Senior DevOps at quartermaster – Toronto | Jobyssey

BUILD SOMETHING YOUR NEIGHBOURS WILL LOVE

We’re building Toronto’s dedicated platform for home management to empower the city’s homeowners and to better connect our neighbours and the local Pros they trust.

Our focus is purely on the GTA market right now. We build our property base one street at a time, and our marketplaces one neighbourhood at a time. We’re a local tech company in every sense of the word. We start with integrity, neighbourhood values, and competitive craftsmanship, and we build our business on neighbourhood trust.

We believe in holistic solutions to consumer problems. We believe in high-trust hyperlocal communities. We believe in low commission marketplaces that the best Pros can actually say yes to. And we believe that tech companies should go to work for the locally loved Pros of the GTA rather than trying to get those Pros to effectively work for the tech company. We believe that it’s good business to care. We believe that this problem space deserves a form of digital transformation that the people and Pros of Toronto can trust and invest in.

If this resonates with you and you’re at a point in your career and your life where you want to do something uniquely difficult for a meaningful outcome, you’ve found your next home.

ROLE SALARY BAND

$160,000 - $215,000

ROLE OVERVIEW

The Senior Developer Operations is a key contributor responsible for delivering high-quality, scalable software across the frontend and backend. This role involves building performant UIs, designing robust APIs, modeling data flows, and integrating services that support complex product features.

Working closely with product, design, and engineering teams, the developer drives architecture decisions, leads technical implementation, and mentors others on best practices. They balance hands-on execution with systems thinking, consistently improving code quality, performance, and developer experience. The ideal candidate pairs deep technical skill with a strong product mindset and a focus on reliability, usability, and long-term maintainability.

❤ Competitiveness – We believe that competitiveness is a critical complement to integrity and trust. If we’re not our customer’s best choice, then we’re wasting their time. We believe in the power of healthy competitive markets, and we believe we need to be uniquely competitive to win in this space. We have too much respect for the other players in this space to expect things to be easy. That’s a good thing.

❤ Empowerment – Any win we achieve needs to be first and foremost a win that we deliver to others, starting with our customers, and their long term best interests.

VACATION AND BENEFITS

We know the power it takes to be successful in a challenging mission and we want to ensure our team is rested and ready to go.

We offer 30 days of PTO annually, which can be used for vacation, personal days, or illness. Five of these days are designated as company-wide closures around the start and end of the year.
In addition, our benefits plan covers health, dental and wellness to add that extra pep in our step, and help us sleep at night.
We have a tech allowance benefit to help set you up for work.
We have pregnancy and parental leave policies, and we’re ready to support your family’s next stage of growth.

EMPLOYEE OWNERSHIP:

We’re a team on a mission. We expect a high degree of ownership from each other and we pair that with higher than usual employee ownership in the company.

WHAT YOU WILL BE DOING
Technical Execution & Ownership

Platform Engineering

Design, build, and maintain scalable, secure, and highly available cloud infrastructure.
Develop internal platform services and tooling that improve developer productivity and reduce cognitive load.
Standardize infrastructure patterns and reusable modules.

CI/CD & Automation

Architect and maintain robust CI/CD pipelines for multiple services and environments.
Drive automation across build, test, deployment, and release processes.
Implement progressive delivery strategies (e.g., blue/green, canary deployments).

Infrastructure as Code (IaC)

Define and manage infrastructure using tools such as Terraform, Pulumi, or CloudFormation.
Enforce best practices for versioning, testing, and reusability of infrastructure code.

Observability & Reliability

Build and maintain monitoring, logging, and alerting systems.
Define and track SLIs/SLOs and improve system reliability through data-driven decisions.
Lead incident response, root cause analysis, and postmortems.

Cloud & Security

Optimize cloud resource usage, performance, and cost.
Implement security best practices, including IAM, secrets management, and compliance controls.
Collaborate with security teams to enforce policies and standards.

Collaboration & Leadership

Partner with engineering teams to improve deployment workflows and system reliability.
Mentor junior engineers and promote DevOps and platform engineering best practices.
Contribute to architectural decisions and technical strategy.

Agile Process & Delivery

Drive backlog refinement, estimation, and sprint planning across cross-functional squads with fullstack responsibilities
Own release readiness for features, including end-to-end testing, canary rollout strategies, and post-deployment observability
Establish and maintain CI/CD pipelines for web and backend services using GitHub Actions, CircleCI, or similar tools
Integrate code coverage, static analysis, and test automation into delivery pipelines to support velocity without sacrificing stability
Continuously improve team workflows via retrospectives, tooling improvements, and process experimentation

WHAT YOU BRING
Candidates should have 6+ years of experience in DevOps, Site Reliability Engineering (SRE), or platform engineering roles, with at least 2+ years leading technical initiatives or mentoring engineers. They must be proficient in scripting or programming languages such as Python, Go, or Bash, and have strong experience working with cloud platforms (e.g., AWS, GCP, or Azure).

Expertise in building and maintaining CI/CD pipelines, managing infrastructure as code (e.g., Terraform, Pulumi), and operating containerized workloads (Docker, Kubernetes) is essential. Candidates should have hands-on experience with observability tooling (monitoring, logging, alerting), as well as a solid understanding of distributed systems, networking, and security best practices.

They should be confident in owning infrastructure and platform architecture decisions, improving system reliability, and driving automation across the software delivery lifecycle. Experience collaborating closely with engineering, product, IT and data teams is critical, along with a strong ability to mentor peers and promote DevOps best practices.

Familiarity with performance optimization, incident management, and secure infrastructure design is expected. The ideal candidate builds scalable, resilient platforms, improves developer experience, and thrives in fast-paced, cross-functional environments.

THIS IS A GOOD FIT FOR YOU IF…

You’re mission-driven and looking to solve the mission’s hardest problems.
You’re at a point in your life and your career where you want to tackle a uniquely demanding job to produce meaningful impact.
You’re keen to work in-person with a team.
You show up like an owner.
You want to value the equity and solve for others.

TEAM VALUES

❤ Integrity – We prioritize integrity over comfort, convenience, and the short-cuts of success that drive metrics but undermine trust.

❤ Trust – We cannot win unless we win on trust. Trust is hard to earn and easy to lose. We need to be built for it in our DNA.

LOCATION

Hybrid #LI-HYBRID

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