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Director Information Technology

Western Springs, Illinois, 60558, United States
September 24, 2018

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708-***-**** Western Springs, IL PROFILE

Results-oriented, collaborative Information Technology executive with nearly 20 years of Infrastructure Operations experience. Strategic thinker and relationship-builder with a passion for the use of technology to improve and innovate the user experience, outcomes and company goals. Hands-on leader with a broad, deep knowledge of various platforms, operating systems and applications. Certifications and Core Expertise

Cisco Certified Network Associate (CCNA) IT Data Analytics

VMware Certified Administrator VNX Certified SAN Administrator

ITIL Foundations Certification SIEM

Certified Citrix Administrator Hyper converged Technology


Azure Cisco Switches and Firewalls

Project Management Site Recovery Manager (SRM)

VOIP All scripts Connect R Certified Administrator

SDLC Avamar Backup Certification

Vulnerability Management IT Mergers & Acquisitions

Microsoft Certified System Engineer (MCSE) for

Windows Server 2000,2003,2008

Risk Management

Budgeting, Planning and Forecasting



Director Infrastructure

Leading team of 24 IT professional with 3 direct reports, Network Manager, Server/Storage manager Service Desk manager.

Lead redesign and implementation of new global datacenters Canada, US.

Designed and lead on the fly build and conversion of end of life infrastructure (500 plus servers) to new infrastructure with zero downtime.

Redesigned enterprise WAN using SD-Wan technology.

Implemented DRAAS for real-time disaster recovery.

Implemented enterprise level cloud IP phone system in US and Canada.

Designed and implemented enterprise service desk.

Negotiated 4M Microsoft EA.

Implemented cloud/hybrid for storage and application design.

Advanced level of building SLA’s within the business and staff.

Built “critical situation” processes within IT to maintain service to the business. PSAV, Schiller Park, IL 2016 – 2017

Director, Infrastructure and Application Services

Team leadership responsibilities for seven direct reports.

Defined and managed a $7M capex/opex budget for a $1.9B global company.

Reduced Data Center footprint by 60% using hyper-converged technology, Azure and Amazon AWS.

Project Manager of data center globalization project; led team of 12 across 3 countries.

Led migration of CRM to on premise.

Designed and implemented IT merger and acquisition policies and procedures using ITIL methodology. CRAIG CYPRESS Page 2

Created and maintained strategic partnerships to support infrastructure vision.

Collaborated with senior leadership and business areas to determine technology needs and priorities.

Focused on remaining current on industry best practices and trends.

Developed 3–5 year infrastructure strategy to save $1M.

Built Disaster Recovery site and introduced real-time high availability for core applications (Oracle, Exchange, and A/D).

PRONGER SMITH MEDICAL CARE, Tinley Park, IL 2009 – 2016 Director, Information Technology, 2012 – 2016

Responsible for all technical aspects of $100M, 70-provider, multiple-location health care facility, reporting to CEO.

Developed, maintained and executed five-year strategic technology plan.

Led, managed and mentored 12-member technical staff with full P&L responsibility of $2M budget.

Ensured technical strategies aligned and supported company goals.

Identified, evaluated, negotiated, and contracted with and maintained relationships with 50 technology vendors.

Collaborated with department directors to ensure workflow efficiency.

Led infrastructure design and installation for new Allscripts Electronic Medical Record (EMR) system.

Implemented All Scripts EMR and PM system, Orchard LIS, VOIP/switch infrastructure, NextGen EMR for Ophthalmology, ICD 10 with charge passing.

Developed mobile secure platform to enable doctors to share data.

Built and maintained 70 interfaces into EMR.

Responsible for patient portals: Follow My Health and NextGen.

Partnered with BlueCross BlueShield (BCBS), University of Illinois Circle, and Rush University Medical Center to establish a local HIE; one of the first medical centers to send patient data to HIE. Network Systems Manager, 2009 – 2012

Supported company growth through the technology expansion to new 40,000 sq. ft. facility.

Architected WAN connection for three campuses.

Designed and implemented two CX240 Sans and one VNX San with 150tb of data.

Led design of a three-facility, centralized Picture Archiving and Communication System


Designed and implemented Disaster Recovery solution with real-time failover.

Built three VMWare farms and 20 Citrix servers.

Upgraded mail system to Exchange 2010.

Refreshed and replaced entire switch infrastructure.

Installed companywide wireless network (Meraki). MARSH MCLENNAN/CSSTARS, Chicago, IL 2006 – 2009

Senior Systems Administrator

Led migration of 48 servers from Windows 2003 to Windows 2008.

Implemented Xerox DocuShare 6.0 worldwide.

Responsible for requirements gathering, solution evaluation, selection and architecture design for implementation of DocuShare.

Developed, standardized and communicated procedures for end users.

Designed and developed Configuration Management solution for client customization to STARS product using DocuShare.

Led Chicago Disaster Recovery Program with IBM center in Boulder, CO.

Designed and implemented enterprise McAfee ePolicy Orchestrator.

Administered 300 Windows servers supporting 35,000 users from over 1,000 clients worldwide.

Administered 58 servers Citrix 4.0 Presentation Server Farm running the STARS PE Risk Management product.

Implemented enterprise monitoring tools including HP SIM server, IP-Sentry and Servers Alive. CRAIG CYPRESS Page 3

Implemented VMware ESX Servers with 100 virtualized servers. AMSTED INDUSTRIES INCORPORATED, Chicago, IL 2004 – 2006 Network Administrator

Primary Sarbanes Oxley IT compliance officer.

Led requirements gathering, research, purchase and roll-out of Laser Fiche Document imaging solution.

Built corporate intranet using Cold Fusion and intranet connections.

Installed Cisco wireless access and Cisco VOIP phone system.

Administered company-wide WAN, wireless network, VPN, PAL, Remote Email, and RPC.

Supported and maintained Great Plains, FDC and XRT applications.

Administered 13 Windows 2003 servers running internal applications for Legal, Treasury and Human Resources.

Researched, purchased and administered Ecora Patch Management Software.

Purchased and installed Backup Exec 10.0 with overland tape unit.

Built and maintained Citrix servers.

Held Budget/P&L responsibility.

STYLECLICK/MVP.COM, Chicago, IL 2000 – 2003

Operations Engineer

Implemented e-commerce Web farm of 100 servers that produced $30M in sales per year.

Achieved uptime in excess of 99.7% for websites in 2001.

Implemented Servers Alive and Dotcom Monitors to ensure reliability.

Dotcom-Monitored test sites across the US every three minutes, 24/7.

Implemented 24/7 team coverage to handle and resolve issues.

Built and maintained five e-commerce sites and seven portals.

Built virtual directories and implemented code on all servers via script-based tools.

Migrated Web farm from NT to Windows 2000; ran in mixed mode for legacy applications.

Lead Engineer for installation of Unity Mail outbound e-mail service, which sent direct e-mail campaigns to 1M recipients daily.


B.A. in Interdisciplinary Studies, Governors State University, University Park, IL

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