I am a Senior Software Engineer with 9+ years of experience delivering enterprise-grade software solutions across the Finance, Insurance, and Healthcare sectors. I specialize in .NET, cloud-native architectures, DevSecOps, and data-driven engineering, with a strong focus on secure system design, modernization, and compliance (HIPPA, PCI-DSS, SOC 2). I have led development teams and collaborated with cross-functional stakeholders to build scalable, high-performance applications that drive measurable business outcomes. I design modern architectures using Azure and AWS, implement secure APIs with OAuth 2.0 and OpenID Connect, and champion DevSecOps practices across multi-region deployments to ensure reliability, security, and compliance.

Caleb Greenwood

I am a Senior Software Engineer with 9+ years of experience delivering enterprise-grade software solutions across the Finance, Insurance, and Healthcare sectors. I specialize in .NET, cloud-native architectures, DevSecOps, and data-driven engineering, with a strong focus on secure system design, modernization, and compliance (HIPPA, PCI-DSS, SOC 2). I have led development teams and collaborated with cross-functional stakeholders to build scalable, high-performance applications that drive measurable business outcomes. I design modern architectures using Azure and AWS, implement secure APIs with OAuth 2.0 and OpenID Connect, and champion DevSecOps practices across multi-region deployments to ensure reliability, security, and compliance.

Available to hire

I am a Senior Software Engineer with 9+ years of experience delivering enterprise-grade software solutions across the Finance, Insurance, and Healthcare sectors. I specialize in .NET, cloud-native architectures, DevSecOps, and data-driven engineering, with a strong focus on secure system design, modernization, and compliance (HIPPA, PCI-DSS, SOC 2).

I have led development teams and collaborated with cross-functional stakeholders to build scalable, high-performance applications that drive measurable business outcomes. I design modern architectures using Azure and AWS, implement secure APIs with OAuth 2.0 and OpenID Connect, and champion DevSecOps practices across multi-region deployments to ensure reliability, security, and compliance.

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Experience Level

Expert
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Expert
Expert
Expert
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Expert
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Work Experience

Senior Software Engineer | Technical Lead, Finance & Insurance Digital Modernization at Deloitte
June 1, 2023 - December 1, 2025
Led modernization of healthcare data management platforms from monolithic .NET Framework apps to distributed .NET Core microservices hosted on Azure Kubernetes Service (AKS), delivering seamless policy administration across 10+ client regions and achieving high availability. Implemented secure API ecosystems with Azure API Management and OpenID Connect, built CI/CD pipelines and automated testing to support compliance (HIPPA, PCI-DSS, SOC 2). Designed data analytics and observability solutions (Grafana, Application Insights, DataDog) to monitor 25+ Azure services, enabling cost optimization and faster incident response. Established cross-region failover strategies using Azure Traffic Manager and Load Balancer, achieving 99.95% SLA compliance. Built reusable .NET libraries and WCF services with centralized logging and thread-safe design to improve reliability by ~20%. Mentored 4 junior engineers and 2 QA analysts, and presented modernization roadmaps to executives. Implemented AI-driven
Frontend Master, Enterprise Software & Government Cloud Solutions at IBM
May 1, 2018 - May 1, 2023
Delivered responsive ASP.NET MVC and Web API solutions to automate complex enterprise document workflows, improving operational efficiency by 25%. Redesigned front-end experiences using Angular, TypeScript, and Bootstrap, reducing page load times by 38%. Built reusable .NET libraries and WCF services with centralized logging and thread-safe design, improving application reliability by 20%. Created advanced data visualizations using Grafana and Application Insights dashboards to optimize costs and monitor 25+ Azure services, identifying ~$30K annual savings. Collaborated with Deloitte’s health care clients to define digital transformation roadmaps and align architecture with regulatory standards (HIPA A, HITRUST, SOC 2). Implemented CI/CD pipelines with Azure DevOps, YAML templates, and policy gates to enforce code quality and automated regression testing. Configured Azure API Management, Key Vault, and Managed Identities to secure data exchanges between cloud microservices and on-pre

Education

Bachelor of Science in Computer Systems Networking and Telecommunications at Ohio University
August 1, 2011 - May 1, 2015

Qualifications

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Industry Experience

Financial Services, Healthcare, Software & Internet