[Hiring] Director of Engineering, Cloud & Reliability @Boulevard

Role Description

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

Benefits

• 401(k) match plus dental, medical, vision, and life insurance.
• Flexible vacation day policy.
• Fully remote work with a monthly work from home stipend.
• Family planning resources and specialized support programs.
• Equity opportunities to grow with Boulevard.
• Boulevard Bucks Learning and Development program to explore businesses in the market we serve.