Director of Engineering, Cloud & Reliability

Who is Boulevard? Boulevard provides the first and only client experience platform for appointment-based, self-care businesses. We empower our customers to give their clients more of the magical moments that matter most. Before launching in 2016, our founders spent months interviewing salon managers and working behind front desks to understand their pain points so we could design a modern, user-friendly platform that meets the unique needs of their business. Our roots may be in hair salons, but we are built for the broader self-care industry, including many types of salons, spas, medspa, barbershops, and more. Our technology not only helps our customers survive but thrive. Take a look at  how we (and YOU) can make that happen .  We have an insatiable curiosity and embrace experimentation. We believe that simple solutions require the most sophistication, and we design each and every detail to maximize potential, power, and impact. Do our values match? Read through our story and what we value the most . Our team values and celebrates our diverse backgrounds. Being open about who we are and what we do allows us to do the best work of our lives. We believe in equal opportunity for all, and you should too. Come do the best work of your life at Boulevard. We're hiring a Director of Engineering - Cloud & Reliability to lead our infrastructure transformation and establish industry leading reliability practices. This role will be instrumental in evolving Boulevard's infrastructure into a scalable, reliable, secure, and highly available platform that supports our rapid growth and customer needs across a spectrum of market segments (Small Business, Franchises, Enterprises). Reporting to the SVP of Engineering, you'll lead a team of infrastructure and reliability engineers while driving the technical strategy for our cloud infrastructure, DevOps practices, and platform capabilities. Your work will directly enable the Engineering & Data teams to deliver APIs, services, customer-facing products and data capabilities at scale by providing robust, self-service infrastructure foundations. You'll architect and implement modern infrastructure practices including containerization, infrastructure-as-code, advanced CI/CD pipelines, and comprehensive observability systems. This role is perfect for a technical leader who wants to build the infrastructure platform that becomes the backbone of Boulevard's next phase of growth. Domains of Ownership Cloud Infrastructure & Platform - Design, implement, and maintain scalable AWS infrastructure including multi-region deployments, and infrastructure-as-code 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 Boulevard services Infrastructure Automation - Build self-service infrastructure capabilities and advanced automation using Terraform and GitOps practices Security & Compliance - Establish comprehensive security practices, manage compliance frameworks (PCI, HIPAA, SOC 2), and implement security-by-design principles Key Projects & Initiatives EKS Migration & Containerization : Lead the migration from current infrastructure to Amazon EKS, implementing container orchestration and services-ready architecture Multi-Region DR Implementation : Design and implement hot-hot disaster recovery with automated failover, load balancing, and regular testing procedures CI/CD Pipeline Transformation : Modernize deployment pipelines to support faster, more reliable deployments Advanced Observability : Enhance comprehensive monitoring, alerting, and incident response using DataDog, enabling proactive issue detection and resolution Security Framework : Establish enterprise-grade security practices, compliance frameworks, and automation to support Data team's governance requirements Infrastructure-as-Code Evolution : Scale Terraform usage, implement GitOps practices, and create self-service infrastructure capabilities Database Scaling : Address current RDS limitations and implement scalable database architecture What you'll do here: Technical Leadership : Define and execute the long-term infrastructure and security strategy, ensuring scalability, reliability, and security as Boulevard grows Team Building : Lead, mentor, and grow a team of infrastructure and reliability engineers, establishing best practices and fostering a culture of operational excellence Cross-functional Collaboration : Partner closely with Product, Services and Data Engineering teams to provide the infrastructure foundation for their initiatives Architecture & Design : Drive architectural decisions for cloud infrastructure, security systems, and operational practices Operational Excellence : Establish monitoring, alerting, and incident response practices that ensure high availability and performance Compliance Management : Ensure compliance with industry standards (PCI, HIPAA, SOC 2) and implement security controls What you'll need to thrive: 10+ years of experience in cloud infrastructure and platform engineering, with 5+ years leading infrastructure teams of 5-15 engineers Deep experience with AWS services including EKS, RDS, VPC, IAM, and infrastructure automation using Terraform Proven experience migrating applications to Kubernetes/EKS and implementing container-based architectures Strong background in security practices, compliance frameworks (PCI, HIPAA, SOC 2), and security automation Experience transforming CI/CD pipelines, implementing GitOps practices, and enabling rapid software delivery Expertise with monitoring and observability tools (DataDog, Prometheus, Grafana) and implementing comprehens