Windows Server Administrator Jobs in Indiana (NOW HIRING)

AI and Security Administrator 
Location: Hybrid - Indianapolis, IN

Alera Group was founded in 2017 and has grown to become the 14th largest broker of U.S. business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, and Financial Services. With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service..

• Make an Impact: Your work supports businesses and individuals in protecting what matters most.

• Grow With Us: We invest in development, mentorship, and long-term career growth.

• The Collaborative Way: We believe in accountability, teamwork, and shared success across all offices and lines of business.

• National Strength. Local Heart: Scale, resources, and expertise — with relationships that feel personal.

Position Summary:
Reporting to the Director of Technology, the AI and Security Administrator is an Exempt position that will use specialized knowledge and skills obtained through education, experience, specialized training and/or certification to support, maintain and improve Vital Incite’s operations.  The AI and Security Administrator is responsible for enabling and securing Microsoft 365 Copilot and related AI capabilities in a HIPAA-regulated environment. This role designs and manages AI agents, helps users get value from Copilot through prompt coaching and support, and implements controls to protect sensitive data using Microsoft Purview and Microsoft security tooling. In addition, the role supports core IT operations including Windows Server administration and cloud administration across Azure and Google Cloud Platform (GCP).  This is a hands-on position requiring a strong balance of security mindset, practical AI enablement, and systems administration.

Essential Responsibilities:

• Design, build, test, and maintain AI agents for business workflows (e.g., policy Q&A, ticket triage, report generation, onboarding support) using Microsoft 365 Copilot extensibility tools
• Configure agent data sources and access boundaries (SharePoint, OneDrive, Teams, approved repositories) to ensure least-privilege and HIPAA-safe usage.
• Provide end-user training, office hours, and 1:1 support to improve Copilot adoption and safe usage.
• Monitor agent and Copilot usage patterns and recommend improvements (quality, reliability, compliance alignment).
• Implement and manage controls to protect PHI and sensitive business data used with Copilot and across Microsoft 365.
• Ensure Purview policies align with business workflows (minimizing friction while maintaining compliance).
• Administer core Microsoft 365 security and identity features, such as:  Entra ID identity and access management, Conditional Access and MFA policy enforcement (as applicable), Role-based access control and privileged access practices
• Support secure configuration of Teams, SharePoint, OneDrive permissions, external sharing, and guest access policies.
• Administer Windows Server environments including:
  • Active Directory (on-prem and/or hybrid), Group Policy, DNS/DHCP, file services
  • Patch management and vulnerability remediation
  • Backup/restore operations and disaster recovery readiness
  • Endpoint security best practices and troubleshooting
  • Assist in the management of system upgrades, communications and documentation of system design.
• Maintain system documentation (diagrams, runbooks, standard operating procedures).
• Support infrastructure and security tasks in Azure and GCP, including: 
  
  • Identity integration, networking basics, storage permissions, and security configurations
  • VM and managed service administration relevant to company workloads
  • Logging/monitoring and cost-awareness recommendations
• Participate in architecture and vendor discussions related to cloud services and security posture.
• Participate in IT ticket triage and issue resolution, balancing project work with daily operations. 
• Maintain clear documentation and change tracking for security policies, AI agents, and infrastructure changes. 
• Contribute to continuous improvement—automation, scripting, standardization, and proactive risk reduction.
• Assures that the Organization maintains all aspects of effective technology security, while allowing efficient/effective product delivery.  This includes assisting with maintaining SOC 2, Type 2 and HITRUST certifications that include HIPAA considerations and addressing all third-party stakeholder security audits.
• Manage security of file transfer processes including user accounts and encryption.
• Support end user hardware/software/user accounts.

Benefits:
Alera Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more.

Work Model:
This role is Hybrid at our Indianapolis office. In office Mondays & Wednesdays. Work from home on Tuesday, Thursday, and Friday. 

Professional Development – Alera Group Academy

At Alera Group, growth isn’t left to chance. Through Alera Group Academy, we provide structured development opportunities designed to help you expand your expertise and build a meaningful career.

You’ll have access to:

• Role-specific learning paths

• Leadership development programs

• Technical and compliance training

• Industry certifications and continuing education support

• Peer learning and knowledge-sharing communities

Whether you’re deepening your technical expertise or preparing for leadership, we’re invested in helping you grow.

We're an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.

Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.

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