Cloud Operations Technician:  

We are looking for an experienced Cloud Operations Technician to join our Cloud Operations team in Penticton, BC!

Windward Software has recently undertaken calculated growth, which has featured the launch of the company's new service, Windward System Five on Cloud. This new service will evolve: moving from ‘lift & shift’ to a cloud-native solution. We are also building upon our Windward Integration Platform to include managed integrations to Polaris, Mega Group, NetSuite, and additional third-party applications.

The Cloud Operations Technician will be responsible for provisioning, securing, and maintaining the company's cloud-based infrastructure. You will be part of a small team that works closely with Development and Client Services personnel in delivering professional and exciting services to Windward Software's clients.

You are a skilled IT professional, who continuously learns and hones your trade, and has a true passion for the work. You understand the importance of deadlines, teamwork and good strong work ethic.

Position Responsibilities:

  • Building and implementing an ‘infrastructure as code’ based solution.
  • Onboarding / offboarding.
  • Cost reporting and analysis.
  • Applying and developing best practices across all aspects of work.
  • Designing, implementing, and maintaining servers, storage, networks, and security infrastructure.
  • Designing, implementing, and testing disaster recovery and business continuity infrastructure.
  • Creating and implementing automation for cloud platforms, as well as monitoring and alerting processes.
  • Troubleshooting production issues and responding to after-hours escalations.
  • Helping to develop and implementing processes and best practices designed to increase productivity and dependability.
  • Communicating directly with customers, as required.
  • Escalating issues and challenges to the CTO.
  • Ensuring key performance indicators are recorded, monitored, and communicated on a regular basis.
  • Device configuration.
  • Completing Windward System Five on Cloud installations, updates, and maintenance.
  • Developing and applying best practices for data management (e.g., backups & recovery).


  • B.Sc . in Computer Science or equivalent discipline or industry experience.
  • IT Professional preferably MSCA/MCSE certified with 3-5 years experience in the following:
    • Windows Server 2012 / 2016 operating systems
    • Exceptional problem-solving skills
    • Networking / DNS / DHCP
    • Active Directory Domain Services / Group Policy
    • Virtualization (Hyper-V) / Windows Failover Clustering / Remote Desktop Services
    • Azure / AWS Cloud Technologies
  • Familiarity with web applications and relational databases.

On-the-job training will be provided for our proprietary Windward System Five business management solution suite as well as continuous upgrading of skills to meet the business requirements of the future.

Technologies (non-exhaustive):

  • Azure (VM, Web Apps, Logic Apps, NSG, Load Balancer, Health Probes, Application Gateway, Availability Groups, AAD, Log Analytics, Operations Management Suite, Azure Storage)
  • PowerShell
  • Windows Server 2016
  • Windows Active Directory / Domain Services
  • Remote Desktop Services
  • Azure SQL Database, Actian PSQL

Working Conditions and Requirements:

  • This is a supportive technical role and requires that the work be performed in the Windward Software Penticton office (schedule to be determined).
  • On-call, emergency, and extended work hours are to be expected.

We offer:

  • A comprehensive benefit package.
  • Lakes, beaches, wineries, all in our backyard!  Take your lunch break at beautiful Skaha Beach – literally just a block away.
  • We have a huge staff lounge area with gym equipment, pool table and showers onsite.
  • Tickets for events at the South Okanagan Events Centre (SOEC).
  • Social activities such as golf tournaments, holiday festivities, etc.


Send your details to and don’t forget a cover letter!  While we appreciate all interest, only those selected for further review will be contacted.  Thank you.

Job Info

Location: Penticton, BC, Canada

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