Senior Help Desk Lead – Microsoft 365 & SaaS Support

LawToolBox

Denver (CO)

Hybrid

USD 90,000 - 130,000

Full time

14 days+

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Benefits offered by this job

401(k)

401(k) matching

Dental insurance

Employee assistance program

Health insurance

Life insurance

Parental leave

Tuition reimbursement

Vision insurance

Job summary

LawToolBox in Denver seeks a Senior Help Desk Manager to own the support operation end-to-end for a demanding client base of attorneys, IT admins, and Microsoft Partners. You will drive processes, SLAs, and knowledge-base quality while resolving Tier 2/3 issues across SharePoint, Teams, Exchange, and Entra ID.

You bring 5+ years in technical support, deep Microsoft 365 expertise, and a proven ability to lead a support function independently.

Qualifications

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.
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.

Responsibilities

Own the help desk function end to end, designing workflows, escalation paths, and SLA targets.
Provide Senior-Level Technical Support across the full LawToolBox and Microsoft 365 stack: SharePoint, Teams, Exchange, Entra ID, OneDrive, and integrations.
Serve as internal and external authority on Microsoft 365, diagnosing tenant configurations and permission issues across diverse client environments.
Manage client relationships with a focus on legal and IT audiences, communicating clearly and professionally.
Diagnose and resolve client-side issues, document patterns, and develop repeatable resolution guides.
Own knowledge base content and ensure accuracy, usefulness, and easy searchability.
Track metrics for volume, resolution time, escalations, and CSAT; report to Customer Success and leadership.
Support onboarding and implementation with customers to ensure proper configuration in the Microsoft environment.