Senior Systems Engineer

Cprime, a Goldman Sachs and Everstone Capital portfolio company, is more than just a full-service consulting firm – we are your strategic partner for driving innovation and agility in your business. Cprime is trusted around the globe to provide strategic and technical consulting, coaching, and training to businesses leading their industry in digital transformation. With over two decades of experience, we have honed our expertise to help organizations adapt at the speed the market demands. In a world where every business is reliant on software, it’s time to embrace change, or be left behind.

We’re more than consultants; we’re passionate problem solvers on a mission to help your organisation thrive in a technology-driven world. We’ve created a dynamic environment with strong innovation where growth is encouraged and diversity is celebrated. We continuously challenge each other to work smarter and adapt new ideas. Our Cprimers are given the flexibility to work, opportunities to collaborate, and have fun along the way.

Job Summary

We are seeking a skilled and detail-oriented Senior Systems Engineer with hands-on experience in Google Workspace and Microsoft 365, including expertise in migrating from G Suite to Microsoft 365. The ideal candidate will have a strong background in managing cloud platform migrations, ensuring data integrity, minimal downtime, and a seamless user experience throughout the transition.

In this role, you will collaborate closely with cross-functional teams to plan, execute, and support the end-to-end migration process. Your focus will be on enabling a smooth transition while maintaining system performance, user productivity, and adherence to security best practices.

• Lead end-to-end email migrations from Google Workspace (G Suite) and other third-party platforms to Office 365, ensuring minimal downtime and data integrity.
• Perform comprehensive Office 365 administration and configuration, including Exchange Online, SharePoint, Teams, and OneDrive.
• Integrate cloud-based anti-spam and encryption solutions to secure inbound and outbound mail flow.
• Utilize PowerShell scripting to extract detailed logs, perform health checks, automate tasks, and generate compliance reports.
• Execute eDiscovery, enable Data Loss Prevention (DLP), and maintain security compliance using the Microsoft 365 Security & Compliance Center.
• Resolve Directory Synchronization (DirSync) issues using Azure AD Connect, and manage user object sync between on-prem AD and Azure AD.
• Create and manage Transport Rules, Legal Holds, Email Archiving, Retention Policies, and Journaling to meet regulatory and business requirements.
• Monitor and retrieve tenant audit logs, manage mailbox deletions, configure alerts, and perform backup and restoration of user email accounts.
• Support multiple email migration methods (IMAP, Cutover, and G Suite migration).
• Collaborate with Microsoft Support to troubleshoot and resolve escalated Office 365 issues.
• Perform data migrations including emails, calendars, contacts, and files (e.g., Gmail to Outlook, Google Drive to OneDrive/SharePoint).
• Configure and optimize core Microsoft 365 services to meet business and user collaboration needs.
• Use leading migration tools such as BitTitan, CloudM, and Microsoft Migration Manager to automate and streamline transitions.

• Create, modify, and manage user accounts, groups, and OUs in accordance with organizational policies.
• Monitor and troubleshoot directory replication, authentication failures, and login issues.
• Administer role-based access controls (RBAC) across messaging and collaboration platforms.
• Support Exchange Hybrid configurations, ensuring proper federation between on-prem AD and Exchange Online.
• Audit directory changes, monitor Kerberos tickets, and analyze logs using Event Viewer and third-party tools.
• Provide support for Single Sign-On (SSO) integrations across Office 365, Active Directory, and SaaS applications.
• Assist in domain controller maintenance, patch management, and schema upgrades as part of infrastructure upkeep.

• Manage user provisioning, licensing, and access permissions in Microsoft 365 and Azure Active Directory.
• Configure and enforce security & compliance policies, including email filtering, DLP, and MFA.
• Provide post-migration support and troubleshoot user issues to ensure a smooth operational experience.
• Training & Documentation:
• Develop user guides and deliver training sessions to support a smooth transition to Microsoft 365.
• Maintain clear documentation of migration procedures, configurations, and best practices for future use.

• Engage with stakeholders to gather requirements and provide regular updates during migration projects.
• Coordinate with IT support teams to ensure ongoing system stability and optimal performance.

• 6+ years of Proven experience managing messaging administration, IT infrastructure, Active directory or system administration in Google Workspace and Microsoft 365 administration 
• Strong knowledge of Microsoft 365 services like Exchange, SharePoint, OneDrive, Teams.
• Manage and maintain Active Directory (AD) and Azure Active Directory (AAD) environments to ensure accurate identity management and secure authentication.
• Implement and manage Group Policy Objects (GPOs) to enforce security, desktop, and messaging configurations across the enterprise.
• Configure and troubleshoot Azure AD Connect for synchronization between on-premises AD and Microsoft 365/Azure AD.
• Perform regular AD health checks, backups, and restore operations to ensure high availability and business continuity.
• Collaborate with the security team to implement and monitor multi-factor authentication (MFA) and conditional access policies.
• Proficiency in PowerShell scripting for automating administrative tasks for Microsoft 365 administration.
• Understanding of DNS, SMTP, IMAP, and related email protocols. (SPF, DKIM, DMARC).
• Experience with third-party migration tools (like BitTitan or CloudM).
• Excellent troubleshooting and communication skills.
• Excellent problem-solving skills and attention to detail.

• Strong organizational and project management skills.
• Ability to work independently and in a team environment.
• Clear communication skills to work with both technical and non-technical stakeholders.

• Relevant certifications (e.g., Microsoft 365 Certified: Messaging Administrator Associate - Enterprise Administrator Expert, Microsoft 365 Messaging Administrator.
• Knowledge of Google Workspace APIs and tools.
• Familiarity with email security tools (e.g., Proofpoint, Mimecast) is a plus.

• Bachelor’s degree in computer science, Information Technology, or a related field.

What We Believe In

At Cprime we believe in facilitating social justice action internally, in industry, and within our communities.  We believe part of our mission is to expand the minds, hearts, and opportunities of our Cprime teammates and within the broader community to include those who have been historically marginalized.

Equal Employment Opportunity Statement    

Cprime is an equal-opportunity employer that is committed to diversity and inclusion in the workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by federal, state, or local laws.