Lead Site Reliability Engineer - Canada, Remote

Our Team

The Incident Response Team sits at the intersection of every customer-impacting failure across Vista. We coordinate response to critical incidents, drive learning out of every event, and partner with engineering teams across the organisation to make Vista more reliable. Today the team is strong on incident handling, and we are deliberately raising the engineering bar to match.

What You Will Do

• Identify patterns of failure across the organisation. Analyse incidents and post-incident reviews to find the recurring technical root causes behind customer impact, rather than treating each incident as a one-off.

• Prioritise the biggest improvement levers. Focus reliability effort where it most reduces Mean Time to Detect and Mean Time to Resolve, and where it proactively prevents the next incident from happening at all.

• Turn those patterns into the right engineering intervention and influence the teams who can build it. This includes safe deployment defaults, secret and credential rotation, resilience patterns such as circuit breakers and fallbacks, observability and alerting standards, contract testing, and infrastructure pre-flight validation. You drive the what and the why; the owning teams build it.

• Help teams hands-on, in their code, through Merge Requests, pairing, code review, and active technical support, favouring the simplest intervention that prevents recurrence over the most elaborate one.

• Disseminate and evangelise improvements across the organisation. Identify best practices, document them, and transfer the learning to other teams so that local fixes become shared practice and improvements compound rather than stay siloed.

• Lead the technical conversation in post-incident reviews and operational forums. Ask the questions that surface missing monitoring, untested failure modes, incomplete rollback strategies, and unaddressed dependency risks, and steer toward the simplest solution that holds.

• Help the Incident Response Team grow its engineering practice by pairing on real work, sharing what good engineering looks like in our context, and running internal learning sessions that bring the team from incident-response specialists toward incident-response engineers.

• Partner across teams without direct authority. Work with Platform Engineering, Deployment Platform, Developer Productivity, and senior engineers across Vista; contribute as a reviewer on proposals that touch reliability, deployment safety, observability, or operational readiness; and take part in the team's on-call rotation, contributing incident leadership when shared coverage requires it.

Your Qualifications

At VistaPrint, we are striving to hire individuals that add new ideas and perspectives to our teams and enhance our culture. No matter your background or work experience, we strongly encourage you to apply—even if you feel that you don’t meet the exact requirements or have the same qualifications. You might be a great candidate for this or other opportunities.

• 5 or more years of hands-on Site Reliability, Platform, or Infrastructure Engineering experience in a large-scale, distributed production environment, with proficiency in at least one programming language (e.g., Python, Go, TypeScript, Java) and a track record of code shipped to production

• Demonstrated experience driving adoption of a reliability or platform pattern (e.g., progressive delivery, observability standard, resilience library, secret rotation) across teams that did not report to you, with measurable outcomes.

• Strong systems thinking and a demonstrable bias toward simple solutions - able to read an incident or a design and identify the underlying class of problem (retries, cascading failures, queueing behaviour, partial failures, head-of-line blocking) and the smallest, cheapest intervention that addresses it. Comfortable choosing a post-deploy curl check over a full sandbox environment when the simpler intervention would prevent the same incident.

• Hands-on experience with the modern reliability stack: at least one major cloud platform (AWS, Google Cloud, or Azure), an observability platform (for example New Relic, Datadog, or Grafana), defining and operating against Service Level Objectives, continuous integration and deployment pipelines, and infrastructure-as-code (for example AWS CDK, Pulumi).

• Hands-on exposure to Artificial Intelligence and Large Language Model tooling in an engineering context, for example integrating Large Language Models into workflows or operational tooling, or using Artificial Intelligence meaningfully in your own engineering.

Nice to Have

• Prior experience formally mentoring engineers, running internal learning programmes, or growing the engineering capability of a team that started from a non-engineering baseline.

• Experience designing or running chaos engineering, GameDays, or failure-injection programmes.

• Experience working in a globally distributed engineering organisation with Follow-the-Sun or 24/7 coverage models.

• Experience integrating with or extending modern incident management and service-catalogue tooling (e.g., incident.io, PagerDuty, Cortex, Backstage) at the API or workflow level - not just as a user.

• Experience building internal developer platforms, paved-road tooling, or "golden path" patterns that other engineering teams adopt by choice.

Why You'll Love Working Here

There is a lot to love about working at VistaPrint. We are an award winning Remote-First company. We’re an inclusive community. We’re growing (which means you can too). And to help orient us all in the same direction, we have our Vista Behaviors which exemplify the behavioral attributes that make us a culturally strong and high-performing team.

About Us

VistaPrint is the design and marketing partner to millions of small businesses around the world. For over 20 years we’ve been inspired by small businesses, and we work incessantly to deliver solutions to their evolving needs. Together, VistaCreate, 99designs by Vista and VistaPrint represent a full-service design, digital and print solution, elevating small businesses’ presence in physical and digital spaces and powering them to achieve success. VistaPrint is focused on making great marketing and design accessible to every small business owner, allowing them to create a cohesive brand image for use in-store, online and on-the-go.

Commitment to Diversity, Equity, & Inclusion

VistaPrint exists to help our customers live their dreams. Each dream is unique – and the VistaPrint team needs to be as well. We believe in the unique contributions of everyone within a diverse global organization. We are collaborative, inclusive, and innovative. We strive to role model and live an inclusive culture of fairness, respect and belonging for all. And we work together to empower each other, creating a space in which each of us can spark our next great idea.

Equal Opportunity Employer

VistaPrint, a Cimpress company, is an Equal Employment Opportunity Employer. All qualified candidates will receive consideration for employment without regard to race, color, sex, national or ethnic origin, nationality, age, religion, citizenship, disability, medical condition, sexual orientation, gender identity, gender presentation, legal or preferred name, marital status, pregnancy, family structure, veteran status or any other basis protected by human rights laws or regulations. This list is not exhaustive and, in fact, in many cases, we strive to do more than the law requires.