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vCISO Cybersecurity Professional with 25+ years of experience delivering enterprise-scale solutions for Fortune 500 companies. I help organizations navigate complex technology challenges, whether it’s adopting AI, securing systems, migrating platforms, or scaling operations. I bring a strategic mindset paired with hands-on technical expertise to every engagement. Key areas of expertise include: • Cybersecurity & Risk Management (CISSP, CISM certified) • Cybersecurity & Artificial Intelligence (AAISM certified) • Generative AI (ChatGPT, Claude, CustomGPTs, private LLM deployments, AnythingLLM, RAG pipelines) • Microsoft 365 & GSuite Administration (setup, automation, security, and onboarding) • Identity & Access Management (Okta, SSO, MFA) • Security Audits, Patch Management, and Incident Response • Large-Scale IT Project Management • IT Mergers & Acquisitions • Team Management and IT Leadership • Cloud Services (AWS, Azure) U.S.-based and available for ongoing consulting or focused project work. If you’re looking to modernize your tech stack, adopt AI securely, or untangle a messy IT environment with security, resilience, and best practices at the core I’m here to help.

Your Google Workspace environment has security gaps you probably don't know about yet. I'm a Google Workspace specialist with nearly a decade of experience across SMB, enterprise, and FedRAMP-regulated environments. I help business owners and IT leads fix the things that keep them up at night, excessive super admin access, missing MFA, AI tools connected to the wrong accounts, backdoor access from former employees, and domain sprawl. My engagements are milestone-based and fixed-price. You approve each phase before I proceed. No surprises, no runaway hours. What I do: GWS security audits — super admin reduction, OAuth app enumeration, SPF/DKIM/DMARC Identity hardening — YubiKey MFA, dedicated admin accounts, custom roles OU architecture and Shared Drive governance SAML SSO + JIT provisioning (replacing broken SCIM setups) AI governance — safely deploying Gemini and Claude without exposing super admin scope Onboarding/offboarding automation via Google Chat chatbot (no super admin required) Apple Business Manager + MDM for device fleets Advanced GAM for bulk operations and auditing Who I work with: Fast-growing SMBs that scaled quickly and now realize their GWS environment hasn't kept pace with the business. Companies about to deploy AI tools who want guardrails in place first. Anyone who's had a security incident, or wants to avoid one. My background: SADA Systems, Meta (Senior GWS SME), Salesforce (FedRAMP High), and several Google Cloud partners. I know what enterprise-grade GWS administration looks like, and I bring that to SMB engagements at a fraction of the cost. All work performed remotely. Off-hours scheduling available to minimize disruption to your team. Ready to start? Send me a message or book a 30-minute consultation call.

With over a decade in IT and a specialization in Jamf and mobile device management, I deliver top-notch expertise to streamline your deployments and automation processes. 🥇Expert-Vetted ✅ Highest earnings & rating for Jamf Freelancer ✅ 100+ Jamf Pro deployments ✅ 60+ Intune deployments ⚙️ Zero-Touch Deployments: Expert in macOS setups with DEPNotify & Jamf Connect Notify ⚙️ Advanced Scripting: Enhance Jamf workflows with custom scripts ⚙️ Jamf Connect & SSO Integration: Seamless workflows with Okta, Entra ID, and GSuite ⚙️ Custom Scripting & pkg Creation: Tailored solutions for your unique needs 💼 Okta SSO | 💼 Entra ID SSO | 💼 Google Workspace Federation ⏱ Full-time Independent Freelancer 🏢 Supporting deployments and automation for 5 large Jamf MSPs. 🗣 Communication is key – I prioritize clear and consistent communication to ensure project success. A diverse Systems Engineer with 11+ years of experience in developing and maintaining IT systems, and 10 years of experience in mobile device management. Technical expertise spreads across server and backup administration, cloud security, software support, asset management, vendor management, and customer support. Specializes in saving man-hours and money for the enterprise.

Misconfigurations, shadow identities, and unsecured AI pipelines silently raise breach odds. I partner with business owners to close those gaps fast! What I’ll Deliver • Cloud-native hardening – Entra ID Conditional Access, AWS IAM least-privilege, GCP VPC SC, Microsoft Defender & Purview tuning • AI security & governance – Threat modeling for LLM/agentic systems, secure Vertex AI/Bedrock pipelines, TRiSM-aligned policies • Compliance-ready architecture—ISO 27001, SOC 2, HIPAA evidence packs, Zero-Trust roadmaps • Incident preparedness—24-hour containment playbooks, forensic workflows, automated Sentinel/Chronicle detections Proven Impact • 70 % cut in high-risk privileges across multi-cloud estate • Inbox placement boosted from 60 % to 95 via SPF/DKIM/DMARC • ISO 27001 audit pass in six weeks—saving $40K in outside fees Want me to walk you through the three quickest wins I already see? Message me What my clients say: Top rated : "Best investment I made on Upwork, Ray is quick, thoughtful, organized and made this project SO easy. He's incredibly communicative and so on top of it. 10/10 "Ray did an excellent job solving some email delivery issues for us. He was extremely timely and his communication was consistent and clear. Definitely recommend Ray!" Microsoft 365 Security | Azure Security | Cloud Security Consulting | ISO 27001 Implementation | SOC 2 Readiness | Google Workspace Security | Email Deliverability | SPF | DKIM | DMARC | Microsoft Intune | Conditional Access | Microsoft Defender for Endpoint | Risk Assessment | Vulnerability Assessment | Compliance Consulting

As a skilled IT professional with over five years of experience, I specialize in system administration for MSP's, cloud services, and technical support. My expertise includes managing and securing IT infrastructures, automating processes, and providing top-tier support to ensure seamless operations. Key Expertise: • System Administration: Expert in Active Directory, Windows Server, and Hyper-V management. • Cloud Services: Leading cloud migrations, integrating with Azure AD, and managing AWS and Google Cloud. • Technical Support: Providing tier 2 and tier 3 support, resolving complex issues, and using tools like NinjaRMM and Zendesk. • Automation and Scripting: Proficient in PowerShell for efficient task automation. • Backup and Recovery: Deploying and managing Veeam Data Protection for data integrity. Why Work with Me? I deliver high-quality, reliable IT solutions tailored to your needs. My collaborative approach ensures I understand your challenges and goals, providing the best outcomes. Let’s streamline your IT operations and drive your business growth together.

My name is Temidayo Frank Obasoyen. I am a Microsoft 365 Enterprise Administrator, Microsoft Security Administrator Associate, Messaging Administrator Associate, Microsoft Teams Administrator Associate, Azure Security Engineer Associate. I help organizations set up Microsoft 365 tenants and provide worldwide Microsoft 365 Technical Support to IT managers, IT directors, Head of IT, CTO, and CEOs of organizations globally. I support hybrid and cloud-only Microsoft 365 deployment for the following regions: EMEA, NOAM, and APGC clients. I have experience creating technical architecture documents and SOP creation for operation. I have experience work daily on incidents, problems, and service requests under the direction of an Infrastructure Specialist. I have experience working with a team and help provide technical suggestions related to tickets. I have experience collaborating with Internal and customers for troubleshooting incidents and adhere to critical incident procedures. I have experience communicating with customers on project status reports and dashboards, meeting agendas and minutes, and executive information. I have a Windows 11 Pro PC with the latest updates installed, 16 GB RAM, Core i7, 500 GB HDD with no 3rd-party antivirus software installed and 11th generation. I am fluent in English and with excellent chat skills. I have a work environment conducive to the job (with internet speeds greater than 70 MBs). I have a decent headset/mic for customers to hear me. The following are my experience with Microsoft Office 365 but not limited to them: • Strong understanding of day-to-day functionality in Office 365 services like Microsoft Teams, OneDrive for Business, Exchange Online, and Active Directory • Supports Microsoft Office 365 Exchange Online users using MS Office Outlook 2016 and OWA • Installation and Activation of Office Applications O365 channels and Patching deployment • Mailbox management like Mailbox permission, delegation, quota management, mail tracking, and mail transport rule creation/modification • Experience in handling migration issues from on-premises to cloud • Troubleshoot issues related to Mail-flow, Shared Mailbox, Distribution List, User Mailbox, Anti-spam, Anti-malware, Security and Compliance • Experience in managing Hybrid environments, Exchange Online Protection, DirSync/ADFS Environment • Managing Identities and Synchronization between the Microsoft Cloud and the On-Premises Environment. • Good understanding of DNS, Hybrid Email Routing, Email Tracking, SMTP/ Application Mail Relay, Backup and Restore, Disaster recovery concepts • Exchange Online, Azure Active Directory, Azure AD synchronization • Administration of Cloud services using GUI and Microsoft PowerShell, Azure Module PowerShell, Exchange Management Shell, SharePoint Management Shell, Skype for Business Management Shell, and Microsoft Teams Management Shell. • Managing Identities in Microsoft Azure Active Directory • Managing Cloud Security and Data with Retention policies, DLP (Data loss prevention) policies, Litigation hold & eDiscovery. • Exchange Online administration (user & permission, transport rules, spoofing & phishing prevention, configuration, and setup) • Real-time experience on Microsoft Office 365, SharePoint Online, PowerApps, Power Automate, and SharePoint Framework • Managing user accounts and user licenses through the Office 365 admin center in the Microsoft cloud platform or Windows PowerShell cmdlets • Perform scripting administration tasks and reporting using PowerShell or other scripting technology developing scripts for automating processes within the environment • Configure and implement large scale Active Directory environment •Good understanding and work experience with various mobility solutions •Troubleshooting skills on Outlook 2013 and 2016 •Good knowledge of Office 365 Groups Implementation, Security, Troubleshooting and Event Log Administration •Evaluate symptoms and determine the root cause of complex client issues reported by various stakeholders and end-users •Experience on Migration Tools like Quest Migration or any other third-party tool for Inter and Intra Exchange Organization migration for Exchange 2003/2007/2010/2013 and Office 365. •Troubleshooting experience on Outlook and Office • Excellent customer service skills. • Microsoft Office 365 Deployment and Administration • Microsoft SharePoint Online/OneDrive For Business, Exchange Online/Outlook, Skype for Business/Teams Deployment, support, and Administration • Managing Identities and Synchronization between the Microsoft Cloud and the On-Premises Environment. • Managing Cloud Security and Data with the use of Retention policies, DLP (Data loss prevention) policies, Litigation hold & eDiscovery • Exchange Online administration (user & permission, transport rules, spoofing & phishing prevention, configuration, and setup) • Exchange Online security-related technologies (SPF, DMARC, DKIM, EOP, OME, ATP)