Jason McReynolds

Senior Systems Engineer


Highly technical, customer focused, with a proven ability to lead, help customers solve problems, build solutions, and improve relationships. A passion for technology and over 20 years in IT have developed experience that includes teaching, interacting with all levels within an organization, providing quality customer service, improving process, agile transformation, working with outside vendors, and troubleshooting and solving complex technical issues. Knowledge includes infrastructure design, architecture, integration, security, BC/DR, system build/test/monitor, CI/CD, Android application development, business strategy development, process improvement, and vendor evaluation. Core competencies include Microsoft (Azure, Azure DevOps, Microsoft 365, Windows Server, IIS, Active Directory, Exchange, System Center), Linux/FreeBSD, Apache, PHP, MySQL, Android SDK (and related Android tools), Java, Git, Eclipse, VMware, Hitachi SAN, and Cisco VOIP (Call Manager). Bilingual, albeit a little rusty (English/Spanish).

Technical Summary

Systems: VMware vSphere, Hitachi USP VM and AMS 2500, Microsoft Systems Center Operations Manager, Microsoft System Center Configuration Manager, Windows Server (2012/2008/2003/2000), Windows (10/8.1/Vista/XP), Exchange Server (2010/2007/2003), Linux, FreeBSD

Hardware: Cisco routers and switches, IBM, Dell and HP servers and PC’s.

Software & Applications: Azure, Azure DevOps, Microsoft 365, Active Directory, Group Policy, PowerShell, vCenter Server, VMware Consolidated Backup, Apache, IIS, PHP, MySQL, Java, Android SDK, Eclipse, Android Studio, Git, Gradle, Hitachi Device Manager, Cisco CallManager, Cisco IPCC express, Cisco Unity, Postini, Cisco SRST, Veritas, NTbackup, Microsoft Group Policy, Visio.

Networking & Voice: DNS, WINS, DHCP, TCP/IP, SMTP, FTP, H.323, MGCP, SCCP, SIP

Previous Certifications

  • Microsoft Certified Systems Engineer (MCSE): Windows Server 2003
  • Microsoft Certified Systems Engineer (MCSE): Messaging Exchange Server 2003
  • Cisco Certified Network Associate (CCNA)
  • Cisco Unified Communications System Engineer (UCSE)
  • Certified Help Desk Analyst (Help Desk Institute)

Professional Experience

Sr. Systems Engineer, Phreesia, Portland, OR

January 2022 – Present

  • Temporarily continued duties as IT Director of Insignia Health
  • Collaborated with management to assist with the merger of Insignia Health IT with Phreesia IT
  • Continued to work on improving Insignia Health processes, procedures and security by collaborating with Phreesia resources.
  • Documented web tier server build process and scripted build and configuration of web servers.
  • Continued to work with developers to streamline and improve deployment process using Azure DevOps.

IT Director, Insignia Health, Portland, OR

September 2021 – January 2022

  • Responsible for bringing in new tools to help with security and compliance.
  • Responsible for training and managing existing employees and growing the engineering department.
  • Responsible for managing and improving compliance and security practices.
  • Responsible for vendor management and relationships.
  • Played a key role in recent acquisition in regards to providing detailed information about processes and procedures as well as making sure tasks were completed reliably and on time.
  • Responsible for working with management and other teams to understand customer and business needs and improve IT processes, procedures and efficiency.

Senior Systems Engineer, Insignia Health, Portland, OR

March 2021 – September 2021

  • Automated and improved deployment process using Azure DevOps – cut deployment time from hours to minutes and improved efficiency and reliability.
  • Implemented changes in Azure to reduce costs by about 5% and saving the company over $1000/mo.
  • Responsible for managing, maintaining and improving solutions in Azure.
  • Mentor junior administrators in regards to automation, scripting and DevOps.
  • Script solutions for application installation, management and deployment as well as vulnerability remediation using PowerShell.
  • Manage, improve and create documentation for existing processes and procedures.

Sr. Systems Administrator, CorVel, Portland, OR

March 2020 – March 2021

  • Mentor other team members in regards to automation, scripting and DevOps.
  • Script solutions for application installation, management and deployment as well as vulnerability remediation using PowerShell.
  • Responsible for day-to-day support and maintenance of corporate application servers.
  • Responsible for working with manager and other teams to improve relationships and processes to more fully automate and manage systems the team is responsible for.

IT Systems Manager (Infrastructure Engineering), Umpqua Bank, Hillsboro, OR

May 2018 – March 2020

  • Product Owner responsible for IaaS solutions in Azure – delivered automation and solution design for IaaS in Azure – including DR and backup.
  • Assisted with data center hardware refresh for virtualization stack – includes hardware vendor selection, and application migration to new hardware or to Azure.
  • Assist with IT department DevOps transformation by coaching and teaching others.
  • Managed a small team of engineers that worked with business units and internal IT to engineer solutions for IT projects on-prem and in Azure.
  • Worked with business units to improve relationships and better understand their needs to make processes and procedures more efficient.
  • Worked with internal IT teams to help improve processes and procedures to provide higher levels of service to business partners.

IT Systems Manager (Infrastructure & Cloud Engineering), Umpqua Bank, Hillsboro, OR

Mar. 2018 – May 2018

  • Managed a team of four engineers that was responsible for infrastructure virtualization, storage, backup and recovery, and disaster recovery.
  • Responsible for setting goals and direction for associates that reported to me.
  • Responsible for reviewing and maintaining vendor support contracts.
  • Responsible for reviewing and assessing current and future hardware and software needs to come up with 3 to 5-year technology roadmaps.

Systems Engineer, Umpqua Bank, Hillsboro, OR

Feb. 2014 –Mar. 2018

  • Responsible for researching, testing and recommending technologies and methodologies for virtual machine deployment and automation, alert management and monitoring, and system compliance.
  • Created custom reports/checks using PowerShell for server build processes and verification and various reports for management.
  • Responsible for working with other internal teams to design and implement solutions in Microsoft Azure.
  • Responsible for maintaining and managing SCOM infrastructure.
  • Recommended and implemented Derdack Enterprise Alert for SCOM to enhance notifications and alert management.
  • Responsible for managing, maintaining, testing and building production, development and test environments for all virtual systems (VMware and Azure).

Instructor, Saturday Academy, Portland OR

Summer 2015

  • Volunteered and taught two LEGO MINDSTORMS EV3 robotics courses.

Freestyle Development, LLC – Hillsboro, OR

Nov. 2012 – January 2014

  • Android Application Development

Sr Engineer, Distributed Engineering (Windows) – Fiserv, Hillsboro, OR

Oct. 2011 – Nov. 2012

  • Lead Systems engineer for enterprise projects: responsible for solution designs/architecture and implementation.
  • Responsible for working with business units and developers to gather requirements to insure successful design and implementation.
  • Manage and monitor infrastructure with SCCM and SCOM.
  • Currently working on a project to implement and integrate System Center 2012 Orchestrator.

Systems Engineer, Umpqua Bank (contract via VanderHouwen), Hillsboro, OR

April 2011 – Oct. 2011

  • Architected solutions for business applications in a vSphere 4.1/NetApp environment.
  • Managed and monitored infrastructure with SCCM and SCOM.

Technical Lead/Systems Administrator, Bonneville Power Administration (contract via DB Professionals), Portland, OR

Dec. 2010 – April 2011

  • Technical lead for systems in a project to architect a vmware 4.1 environment for the virtulization and consolidation of development and production environments.
  • Designed new OU structure for AD to be used with new vmware environment.
  • Created group policies and documentation for baseline and type server security policies.

Senior Systems Engineer, ServerLogic, Portland, OR

Sept. 2010 – Dec. 2010

  • Managed data center servers for a hosting environment (MS SQL 2005, IIS 6.0, MS Virtual Server 2005, MS Hyper-V, UltraBac).
  • Managed and supported corporate infrastructure (Windows Server 2003/2008, Hyper-V, AD, Exchange 2007, SQL 2005/2008).
  • Re-architected patch management and monitoring for corporate, datacenter and client servers and workstations.

Senior Systems/Infrastructure Engineer

Nov. 2008 – June 2010 – Hollywood Entertainment Inc. – Wilsonville, OR

  • Architected and deployed VMware vSphere 4.0 in a project to virtualize and consolidate corporate offices.
  • Architected and deployed VMware Consolidated Backup (VCB) with NetBackup to manage backups of VMware guests.
  • Managed storage for VMware using Hitachi Device Manager (for Hitachi USP VM and AMS 2500).
  • Planned and transitioned company from Microsoft Exchange 2003 to Microsoft Exchange 2007.
  • Planned and executed migration of data from Veritas Cluster Services (VCS) to new Hitachi ENAS.
  • Configured Microsoft Systems Center Configuration Manager 2007 across multiple AD Domains and Forests to manage Windows Updates, application deployments, system baselines and hardware Inventory.
  • Configured Microsoft Systems Center Operations manager 2005 and 2007 to monitor and audit systems in multiple AD Domains and Forests.
  • Managed and maintained corporate website infrastructure on Windows Server 2003 systems.
  • Rewrote and improved system audit process and Windows patch procedures.

Systems Engineer

June 2008 – November 2008 – ServerLogic – Portland, OR

  • Managed data center servers for a hosting environment (MS SQL 2005, IIS 6.0, MS Virtual Server 2005, MS Hyper-V, UltraBac).
  • Migrated VPN connection and upgraded equipment for local business with 10 locations in 3 states (Cisco ASA, PIX).
  • Migrated servers from Microsoft Virtual Server 2005 to Microsoft Hyper-V.

Systems Engineer

Nov. 2007 – June 2008 – Hollywood Entertainment Inc. – Wilsonville, OR

  • Redesigned Active Directory (AD) to improve management/administration of users, computers and group policies.
  • Migrated users, groups, login scripts and data from Netware to Active Directory and a new Windows managed SAN.
  • Documented migration strategies and processes as well as new guidelines for data shares and Active Directory use.
  • Conducted monthly audits of AD, Netware and Windows environment for SOX compliance.
  • Managed, supported and configured corporate servers (Clustered Exchange 2003, Windows 2000 Server/Windows Server 2003, MSSQL 200/2005/2008, Terminal Services and Windows Server Update Services (WSUS) v3) on IBM servers.
  • Documented installation, configuration and operation guidelines for internal use (used MS Word, Excel and Visio).

Regional Support Specialist

Sept. 2004 – Nov. 2007 –            ADP Dealer Services – Clackamas, OR

  • Technical Commando: frequently sent to critical client sites in order to fix technical/design issues and improve client relationships (MS and Cisco related).
  • Streamlined the client transition process from installation to support to minimize technical problems and improve the client experience.
  • Organized and created classes for supported technologies in order to train employees to better support clients (MS Exchange, Cisco CallManager and Cisco Unity).
  • Managed, supported, configured and upgraded Cisco CallManager (v3.x and 4.x), Cisco CallManager Express, Cisco Unity, Cisco routers and switches for VOIP (H.323, MGCP, SRST), MS Exchange (2000 & 2003), Windows 2000 Server/Windows Server 2003) and Active Directory (including Group Policy), as well as DNS, WINS, DHCP and Backups (Veritas (v8, 9, 10) and MS NTbackup).
  • Documented installation, configuration and troubleshooting procedures for internal and client use.
  • Centralized group resources by designing, implementing and maintaining a custom internal website that provided information and resources to employees within the company (Fedora, Apache, PHP, MySQL).
  • Received the Summit Award in the first half of FY 2006 (Awarded twice yearly for excellent achievement in teamwork, quality and client service).

Technical Support Specialist

April 2002 – Sept. 2004 – Unified Western Grocers – Milwaukie, OR

  • Assistant project manager for researching and recommending a new 3rd party to manage the retail WAN (researched, contacted companies and arranged meetings for proposals).
  • Technical support specialist for retail network: various software applications, operating systems (Unix, Windows 95/98/NT/2000/XP), various Point Of Sale front end systems (NCR, ScanMaster, Retalix) and credit and debit processing hardware and software.

System Administrator

May 2001 – Jan 2004 – ThinkNet – Corvallis OR

  • Architected, implemented and supported web services infrastructure (Apache, PHP, MySQL, Bind, qmail) on FreeBSD and Linux.
  • Designed and maintained firewall and NAT, on FreeBSD and Linux servers.
  • Designed websites using HTML, PHP, MySQL, Java Script, Flash.
  • Planned and implemented migration from FreeBSD to Red Hat 9.

Computer Sales and Service

March 2001 – May 2001 – Exchange Net – Corvallis, OR

  • Pioneered effort to expand business by soliciting local property management companies to provision DSL to apartment buildings.
  • Installed and supported client servers and computers (Windows Server 2000/NT, Windows 98/XP).
  • Managed hosted websites on IIS (Windows 2000 Server).
  • Online and general sales of Internet services, and computers to local businesses and general public.


Oregon State University, Corvallis, Oregon

B.S. Liberal Studies (Music Education and Spanish)

Bilingual (English/Spanish).