Jenna Massardo

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Summary

Technical executive and strategic advisor specializing in developer experience, platform engineering, and enterprise DevOps transformation. I partner with Fortune 500 engineering leaders to modernize software delivery, implement secure development practices, and drive measurable business outcomes. With deep expertise spanning infrastructure automation, policy-as-code, and AI-assisted development, I help organizations scale their engineering capabilities while maintaining security and compliance. Speaker, technical writer, and thought leader with a track record of enabling engineering teams to ship faster, safer, and smarter.

Areas of Expertise

PLATFORM ENGINEERING & DEVELOPER EXPERIENCE

Enterprise DevOps strategy, CI/CD architecture, GitHub Actions & workflows at scale, innersource program design, developer productivity optimization, engineering metrics & DORA adoption

SECURITY & COMPLIANCE

DevSecOps implementation, policy-as-code (Open Policy Agent/Rego), software supply chain security, SBOM strategies, compliance automation, secrets management, security-first architecture

AI-ASSISTED DEVELOPMENT

GitHub Copilot enterprise deployment, AI-augmented workflows, responsible AI adoption strategies, developer enablement for AI tooling

CLOUD & INFRASTRUCTURE

Multi-cloud architecture (Azure, AWS, GCP), Kubernetes & container orchestration, infrastructure as code (Terraform), configuration management at scale

TECHNICAL LEADERSHIP

Strategic technology advisory, enterprise architecture review, technical enablement & training, cross-functional stakeholder alignment, engineering team scaling

Experience

STAFF CUSTOMER SUCCESS ARCHITECT | GITHUB | 2021 - PRESENT

Strategic technical advisor to GitHub’s largest enterprise customers, driving adoption of modern software development practices across organizations with tens of thousands of developers.

Serve as trusted technical advisor to Fortune 500 engineering leadership, providing strategic guidance on DevOps transformation, platform engineering, and secure software delivery
Design and architect enterprise-scale GitHub deployments including Actions CI/CD pipelines, advanced security configurations, and Copilot rollout strategies
Lead technical enablement programs that accelerate customer adoption of GitHub’s platform capabilities, resulting in measurable improvements to developer velocity and security posture
Develop and deliver executive-level presentations on emerging practices including AI-assisted development, software supply chain security, and engineering effectiveness metrics
Author technical content and best practices documentation; contribute to GitHub’s body of knowledge on enterprise DevOps patterns
Collaborate cross-functionally with product, engineering, and sales teams to translate customer needs into platform improvements

SR. CUSTOMER SUCCESS ARCHITECT | STYRA | 2021

Technical lead for enterprise customers implementing policy-as-code and authorization frameworks using Open Policy Agent (OPA).

Designed and implemented authorization architectures for customers adopting cloud-native security patterns
Developed Rego policies and testing frameworks for complex authorization requirements
Delivered technical enablement on policy-as-code principles and OPA ecosystem best practices

LEAD CUSTOMER ARCHITECT | CHEF SOFTWARE (PROGRESS) | 2018 - 2021

Senior technical advisor responsible for driving customer success and product adoption across Chef’s infrastructure automation portfolio.

Partnered with enterprise customers to design compliance-as-code strategies using InSpec, enabling automated audit and security validation across hybrid infrastructure
Led architecture reviews and provided strategic guidance on infrastructure automation at scale
Developed reference architectures, sample code, and technical documentation; authored blog content on DevOps best practices
Conducted technical enablement sessions and peer programming engagements to upskill customer engineering teams

ENGINEERING MANAGER & AUTOMATION ARCHITECT | JACK HENRY & ASSOCIATES | 2014 - 2018

Progressive leadership roles driving infrastructure automation strategy and engineering team development for a Fortune 1000 financial technology company.

Led successful enterprise-wide deployment of configuration management to 11,000+ production servers, establishing compliance automation capabilities
Built and mentored multiple high-performing teams including Systems Management, Operations Monitoring, and Security Infrastructure
Managed distributed engineering teams and contributed to $10M+ technology budget planning
Championed DevOps practices and automation adoption across business units through training, consultation, and internal evangelism
Developed custom automation solutions and internal tooling to improve operational efficiency

Thought Leadership

Technical Blog: dxrf.com/blog — Writing on DevOps, platform engineering, and engineering leadership
Speaking: Internal and customer-facing presentations on enterprise DevOps, GitHub best practices, and AI-assisted development
Open Source: Contributor to documentation and community resources

Caffeine, Code & Chaos