IT Lead

Relay is a digital banking platform that gives self-made business owners the tools and know-how to be great with money—bringing clarity, confidence, and control to every dollar earned, so they can turn hard work into lasting success. We do this by replacing financial guesswork with real visibility, transforming cash flow from a constant source of stress into a clear signal owners can use to run stronger, more resilient businesses.

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.

What You’ll Be Doing

• 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.

Who You Are

• 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.

Bonus Points

• Experience working in startups or high-growth environments.

• Background supporting security and compliance programs (SOC 2, ISO 27001, etc.).

• Experience deploying or managing infrastructure-as-code environments.

• Passionate about financial services, solving hard problems, and creating innovative solutions.

• You’ve contributed to scaling IT systems during major growth phases and can bring lessons learned to help Relay scale confidently.

Physical Requirements

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.

Our Commitment to You

• Competitive salary and meaningful equity: Relay employees are Relay owners, complete with equity and a competitive salary.

• Comprehensive health benefits: enjoy full health benefits from day one. We offer flexible Health or Wellness Spending Accounts and medical, dental, and vision coverage for you and your dependents.

• Flexible vacation and time off: every team member starts with 15 vacation days and 5 flex days to use as needed, plus an extra week of office closure during the end-of-year holidays so you can take time off to recharge and come back better for our customers.

• Parental leave with top-up: we offer 12 weeks off with a 100% salary top-up for all full-time employees, regardless of location, and accessible for all parents: birthing, non-birthing, and adoptive.

• Hybrid work environment: we value meaningful collaboration and connection at our Toronto office 3 days a week, with lunch, snacks, and beverages on us.

• Dog-friendly space: can dogs really make you happy and healthy? We don’t know for sure, but since we don’t want to chance it, our office is 100% floof-friendly.

• Personal and professional growth: through ongoing feedback, mentorship, and coaching, work with peers and leaders who are invested in your growth and success.

• Top-tier equipment: as a Mac-first company, our Toronto offices have everything you need to produce your best work comfortably, from multiple screens to ergonomic seating.

• Social connection: we believe in celebrating our wins with two annual company-wide get-togethers, quarterly team events, happy hours, and special events and networking opportunities with industry leaders.

We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take changes, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.

The Interview Process

• 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

Why Relay Might Be the Perfect Fit For You

• 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.

Our Promise

We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take chances, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.

What’s Important to Us:

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.

At Relay, we believe that diversity is key to building high-performing teams, and creating an inclusive work environment is our priority. We are an equal opportunity employer and welcome people of diverse backgrounds, perspectives, and skills.

We will work with applicants to provide accommodations at any stage of the hiring process. If you require accommodations during the interview process, please email your Talent Partner, and we will work with you to meet your needs.

Disclaimer: For compliance reasons, all offers of employment at Relay are conditional upon a successful background check & employment verification through Certn.