Summary
Overview
Work History
Education
Skills
Early Career Roles
Technical Leadership Expertise
Ai Leadership And Enterprise Modernization
Timeline
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Justin Cain

Phoenix

Summary

Dynamic leader with expertise in Microsoft 365 and Azure modernization, spearheading Cain Technologies' cloud security and identity architecture. Achieved 100% audit readiness with HIPAA-aligned security programs. Proven strategic planner with a focus on Zero Trust methodology, driving impactful MSP architecture design and automation processes. Skilled in vendor management and delivering technology roadmaps.

Overview

26
26
years of professional experience

Work History

Founder / CEO & MSP Architect

Cain Technologies, LLC
Phoenix
01.2024 - Current
  • Founded modern MSP focused on cloud security, identity architecture, and endpoint management using Microsoft 365, Azure/Entra ID, Intune, and Zero Trust methodology.
  • Designed full MSP operating model including service catalog, support workflows, automation pipelines, compliance baselines, tenant governance frameworks, and device lifecycle management standards.
  • Key Achievements:
  • Built a complete standardized Intune and Autopilot onboarding pipeline.
  • Created Cloud Kerberos Trust rollout model for hybrid identity environments.
  • Designed comprehensive MSP security baseline using CIS + Microsoft baselines.
  • Developed PowerShell automation toolkit for onboarding, compliance, and identity cleanup.
  • Built identity-first architecture for SMB and healthcare clients.
  • Delivered fractional-CIO advisory, budget planning, and technology roadmap creation.

CIO / COO

Cain Health, Inc.
Phoenix
01.2007 - Current
  • Executive leader overseeing IT operations, cloud transformation, security, compliance, vendor management, and enterprise systems for a healthcare revenue cycle firm.
  • Directed technology strategy, software development, remote-access architecture, and regulatory compliance across multi-location operations.
  • Key Achievements:
  • Led full modernization from on-prem legacy systems to Microsoft 365 and Azure services.
  • Designed HIPAA-aligned security programs with complete audit readiness.
  • Built secure virtualization strategy using VMware Horizon.
  • Implemented DR/BCP and secure backup architecture.
  • Directed development of healthcare payment analytics and adjudication tools.
  • Introduced identity governance, MFA, Conditional Access, and improved compliance controls.

Interim CIO (Contract)

Wilcox & Flegel
05.2025 - 07.2025
  • Brought in as interim CIO to stabilize systems, modernize identity and security posture, and produce a comprehensive modernization roadmap for a multi-site industrial company undergoing organizational transition.
  • Impact:
  • Performed identity hardening across hybrid/on-prem/Entra environments.
  • Delivered cloud readiness and modernization roadmap.
  • Improved endpoint compliance and operational visibility.
  • Implemented rapid security controls to reduce immediate operational risk.

Lead Internet Developer

Insight Enterprises
Tempe
01.2002 - 01.2007
  • Led enterprise-scale software development teams responsible for global e-commerce platforms and large-scale procurement systems.
  • Designed and integrated high-volume distributed applications supporting millions of daily users.

Principal / Solutions Engineer

Cspace Interactive
01.2001 - 01.2004
  • Developed and implemented integration solutions that improved client system functionalities.
  • Executed comprehensive client requirement analysis to customize solutions for specific needs.
  • Provided ongoing troubleshooting and support, ensuring optimal system performance.
  • Managed multiple projects simultaneously, consistently meeting tight deadlines.
  • Designed websites, portals, and large-scale web applications for various clients.
  • Created secure database schemas for safe user data storage.

Internet Developer

Cyclone Commerce
01.2000 - 01.2001

Designed and implemented websites for marketing and restricted access customer support using PHP and Oracle.

Executed Oracle database design and implementation to enhance data management capabilities.

Developed e-commerce solutions, including SSL and credit card processing systems.

Created back office integration website for CRM and accounting functionalities.

Engineered secure software download processes to protect sensitive information.

Designed XML application interfaces for CRM and accounting systems to streamline operations.

Customized, configured, and maintained PHP/Apache environments using Zend framework.

Education

B.S. - Physics

University of Arizona
Tucson, AZ
05-2000

Skills

  • CIO and COO leadership
  • Strategic planning
  • Microsoft 365 expertise
  • Azure modernization
  • Identity security
  • Conditional access
  • Zero trust architecture
  • MFA enforcement
  • Intune governance
  • Autopilot architecture
  • Security compliance
  • HIPAA regulations
  • CIS benchmarks
  • SOC2 controls
  • Cloud migration strategies
  • Hybrid identity design
  • Azure AD integration
  • Cloud Kerberos trust
  • Enterprise infrastructure management
  • Networking solutions
  • Virtualization technologies
  • VMware expertise
  • AVD deployment
  • Disaster recovery planning
  • Incident response strategies
  • Risk management practices
  • MSP architecture design
  • Standardization initiatives
  • Automation processes
  • Software development leadership
  • SDLC execution
  • Vendor management strategies
  • Budgeting skills
  • IT procurement strategy
  • Microsoft cloud solutions
  • Microsoft 365 governance
  • azure architecture
  • automation pipelines

Early Career Roles

  • Cspace Interactive, Principal / Solutions Engineer, 01/01/01, 12/31/04
  • Cyclone Commerce, Internet Developer, 01/01/00, 12/31/01

Technical Leadership Expertise

Microsoft 365 tenant governance, Azure/Entra ID architecture, administrative roles, privilege hardening, Conditional Access policies, Azure MFA, identity lifecycle management, Intune deployments, security baselines, compliance policies, catalog profiles, Windows Autopilot (white-glove, pre-provisioning, hybrid join), Defender for Endpoint integration, app protection policies, Zero Trust implementation, Cloud Kerberos Trust rollout, Windows Hello for Business, hybrid/modern authentication, SSO/SAML/OAuth integrations, Defender Suite, ASR rules, identity governance, endpoint compliance reporting, encryption policy enforcement, secure network design, firewall policy structure, VPN and conditional access segmentation, Windows Server (AD, DNS, DHCP, GPO), virtualization (VMware, Hyper-V), Azure IaaS, networking, LAN/WAN topology, backup and disaster recovery, cloud migration tooling, PowerShell (advanced scripting), Bash, SQL, PHP, .NET, ColdFusion, automation pipelines and provisioning frameworks

Ai Leadership And Enterprise Modernization

  • Leads AI adoption programs integrating Microsoft Copilot and Azure OpenAI.
  • Builds AI-enabled governance, compliance, and risk management frameworks.
  • Uses AI automation to accelerate provisioning, remediation, documentation, and reporting.
  • Applies predictive analytics to IT operations, resource planning, and cloud optimization.

Timeline

Interim CIO (Contract)

Wilcox & Flegel
05.2025 - 07.2025

Founder / CEO & MSP Architect

Cain Technologies, LLC
01.2024 - Current

CIO / COO

Cain Health, Inc.
01.2007 - Current

Lead Internet Developer

Insight Enterprises
01.2002 - 01.2007

Principal / Solutions Engineer

Cspace Interactive
01.2001 - 01.2004

Internet Developer

Cyclone Commerce
01.2000 - 01.2001

B.S. - Physics

University of Arizona
Justin Cain