Infrastructure AWS Engineer (Windows Security Patching) - Saskatchewan (Remote)

Canada - Saskatchewan

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Guidewire Software
Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. ​We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 400 insurers, from new ventures to the largest and...
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We are seeking an experienced Infrastructure Engineer, who can provide scalable solutions and work independently and be a good team player.This individual will be also responsible for the day-to-day operations, administering, monitoring, troubleshooting, automation, and configuration of Windows servers, but also Linux/VMware, in AWS and on-prem. The focus will be security patching of the OS as well as the applications.This individual will manage and resolve service requests via ServiceNow ticketing system and work closely with internal teams (DevSecOps, Infrastructure, Networking, UC, and AV) and support other customers like Information Security.


  • Manage, coordinate, and implement software upgrades, patches, hot fixes on Linux/Windows/ESXi systems as well as on applications, using tools like SCCM, MePM, AWS Systems Manager, Satellite, etc.
  • Maintain OS configuration using Configuration Management tools like Ansible
  • Support file/printer servers and manage AD resource permissions
  • Manage external digital certificate requests and external DNS provider
  • Investigate and resolve security incidents
  • Fault finding, analysis and of logging information for reporting of performance exceptions
  • Proactively monitoring system performance and capacity planning
  • Create and modify scripts or applications to perform tasks
  • Provide input on ways to improve the stability, security, efficiency, and scalability of the environment
  • Collaborate with other teams and team members to develop automation strategies and deployment processes
  • Maintain best practices on managing systems and services across all environments
  • Must be able to participate in periodic on-call rotation
  • Must be able to work with minimal supervision, is self-motivated and able to define, plan and implement long-term goals, tasks and projects


  • BS in Computer Science or Engineering or information systems or related field (or equivalent experience) required
  • Good understanding of AWS services like EC2, S3, VPC, Route53 and Kubernetes
  • 7+ years Linux/Windows/VMware systems administration experience
  • Scripting skills: highly skilled in a at least one typical scripting languages (shell/bash, PowerShell, Perl, python, ruby)
  • Knowledge of infrastructure automation tools such as Ansible, Terraform, AWS Systems Manager, etc.
  • Experience designing and maintaining AWS-based systems
  • Experience configuring Linux/Windows guests in a VMware ESXi environment
  • Experience supporting Microsoft Exchange, preferably in a hybrid environment
  • Strong understanding of Active Directory and related technologies, especially DNS and DHCP
  • Understanding and management of Microsoft applications: ADFS, PKI, SCOM, KMS, MBAM, RDS, IIS, and SQL is a plus
  • Management and deployment of Datadog, Flexera agent, CrowdStrike agent, CyberArk Endpoint, and similar tools
  • 2+ years of Office 365 experience including migrations from on-premises highly desired
  • Excellent problem solving, multitasking, troubleshooting skills and attention to details are required to work in this challenging and dynamic environment
  • SCCM experience for patch management, application deployment, and OS deployment is a plus
  • Comfortable working with third parties and managed service provider
  • Strong knowledge related to email security (SPF, DKIM, and DMARC) and security best practices in general and mail client/server troubleshooting
  • Strong documentation skill, analytical, organizational, and problem-solving skills, as well as accuracy and attention to detail
  • Very strong interpersonal, customer service, result oriented and team building skills are essential
  • Jamf experience for MACs management is a plus
  • Any AWS certifications or Office 365 MCSA will be plus
About GuidewireGuidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently.
Guidewire combines core, data, digital, analytics, and AI to deliver our platform as a cloud service. More than 400 insurers, including the largest and most complex in the world, run on Guidewire.
As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1000+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of add-ons that accelerate integration, localization, and innovation.
Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.
Disability Accommodations and Guidewire’s Appeals Process. Guidewire provides accommodations to the hiring process to create a fair opportunity for candidates with disabilities to contend for open positions. Accommodation requests should be directed to (650) 356-4940 or If things do not go as hoped, we invite you to use our appeals process. Guidewire promises to independently review any denied accommodation and any decision not to offer you the position. The appeals process is the same in either case. Within five business days of receiving a notice of denial of an accommodation, or receiving a notice of your non-selection for a vacancy, call (650) 356-4940 or e-mail to make an appeal. Guidewire will assign a new decision-maker to review the request and/or hiring decision, who will then notify you in writing of a decision within 10 business days.
Job region(s): Remote/Anywhere North America
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