Senior Cloud Engineer (Agentic Infrastructure)

• 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

• 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

Benefits

• Health Insurance: Comprehensive medical , dental, and vision coverage

• Fertility and family forming: Through a partnership, Handshake offers comprehensive family benefits, including infertility treatments and a $15K stipend, to its employees.

• LGTBQ+ coverage: All medical plans cover transgender services.

• Mental health: Discounts on a variety of wellness apps and an Employee Assistance Program with access to five free counseling sessions.

• Tax savings: Tax-advantaged benefits to save money on healthcare, dependent care, and other expenses.

• Life & disability insurance: Essential benefits and automatic coverage with basic life insurance, plus short-term and long-term disability coverage.

• 401k match: Dollar-for-dollar match up to 1% of pay, with a max of $1,200 per year.

• Equity: Our equity program includes grants at hire, refresher grants after two years of tenure, and grants alongside promotions.

• Financial management: Handshake partners to provide free professional financial planning services.

• Learning & development: Employees are provided with an annual stipend to use towards professional development, career development workshops, manager trainings, and 1-on-1 coaching through external partnerships

• Community leader support: Employee Resource Group leaders are compensated with a quarterly bonus for the high-impact work the role requires

• Parental leave: Leaves of 16 weeks for birth-giving parents and 10 weeks for non-birth-giving parents; the policy applies to adoptions as well. Handshake also partners to provide one-on-one coaching on preparing for leave and coming back from leave

• Flexible time off: No accrued time off or waiting period to take vacation. Two paid flexible holiday days off to observe holidays that closely align with religious, cultural, and personal needs

• Sabbatical: Paid six-week sabbatical to recharge and reset beginning at six years of continuous, full-time employment, and every four years thereafter

• Volunteer time off: Two days off for social and civil activism, volunteer work, and/or any related activities, including attending and participating in protests- A collaborative spirit and a bias toward documentation, standards, and shared ownership

• Fluency with modern CI/CD tooling — Buildkite, GitHub Actions, or similar — and a strong GitOps mindset with tools like ArgoCD or Flux

• Strong proficiency with Infrastructure as Code, particularly Terraform or experience with Crossplane or similar policy-driven IaC

• Experience designing container-based and Kubernetes-native architectures

• 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 communication skills — you can explain a complex architectural decision to an engineer and an executive alike

• A genuine curiosity about applying AI and automation to infrastructure problems — whether that’s smarter alerting, self-healing systems, or LLM-assisted runbooks

• Exposure to Cloud Security practices, and experience with IAM, SIEM, scanning, etc

• Background in platform engineering or developer experience (DX)

• Familiarity with FinOps practices and cloud cost optimization

• Experience with service mesh architectures (Istio, Linkerd)