[Remote] VP, Cloud Engineering and Modernization

Note: The job is a remote job and is open to candidates in USA. Crawford & Company is seeking a visionary VP of Cloud Engineering & Modernization to lead and scale their cloud-native platforms. This role is responsible for driving cloud strategy, modernization, and continuous improvement across the company's infrastructure while ensuring security, resilience, and cost-efficiency.

Responsibilities

• Own and drive the enterprise cloud engineering strategy and its inputs into modernization strategy, roadmap, and delivery operating model (intake, prioritization, execution, and reporting) aligned to business and technology objectives
• Lead and govern end-to-end migrations of applications and workloads from on-premises environments to Azure and AWS, including assessment, dependency mapping, wave planning, and cutover execution
• Partner with application-teams to define migration approaches (rehost, replatform, refactor, retire) and ensure target-state architecture meets requirements for resiliency, performance, and supportability
• Establish, contribute to, and programatically enforce standards for Infrastructure such as Code, CI/CD, configuration management, and automated provisioning to enable repeatable delivery
• Provide leadership to Cloud Platform Engineering/Cloudops Migration teams and manage vendor/partner resources to deliver programs on schedule and within budget
• Drive operational readiness for migrated workloads, including monitoring, alerting, backup/restore, DR, incident/problem management, runbooks, and call/ escalation processes
• Collaborate with Security, Privacy, Risk, and Compliance to incorporate their requirements into cloud engineering
• Partner with FinOps and Cloudops Delivery and migration teams to implement cloud cost management practices, including tagging standards, budgets/forecasting, and ongoing optimization across Azure and AWS
• Define KPIs and reporting for platform health and migration outcomes (availability, performance, cost, security posture, delivery velocity), and communicate status, risks, and decisions to senior stakeholders
• Evaluate and introduce new cloud services, tooling, and reference architectures to improve reliability, security, scalability, and engineering efficiency
• Serve as an escalation point for critical cloud and migration issues, leading root cause analysis and driving preventative improvements
• Develop and maintain documentation (architecture standards, migration playbooks, landing zone patterns, runbooks) to ensure consistent execution and knowledge transfer
• Coach and mentor engineering leaders and senior engineers; support talent development, hiring/interviewing, and performance goals under supervision of the Chief AI, Data and Cloud Officer of the company

Skills

• Bachelor's degree preferred
• Deep understanding of cloud architectures and core services across Azure and AWS; ability to define reference architectures, landing zones, and platform standards for enterprise adoption
• Proven expertise in large-scale data center-to-cloud migration programs, including discovery/assessment, dependency management, wave planning, and cutover execution
• Strong hands-on knowledge of Infrastructure as Code and Automation
• Advanced understanding of cloud networking, identity and access management, security controls, encryption/key management, and logging/monitoring patterns
• Experience with containers and orchestration (Docker, Kubernetes) and modern application platform patterns
• Working knowledge of FinOps principles, cost governance, tagging strategies, budgeting/forecasting, and optimization techniques
• Demonstrates strong leadership, manages stakeholders effectively, and communicates well; skilled at influencing both technical and non-technical teams to achieve results even in uncertain situations
• Strong documentation and program execution skills, including creation of playbooks, runbooks, standards, and KPI-based reporting
• 15+ years of experience in building and scaling cloud-native platforms
• 10 + years leading technical teams and/or large cross-functional programs, including vendor/partner management and matrix leadership
• Demonstrated success leading enterprise migration and modernization initiatives, with accountability for delivery timelines, risk management, and operational stabilization
• Experience building or operating multi-cloud or hybrid environments, including landing zone design, network connectivity, identity integration, monitoring, and governance controls
• Strong track record establishing engineering standards and operating procedures (IaC, CI/CD, automation, security-by-design) to improve consistency and efficiency
• Experience partnering with Security, Privacy, Risk/Compliance, and Internal Audit on control design and evidence collection in cloud environments
• Relevant cloud certifications preferred (e.g., Flexara Web Services Certified Solutions Architect)

Benefits

• Pay and incentive plans that recognize performance excellence
• Benefit programs that empower financial, physical, and mental wellness
• Training programs that promote continuous learning and career progression while enhancing job performance
• Sustainability programs that give back to the communities in which we live and work
• A culture of respect, collaboration, entrepreneurial spirit and inclusion

Company Overview