Senior IT Administrator & Internal Tooling Lead

Written By Rachel Yockey

Entegrata is an Indianapolis-based legal technology company transforming how law firms manage and use their data. Our data lakehouse platform, built on the Microsoft Azure stack, helps firms centralize disparate data sources securely and turn them into production-ready analytics through a proprietary legal data model and pre-built Power BI reports. Founded in 2023, we’re a fast-growing, venture-backed team on a mission to be the data platform of choice for the legal industry.

The Role

We’re looking for an experienced Senior IT Administrator & Internal Tooling Lead to wear two hats. First, you’ll run our day-to-day IT operations and be the go-to person for every employee’s technology needs across a mixed Windows and macOS fleet. Second, when you’re not in the queue, you’ll lead the buildout of our internal tooling: quality-of-life automations, internal integrations, and the systems that make the whole company faster.

A core part of that second hat is building and maintaining our internal uses of Claude and the company OS we’re standing up on top of it: the internal platform, workflows, and automations that connect our tools and put AI to work for the team. This is the high-leverage, build-something work that compounds over time.

This is a hands-on, individual-contributor role. One moment you’re helping an employee set up their laptop and licenses; the next you’re scripting an automation in PowerShell, wiring up a Slack Workflow, or building an internal Claude integration. You’ll do the day-to-day work yourself and partner closely with our security team on access, identity, and compliance: security guides the guardrails, and you keep IT running smoothly and the team productive.

This is a hybrid position based in Indianapolis, IN, with three days a week in our Keystone Crossing office.

What You’ll Do: IT Operations

  • Provide IT help desk support for all employees: fielding requests, troubleshooting hardware and software issues, and resolving problems quickly and patiently.

  • Own laptop and hardware procurement and the full device lifecycle: sourcing, ordering, imaging, deploying, tracking, and retiring equipment.

  • Set up and manage software licenses and accounts for employees, including assigning and tracking Microsoft 365 and other application licenses.

  • Manage device deployment, configuration, and lifecycle through Microsoft Intune across Windows and macOS fleets.

  • Administer Microsoft Entra ID (Azure AD) identity, including Entra group management, user provisioning, and access assignments.

  • Configure and maintain Microsoft Entra Global Secure Access (GSA) for secure remote access and VPN connectivity.

  • Own and manage the Apple business and user management portal

  • Own vendor management end to end: onboarding new tools, managing seats and licenses, and handling payments, renewals, and procurement.

  • Maintain and support Microsoft Azure infrastructure and core IT services.

  • Partner with the security team to implement and maintain access, identity, and compliance requirements in day-to-day operations for alignment with our SOC 2 and other security compliance regulations.

What You’ll Do: Internal Tooling & DevEx

  • Lead the buildout and maintenance of our internal uses of Claude: integrations, internal assistants, and AI-powered workflows that make the team more productive.

  • Help architect and build the company OS: the internal platform, automations, and connective tissue we’re building on top of our AI and SaaS stack.

  • Develop automation and tooling using Bash, PowerShell, and Python to streamline routine operations and eliminate manual work.

  • Build cross-tool workflows and integrations using GitHub Actions, Slack Workflows, and Azure Logic Apps.

  • Identify quality-of-life improvements across the org and ship them: the small automations and internal tools that quietly remove friction.

  • Maintain, document, and harden internal tooling so it stays reliable and secure as the company scales.

What Success Looks Like (First 12 Months)

By month 3:

  • You have a solid working understanding of our fleet, Intune/Entra configuration, and the support queue, and the help desk is running smoothly with fast, reliable response times.

  • Device lifecycle, licensing, and vendor renewals are under control, with no surprises.

  • You’ve mapped the highest-friction manual processes across the company and have a clear point of view on the first automation and internal Claude tooling wins.

By month 6:

  • The help desk runs on documented runbooks, with routine requests automated or self-service where it makes sense.

  • You’ve shipped your first internal Claude integrations and a handful of quality-of-life automations that the team is actively using.

  • The first building blocks of the company OS are in place, connecting our core tools and workflows.

By month 12:

  • IT operations are stable, well-documented, and low on firefighting.

  • Internal Claude tooling is something the team relies on daily, with measurable time saved across the org.

  • The company OS has real infrastructure: connected workflows across our stack that are owned, documented, and maintained.

  • You’ve built credibility internally as the person who both keeps IT running and makes the whole company faster.

What We’re Looking For

  • 5+ years of IT management experience, with deep expertise in Microsoft Azure and Microsoft Intune.

  • Proven experience running IT help desk / end-user support for an organization.

  • Experience with hardware procurement and device lifecycle management.

  • Experience managing software licensing (e.g., Microsoft 365 license assignment and tracking).

  • Hands-on experience with Microsoft Entra ID, including Entra group management and user provisioning.

  • Experience administering Global Secure Access or comparable VPN / secure remote access solutions.

  • Proven experience managing both Windows and macOS environments.

  • Strong vendor management experience, including provisioning, licensing, and handling payments and renewals.

  • Proficiency scripting in Bash and PowerShell; working proficiency in Python.

  • Hands-on experience building automations and integrations with tools like GitHub Actions, Slack Workflows, and Azure Logic Apps.

  • Comfort working with APIs and integrating SaaS tools, including connecting third-party services into custom workflows.

  • A practical awareness of security fundamentals as they apply to endpoints, identity, and access.

  • A builder’s instinct: you spot friction and ship the tool that fixes it.

  • Excellent troubleshooting skills and strong, patient communication with non-technical employees.

Nice to Have

  • Experience building with LLM APIs or AI agent tooling (e.g., the Claude API, prompt engineering, or internal AI assistants).

  • Prior experience standing up internal platforms, developer tooling, or “company OS” style systems.

  • Some exposure to compliance or security practices (e.g., access reviews, Conditional Access, or frameworks like SOC 2 or ISO 27001): a plus, not a requirement.

  • Relevant certifications (e.g., Microsoft Certified: Azure Administrator, Endpoint Administrator, or Identity and Access Administrator).

What We Offer

  • Competitive startup salary

  • Medical, dental, and vision insurance

  • 401k plan with match

  • Unlimited Paid time off

  • Company holidays

  • Professional growth and development opportunitie

If you’re ready to shape the future of legal data and work with a high performing development team, apply here!

Rachel Yockey
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