Help Desk Lead

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. You'll need to earn their trust quickly and keep it., You are the help desk. You design and continuously improve how support operates - ticket workflows, escalation paths, response standards, SLA targets, and quality benchmarks. You don't wait to be told what's broken; you identify it, fix it, and build systems to prevent it from recurring.

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. You're the person escalations land with, and you resolve them. You know when to loop in Engineering and how to give them exactly 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. That means diagnosing tenant configuration issues, permissions problems, sync failures, Exchange routing, Teams channel behavior, and SharePoint permission inheritance - and doing it across a wide range of client environments managed by different IT teams and Microsoft Partners. You communicate technical findings clearly to both IT-fluent and non-technical stakeholders.

Client Relationship Management - Legal & IT Audience: Support a sophisticated mix of clients: attorneys and legal professionals who need fast, clear answers without jargon; IT staff and Microsoft Partners who need technical depth and collaborative troubleshooting. You adapt your 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. You document patterns, build repeatable resolution guides, and work proactively to reduce the volume of these contacts over time.

Knowledge Base Ownership: Own the help center as a strategic asset. You write and maintain support documentation that serves multiple audiences - end users, IT admins, and Microsoft Partners - and you keep it accurate, searchable, and genuinely useful. You identify gaps from ticket trends and close them before they become repeat contacts. Your knowledge base is a reflection of the standard you hold yourself to.

Ticket Operations & Trend Reporting: Maintain a clean, well-prioritized queue and track the metrics that matter: volume by category, resolution time, escalation rate, recurring issues, and customer satisfaction. You report regularly to Customer Success and leadership, surface emerging product issues to Engineering and Product, and use data to continuously raise the bar on support quality.

Onboarding & Implementation Support: Partner with Customer Success during client onboarding to ensure new law firms and legal teams are properly configured in the Microsoft environment - correct permissions, integrations, and a seamless first experience with LawToolBox. A well-executed setup means fewer support contacts, a better client relationship, and a stronger foundation for retention.

Do you have experience in Ticketing system technical support?, You bring deep Microsoft 365 expertise, a process-builder's mindset, and the communication skills to meet every type of user where they are - whether that's a managing partner who just wants it fixed, or an IT admin who wants to understand exactly why it broke., * 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, not just end users - you can go deep technically and hold your own in a collaborative troubleshooting session
• Proven ability to own a support function independently: building and refining workflows, maintaining documentation, and driving quality without being managed to it
• Strong written and verbal communication - you write clear, professional support documentation and can explain a complex issue to a frustrated attorney 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 - you understand the stakes of their environment and bring the appropriate sense of urgency
• Process-oriented and self-directed - you see what needs to be built, build it, and hold yourself accountable to the outcome

Nice to Have

• 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

Pulled from the full job description

• Tuition reimbursement
• Parental leave
• 401(k)
• Health insurance
• 401(k) matching
• Vision insurance
• Dental insurance, Our technology is second only to our people. Our Team events are imagined, organized, and led by new hires. Team building is core to who we are and what makes our culture. Get a front row seat to an industry leading company that is paving the way for SaaS based companies that can scale and rapidly grow.

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.

Pay: $70,000.00 - $80,000.00 per year, * 401(k)

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

LawToolBox is on a mission to transform the way legal professionals practice law. We are 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. Our platform gives attorneys something they've never had before: matter-specific AI that understands their work. It surfaces insights from Outlook threads, co-authored Word documents, and Teams and Zoom transcripts so lawyers can get up to speed fast, work smarter, and focus on the work with the biggest impact.