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AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.
At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.
We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.
We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD.
We are seeking a seasoned Senior Modern Workspace Engineer with deep technical expertise across the Microsoft 365 ecosystem. This is a senior-level, hands-on engineering role focused on design, implementation, troubleshooting, and Tier-3 support of enterprise Modern Workplace environments for Fortune 1000 and upper-mid-market clients.
You will act as the technical escalation point for complex issues spanning Microsoft Endpoint Manager (Intune), Azure AD/Entra ID, Windows Autopilot, Defender for Endpoint, Exchange Online, SharePoint Online, OneDrive, Teams governance, and Power Platform administration.
Responsibilities
- Architect, deploy, and optimize large-scale Microsoft 365 Modern Workplace solutions (5,000–150,000+ seats)
- Serve as final escalation point for critical production incidents involving Intune, Autopilot, Windows 365 Cloud PC, Entra ID Conditional Access, Defender for Endpoint, and Teams
- Perform advanced troubleshooting of device compliance, application deployment failures, provisioning issues, BitLocker recovery, and hybrid identity sync problems
- Design and implement enterprise-grade Conditional Access policies, Intune configuration profiles, compliance policies, and Windows Update rings
- Lead Autopilot migrations (on-prem ConfigMgr → full cloud Autopilot) and Windows 365 Cloud PC deployments
- Build and maintain PowerShell/PnP/Graph API automation for tenant-wide governance and lifecycle management
- Optimize Microsoft Teams environments (voice, meetings, governance, retention, data loss prevention)
- Integrate and troubleshoot Defender for Endpoint, Defender for Office 365, and Microsoft Purview (Information Protection, DLP, Insider Risk)
- Conduct performance and security reviews of Entra ID, SharePoint, and OneDrive configurations
- Create and deliver technical run-books, root-cause analysis reports, and proactive health assessments
- Mentor mid-level engineers and contribute to internal knowledge base and tooling
- Participate in a 24×7 on-call rotation (with generous premium on-call compensation)
- 8+ years of progressive experience in Microsoft endpoint and cloud identity management
- Expert-level knowledge of Microsoft Intune, Entra ID (Azure AD), Autopilot, Windows 365, and Co-management
- Advanced PowerShell and Microsoft Graph API scripting (automation is a daily activity)
- Proven track record resolving complex, enterprise-scale Modern Workplace incidents
- Deep understanding of Entra ID Conditional Access, MFA, identity protection, and privileged identity management
- Hands-on experience with Defender for Endpoint advanced hunting, attack surface reduction, and ASR rules
- Strong knowledge of Microsoft Teams administration (including Teams Phone / Direct Routing if certified)
- Experience with large SharePoint Online migrations, sensitivity labels, and retention policies
- Excellent communication skills and prior client-facing consulting or enterprise support experience
Why AHEAD:
Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.
We fuel growth by stacking our office with top-notch technologies in a multi-million-dollar lab, by encouraging cross department training and development, sponsoring certifications and credentials for continued learning.
USA Employment Benefits include:
- Medical, Dental, and Vision Insurance
- 401(k)
- Paid company holidays
- Paid time off
- Paid parental and caregiver leave
- Plus more! See benefits https://www.aheadbenefits.com/ for additional details.
The compensation range indicated in this posting reflects the On-Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.
AHEAD Chicago, Illinois, USA Office
401 N Michigan Ave, Chicago, IL, United States, 60611
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
