Senior Software Engineer – Sustaining Automation

Chainguard

Senior Engineer designing automation systems for secure container images at Chainguard. Leading technical initiatives, development, and quality improvements in software supply chains.

Posted 6/13/2026full-timeRemote • 🇨🇦 CanadaSenior💰 $157,000 - $184,000 per yearWebsite

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Hard Skills

GoAI integrationLLM integrationsystems architecturedeveloper toolsCLI developmentautomation platformsLinuxcontainerizationDocker

Soft Skills

communicationcollaborationautonomytechnical writing

Tools & Technologies

package managersapkaptrpmMakeBazelKubernetesOCIcontainer registries

Industry Keywords

scalable systemsquality gatestest generationvalidation frameworksprompt engineering

Tech Stack

Tools & technologies

DockerGoKubernetesLinux

About the role

Key responsibilities & impact

Architect the automation platform: Design the end-to-end system that orchestrates package creation, test generation, and image building. Own the technical vision and make decisions that will scale.
Build AI-powered tooling: Develop LLM-integrated, agentic pipelines for manifest generation, test scaffolding, and validation. Design prompt architectures, evaluation loops, and quality gates.
Write production Go: This is a hands on role! You'll develop CLI tools, services, and integrations alongside your team.
Build quality tooling: Develop tooling and automation that improves customer reliability, including test generators, validation frameworks, and quality gates.
Shape the roadmap: Collaborate with engineering leadership to identify the highest-impact problems and ensure they get solved. Participate in long-term planning for the organization.

Requirements

What you’ll need

5-7 years of software engineering experience, with a track record of designing and building complex systems
Strong Go expertise
Experience with AI/LLM integration: building systems that use language models for code generation, automation, or developer tooling. Familiarity with prompt engineering, evaluation, and guardrails
Systems architecture skills: ability to design loosely-coupled, scalable systems and make pragmatic trade-offs
Experience building developer tools, CLIs, or automation platforms
Deep Linux and build systems knowledge: experience with package managers (apk, apt, rpm), build tools (Make, Bazel, language-specific toolchains), and containerization
Container ecosystem expertise: Docker, OCI, container registries, Kubernetes
Strong communication skills: ability to write clear technical documents, work autonomously, and collaborate across teams.

Benefits

Comp & perks

Flexible & Remote-First Culture: Work remotely with team meetup opportunities, bi-annual destination summits, and a monthly stipend for coworking spaces, phone and internet costs.
Our Approach to Equity: Receive stock options upon hire and promotion. Plus, you can participate in secondary offerings and have 10 years to exercise your options (yes, you read that correctly: 10 years!).
100% Covered Health Insurance: We cover 100% of your health, vision and dental insurance premiums for you and your dependents. Nothing comes out of your paycheck.
∞ Flexible Time Off: Take the time you need – to do our best work, we need to recharge and reset.
18 Weeks Paid Parental Leave: We offer 18 weeks for birthing parents and 12 weeks for non-birthing parents, with the option to use it all at once or throughout your child's first year.