Who you are

• You bring deep SRE expertise and senior-level leadership experience
• You’ve operated at scale, navigated inflection points, and understand how reliability strategy must evolve as companies grow
• You have 5+ years of experience managing engineering teams and 8+ years in Site Reliability, Platform, or Infrastructure roles
• You’ve owned and materially improved reliability, scalability, and performance in production systems
• You’ve defined and driven reliability or platform strategy across teams or at an organizational level
• You’ve built, evolved, or restructured SRE or platform functions in growing companies
• You’ve led teams through significant production incidents and operational challenges, acting as a credible escalation leader
• You demonstrate strong technical judgment in cloud-native systems (e.g., AWS) and modern infrastructure practices (IaC, CI/CD, observability)
• You’ve influenced engineering and product leadership on reliability tradeoffs, long-term investments, and operational risk
• You’re comfortable operating at multiple altitudes; from technical design discussions to executive-level conversations about impact and strategy
• You lead with calm authority, set a high bar for ownership and accountability, and develop strong, opinionated engineers into even stronger leaders
• You thrive in fast-moving environments where reliability practices must continuously evolve
• If you’re energized by complex systems, organizational leadership, and building resilient platforms customers rely on every day, we'd love to meet you!
• You’ve scaled an SRE or platform organization through a significant growth phase
• You have experience in fintech or other regulated, high-availability environments
• You’ve implemented SLO frameworks, error budgets, and capacity planning at scale
• You’ve led through organizational change or multi-team transformation
• 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

What the job involves

• As Relay continues to scale, the reliability, performance, and resilience of our platform are no longer just technical concerns
• They are core to our customer experience and business success
• This is a senior leadership role responsible not only for guiding a strong team of Site Reliability Engineers, but for shaping how reliability strategy influences engineering and product decisions across the organization
• You will define the direction of the SRE function, drive alignment on operational excellence, and help the company anticipate and navigate scale inflection points before they become risk
• Lead and evolve Relay’s Site Reliability Engineering function, setting strategic direction as the company scales
• Define and drive the long-term reliability roadmap, making principled tradeoffs under real business and capacity constraints
• Serve as the senior reliability voice in engineering and product leadership discussions
• Influence how reliability considerations are embedded into product planning, architecture decisions, and delivery processes
• Act as a senior escalation point during critical production incidents, ensuring clear communication and durable follow-through
• Strengthen Relay’s observability, performance, and operational maturity practices across teams
• Establish and reinforce standards around SLOs, operational readiness, incident management, and continuous improvement
• Partner with Engineering, Product, Data, and Finance stakeholders to balance velocity, risk, performance, and cost
• Build and develop a high-performing SRE organization capable of supporting future growth

The application process

• Stage 1: A 1-hour Google Meet call with a member of the People team
• Stage 2: A 1-hour Google Meets video call with the hiring manager (VP of Engineering)
• Stage 3: A 1-hour in-person interview with a member of Relay’s senior leadership team
• Stage 4: A 1-hour live technical assessment via Google Meet, or in person, with a panel of interviewers (technical leaders & stakeholders)

Benefits

• Competitive salary and meaningful equity: Relay employees are Relay owners, complete with equity and a competitive salary. Since 2023, 66%+ of employees have received salary increases, with multiple new team members joining just last year.
• 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.
• Personal and professional growth: Through ongoing feedback, mentorship, and coaching, work with peers and leaders who are invested in your growth and success. Even with more than half of our team joining in the last 12 months, almost 20% have received promotions in the last year alone.
• 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
• Comprehensive health benefits: Enjoy full health benefits from day one: no probation period required. We offer flexible Health or Wellness Spending Accounts and medical, dental, and vision coverage for you and your dependents.
• Hybrid work environment: We value meaningful collaboration and connection at our Toronto office three days per week, with lunch, snacks, and beverages on us.
• 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.
• 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.
• 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.
• Award-winning workplace: As a winner of CB Insights' Fintech 100, Deloitte Canada's Technology Fast 50, Forbes Fintech 50, and the CIX Top 10 Growth Award, Relay is a recognized innovative and high-growth company.