[Hiring] Director, Cloud Engineering @Bridgeway Benefit Technologies

Bridgeway is seeking a Director of Cloud Engineering to lead the strategy, modernization, and operational excellence of our infrastructure and developer enablement Cloud. This role defines and executes the vision for reliability, scalability, security, and automation across our technology ecosystem. You will shape enterprise-wide Cloud strategy, champion DevOps and Site Reliability Engineering practices, and enable teams to deliver secure, high-quality software. You will also lead a high-performing engineering team and serve as a trusted advisor to executive and business stakeholders. This is a high-impact opportunity to drive the transformation of our Cloud into a highly automated, resilient environment that supports Bridgeway’s long-term growth and innovation.

The is a remote position with preference given to East Coast candidates; <5% travel expected. After-hours/on-call availability required.

Key Responsibilities

• Define and execute the enterprise Cloud engineering and DevOps strategy aligned with Bridgeway’s business and technology objectives
• Establish and maintain a multi-year roadmap for reliability, scalability, automation, CI/CD, and cloud modernization
• Provide architectural leadership to ensure Cloud investments deliver measurable business value
• Provide hands-on support as needed
• Define and enforce Infrastructure as Code (IaC) standards using Terraform, ensuring consistent, repeatable, and auditable infrastructure deployments across all environments
• Establish Terraform module libraries and governance practices to promote reusability, reduce configuration drift, and accelerate infrastructure provisioning
• Lead the adoption of GitOps workflows for infrastructure management, integrating Terraform with CI/CD pipelines for automated plan, review, and apply processes
• Lead the implementation and governance of secure networking solutions using modern VPN technologies such as Tailscale, WireGuard, and traditional IPsec tunnels
• Partner with executive leadership to communicate Cloud strategy, progress, and outcomes
• Oversee the design, implementation, and optimization of cloud infrastructure, CI/CD pipelines, and developer enablement Clouds
• Establish KPIs and metrics to measure reliability, delivery efficiency, and Cloud maturity
• Lead enterprise-wide standards, policies, and governance for Cloud and DevOps practices
• Lead, mentor, and develop a team of Windows and Linux-focused engineers
• Build a culture of accountability, continuous improvement, and operational excellence
• Oversee talent strategy including hiring, performance management, succession planning, and career development
• Foster a collaborative, inclusive, and high-performance engineering organization
• Act as a primary escalation and decision authority for Cloud-related risks and challenges
• Partner with Product, Engineering, Architecture, Security, and Business leaders to translate business needs into scalable technical solutions
• Evaluate emerging cloud technologies and make architecture decisions aligned with business objectives
• Oversee cloud cost management and budget optimization
• Serve as a change agent, driving adoption of modern engineering practices and emerging technologies
• Design and drive implementation of IP Address Management (IPAM) solutions such as NetBox, Infoblox, or AWS IPAM Services
• Architect and manage multi-account (AWS) or multi-tenant (Azure) environments with complex interconnection and governance requirements
• Lead migrations from traditional on-premises deployment patterns to leverage cloud-native services
• Design and maintain Kubernetes environments with proper security controls, network segmentation, and namespace isolation
• Partner with development teams to transition application deployments from traditional server installations to containers and serverless architectures
• Interface with development teams to identify pain points and lead continuous improvement initiatives
• Ensure Cloud availability, resilience, security, and compliance
• Support security and compliance teams with evidence gathering and audit interviews for SOC 2 and similar frameworks
• Design and maintain centralized logging configurations that aggregate and correlate system, application, cloud, and SaaS logsImplement advanced monitoring and alerting structures to ensure availability and assist development teams in identifying application errors and performance concerns
• Troubleshoot complex technical issues across all levels of the stack while marshalling appropriate resources and providing timely updates to stakeholders
• Deliver root cause analysis reports with actionable recommendations to prevent recurrence
• Lead incident management, root cause analysis, and continuous improvement efforts
• Drive automation-first practices using tools such as Python, Terraform, Ansible, and CI/CD Clouds.
• Coach and mentor traditional systems administrators on cloud concepts, enabling them to maintain and optimize cloud services

Qualifications

• 10+ years of experience in infrastructure, Cloud, Cloud engineering, or DevOps roles, with at least 3 years in leadership or management positions
• 5+ years of hands-on experience designing and operating cloud environments
• Proven experience leading enterprise DevOps and Cloud transformation initiatives
• Demonstrated success managing and developing high-performing technical teams, including full human capital responsibility
• Strong expertise in cloud architecture, automation, CI/CD, and reliability engineering
• Exceptional communication skills with the ability to influence executive, technical, and non-technical stakeholders
• Hands-on experience architecting and deploying systems that meet advanced security compliance requirements including HIPAA, HITRUST, and NIST frameworks
• Experience implementing and managing Entra ID as a primary identity provider with SAML and OAuth integrations across internal and external systems
• Proficiency developing and maintaining build and deployment pipelines supporting multiple teams with distinct requirements across multiple languages and frameworks
• Hands-on experience designing and implementing Terraform configurations for multi-cloud environments, including state management, workspace strategies, and remote backend configurations
• Proficiency establishing Terraform governance frameworks including Sentinel policies, code review standards, and module registries
• Experience migrating legacy infrastructure to IaC patterns using Terraform import and refactoring strategies
• Hands-on experience designing and operating enterprise secure network solutions including IPsec site-to-site tunnels and modern overlay networks such as Tailscale or WireGuard
• Bachelor’s degree in Computer Science, Engineering, or related field

Bridgeway is an equal opportunity employer.