help desk role, with at least 2 years supporting a SaaS product in a senior or lead capacity.
• Deep, hands-on expertise with Microsoft 365—SharePoint, Teams, Exchange, Entra ID (Azure AD), OneDrive, and the M365 Admin Center.
• Experience supporting IT administrators and Microsoft Partners, with the ability to go deep technically in collaborative troubleshooting sessions.
• Proven ability to own a support function independently: building and refining workflows, maintaining documentation, and driving quality without direct management.
• Strong written and verbal communication—write clear, professional support documentation and explain complex issues to frustrated attorneys in plain English.
• Experience with ticketing platforms such as Freshdesk, Zendesk, or similar, and a disciplined approach to queue management and SLA adherence.
• Comfortable working with a legal professional client base—understand the stakes of their environment and bring appropriate urgency.
• Process-oriented and self-directed—see what needs to be built, build it, and hold yourself accountable to the outcome.

Qualifications

• Experience supporting legal technology platforms or working within a legal services organization.
• Microsoft certifications (MS-900, MS-700, MS-203, or equivalent).
• Familiarity with Microsoft Power Platform—Power Automate, Power Apps.
• Experience collaborating with or supporting Microsoft CSPs or managed service providers.
• Background in knowledge management, technical writing, or customer education.
• Exposure to CRM platforms such as HubSpot or Salesforce.

Work Environment

We’re hybrid workers, spending 2 days a week at a vibrant co-working space 20 minutes south of downtown Denver, just steps from the Arapahoe light-rail station.

Benefits

• 401(k)
• 401(k) matching
• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Parental leave
• Tuition reimbursement
• Vision insurance

About Us

Our technology is second only to our people. Team events are imagined, organized, and led by new hires. Team building is core to who we are and what makes our culture. We invest in people and help them build on their strengths, provide leadership opportunities partnering with leading SaaS companies and technology giants like Microsoft. We provide a career path to develop core skills needed to be an effective leader. Our entrepreneur’s mindset provides a place where everyone can own their career path.

Highlights:

• First legal app to be certified for Microsoft Copilot in 2023.
• Deployed globally in Microsoft Innovation Hubs as M365 Copilot for Legal.
• 1st Place, SharePoint Integration – Best SharePoint Solution.
• 2nd Place, App for Teams – Best Office Integration.