Senior Software Engineer (Sustaining Automation)

Remote from: USA, Canada +1 more, Europe
Salary, yearly, USD: 157,000 - 184,000
Department: Software Engineering
Employment type: Full Time,
Job posted: 15 Jun 2026
Apply before: 15 Jul 2026
Experience level: Senior
Views / Applies: 13 / 5

About company

About Chainguard

Securing the software supply chain with hardened container images and comprehensive supply chain security solutions.

Computer & Network Security
2021

Actively Hiring

AI Summary

Chainguard, a leader in software supply chain security, is seeking a Senior Software Engineer to lead a new greenfield automation team. You will architect the platform for delivering secure container images, build AI-powered tooling using Go and LLMs, and drive technical decisions for scalable systems. This role requires deep expertise in Go, LLM integration, and container ecosystems, offering an opportunity to shape the future of fulfillment at a high-growth company backed by top VCs. You'll work with a small team to design end-to-end pipelines, develop CLIs, and improve customer reliability through quality tooling.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role demands 5-7 years of experience with strong systems architecture and Go expertise, plus emerging skills in AI/LLM integration, making it challenging but not at the principal level.

Salary Analysis

AI Insight The offered salary range of $157,000-$184,000 is competitive for a senior software engineer role, aligning with the market median of ~$170,000. It reflects the specialized skills required in automation and AI, but may be on the higher end for generalist roles.

Key Skills

Go AI/LLM Automation Developer Tools Container Security Kubernetes Software Supply Chain Cloud Native Open Source DevOps

Cover Letter Sample

Dear Hiring Manager,

I am thrilled to apply for the Senior Software Engineer (Sustaining Automation) role at Chainguard. With over 6 years of experience building scalable systems in Go and a passion for AI-driven developer tooling, I am excited about the opportunity to architect the automation platform that powers Chainguard's secure container images. My background includes designing CLI tools, integrating LLMs for code generation, and leading cross-functional initiatives to improve engineering quality.

I am particularly drawn to Chainguard's mission of securing the software supply chain and am eager to contribute to a greenfield project where I can shape technical decisions from day one. My experience with container ecosystems and open-source contributions aligns well with your needs, and I am confident I can drive the development of AI-powered pipelines and quality tooling.

Thank you for considering my application. I look forward to the possibility of discussing how my skills can help Chainguard scale its impact.

Sincerely,
[Your Name]

Possible Interview Questions

Describe your experience designing and building a scalable automation system. What architectural decisions did you make and why?

In my previous role, I led the design of a CI pipeline that processed thousands of builds daily. We chose a microservices architecture using Go for its performance and concurrency, with Kafka for event-driven orchestration. This allowed us to decouple components like build triggers, test execution, and artifact storage, enabling independent scaling. We also implemented a retry mechanism and idempotency keys to handle failures gracefully.

How have you integrated LLMs into a production system for code generation or automation? What challenges did you face?

I built a tool that used GPT-4 to generate boilerplate code for microservices. Challenges included ensuring output quality through prompt engineering and implementing validation gates that checked syntax and style. We also added an evaluation loop where human reviewers approved or rejected suggestions, which fed back into fine-tuning the prompts. This reduced manual coding time by 30% while maintaining code quality.

Walk me through a complex technical problem you solved in Go, particularly involving concurrency or systems-level programming.

I developed a high-throughput file watcher that needed to process millions of events per day without missing or duplicating them. I used Go's goroutines and channels with a fan-out/fan-in pattern, along with an in-memory ring buffer for deduplication. I also implemented graceful shutdown using context cancellation. The solution handled the load with minimal latency and was deployed in production without incidents.

How do you approach technical leadership on a new team? Can you give an example of guiding technical decisions?

On a new team, I first focus on understanding the business goals and constraints. For a greenfield project, I facilitated architecture discussions using lightweight design documents and RFCs. I encouraged the team to evaluate trade-offs between simplicity and scalability. In one case, I advocated for a modular design that allowed incremental adoption, which later enabled us to replace a component without downtime.

Explain your experience with container build systems like melange/apko or traditional package managers. How would you design a test generator for container images?

I have experience with APK and RPM package managers, and I've used Buildah and Dockerfiles for containerization. For a test generator, I would design a system that scans image layers and dependencies, then generates tests with structured assertions (e.g., 'assert package X is present') using a template engine. Integration with CI would allow running these tests on every image rebuild, and results would be reported back to the team.

Chainguard is the trusted source for open source. By delivering hardened, secure, and production-ready builds of all the open source software engineers and AI agents rely on, Chainguard helps organizations build faster, stay compliant, and eliminate risk.
Our customers include Fortune 500 enterprises and global industry leaders, including Anduril, Canva, Fortinet, Hewlett Packard Enterprise, OpenAI, Snap Inc., and Snowflake.
Chainguard is venture-backed by leading investors, including Amplify, IVP, Kleiner Perkins, Lightspeed Venture Partners, Mantis VC, Redpoint Ventures, Sequoia Capital, and Spark Capital.

Who we are

At Chainguard, we are on a mission to secure the software supply chain by default. Our team is founded by the industry’s leading experts on open source software, security and cloud native development.

Chainguard’s product portfolio includes Chainguard Images and Chainguard Services. Customers range from Fortune 500 companies in banking, fintech, government and infrastructure to startups and SMBs. Join us as we help organizations secure their software supply chain from source to production.

The role, in a nutshell

Chainguard delivers the industry’s most secure container images: minimal, zero-CVE, rebuilt daily from source. We’re building a new team focused on automation and tooling to accelerate how we deliver images at scale.

As a Senior Engineer, you’ll be the technical leader for this greenfield effort. You’ll design systems, build AI-powered tooling, and shape the future of our fulfillment platform. You’ll work closely with a small team of engineers, guiding technical decisions and raising the bar for engineering quality.

This is a high-impact role at the intersection of developer tooling, AI/agents, and supply chain security.

What you’ll do

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.

What we’re looking for

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

Nice to haves

Contributions to open-source projects
Familiarity with software supply chain security (SBOM, provenance, signing)
Experience with melange, apko, or Wolfi
Understanding of compliance frameworks (FedRAMP, FIPS, STIG)

Base Salary Range

$157,000—$184,000 USD

About Us

We live and breathe our company values:

We are customer obsessed — We focus on delivering solutions to our customers that create value and make their lives better.
We have a bias for intentional action — We prioritize, plan, try things, and fail fast.
We don’t take ourselves too seriously (but we do serious work) — We are solving an important problem which takes focus, but we also like to enjoy the journey.
We trust each other and assume good intentions — We’re transparent with decisions to empower team members to make well informed decisions.

A few of the benefits we offer:

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.

If your experience is close but doesn’t fulfill all requirements, please apply. We’re building the best team in technology and are focused on hiring “Chainguardians” with unique backgrounds, perspectives, and experiences.

Chainguard is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law.

By submitting your application, you acknowledge that Chainguard will process your personal data in accordance with Chainguard’s Global Candidate Privacy Notice.

Apply now >