Senior Site Reliability Engineer

About

Cloaked is a privacy startup dedicated to rebuilding consumer trust in how personal data is used. Our vision is to create an internet that serves the needs of its users, first and foremost—with individual privacy and opt‑in at the core. Our product is a virtual “cloak” that you use as you visit any website — Facebook, Amazon, etc. It lets you choose to share all, some, or none of your private information based on your personal preference.

We’re looking for a Senior Site Reliability Engineer to take ownership of the critical infrastructure powering our privacy platform. You’ll work directly with our Head of Security and IT to keep services reliable, scalable, and performant as we grow — leading incident response, eliminating toil through automation, and building systems that earn customer trust.

Responsibilities

• Define and maintain SLOs/SLAs that balance user experience with engineering velocity
• Implement comprehensive monitoring and alerting in Datadog to detect production issues
• Build resilient architectures that gracefully handle failures
• Establish error budgets and use them to make data‑driven decisions about feature velocity vs. stability
• Lead incident response as primary on‑call for infrastructure, taking critical load off leadership
• Conduct thorough, blameless post‑mortems to prevent recurrence
• Build and maintain runbooks that enable faster resolution
• Serve as the first line of defense when production issues occur
• Identify and eliminate repetitive manual work through intelligent automation
• Build self‑healing systems that reduce operational burden
• Improve deployment pipelines for faster, safer releases
• Own reliability for a platform running on AWS with Kubernetes, ArgoCD, Cloudflare, and Terraform — tackling challenges like JA4 fingerprint monitoring, cluster upgrades, and scaling infrastructure

Requirements

• Solid experience with Infrastructure as Code (Terraform, CloudFormation, or similar) — building and managing cloud infrastructure programmatically
• Deep Kubernetes experience beyond basic deployments — networking, resource management, storage, security contexts, and debugging complex cluster issues
• Proficiency in Python, Go, or similar languages; you build tools and automate workflows that others want to use
• Experience with CI/CD pipelines (GitLab CI, GitHub Actions, Jenkins) and deployment strategies (blue‑green, canary, rolling)
• Expertise with observability tools (Datadog, Prometheus, Grafana) — distributed tracing, metrics, and log aggregation
• Strong Linux/Unix administration background with deep system‑level understanding
• Production experience with major cloud providers (AWS, GCP, Azure) — networking, compute, storage, and managed services
• Operational experience with databases (SQL and NoSQL) and their performance characteristics
• Deep knowledge of network protocols and troubleshooting (TCP/IP, DNS, HTTP/S, load balancing)
• Ability to define meaningful SLIs/SLOs, calculate error budgets, and make data‑driven reliability decisions
• Experience running incidents under pressure, writing post‑mortems that drive change, and implementing preventive measures
• Ability to profile applications, identify bottlenecks, and optimize resource utilization
• Experience with capacity planning — forecasting growth and scaling infrastructure proactively
• Clear communication of complex technical issues to non‑technical stakeholders
• Documentation that others actually want to read

Nice to Have

• Experience with our stack: AWS, Python, NGINX, Kubernetes, Datadog, ArgoCD, Cloudflare, Terraform, Django
• Experience with AI‑assisted development tools (Cursor, Claude Code)

What We Like

• Take ownership and ship improvements without heavy direction
• Automate yourself out of toil rather than accepting the status quo
• Communicate clearly and collaborate across teams
• Balance pragmatism with engineering excellence
• Embrace blameless culture — focus on systems and processes, not individuals, when things fail

What We Offer

Cloaked is a well‑funded Series A startup based out of NYC. Although we are a distributed team, the NYC team operates with a hybrid model. The office building includes a gourmet cafe, cocktail bar, rooftop work area, and a fully stocked kitchen with drinks and snacks. We frequently organize team outings and socials.

Compensation and Benefits

We offer above‑market rate pay and equity based on the market’s best commercially available data. Compensation is a combination of salary, bonus, and equity.

Benefits

• 401(k)
• Top‑of‑the‑line health, dental, and vision benefits
• Flexible work arrangements and remote work options
• Home office stipend and a new company laptop (plus additional tech as needed)

Perks

• Competitive PTO – minimum vacation per quarter to prevent burnout
• Monthly health stipend – usable for gym memberships, meditation apps, personal trainers, etc.
• Late Night Meals – monthly meal stipend for times when home‑cooked meals aren’t feasible
• Professional Growth – unlimited professional development fund; encouragement to attend conferences and industry events