Senior Cloud Engineer, Agentic Infrastructure

The Role

At Handshake, we believe the infrastructure you build should be as thoughtful as the product it supports. We're looking for a Senior Cloud Engineer on the Agentic Infrastructure team who's excited to shape the foundation that our engineering teams build on - someone who sees infrastructure not as plumbing, but as a product in itself.

As a Senior Cloud Engineer, you'll be at the center of how we design, deploy, and evolve our cloud infrastructure. You'll work closely with engineering, platform, and security teams to define patterns that scale - and make it genuinely easy for developers to do the right thing. You'll codify best practices, champion automation, and bring a modern, opinionated perspective on how cloud-native infrastructure should work.

This isn't a "keep the lights on" role. You'll be architecting systems, writing the playbooks others follow, and pushing us toward a more intelligent, automated infrastructure future.

What You'll Do

• Architect and manage scalable, reliable cloud infrastructure across our production and development environments
• Define and enforce best practices for cloud deployments, making it easy for teams to ship safely and confidently
• Build and maintain CI/CD pipelines (we use Buildkite) and GitOps workflows with ArgoCD to streamline how code gets from commit to production
• Own and evolve our Infrastructure as Code practices using Terraform, Crossplane, or similar IaC tooling
• Drive platform improvements that reduce toil and increase developer velocity
• Explore and implement AI-driven approaches to infrastructure automation, observability, and incident response
• Partner with engineering teams to design systems that are cloud-native from the ground up
• Mentor engineers across the organization on cloud best practices and patterns

You Have

• Deep hands-on experience with GCP (strongly preferred), AWS, or Azure - you've run production workloads at scale and know where the bodies are buried
• Strong proficiency with Infrastructure as Code, particularly Terraform or experience with Crossplane or similar policy-driven IaC
• Fluency with modern CI/CD tooling - Buildkite, GitHub Actions, or similar - and a strong GitOps mindset with tools like ArgoCD or Flux
• Experience designing container-based and Kubernetes-native architectures
• A genuine curiosity about applying AI and automation to infrastructure problems - whether that's smarter alerting, self-healing systems, or LLM-assisted runbooks
• Strong communication skills - you can explain a complex architectural decision to an engineer and an executive alike
• A collaborative spirit and a bias toward documentation, standards, and shared ownership

Bonus Points

• Familiarity with FinOps practices and cloud cost optimization
• Background in platform engineering or developer experience (DX)
• Exposure to Cloud Security practices, and experience with IAM, SIEM, scanning, etc.
• Experience with service mesh architectures (Istio, Linkerd)

We Offer

• Handshake delivers benefits that help you feel supported - and thrive at work and in life.
• The below benefits are for full-time US employees.
• Ownership: Equity in a fast-growing company
• Financial Wellness: 401(k) match, competitive compensation, financial coaching

Benefits

Family Support: Paid parental leave, fertility benefits, parental coaching:

• Wellbeing: Medical, dental, & vision, mental health support, $500 wellness stipend
• Growth: $2,000 learning stipend, ongoing development
• Remote & Office: Internet, commuting, & free lunch/gym in our SF office
• Time Off: Flexible PTO, 15 holidays + 2 flex days
• Connection: Team outings & referral bonuses