Director of Engineering, Cloud & Reliability - Boulevard

About 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.

Our roots may be in hair salons, but we are built for the broader self-care industry, including many types of salons, spas, medspas, barbershops, and more. Our technology not only helps our customers survive but thrive.

Role Overview

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.

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 the 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

• 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 comprehensive alerting strategies.
• Proven ability to work with Product Engineering, Data Engineering, and Platform Services teams to enable their technical initiatives.

Benefits & Perks

• 401(k) match plus dental, medical, vision, and life insurance.
• Flexible vacation day policy.
• Fully remote work environment with a monthly work-from-home stipend.
• Family planning resources and specialized support programs.
• Equity options to grow with Boulevard.
• Boulevard Bucks Learning and Development program.