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Karolina O'Connor
Severn, MD  •  (410) 643-8419  •  karolina@nerdycyberchick.com  •  linkedin.com/in/karolina-o-connor
Cloud & Identity Engineer / Microsoft 365 Administrator
Professional Summary

Microsoft 365 and Cloud Infrastructure specialist with 7+ years managing security posture, identity, and operations across ~30 client environments. Deep hands-on experience in Entra ID, Conditional Access, MFA troubleshooting, Exchange Online mail flow, Intune/MDM enforcement, and Microsoft Defender investigation. Known for resolving complex, multi-layered issues end-to-end and translating security requirements into practical, user-ready policy.

Core Skills
  • Identity & Access Management: Entra ID, Conditional Access, MFA, sign-in/session troubleshooting, hybrid identity, SSPR
  • Microsoft 365 Administration: M365 admin center, Exchange Online, Teams, SharePoint/OneDrive, licensing
  • Security Operations: Microsoft Defender for Office 365, SOC alert triage, EDR rule tuning, threat investigation & remediation
  • Email & Mail Flow: connectors, transport rules, deliverability troubleshooting, DMARC/DKIM/SPF implementation
  • Endpoint & MDM: Microsoft Intune (Windows & macOS), compliance policies, security baselines, Apple Business Manager
  • Automation: PowerShell (Exchange/Graph API), scripting for administration and reporting
  • Networking & Perimeter: SonicWall VPN/firewall, segmentation, structured cabling, LAN/WAN troubleshooting
  • Governance: SharePoint permissions, external sharing, guest access governance, data lifecycle
Professional Experience
Senior Systems & Infrastructure Engineer
Mar 2023 – Present
Smart Computing Solutions, Inc. (MSP) — Severn, MD
  • Own Microsoft 365 and cloud operations across ~30 client organizations, accountable for stability, security posture, and end-to-end issue resolution.
  • Build and maintain Entra ID configurations including Conditional Access; troubleshoot MFA, sign-in failures, and session/access issues across multiple tenants.
  • Administer Exchange Online connectors, mail flow rules, and delivery troubleshooting; support hybrid identity as clients transition cloud-first.
  • Investigate and respond to Microsoft Defender for Office 365 security alerts; perform SOC triage and threat remediation end-to-end.
  • Manage Intune/MDM policies across Windows and macOS; develop scripts for app delivery and configuration enforcement.
  • Drive email security hardening: DMARC/DKIM/SPF implementation, phishing/spoofing response.
  • Design SharePoint/OneDrive permissions, external sharing governance, and execute file migrations.
  • Administer SonicWall environments (VPN, firewall rules); network-level troubleshooting and structured cabling projects.
  • Deployed Copilot 365 in a small M365 environment; developed Copilot readiness/adoption plan for a nonprofit (~40 users).
Systems Engineer
Aug 2018 – Sep 2020
Livanta, LLC — Annapolis Junction, MD (Healthcare / Federal)
  • Administered Windows Server, Active Directory, and core infrastructure in a regulated healthcare environment.
  • Managed Hyper-V/VMware virtualization, patching cycles, and backup/DR operations.
Education
Bachelor of Science in Cybersecurity — Full Sail University
2020 – 2023
🏆 Valedictorian ⭐ Master's Achievement Award
Certifications
  • Kaseya Certified Expert — IT Glue (Oct 2024, expires Oct 2026)
  • Kaseya 365 Endpoint / OPS Certifications
  • Microsoft Certified — MCSA: Windows Server, MCITP: Enterprise Administrator, MCP, MCTS (multiple)
Cloud & M365 Identity & Access Security & Threat Infrastructure
Cloud & Identity Engineer · MSP Lead · Annapolis, MD

I Build &
Secure Networks.
Then document them too.

Senior engineer managing cloud infrastructure, identity, and security across 30+ organizations. Microsoft 365, Entra ID, Intune, SonicWall — if it runs on a network, I own it end to end.

Microsoft 365 Entra ID Conditional Access Intune + ABM Copilot 365 SonicWall macOS Threat Hunter DMARC / DKIM / SPF
30+
client organizations
7+
years experience
100+
environments managed
BS
cybersecurity · valedictorian
Active

Threat investigation & remediation — I dig in, trace the path, contain the damage, and clean up the mess. End to end, every time.

Microsoft Copilot 365 — deployed in production and building readiness plans for nonprofit environments.

core stack
Cloud & Identity
Microsoft 365Entra ID Conditional AccessExchange Online SharePoint / OneDriveCopilot 365 Teams Admin
Endpoint & MDM
Microsoft IntuneApple Business Manager Windows AutopilotCompliance Policies Security BaselinesmacOS MDM
Security & Threat
Threat HuntingIncident Remediation SOC TriageEDR / Datto AV DMARC/DKIM/SPFEmail Security Defender for O365
Networking & Infra
SonicWallSecure Edge VPN LAN / WANSwitching WirelessStructured Cabling Windows ServerHyper-V
Automation
PowerShellGraph API Exchange Online PSBash / Shell
MSP Operations
Autotask PSADatto RMM IT GlueRocketCyber Capital PlanningSOPs Project Lead
portfolio
Cloud & M365 Administration
Microsoft 365 & Cloud Operations
Day-to-day ownership of M365 tenants — Exchange, SharePoint, Teams, licensing, mail flow, and everything in between across ~30 client organizations.
Exchange Online Mail Flow & Domain Protection
  • Configured connectors and transport rules for complex multi-tenant routing scenarios
  • Resolved deliverability failures, NDR analysis, and hybrid mail flow issues
  • Implemented DMARC/DKIM/SPF from scratch across dozens of domains; remediated misconfigured records causing spoofing and spam failures
Exchange OnlineTransport RulesDMARC/DKIM/SPFDeliverability
SharePoint & OneDrive Governance
  • Designed and administered SharePoint permissions and external sharing policies across education and nonprofit tenants
  • Executed large-scale file migrations using PnP PowerShell and SPMT
  • Resolved SharePoint storage crises and OneDrive sync/licensing issues at scale
SharePointOneDrivePnP PowerShellGovernance
Microsoft Copilot 365 Deployment & Readiness
  • Deployed Copilot 365 in a live M365 environment (12 users); managed licensing and onboarding
  • Developed a Copilot readiness and adoption plan for a nonprofit (~40 users), including data governance and sensitivity label readiness
Copilot 365M365 LicensingReadiness Planning
Identity & Access Management
Entra ID & Zero Trust Identity
Hands-on Entra ID administration across hybrid and cloud-native environments — Conditional Access, MFA, sign-in troubleshooting, and identity lifecycle management.
Conditional Access Policy Design & Troubleshooting
  • Built and maintained Conditional Access policies across multiple client tenants with varying compliance requirements
  • Resolved MFA registration failures, legacy auth blocks, and sign-in/session policy conflicts
  • Balanced security posture with usability — minimized user disruption while enforcing Zero Trust access controls
Entra IDConditional AccessMFAZero Trust
Intune MDM — Windows & macOS Policy Deployment
  • Managed compliance and device configuration policies for Windows and macOS endpoints across 30+ environments
  • Deployed apps, enforced security baselines, and built enrollment workflows using Apple Business Manager and Windows Autopilot
  • Troubleshot Intune enrollment failures, policy conflicts, and compliance reporting gaps
IntuneWindowsmacOSABMAutopilot
Hybrid Identity & Active Directory Migrations
  • Supported hybrid AD environments during cloud-first migrations; resolved Kerberos and Group Policy failures
  • Performed AD metadata cleanup, DNS decommission, and domain controller migrations
Active DirectoryHybrid IdentityDNSKerberos
Security & Threat Response
Threat Hunting & Incident Remediation
End-to-end security incident response — from initial alert to full remediation. I trace the path, contain the damage, and close the gap.
Credential Spray & Email Compromise Response
  • Investigated and contained a credential spray attack on a client email environment; traced attacker activity through Defender audit logs
  • Remediated compromised accounts, reset sessions, and implemented targeted Conditional Access to prevent recurrence
  • Coordinated DKIM/DMARC hardening and domain cleanup following the incident
Incident ResponseDefender for O365BECDMARC
EDR Tuning & SOC Alert Management
  • Tuned EDR alert suppression rules to reduce false-positive ticket noise across MSP environments
  • Triaged RocketCyber and Datto EDR alerts; escalated and contained confirmed threats
  • Isolated compromised endpoints and coordinated remediation across client sites
EDRSOC TriageRocketCyberDatto AV
Email Security Hardening (Multi-Client)
  • Deployed DMARC/DKIM/SPF from scratch across dozens of domains in GoDaddy, Cloudflare, and other DNS providers
  • Identified and removed orphaned MX records, legacy selectors, and conflicting SPF includes
  • Reduced spoofing exposure and improved deliverability across all treated environments
DMARCDKIMSPFCloudflareDNS
Infrastructure & Networking
Network Builds & Infrastructure Projects
Physical and logical infrastructure — SonicWall, structured cabling, server builds, and everything that makes the network actually run.
SonicWall TZ470 RMA & Network Rebuild
  • Managed SonicWall TZ470 RMA swap, firmware upgrade, and full network cutover with minimal downtime
  • Reconfigured VPN tunnels, firewall rules, and VLAN segmentation post-swap
  • Validated connectivity and resolved subnet routing issues following the migration
SonicWallVPNFirewallVLAN
Hyper-V / NTP Infrastructure Remediation
  • Diagnosed and resolved Hyper-V time sync / NTP misconfiguration causing nightly Kerberos authentication failures
  • Reconfigured W32Time service hierarchy on domain controllers; eliminated recurring event log errors
Hyper-VWindows ServerNTPKerberos
Structured Cabling & Site Buildouts
  • Delivered structured cabling, patch panel termination, and switch infrastructure for commercial office buildouts
  • Designed and documented network topology for MSP client environments
Structured CablingLAN/WANNetwork Design
experience
Senior Infrastructure / Systems Engineer
Smart Computing Solutions, Inc. MSP
March 2023 – Present
  • Own and operate Microsoft 365 and cloud infrastructure across ~30 client organizations — accountable for stability, security posture, and end-to-end resolution.
  • Administer Entra ID identity configurations: Conditional Access, MFA, sign-in troubleshooting, and hybrid identity support.
  • Manage Exchange Online mail flow, connectors, transport rules, and deliverability; implement DMARC/DKIM/SPF across client domains.
  • Perform threat investigation and incident remediation end-to-end — from Defender alert to full containment and cleanup.
  • Deploy and manage Intune/MDM policies for Windows and macOS; Apple Business Manager and Autopilot workflows.
  • Administer SonicWall environments, VPN tunnels, and firewall rules; deliver structured cabling and network buildouts.
  • Develop SOPs, runbooks, and documentation (IT Glue / NetworkGlue) for 100+ managed environments.
M365Entra IDIntune macOS + ABMSonicWallThreat HuntingDMARC/DKIM/SPF
Systems Engineer
Livanta, LLC Healthcare / Federal
August 2018 – September 2020
  • Administered LAN/WAN infrastructure, Windows Server, Active Directory, and enterprise backups in a regulated healthcare environment.
  • Managed virtualization platforms (Hyper-V/VMware), patching cycles, and disaster recovery operations.
  • Supported internal IT operations and infrastructure upgrades for a federal healthcare contractor.
Windows ServerActive DirectoryHyper-VVMwareHealthcare IT
Karolina O'Connor
Cloud & Identity Engineer · Senior MSP Lead
I build secure infrastructure, own hard problems end to end, and actually document what I do. 30+ clients, 7+ years, zero shortcuts.
education
Bachelor of Science — Cybersecurity
Full Sail University
2020 – 2023
🏆 Valedictorian ⭐ Master's Achievement Award
certifications
MCSA: Windows Server
Microsoft Certified Professional (MCP)
MCITP: Enterprise Administrator
MCTS: Windows Server (multiple)
Kaseya Certified Expert — IT Glue
Kaseya 365 Endpoint / OPS
certifications & badges
IT Glue Certified Expert
Certified Expert — IT Glue
Kaseya University
Issued Oct 2024 · Expires Oct 2026
Kaseya 365 Endpoint KCA
Certified Administrator — Kaseya 365 Endpoint
Kaseya University
Issued Oct 2025 · Level 2
Microsoft Certifications
MCSA: Windows Server
MCP — Microsoft Certified Professional
MCITP: Enterprise Administrator
MCTS: Windows Server (multiple)
contact

Available for cloud infrastructure, M365 administration, identity engineering, and security consulting engagements. Let's talk.

Email
karolina@nerdycyberchick.com
LinkedIn
linkedin.com/in/karolina-o-connor
Resume
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Website
nerdycyberchick.com