Staff Site Reliability Engineer

Hey there! We’re ContactMonkey 👋

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Staff Site Reliability Engineer

You are not just building infrastructure—you are radically improving the daily lives and productivity of every engineer. As our Staff Engineer, Developer Experience, your primary mandate is to unlock engineering velocity. You will leverage your expertise in SRE and cloud infrastructure to eliminate friction, automate toil, and build the self-service platforms that allow developers to ship code faster, test more robustly, and troubleshoot independently. While you will ensure stability, security, and compliance (the essential housekeeping), your success will be measured by your measurable impact on the team's agility and innovation pipeline. You are the champion who enables engineers to focus on product, not platform.

Your impact

• Engineering Velocity: Deliver robust, production-mirroring environments that empower engineering teams to confidently test, develop, and experiment—reducing environment-related defects and accelerating iteration cycles.

• Cost & Performance Optimization: Lead infrastructure optimization with autoscaling and rightsizing initiatives to achieve significant cost savings and enhance service performance.

• Release Automation: Automate build, test, and deployment pipelines to increase deployment frequency, reduce manual effort, and establish a high-velocity CI/CD practice (GitHub Actions).

• Reliability & Insights: Build and maintain comprehensive observability platforms (Grafana, Datadog, Sentry, Prometheus, Loki) that provide actionable insights and improve service reliability and uptime.

• Security & Agility: Own implementation of security best practices for identity and access management, and secrets management, ensuring agility and security in the absence of dedicated ops or security teams.

• Infrastructure Governance: Champion Infrastructure-as-Code (Terraform, Terragrunt) and container orchestration best practices (Kubernetes) for stable, maintainable infrastructure.

• Organizational Growth: Mentor peers, lead by example, and foster a culture of shared ownership, proactive problem-solving, and continuous knowledge sharing.

• Compliance: Embed regulatory controls (SOC2, GDPR) directly into infrastructure and operational processes for audit readiness.

• Technical Modernization: Modernize legacy infrastructure with scalable, maintainable solutions aligned with long-term business and technical goals.

About you:

• 7+ years in SRE, cloud infrastructure, or DevOps roles supporting complex distributed systems.

• Expertise in observability, metrics, alerting, and incident response with a data-driven approach.

• Proficient with AWS, Terraform, Terragrunt, Kubernetes, and scripting

• A strong collaborator and product thinker who views developer experience as their primary product, focused on measurably improving the daily workflow and speed of feature teams.

• Skilled in balancing rapid innovation with robust security and compliance.

• Experience implementing compliance frameworks within infrastructure and operational processes.

How you can stand out:

• Exceptional Cross-Functional Leadership: A highly open, approachable, and non-confrontational collaborator who can engage effectively with individual engineers, engineering leaders, and confidently present and discuss strategic platform direction with senior leadership (VP and C-level) at the appropriate business altitude.

• Proven ability to lead platform initiatives with a documented track record of unlocking developer productivity and accelerating time-to-market.

• Experience migrating legacy systems to cloud-native, scalable platforms.

• Track record of mentoring engineers and building collaborative, high-impact teams.

• Strong operational excellence and security mindset in cloud environments.

• Experience with Go and/or Nix

What we bring to the table

🏥 100% employer-paid benefits and a health spending account from day one

🌎 Work from anywhere in the world for up to 4 weeks

💰 Stock option plan for a stake in our success

🏝 Generous vacation package to take well-deserved breaks

📚 Personal development budget to fuel your growth

🧖 One personal day and one volunteering day to give back to the community

🍎 Five health days per year

💼 Beautiful downtown Toronto office for hybrid work—stocked with all the best snacks

Who We Are

Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.

Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.

We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:

• Ranked by the Globe & Mail as one of Canada’s fastest-growing companies

• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years

• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America

• Raised a record $55 million Series A financing for a Canadian tech company in 2023

Diversity is our strength

At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.