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Director of Engineering, Cloud & Reliability

Boulevard - Remote - Remote - posted 2026-04-08

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Boulevard is a client experience platform for appointment-based self-care businesses (salons, spas, medspa, barbershops). Founded in 2016, the company serves small businesses through enterprises with modern, user-friendly software that helps customers thrive. You will lead Boulevard's infrastructure transformation as Director of Engineering, Cloud & Reliability, reporting to the SVP of Engineering. You'll manage a team of infrastructure and reliability engineers while owning the technical strategy for cloud infrastructure, DevOps practices, and platform capabilities that enable rapid growth across market segments. Key responsibilities include: **Cloud Infrastructure & Platform**: Design and maintain scalable AWS infrastructure with multi-region deployments and infrastructure-as-code practices. **DevOps & CI/CD**: Transform deployment pipelines, implement container orchestration, and enable rapid, reliable software delivery. **Observability & Reliability**: Implement comprehensive monitoring, alerting, and incident response using DataDog and related tools. **Disaster Recovery & Business Continuity**: Establish DR infrastructure, failover systems, and business continuity planning across all services. **Infrastructure Automation**: Build self-service infrastructure capabilities and advanced automation using Terraform and GitOps practices. **Security & Compliance**: Establish comprehensive security practices and manage compliance frameworks (PCI, HIPAA, SOC 2). Major initiatives include EKS migration and containerization, multi-region disaster recovery implementation, CI/CD pipeline modernization, advanced observability enhancement, enterprise-grade security framework establishment, infrastructure-as-code evolution, and database scaling to address RDS limitations. This role is ideal for a technical leader who wants to build the infrastructure platform that becomes the backbone of Boulevard's next growth phase. You'll architect modern infrastructure practices including containerization, infrastructure-as-code, advanced CI/CD pipelines, and comprehensive observability systems.

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