Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London.

OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth.

OdysseyRe is rated A+ (Superior) by AM Best and A+ (Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH.

Position Summary

We are looking for a talented Cloud Engineer who has the experience and knowledge

necessary to help build out our existing Azure cloud infrastructure and troubleshoot problems as

they arise.  This is a Junior Level position within our Public Cloud Operations team. This role is responsible

for building, maintaining, and monitoring core systems and applications.  They will also be asked to contribute to the design and maintenance of new and existing cloud designs, CI/CD pipelines, automation and scripting efforts, performance monitoring and tuning, process automation and capacity planning.  This role will also provide Windows Server Support as well as contribute to our on-call support rotation.  Position requires after hours support, occasional weekend work and a flexible work schedule.  General

supervision will be provided for this position but the ideal candidate would have the maturity and drive to self-educate, adapt, and contribute to unstructured and often dynamic work environments.  The position requires understanding the overall business

process and structure while being in full alignment with IT and Company Policies / Procedures / Approved Architecture and Engineering Practices.  

Essential Duties

1. Monitoring and Troubleshooting Azure Cloud environments.   This includes but is not limited to Virtual Machines, vNets, Subnets, NSG’s, APIM, WEB Apps, Logic Apps, vWAN, Express Route, Monitoring, Azure Policies, etc.
2. Performs daily maintenance tasks, system and application log reviews, break-fix support
3. Knowing when to ask for help / assistance from more Sr. Level Resources.
4. Prioritizing “Stability and Security” in everything we do.
5. Routine systems and application patches and upgrades
6. Ability to collaborate in a geographically diverse, Agile based delivery system.
7. Contributing to Cloud infrastructure design, build, configuration and capacity planning
8. Solid understanding of Azure service offerings and ability to design secure hybrid solutions
9. Experience with data platforms and analytics tools a plus
10. Windows (required) and Linux (desired) server installation, configuration, tuning, monitoring and break-fix support
11. Application functional and performance monitoring, root cause analysis and resolution
12. IT Automation and Configuration Management Skills; Ansible, Bicep (desired), PowerShell, and Terraform experience
13. Kubernetes experience building and maintaining clusters, auto scaling and monitoring a plus
14. Knowledge of scripting with one or more tools - PowerShell, Batch, Shell, SQL, Python or Perl
15. Works with project teams to help determine and advise the technical scope for new projects
16. Produce and maintain high quality technical documentation for systems, applications, scripts, automation and processes

Skills, Knowledge and Abilities

1. Extensive Windows OS, Cloud Service, application and network troubleshooting experience
2. Solid experience in overseeing the design and implementation of systems, applications and related

processes both on premise and in the cloud

3. Strong written, oral, and inter-personal communication skills
4. Ability to solve complex problems quickly and completely
5. Good project management skills
6. Must be highly self-motivated and directed, an independent thinker, organized and detail-oriented
7. Ability to work independently with little guidance and in a collaborative team environment
8. Adherence to established processes and procedures
9. Strong understanding of computer technologies and the direction of new technologies
10. Competence with documenting, flowcharting and project management tools and procedures
11. Ability to plan and organize effectively
12. Knowledge of applicable IT security, confidentiality and data privacy practices - maintains

confidentiality of company-sensitive data

13. Keeping direct supervisors informed of activities and situations which will impact the achievement of

corporate and department goals and objectives

14. Performing other related duties, as required, to achieve the goals and objectives of the Company and Department

Technical Requirements

Powershell, Bicep, Terraform in an Azure setting.

Windows Server (2012 thru 2022)

Linux – Redhat Enterprise Linux experience a plus

Azure general administration and solution design experience

Containers, Kubernetes and Helm experience a plus

Application Performance Monitoring

Server performance and capacity monitoring tools (DataDog, SCOM, Dynatrace, Foglight, Extrahop)

Server clustering and H/A concepts

Enterprise job scheduling and automation

General web development architecture knowledge

Windows \ PowerShell \ Python \ Linux Shell scripting

Basic AD management experience

Experience with Microsoft Office tools

Experience & Education Requirements

Bachelor’s degree in Computer Science, a related field, or equivalent technical education in a directly

related area.

5 to 7 years hands-on experience directly related to the duties and responsibilities specified

Knowledge of Insurance and Reinsurance a plus.

Ability to establish and maintain professional relationships with others on the Team and Business.

We are an E-Verify employer - all hired positions require successfully passing an E-Verify Check.  

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