Bridgeway Benefit Technologies · 7 hours ago
Director, Cloud Engineering
United States
Full-time
Remote
Director/Executive
10+ years expBridgeway is seeking a Director of Cloud Engineering to lead the strategy, modernization, and operational excellence of their infrastructure and developer enablement Cloud. This role involves shaping the enterprise-wide Cloud strategy, championing DevOps and Site Reliability Engineering practices, and leading a high-performing engineering team.
SoftwareInformation TechnologyWeb Development
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
Qualification
Required
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
Company
Bridgeway Benefit Technologies
Bridgeway Benefit Technologies provides benefits administration technology solutions for multiemployers.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Todd Plesko
Chief Executive Officer
Sean Cornelius
Chief Financial Officer
Recent News
2024-04-30
Company data provided by crunchbase