Senior Cloud Engineer, Agentic Infrastructure

AI Chopping Block; San Francisco, Northern (CA, KY); Hybrid; USD 180,000 - 230,000; Full time

Benefits offered by this job

Equity in the company

401(k) match

Parental leave

Medical, dental, & vision

Mental health support

Learning stipend

Remote & Office: SF office perks

Flexible PTO

Team outings

Job summary

Handshake is seeking a Senior Cloud Engineer on the Agentic Infrastructure team to shape the foundation of our cloud systems. You will design, deploy, and evolve cloud infrastructure, collaborating with engineering, platform, and security to scale patterns that make it easy for developers to ship safely.

This role goes beyond keeping the lights on; you will architect systems, write playbooks, push toward intelligent automation, and mentor engineers on cloud best practices, encouraging a

Qualifications

• Deep hands-on experience with GCP, AWS or Azure at scale.
• Strong IaC experience with Terraform or Crossplane.
• Fluency with CI/CD tooling and GitOps (ArgoCD).
• Experience designing Kubernetes-native architectures.
• Ability to explain complex architectural decisions to engineers and executives.
• Collaborative, documentation-first mindset.

Responsibilities

• Architect and manage scalable cloud infrastructure across production and development environments.
• Define and enforce best practices for cloud deployments.
• Build and maintain CI/CD pipelines (Buildkite) and GitOps with ArgoCD.
• Own and evolve Infrastructure as Code with Terraform/Crossplane.
• Drive platform improvements to reduce toil and increase developer velocity.
• Explore AI-driven approaches to infrastructure automation and observability.
• Partner with engineering teams to design cloud-native systems.
• Mentor engineers on cloud best practices and patterns.

Skills

GCP/AWS/Azure

Terraform / Crossplane

Buildkite / GitHub Actions

Kubernetes / containers

AI for infra automation

Communication

Documentation & collaboration

Tools

ArgoCD

Crossplane

Terraform

Buildkite

GitHub Actions

Job description

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family & peers can see & feel

• Work hand-in-hand with world-class AI labs, Fortune 500 partners & the world's top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, & Palantir, among others

• Build a massive, fast-growing business with billions in revenue

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

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

Explore our mission, values, & comprehensive US benefits at joinhandshake.com/careers.