System Administrator



Posted on Friday, June 16, 2023

System Administrator

At Carebook, our mission is to create a world of connected health that empowers individuals and brings organizations towards a proactive and lifelong commitment to wellbeing. We believe in a world where everyone has the opportunity to be actively engaged and fully supported in managing and improving their overall health.

Established in 2014, Carebook is a publicly-traded company that acquired both InfoTech and CoreHealth Technologies in 2021, allowing us to expand our family of SaaS platforms to support the well-being journeys of over 3.5 million people and cater to Fortune 10 and 500 companies.

With well-being at the heart of everything we do, when you work at Carebook, you’re joining a multi-disciplinary team, passionate about solving problems through innovative technology and collaboration with a culture grounded in personal growth and well-being.

Having become certified a Great Place To Work and made the Best Workplaces in Quebec and Best Workplaces for Inclusion lists in 2022, our focus on our people shows and, although our team may be spread across the country as a remote company, we always have a team-first mentality in a remote-first and flexible environment so you can do your best work anywhere in Canada or at one of our office locations in Montreal, Winnipeg or Kelowna!

We are seeking a highly skilled and motivated System Administrator to join our dynamic team at Carebook. As a System Administrator, you will play a crucial role in maintaining the stability, security, and scalability of our infrastructure to ensure seamless operations for our clients.


  • System Maintenance and Support:
    • Administer, monitor, and optimize our cloud-based systems and network infrastructure.
    • Perform regular system maintenance, including updates, patches, and backups.
    • Troubleshoot and resolve system and network issues promptly to minimize downtime.
  • Security and Compliance:
    • Implement and maintain robust security measures to protect our systems and data.
    • Ensure compliance with industry standards and regulations (e.g., GDPR, HIPAA).
    • Conduct regular security audits and vulnerability assessments.
  • Infrastructure Management:
    • Manage our cloud infrastructure, including virtualization, storage, and networking.
    • Deploy and configure servers, databases, and applications as per business requirements.
    • Collaborate with cross-functional teams to plan and implement infrastructure projects.
  • Monitoring and Performance Optimization:
    • Monitor system performance and proactively identify areas for improvement.
    • Optimize system configurations to ensure optimal performance and scalability.
    • Implement and maintain monitoring tools to track system health and performance metrics.
  • Documentation and Knowledge Sharing:
      • Create and maintain comprehensive system documentation, including procedures and configurations.
      • Share knowledge and provide guidance to team members on system-related matters.
      • Develop and enforce best practices for system administration and operational procedures.


    • Degree or Certification in Computer Science, Information Technology, or a related field.
    • Proven experience as a System Administrator, preferably in a SaaS environment.
    • Strong knowledge of cloud-based infrastructure, such as AWS, Azure, or Google Cloud.
    • Proficiency in Linux/Unix and Windows Server administration.
    • Familiarity with virtualization technologies (e.g., VMware, Hyper-V).
    • Solid understanding of networking protocols, security principles, and firewalls.
    • Experience with scripting languages (e.g., Bash, PowerShell) and automation tools.
    • Ability to troubleshoot complex system and network issues efficiently.
    • Excellent communication and collaboration skills.

    Perks of Working at Carebook

    • Employee Stock Option Plan for everyone (ESOP)
    • High-quality Benefits – We offer comprehensive programs for compensation, health benefits (including telemedicine service with Maple available to both yourself & your family 24/7) and recognition
    • Work-Life Balance – Remote-first hybrid work model + flexible hours
    • Regular in-person or virtual events/get-togethers [Optional]
    • EDI and Wellness Committees to partake in to prioritize & promote diversity, health and wellness
    • Personal & Professional Development – Mentorship Program designed to promote our employees’ personal growth, professional development and continuous learning

    Diversity, Equity, and Inclusion

    Carebook is an Equal Opportunity Employer. We’re dedicated to fostering an inclusive workplace and culture that is directly impacted by the various perspectives, backgrounds, and experiences of our Team Members. We’re committed to this because our core values demand it - values like Respect, Curiosity & Creativity and One Team. We believe that everyone can contribute something unique to the company, to our products and that teamwork makes the dream work. For these reasons, applicants from all backgrounds are encouraged to apply.