Senior Microsoft 365 Lead

The Kennedy Group; Chicago (IL); On-site; USD 140,000 - 210,000; Full time

Job summary

The Kennedy Group is seeking a senior Microsoft 365 Cloud Engineer/Architect to shape and operate a globally critical Microsoft 365 environment from Chicago. This is an end-to-end ownership role, not a general admin, accountable for the platform in production.

You will drive architecture, automation, observability and continuous improvement across a distributed team of specialists for a large-scale enterprise.

Qualifications

• The candidate must have 7+ years in senior Microsoft 365 roles, as a Lead, Architect, or Engineer in enterprise settings.
• Deep hands-on experience with SharePoint Online and Exchange Online in complex hybrid environments.
• Strong expertise in identity, access architecture and Entra/Azure AD with MFA and B2B concepts.

Responsibilities

• Define architecture and technical direction for a global Microsoft 365 platform (collaboration, messaging, identity, device access).
• Lead end-to-end architectural decisions from design through rollout and adoption across regions.
• Simplify and modernize the environment, reducing legacy tech and complex dependencies.
• Own SharePoint Online content architecture, governance, permissions, and lifecycle management.

Skills

Microsoft 365 Architecture

SharePoint Online

Exchange Online

Entra ID / Azure AD

Conditional Access

PowerShell

Microsoft Graph

Azure CLI

Terraform

GitHub Actions / IaC

Log Analytics / Azure Monitor

Intune / MDM

Hybrid Identity

Leadership & Mentoring

Stakeholder Communication

Financial Services domain knowledge

Education

Bachelor’s degree in Computer Science/Information Systems

Tools

Terraform

Azure CLI

GitHub

Log Analytics

Job description

A global technology-driven trading and financial services firm is looking to hire a senior Microsoft 365 Cloud Engineer/Architect to help shape and operate a globally critical Microsoft 365 environment.

This is not a generalist Microsoft 365 administration role. We're looking for an engineer who has owned a Microsoft 365 tenant end-to-end in a complex enterprise environment and is comfortable being accountable for the platform in production

You’ll work as part of a distributed team of senior Microsoft 365 specialists, driving architecture, automation, observability and continuous improvement across a global enterprise environment.

The Role

• Define the architecture and technical direction for a global Microsoft 365 platform spanning collaboration, messaging, identity and device access.
• Lead architectural decisions end-to-end, from solution design and peer review through implementation, global rollout and adoption.
• Simplify and modernise the environment, reducing legacy technology, hybrid complexity and unnecessary architectural dependencies.
• Own collaboration and content architecture, including SharePoint Online, information architecture, governance, permissions and lifecycle management.
• Lead enterprise messaging architecture, covering Exchange Online, global mail flow, routing, hybrid integration and coexistence.
• Design identity and access foundations, including authentication, access controls, lifecycle management and hybrid identity integration.
• Architect Azure, mobile and observability capabilities supporting Microsoft 365, including Intune, iOS/Android access, monitoring, telemetry and automated remediation.
• Drive operational excellence and automation, building self-healing capabilities and production-grade automation that improves reliability, reduces incidents and continuously enhances the platform.

Required Skills & Experience

• 7+ years' experience as a senior Microsoft 365 Engineer, Technical Lead or Architect, ideally owning large-scale enterprise platforms.
• Deep hands-on expertise in SharePoint Online and Exchange Online, including complex mail-flow and hybrid environments.
• Strong identity and access architecture experience, particularly with Entra ID / Azure AD and Entra ID Connect.
• Strong knowledge of Conditional Access, tenant restrictions, B2B, RBAC, enterprise applications, service principals and Application Proxy.
• Proven experience simplifying and modernising complex hybrid Microsoft environments.
• Advanced PowerShell engineering skills, with practical experience using Microsoft Graph, Azure CLI, Terraform and GitHub-based Infrastructure-as-Code.
• Strong experience with Azure monitoring and observability, particularly Log Analytics and KQL.
• Hands-on experience designing and operating Azure infrastructure, including policies, subscriptions, Workbooks, Storage Accounts, VNets and Traffic Manager.
• Experience with Microsoft Intune/MDM, including policy and configuration for iOS and Android across both BYOD and corporate-managed environments.
• Strong architecture, communication and leadership skills, with the ability to influence senior technical stakeholders, mentor engineers and independently deliver complex global initiatives.
• Microsoft certification in Azure or Microsoft 365.
• Enterprise environments with significant Microsoft technology adoption, particularly Financial Services, Big Tech/SaaS, Cloud, Logistics & Transportation, Resources & Mining or Managed Services.
• Previous experience at Principal Consultant, Architect or Technical Lead level.
• Experience across Microsoft 365 Defender, Purview, advanced compliance, Logic Apps, Power Automate or Microsoft Copilot/AI agents.
• Experience working within trading, financial services or other highly resilient, low-tolerance production environments.