IT Lead, Relay

• You have 6+ years of progressive IT Operations experience, including mentorship responsibilities
• You have hands-on experience managing SaaS applications at scale (e.g., Google Workspace, Jira, Slack, Cloudflare)
• Familiarity with MDM and endpoint management tools (e.g., Kandji, Jamf, or Intune)
• Exposure to identity and access management (IAM) systems such as Okta or JumpCloud
• You’re skilled in managing office network infrastructure - firewalls, switches, and access points - and thrive in both cloud and on-prem environments
• You’re comfortable establishing, automating, and scaling IT processes to support a fast-growing, hybrid company
• You’re proficient with configuration management tools such as Ansible, Puppet, Terraform, or Chef, and can script in Bash or a similar language
• You’re highly collaborative, proactive, and motivated to elevate the reliability and security of our internal systems
• Able to work on-site at our Toronto office a minimum of 3 days a week
• You embody a hands-on mindset, and don’t hesitate to roll up your sleeves when needed
• This role may involve physical activities such as lifting and moving materials up to 50 pounds, bending, stretching, reaching, frequent walking, and ascending/descending ladders and stairs, all within reasonable accommodation
• You push relentlessly for reinvention: You’re built to constantly ask, “How can this be better?” Change excites you and you drive it
• You crave autonomy: We trust our team with big challenges and the freedom to solve them. If you’re someone who takes initiative, is comfortable taking risks, and seeks input when needed, you’ll find the freedom here empowering
• You own your work: You take pride in your work, follow through on commitments, and feel a deep sense of responsibility for outcomes, not just tasks
• You treat comfort as a red flag: You seek growth. When things feel too comfortable, you lean into change. You’re excited about stepping into the unknown and navigating new terrain to create something better alongside your team
• You care about impact, not noise: You care deeply about the substance of your work. You measure success by results, not recognition and you let your work speak for itself
• You’re energized by complexity and ambiguity: You enjoy tackling problems that don’t come with a playbook. You’re comfortable building from scratch, iterating as you go, and collaborating to shape the best path forward
• You seek out feedback: We value directness, clarity, and respect. We believe honesty fuels great work and career growth. You see feedback as a tool for learning and improvement, and you know that open, honest dialogue is key to achieving the best results — together
• You’re here for more than a job: At Relay, everything we do is in service of our mission to help small businesses thrive. To drive impact and have purpose here, that mission must matter to you too
• Research shows that women-identifying and other marginalized individuals often apply only if they meet 100% of the qualifications. But no one is a perfect match on paper. If this role excites you, we’d love to hear from you and figure out together if it’s a great fit

Desirable

• Relay’s IT team builds and maintains the systems and infrastructure that power our people and secure our business. As a Lead IT Operations professional, you’ll drive the next phase of our IT maturity - ensuring reliability, security, and scalability across our growing organization
• You’ll play a key role in shaping how technology empowers every team at Relay to work safely, efficiently, and creatively
• Help lead and administrate IT Operations at Relay, fostering a collaborative, high-performing environment
• Develop, implement, and enforce IT policies, standards, and best practices across all sites, ensuring compliance with company security standards and industry regulations
• Design, implement, and maintain site disaster recovery plans, ensuring business continuity and data integrity
• Oversee the procurement, deployment, and lifecycle management of a diverse fleet of IT equipment, including laptops, high-performance workstations, and specialized computing infrastructure
• Help manage vendor relationships, IT-related budgets, expenses, and asset tracking
• Strategically manage and optimize the service desk workflow, ensuring efficient resolution of tickets received via JIRA, email, instant messaging, and verbal requests
• Help design, configure, and maintain a high-throughput, on-premise network infrastructure
• Collaborate closely with Engineering and Research teams to ensure seamless integration, security, and optimal performance of systems supporting Relay’s development environment
• Drive continuous improvement initiatives for IT processes and systems, leveraging automation and innovative solutions
• Lead the selection, implementation, and management of SaaS applications at scale (e.g., Google Workspace, Jira, Slack, Cloudflare), ensuring their efficient and secure operation
• Develop and implement robust configuration management strategies using tools such as Ansible, Puppet, or Chef

• Stage 1: A 45-minute interview with our Senior IT Manager
• Stage 2: A 45-minute in person values interview with a member of our Leadership Team
• Stage 3: A case study & 60-minute presentation with our Senior IT Manager, and our Compliance & Privacy Lead