Director, Cloud & Reliability — Fully Remote

Boulevard; United States; Remote; USD 220,000 - 270,000; Full time

Benefits offered by this job

Competitive base pay

Equity participation

Medical coverage 100% employee premium

HSA $1,200 employer contribution

Dental, vision, life, disability保险

Parental leave (12 weeks)

Flexible PTO + 10 holidays

Remote with home office stipend

Boulevard Bucks $200 quarterly

One Medical membership

Employee Assistance Program

Job summary

Boulevard is seeking a Director of Engineering, Cloud & Reliability to lead the infrastructure transformation for a scalable, highly available platform used by self-care businesses across North America.

You will mentor a team of infra and reliability engineers, drive cloud strategy, and ensure PCI/HIPAA/SOC 2 compliance while enabling product and data teams with self-service capabilities. This role is fully remote within the US and Canada.

Qualifications

• 10+ years of experience in cloud infrastructure and platform engineering.
• 5+ years leading infrastructure teams of 5-15 engineers.
• Deep experience with AWS including EKS, RDS, VPC, and IAM, and Terraform.
• Proven experience migrating applications to Kubernetes/EKS.
• Security practices, PCI HIPAA SOC 2 compliance experience.
• Experience transforming CI/CD pipelines and enabling GitOps.
• Monitoring/observability with Datadog, Prometheus, Grafana.

Responsibilities

• Define and carry out long-term infrastructure and security strategy for scalable platform.
• Lead and grow a team of infra and reliability engineers; foster operational excellence.
• Migrate to Amazon EKS; bring containerized, service-ready architecture.
• Design multi-region disaster recovery with automated failover and testing.
• Modernize CI/CD pipelines; scale Terraform and GitOps for self-service infra.
• Strengthen monitoring/alerting with Datadog; improve incident response.
• Drive architectural decisions across cloud infra, security, and operations; scale DB.
• Partner with Product Eng, Data Eng, and Platform Services to enable initiatives.

Skills

Cloud infra

AWS EKS RDS

Terraform

Kubernetes migration

PCI HIPAA SOC2

CI/CD GitOps

Datadog monitoring

Team leadership

Cross-functional collaboration

Tools

Kubernetes

Prometheus

Grafana

Datadog

Job description

Boulevard is seeking a Director of Engineering, Cloud & Reliability to lead the infrastructure transformation for a scalable, highly available platform used by self-care businesses across North America.

You will mentor a team of infra and reliability engineers, drive cloud strategy, and ensure PCI/HIPAA/SOC 2 compliance while enabling product and data teams with self-service capabilities. This role is fully remote within the US and Canada.