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Microsoft 365 Cloud Tech Lead

Optiver · Chicago, IL · Enterprise

Posted Oct 2, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you removed hybrid complexity or legacy patterns from a Microsoft 365 tenant. What did you cut and how did you do it safely?

What they are checking: Their track record with systemic simplification, which the posting calls out directly.

Tell me about a global rollout you led from design through adoption. What did you do to get people to actually use it?

What they are checking: Full ownership of change through adoption, not just technical deployment.

What would you do

Microsoft 365 here is treated as critical production infrastructure. What changes about how you operate it when you take that seriously?

What they are checking: Whether they bring production-grade discipline like change control, observability and rollback to collaboration tooling.

You propose an architectural change and a peer in another office disagrees during validation. How do you work through it?

What they are checking: Ability to work in a distributed peer group where decisions are validated rather than dictated.

A Microsoft service degradation hits during market hours. What do you do in the first thirty minutes?

What they are checking: Incident leadership when the root cause sits with a vendor and the business impact is immediate.

About the work

Walk me through a global Exchange Online mail flow design you owned, including routing, connectors and security controls.

What they are checking: Real ownership of enterprise messaging architecture at global scale, not just admin tasks.

How do you design SharePoint and Teams information architecture, permissions and lifecycle management so they don't sprawl?

What they are checking: Governance thinking that keeps content platforms usable and secure over years, not months.

How have you used CI pipelines and code to manage Microsoft 365 configuration changes?

What they are checking: Whether they treat platform configuration as code, which the team says is central to its work.

Describe a self-healing automation you built. What did it detect, and what did it fix on its own?

What they are checking: Practical automation skill and judgment about what is safe to remediate without a human.

How would you approach Entra ID conditional access and device access policies for traders who need fast, reliable mobile access?

What they are checking: Balancing identity security with the availability needs of a trading workforce.

What do you monitor to know the Microsoft 365 platform is healthy before users start reporting problems?

What they are checking: Observability mindset and knowing which signals predict user impact.

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The full job description

As published by Optiver.

Optiver's Global Enterprise Clients team owns the global Microsoft 365 platform — collaboration, messaging, identity, and mobile access — that our entire worldwide workforce runs on every day. It's treated as critical production infrastructure, not a back-office system. You'll join an established, distributed group of Microsoft 365 Cloud Technical Leads spread across our global offices, operating a single global platform, in a hands-on role with real architectural influence: engineers here design solutions, validate them with peers, and implement them directly. Observability, continuous capability uplift, CI-driven change, and self-healing automation are central to how we keep this platform reliable at scale. What you'll do • Set direction and design standards for our global Microsoft 365 platform across collaboration, messaging, identity, and device access • Lead arcitectural decisions end-to-end — design, peer validation, implementation — driving change from inception through global rollout and adoption, with full ownership of global deliverables • Drive systemic simplification, reducing legacy patterns, hybrid complexity, and accidental architecture • Define and operate our collaboration and content platforms, including information architecture, governance, permissions, and lifecycle management • Own enterprise messaging architecture, including global mail flow, routing, hybrid integration, and coexistence • Architect identity and access foundations, covering authentication models, access control, lifecycle management, and hybrid integration • Define and own mobile access architecture for iOS and Android • Architect the Azure foundations that support Microsoft 365, identity, automation, monitoring, and remediation • Treat observability as non-negotiable — design deep monitoring, alerting, and telemetry, using tooling that surfaces systemic risk and informs decisions • Own BAU operations for the platform, including incidents, degradations, change execution, and continuous improvement • Design, implement, and operate self-healing automation that closes the loop between detection, remediation, and prevention • Build and maintain production-grade automation using industry-standard tooling, including AI-assisted development where it accelerates delivery without reducing ownership What you'll get You'll join a culture of collaboration and excellence, surrounded by curious thinkers and creative problem-solvers. Motivated by a passion for continuous improvement, you'll thrive in a supportive, high-performing environment alongside talented colleagues, collectively tackling some of the toughest challenges in the financial markets. In addition, you'll receive: • The opportunity to work alongside best-in-class professionals from over 40 different countries • Highly competitive compensation package, including a global profit-sharing pool and performance-based bonus structure • 401(k) match up to 50% • Comprehensive health, mental, dental, vision, disability, and life coverage • 25 paid vacation days alongside market holidays • Extensive office perks, including breakfast, lunch and snacks, regular social events, clubs, sporting leagues and more Who you are • 7+ years' experience as a senior Microsoft 365 engineer or architect, owning and operating mid-to-large enterprise platforms • Deep hands-on expertise in SharePoint Online platform engineering and Exchange Online mail flow, including hybrid scenarios • Strong command of identity and access architecture, including Entra ID / Azure AD and Entra ID Connect (Conditional Access, tenant restrictions, B2B, RBAC, enterprise apps, service principals, app proxy) • Proven track record simplifying complex hybrid environments • Strong PowerShell engineering skills and comfort with Microsoft Graph, Azure CLI, Terraform, and GitHub-based Infrastructure-as-Code workflows • Highly proficient with Log Analytics and KQL • Comfortable designing and operating Azure resources — policies, subscriptions, workbooks, storage accounts, VNETs, Traffic Manager • Experience defining and owning MDM/Intune policy and configuration for iOS and Android, across both BYOD and corporate-managed settings • Comfortable debating architecture with senior peers and backing decisions with data • A clear, trusted communicator and technical mentor who raises the bar for others • Thrives in a high-ownership, continuous-improvement environment, with demonstrated experience owning initiatives end-to-end — from conception through implementation, rollout, skills transfer, and sustained operation • Able to autonomously run and deliver global projects across a distributed team and time zones, and drive change without heavy oversight Experience that helps • Tertiary qualification in Computer Science or a related field; recent (~3 years) Microsoft certification in Azure or M365 • Background in an enterprise environment with heavy Microsoft platform adoption — Financial Services, Logistics & Transportation, Resources & Mining, Big Tech/SaaS/Cloud, or as a Managed Service Provider or Microsoft integration partner — particularly in large-user-base, campus-style environments • Prior experience at Principal Consultant or Architect level, in presales design and engineering, or in project management • Exposure to Microsoft 365 Defender and threat protection, Purview or advanced compliance tooling, Logic Apps/Power Automate/workflow platforms, or building and maintaining AI Copilot agents • Experience in a trading firm or other ultra-low-tolerance production environment Who we are At Optiver, our mission is to improve the market by injecting liquidity, providing accurate pricing, increasing transparency and stabilising the market no matter the conditions. With a focus on continuous improvement, we prioritise safeguarding the health and efficiency of the markets for all participants. As one of the largest market making institutions, we are a respected partner on 100+ exchanges across the globe. Our differences are our edge. Optiver does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, or other legally protected characteristics.  

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