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Calvin D.

Calvin D.

Microsoft365 Security & Compliance | GCC | Google Workspace | AI&Azure

I help organizations secure, migrate, and manage Microsoft 365 and Azure environments, with a specialty in regulated industries where compliance is not optional. Healthcare companies under HIPAA, federal contractors pursuing CMMC Level 2, and firms working toward NIST 800-171 are the clients I have helped to achieve results. Over 20 years in IT, the last several focused exclusively on Microsoft security, cloud infrastructure, and AI implementation. I work across Business, GCC, and GCC High tenants, which means I understand the differences in licensing, feature availability, and configuration that trip up generalists. I can help with M365 migrations from IMAP and Google Workspace, or other cloud platforms. I handle tenant provisioning, mailbox migrations, SharePoint and OneDrive data management, DNS cutover, and user training. Whether you are moving from Gmail and Google Drive to Microsoft 365, consolidating multiple tenants, or upgrading from Business to GCC High, I can plan the migration to protect data integrity and minimize downtime. Google Workspace administration and migrations. I manage Google Workspace environments and can help with transitioning organizations from Google to Microsoft 365 when business or compliance requirements demand it. I will handle the full lifecycle: audit of the existing Google environment, map mailboxes and Drive structures to their M365 equivalents, execute the migration, and decommission the old tenant. Azure infrastructure and security. I can configure and manage Azure virtual machines, networking, and resource groups for organizations that need cloud compute alongside their M365 environment. I will build and enforce Azure Policy assignments to maintain compliance guardrails across subscriptions, ensuring resources are deployed only in approved regions, with required tagging, and within approved configurations. Regarding organizations adopting Windows 365 Cloud PC, I will handle provisioning, network configuration, Intune integration, and Conditional Access policies so users get a fully managed desktop experience that meets the same security and compliance standards as your physical endpoints. AI implementation and security for business environments. I can deploy and configure Microsoft Copilot across M365 apps, set up the data governance and sensitivity labels required before a safe Copilot rollout, and train teams on effective use. I can also implement AI tools like Claude and ChatGPT into business workflows, building automation, internal knowledge retrieval, and content generation systems while ensuring data stays within your compliance boundaries. If you are adopting AI and need someone who understands both the capability and the security implications, that is exactly where I operate. Security stack deployment and tuning across Defender for Endpoint, Defender for Identity, Defender for Office 365, and Microsoft Sentinel. I build detection rules, configure alerting, and make sure the tools are actually catching threats, not just installed. Intune and Entra ID for device management, Conditional Access policies, and zero trust architecture. I set up compliant device enforcement, app protection policies, and identity governance so your environment meets the frameworks your auditors care about. Purview for data classification, sensitivity labels, DLP policies, and retention. If you need to prove to an auditor that PII or CUI is being handled correctly, this is where I live. SharePoint governance, Teams provisioning and voice configuration, and Exchange Online mail flow and transport rules. I build these to scale, not just to work on day one. I have delivered projects for healthcare organizations, financial firms, government contractors, and various small businesses. I scope tightly, communicate clearly, and I am available for both project-based engagements and ongoing advisory work. If you have a compliance deadline, a migration on the horizon, an AI rollout to get right, or a security gap you need closed, send me a message with the details and I will tell you exactly how I would approach it.

🇺🇸Evanston, United States$100/hr100% JSS4.76 (3)Since Aug 2016

Earnings and projects

MRR
$40

Last 6 months ÷ 6

World#155,316 / 412k
🇺🇸Country#20,713 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $237

Total earnings
$1.4k
World#363,316 / 412k
🇺🇸Country#55,710 / 62.1k
Per project
$238

$237 in the last 6 months

World#250,924 / 412k
🇺🇸Country#40,120 / 62.1k
Projects, last 6 months
1
100% fixed0% hourly
World#128,092 / 412k
🇺🇸Country#16,472 / 62.1k
Projects in all
6

Across 7 contracts

57% fixed43% hourly
World#250,290 / 412k
🇺🇸Country#35,789 / 62.1k

Earnings, last 30 days

$1.4kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$1,400$1,420$1,440$1,460Oct 8Oct 23Nov 7

Skill rankings: Top 32% in Information Security Threat Mitigation

Ranked by MRR among everyone on Upwork with the skill.

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  8. #478Information Security1,158 freelancers · 🇺🇸 #121Top 41%