Site Reliability Engineer

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.

$210,000 - $260,000 a year

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. This is a high-impact role for an engineer who thrives on ownership and engineering excellence.

What will you do?

-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 — you'll tackle real challenges like JA4 fingerprint monitoring, cluster upgrades, and scaling infrastructure.

What skills and experiences will help you?

-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, 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

What's 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 do 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 is home to several amenities, including a gourmet cafe, cocktail bar, and a rooftop work area.

We have a fully built out kitchen packed with drinks and snacks. The Cloaked team has diverse interests and so we frequently embark on team outings and go out for socials!

Compensation and Benefits

We offer above market rate pay and equity based off of the market's best commercially available data. Your compensation will be a combination of salary, bonus and equity.

Benefits

Cloaked employees have 401K, as well as top of the line Health, Dental, and Vision benefits.

We offer flexible work arrangements and the ability to work remotely as needed. Cloaked provides a home office stipend in addition to a new company laptop (and other tech depending on the role).

Perks

🌴Competitive PTO: We encourage employees to take a minimum # of vacation per quarter. We see PTO as a preventative burnout measure and are committed to changing the industry standard.

🤸Monthly health stipend: Used for any kind of physical, mental or emotional care you’d like to take for yourself, be it a gym membership, a meditation app, or time with a personal trainer.

🥗 Late Night Meals: We understand that sometimes work can get in the way of meal prep. In response to that, we offer employees a monthly meal stipend to be used when they don't have time to get a home cooked meal going!

🧠 Professional Growth: Opportunities for career development and personal growth are provided to all employees who seek to further their knowledge and capabilities through an unlimited professional development fund. Additionally team members are encouraged to regularly attend conferences and industry events.

We are really excited about having you join our mission-driven team and help us build the future of online privacy!

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.