Senior System Engineer (Chicago)

JOB SUMMARY

The Senior MS Systems Engineer administers, engineers, secures, automates, and supports Microsoft 365 and related enterprise applications. The role handles advanced troubleshooting, configuration, integrations, testing, deployment, lifecycle management, and service improvement across collaboration, identity, endpoint management, security, compliance, automation, analytics, and AI services.

Working with IT, Security, Legal, Human Resources, business owners, and vendors, the engineer translates business and control requirements into reliable solutions, clear documentation, and effective support. Periodic evening or weekend work may be required for incidents, planned changes, releases, and major platform updates.

ESSENTIAL JOB FUNCTIONS

Microsoft 365 Platform Engineering and Administration

• Administer Exchange Online, SharePoint Online, OneDrive, Microsoft Teams, Microsoft 365 Apps, Teams Phone where deployed, Microsoft Intune, and related admin centers.
• Manage users, groups, shared resources, licenses, service plans, roles, application registrations, enterprise applications, and delegated access using least-privilege practices.
• Support Microsoft Entra ID, including authentication methods, MFA, Conditional Access, identity protection, access reviews, Privileged Identity Management, external identities, and single sign-on integrations.
• Plan, test, document, deploy, upgrade, and retire Microsoft 365 configurations, feature releases, patches, integrations, and approved enterprise applications through change management, including pilot groups, rollback plans, deployment reporting, and technical documentation.
• Use PowerShell, Microsoft Graph, REST APIs, and automation runbooks to standardize administration, collect operational data, and reduce manual effort.

Automation, Analytics, and AI

• Support Power Apps, Power Automate, Power Pages, Dataverse, environment governance, data policies, connectors, solutions, service accounts, and application lifecycle management.
• Partner with reporting teams on assigned Power BI and Microsoft Fabric administration or integrations, including workspaces, gateways, semantic models, permissions, refresh operations, and troubleshooting.
• Support Microsoft 365 Copilot, Copilot Studio, agents, connectors, usage reporting, deployment controls, data readiness, and responsible AI governance with Security, Legal, and business stakeholders.
• Automate recurring support, provisioning, reporting, compliance, and monitoring activities with appropriate approvals, logging, and separation of duties.

Operations, Support, and Service Management

• Own escalated Microsoft 365 and enterprise application incidents through diagnosis, root-cause analysis, remediation, and closure.
• Monitor service health, message center notices, audit and sign-in logs, endpoint and security telemetry, queues, jobs, integrations, and capacity; communicate impact and recovery status.
• Maintain incident, request, problem, and change records along with knowledge articles, diagrams, standards, procedures, inventories, and recovery documentation.
• Coordinate with Microsoft and third-party vendors using logs, timelines, reproduction steps, and technical evidence; deliver training and partner with the Service Desk to improve first-contact resolution and escalations.
• Participate in product evaluations, proofs of concept, licensing and roadmap reviews, disaster-recovery exercises, and continuous service improvement.

Team and Professional Responsibilities

• Build effective cross-functional relationships and follow security, privacy, change-management, access-control, vendor-risk, and application-implementation policies.
• Mentor team members and contribute reusable standards, scripts, and documentation.
• Manage assigned work independently, communicate risks and dependencies early, and complete tasks accurately and professionally.

SKILLS, EDUCATION, AND EXPERIENCE

Required

• Bachelor's degree in Information Technology, Computer Science, Management Information Systems, or a related field, or equivalent relevant experience.
• 3 to 5 years of progressively responsible enterprise experience administering or engineering Microsoft 365.
• Hands-on experience with Exchange Online, SharePoint Online, OneDrive, Teams, Microsoft Entra ID, Microsoft 365 Apps and administration, and Microsoft Intune.
• Proficiency with PowerShell and practical experience with Microsoft Graph, APIs, structured data, and automation.
• Understanding of IAM, RBAC, least privilege, Conditional Access, MFA, endpoint compliance, security monitoring, data protection, retention, and eDiscovery.
• Advanced troubleshooting skills across logs, authentication and token flows, network dependencies, client configuration, service health, and root-cause analysis.
• Strong communication, documentation, customer service, prioritization, and cross-team coordination skills; ability to participate in after-hours support and planned changes.
• Working knowledge of SQL Server, SQL queries, reporting, data integration, and enterprise application support.

Preferred

• Microsoft certification such as Microsoft 365 Administrator Expert, Identity and Access Administrator Associate, Endpoint Administrator Associate, Security Operations Analyst Associate, Information Protection and Compliance Administrator Associate, or Power Platform Administrator Associate.
• Experience with Defender XDR, Microsoft Sentinel, Windows Autopilot, Azure Automation, Logic Apps, Power Platform governance, Microsoft Fabric or Power BI administration, Microsoft 365 Copilot, and Copilot Studio.
• Experience with ITIL practices, enterprise change management, incident and problem management, security frameworks, audit evidence, and regulated or publicly traded environments.
• Experience managing financial applications and vertical market SaaS applications.

In return for your excellent skills and abilities, we offer a comprehensive benefits package including: medical, dental, and vision plans, a generous 401(k) employer match, and paid vacations, holidays, and sick time.

We invite you to visit our web site at for additional information regarding our exceptional resort communities.

As an Equal Opportunity Employer, we welcome and thank all applicants.

Estimated compensation for this position:

Annual Salary: $100,000 - $125,000 + Bonus