Director, Cloud Engineering

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 ResponsibilitiesDefine and execute the enterprise Cloud engineering and DevOps strategy aligned with Bridgeway's business and technology objectivesEstablish and maintain a multi-year roadmap for reliability, scalability, automation, CI/CD, and cloud modernizationProvide architectural leadership to ensure Cloud investments deliver measurable business valueProvide hands-on support as neededDefine and enforce Infrastructure as Code (IaC) standards using Terraform, ensuring consistent, repeatable, and auditable infrastructure deployments across all environmentsEstablish Terraform module libraries and governance practices to promote reusability, reduce configuration drift, and accelerate infrastructure provisioningLead the adoption of GitOps workflows for infrastructure management, integrating Terraform with CI/CD pipelines for automated plan, review, and apply processesLead the implementation and governance of secure networking solutions using modern VPN technologies such as Tailscale, WireGuard, and traditional IPsec tunnelsPartner with executive leadership to communicate Cloud strategy, progress, and outcomesOversee the design, implementation, and optimization of cloud infrastructure, CI/CD pipelines, and developer enablement CloudsEstablish KPIs and metrics to measure reliability, delivery efficiency, and Cloud maturityLead enterprise-wide standards, policies, and governance for Cloud and DevOps practicesLead, mentor, and develop a team of Windows and Linux-focused engineersBuild a culture of accountability, continuous improvement, and operational excellenceOversee talent strategy including hiring, performance management, succession planning, and career developmentFoster a collaborative, inclusive, and high-performance engineering organizationAct as a primary escalation and decision authority for Cloud-related risks and challengesPartner with Product, Engineering, Architecture, Security, and Business leaders to translate business needs into scalable technical solutionsEvaluate emerging cloud technologies and make architecture decisions aligned with business objectivesOversee cloud cost management and budget optimizationServe as a change agent, driving adoption of modern engineering practices and emerging technologiesDesign and drive implementation of IP Address Management (IPAM) solutions such as NetBox, Infoblox, or AWS IPAM ServicesArchitect and manage multi-account (AWS) or multi-tenant (Azure) environments with complex interconnection and governance requirementsLead migrations from traditional on-premises deployment patterns to leverage cloud-native servicesDesign and maintain Kubernetes environments with proper security controls, network segmentation, and namespace isolationPartner with development teams to transition application deployments from traditional server installations to containers and serverless architecturesInterface with development teams to identify pain points and lead continuous improvement initiativesEnsure Cloud availability, resilience, security, and complianceSupport security and compliance teams with evidence gathering and audit interviews for SOC 2 and similar frameworksDesign 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 concernsTroubleshoot complex technical issues across all levels of the stack while marshalling appropriate resources and providing timely updates to stakeholdersDeliver root cause analysis reports with actionable recommendations to prevent recurrenceLead incident management, root cause analysis, and continuous improvement effortsDrive 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 servicesQualifications10+ years of experience in infrastructure, Cloud, Cloud engineering, or DevOps roles, with at least 3 years in leadership or management positions5+ years of hands-on experience designing and operating cloud environmentsProven experience leading enterprise DevOps and Cloud transformation initiativesDemonstrated success managing and developing high-performing technical teams, including full human capital responsibilityStrong expertise in cloud architecture, automation, CI/CD, and reliability engineeringExceptional communication skills with the ability to influence executive, technical, and non-technical stakeholdersHands-on experience architecting and deploying systems that meet advanced security compliance requirements including HIPAA, HITRUST, and NIST frameworksExperience implementing and managing Entra ID as a primary identity provider with SAML and OAuth integrations across internal and external systemsProficiency developing and maintaining build and deployment pipelines supporting multiple teams with distinct requirements across multiple languages and frameworksHands-on experience designing and implementing Terraform configurations for multi-cloud environments, including state management, workspace strategies, and remote backend configurationsProficiency establishing Terraform governance frameworks including Sentinel policies, code review standards, and module registriesExperience migrating legacy infrastructure to IaC patterns using Terraform import and refactoring strategiesHands-on experience designing and operating enterprise secure network solutions including IPsec site-to-site tunnels and modern overlay networks such as Tailscale or WireGuardBachelor's degree in Computer Science, Engineering, or related fieldBridgeway is an equal opportunity employer.