Open to opportunities

Raymond Maldonado

@raymondmaldonado

Senior IT director specializing in cloud-first infrastructure, cybersecurity, and enterprise operations for multi-site organizations.

United States

Message

What I'm looking for

I’m looking to lead enterprise IT operations and modernization—cloud-first infrastructure, strong cybersecurity, and practical governance—while building teams that improve service delivery, control costs, and deliver reliable outcomes across multi-site environments.

I’m a senior IT director focused on planning, developing, and implementing technology that simplifies business processes and drives organizational goals. I’ve managed end-to-end IT operations for a 600+ person organization across 15+ locations, leading user lifecycle management, system access, and multi-platform integrations while partnering across vendors and internal teams.

I led a full transition to a cloud-first environment, migrating infrastructure to Microsoft Azure, file management to SharePoint Online, and email to Microsoft 365—maintaining business continuity throughout. On the security side, I authored an AI policy, ran annual penetration testing with no significant vulnerabilities, implemented Duo MFA, deployed Mobile Device Management, introduced SentinelOne EDR, and enforced application installation controls with AutoElevate. I also modernized the digital workplace with Zoom, Zoom Phone, and DocuSign, and streamlined provisioning with Microsoft Intune and Autopilot.

Experience

Work history, roles, and key accomplishments

Director of Information Technology Ops

Graham Windham

Jan 2018 - Jun 2026 (8 years 5 months)

Led IT operations for a 600+ person organization across 15+ locations. Directed cloud migration to Microsoft Azure and M365, built the organization's first AI governance policy, managed cybersecurity programs including EDR and MFA, led MSP RFPs, and oversaw infrastructure, helpdesk, and multi-site technology deployments.

Azure Azure AD Microsoft Office Microsoft 365 IT Infrastructure Vendor Management Team Leadership Disaster Recovery IT strategy Endpoint management AI Governance

Assistant Director of IT Operations

Graham Windham

Jan 2011 - Jan 2018 (7 years)

Supported multi-site rollouts of digital workplace and financial/HR platforms, partnering with stakeholders to deploy and adopt new systems. Helped maintain a security baseline through security awareness training and phishing simulations.

Docusign Change Management Stakeholder Management Zoom Zoom Phone DocuSign Accounts Payable Systems Expense Management Platforms Performance Management Systems Security Awareness Training Phishing Simulations

Network Administrator Supervisor

Graham Windham

Jan 2008 - Jan 2011 (3 years)

Supervised network administration and helpdesk operations, coordinating IT support to improve reliability and user outcomes. Partnered with vendors and internal teams to support secure, compliant integrations across locations.

Network Administration Helpdesk Management Team Leadership IT Support Operations Vendor Management Access Permissions Management Security Conscious Deployment Troubleshooting Incident Management Process Improvement Help Desk Management

Network Administrator

Graham Windham

Jan 2003 - Jan 2008 (5 years)

Provided day-to-day network administration and technical support, maintaining reliable operations and resolving user issues. Assisted with maintaining and integrating network infrastructure and related technologies.

Network Administration Technical Support Troubleshooting Systems Administration Endpoint Support Network Monitoring Device Configuration Incident Response