Open to opportunities

John Winfrey

@johnwinfrey

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I am an IT executive with 30+ years leading transformative IT, cloud, and security initiatives.

United States

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What I'm looking for

I am seeking senior IT leadership roles where I can lead cloud and security transformations, mentor technical teams, drive operational excellence, and deliver high-value projects in mission-driven organizations.

I am a purpose-driven IT executive with over three decades of experience architecting and delivering enterprise IT strategies and programs. I have led large-scale projects exceeding $15 million, driven Azure migrations, implemented NIST/CMMC security controls, and delivered measurable outcomes including $60K in annual telecom savings.

I build and mentor high-performing technical teams, implement ITIL-based operations, and design accessibility solutions like Technology Accessibility Labs. My leadership has produced results such as an 80% reduction in critical issues, 99.9% system uptime, 50% faster incident resolution, and substantial improvements in team health and customer satisfaction.

Experience

Work history, roles, and key accomplishments

Current

Director of Information Technology

Current

Ardmore Enterprises

Jun 2024 - Present (1 year 3 months)

Led IT service delivery and HIPAA-compliant operations, established a Technology Accessibility Lab, and implemented an MDM solution; led a telecommunication migration that reduced operating costs by $60,000 per year.

IT Service Delivery HIPAA Mobile Device Management Vendor Management Team Leadership Security

Sr. Service Delivery Manager

ManpowerGroup Public Sector

Oct 2021 - Sep 2023 (1 year 11 months)

Orchestrated IT service delivery and led an Azure migration, reducing critical issues by 80%, cutting incident resolution time by 50% and increasing end-user satisfaction by 70%. Implemented Active Directory and Intune, ensured NIST 800-171/CMMC compliance, and replaced legacy VPN with Palo Alto secure access.

Azure Migrate Active Directory CMMC ITIL Intune Project Management

Sr. Customer Success Account Manager

Microsoft Corporation

Sep 2000 - Sep 2020 (20 years)

Served as strategic advisor and technical lead for large government clients, negotiating a 102% increase in services for the EPA and contributing to five consecutive years of over 30% account growth. Led onboarding and mentoring programs, supported O365/AD/Exchange migrations, and coordinated emergency response for critical incidents.

Customer Success Account Management IT strategy ITIL O365 Migration Crisis Management Mentoring Ad Exchange

Senior Associate/Project Manager

Abacus Technologies

Oct 1996 - Sep 2000 (3 years 11 months)

Managed information security and network projects totaling $15,000,000, led a team of 18 engineers, and implemented 15 LANs supporting federal clients including GSA and the Department of Veterans Affairs.

Project Management Information Security LAN Implementation Team Leadership Network Architecture Federal Contracting

Network System Administrator

Internal Revenue Service

Nov 1992 - Oct 1996 (3 years 11 months)

Installed and administered Windows NT/95 networks supporting over 800 users, supervised a 20-person support staff, and served as technical lead on the IRS-New Carrollton network design team.

Network Administration System Administration Team Supervision LAN Deployment Technical Training Troubleshooting

Education

Degrees, certifications, and relevant coursework

Lions World Services for the Blind

Certificate, Systems Analysis & Systems Design

1991 - 1992

Completed Systems Analysis & Systems Design coursework from 1991 to 1992.

Dale Carnegie

Training, Computer Programming and Management Strategies

1985 -

Completed Computer Programming Training and Management Strategies coursework in 1985.

Tulsa Junior College

Certificate, Business Accounting

1985 -

Completed Basic Business Accounting coursework in 1985.

Business Management Certifications

Professional Certifications, Information Technology / Cybersecurity

Activities and societies: Certifications: Cybersecurity Maturity Model Certification (CMMC); Microsoft Certified Systems Engineer (MCSE) - Windows 2000/2003; Information Technology Infrastructure Library (ITIL); Microsoft Certified Professional (MCP); Microsoft Desktop OS; Microsoft Security Technologies; Microsoft Windows Server; Microsoft Office Framework (MOF) Trainer; Microsoft Solutions Framework (MSF).

Holds multiple professional IT and security certifications including CMMC, MCSE, ITIL, MCP, MOF Trainer, and MSF.