DevOps Engineer II

2 weeks ago

Toronto, Ontario, Canada Wingmate Inc. Full time

DevOps Engineer II

Location: Remote – Canada (Toronto preferred)

Type: Full-Time, Permanent

About Wingmate

Wingmate builds technology that helps field-service and sales organizations operate smarter — connecting field teams, operations, and management in one seamless workflow.

Our SaaS platform powers thousands of businesses worldwide, helping them stay organized, close more deals, and deliver better service.

We're scaling quickly and looking for a DevOps Engineer II who thrives on automation, reliability, and building clean, scalable systems. You'll take ownership of our cloud infrastructure, CI/CD pipelines, and observability stack — ensuring that every deployment is secure, fast, and dependable.

What You'll Do

  • Architect, build, and maintain AWS infrastructure (EC2, ECS/EKS, RDS, S3, CloudFront, Route53, IAM, CloudWatch).
  • Manage and improve our CI/CD pipelines using Jenkins, GitHub Actions, or Bitbucket Pipelines.
  • Implement and maintain infrastructure as code (Terraform or CloudFormation).
  • Automate routine tasks and deployments with Python and Bash scripts.
  • Lead monitoring and observability initiatives using Datadog — build dashboards, tune alerts, and ensure system visibility.
  • Work closely with developers (primarily Ruby on Rails, , and React) to streamline build and release workflows.
  • Champion security best practices and contribute to SOC 2 compliance efforts (audit readiness, access control, data protection).
  • Take ownership of incident response, recovery processes, and continuous improvement initiatives.

What You Bring

  • 4+ years of DevOps or Cloud Infrastructure experience.
  • Deep hands-on knowledge of AWS architecture and operations.
  • Strong background in CI/CD pipeline design and management.
  • Solid experience with Python and Bash scripting for automation.
  • Experience with Datadog (or similar) for system monitoring and alerting.
  • Familiarity with Ruby on Rails application structure and deployment processes.
  • Understanding of infrastructure-as-code principles using Terraform or CloudFormation.
  • Comfort working with Docker and containerized environments (ECS, EKS, or Kubernetes).
  • Knowledge of security, compliance, and governance frameworks (SOC 2 experience a plus).
  • A collaborative mindset — able to work with developers, QA, and product to deliver reliable releases.

Why Wingmate

  • High-impact role with ownership over infrastructure and DevOps culture.
  • Fast-moving, collaborative environment with strong engineering support.
  • Flexible remote work (Canada-based) with autonomy and trust.
  • Competitive compensation and benefits.
  • Opportunity to shape DevOps practices from the ground up as we scale.

Job Type: Full-time

Pay: $100,000.00-$120,000.00 per year

Benefits:

  • Dental care

Work Location: Remote

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