O2E Brands is seeking an experienced and forward-thinking Principal Systems Engineer to lead and manage aspects of IT operations and infrastructure. This individual will be responsible for shaping the technology vision of the organization, ensuring alignment with business goals, and executing strategies that support scalability, performance, and security. This leadership role will encompass hands-on responsibilities ensuring the individual can architect, maintain, and optimize critical systems. The Principal Systems Engineer will work cross-functionally across departments to support secure and reliable technology solutions, while ensuring compliance with internal policies and external regulatory requirements.

???? HYBRID WORK ENVIRONMENT

Our motto "It's All About People" drives us to create a hybrid work model that promotes collaboration, celebration, and connection, while giving you the flexibility to work where it makes sense for you.

• Toronto based team members work in-office every other week (Tues–Thurs; approx. 6 days per month). Core attendance is required from 9 AM – 3 PM on these days to support business priorities.

???? A DAY IN THE LIFE

• Provide strategic direction for IT operations, infrastructure, and systems architecture in alignment with business needs.
• Lead the design, implementation, and management of core IT systems including network infrastructure, cloud environments, storage, identity management, and endpoint management.
• Lead the selection, implementation, and management of enterprise platforms including collaboration suites, endpoint management, device provisioning, and device decommissioning.
• Maintain and continuously improve IT service delivery, support processes, and documentation to meet organizational SLAs and operational goals.
• Develop, implement, and enforce IT policies, standard operating procedures, and system controls to support security and compliance.
• Partner with security and compliance leadership to ensure systems meet regulatory and contractual obligations, including asset inventory management, patch management, and user lifecycle controls.
• Oversee technology procurement, vendor relationships, and licensing across hardware, software, and service agreements.
• Manage endpoint fleet lifecycle to ensure device health, configuration, and performance monitoring across all user platforms.
• Drive automation, configuration management, and efficiency in systems administration tasks and IT workflows.
• Mentor and guide the IT team, fostering a collaborative and accountable environment.

???? WHAT YOU BRING TO THE TABLE

• 7+ years of progressive experience in IT, with at least 3 years in leadership or principal engineering roles.
• Demonstrated success in leading IT operations and infrastructure in a cloud-first or SaaS-based organization.
• Expertise in managing and administering modern collaboration and identity management platforms (e.g., Google Workspace, Okta, Jamf, or similar tools).
• Strong experience with endpoint management across MacOS, Windows, and ChromeOS environments.
• Working knowledge of compliance and security frameworks (SOC 2, PCI, or similar), with experience supporting audit readiness and ongoing control maintenance.
• Proficiency in systems automation and scripting to streamline repetitive tasks and maintain infrastructure at scale.
• Effective communicator with a strategic mindset and a hands-on approach to problem solving.

???? COMPENSATION & BENEFITS

• Competitive Salary (Actual salary offered will be commensurate with education, experience, and internal equity.)
• A Total Compensation Package designed to support your financial, personal, and professional well-being. This includes:
  • Participation in our Company Profit Sharing Program
  • Comprehensive Extended Health & Dental Benefits
  • Generous Paid Time Off, including annual vacation and personal days
  • Hybrid Work Environment, offering flexibility to work both remotely and from our corporate offices
  • Professional Development Opportunities to support ongoing career growth
  • Access to Health and Wellness Programs, including gym facilities at our corporate head office
  • Speak to us to learn more about what we offer

???? THE HIRING PROCESS

• Pre-Screen – Let's talk about your experience, goals & excitement for this role!
• Interviews – Two or more interviews with different team members, including structured competency & scenario-based questions
• Presentation/Assessment
• References & Background Check
• We use audio recording transcription for our interview practices ????