Vice President of Engineering

Madison-Davis, LLC; New York (NY); On-site; USD 320,000 - 520,000; Full time

Job summary

Madison-Davis, LLC seeks a transformational Vice President of Engineering to lead a large-scale modernization initiative. You will accelerate modernization, redefine software delivery, and embed Generative AI across the lifecycle to boost productivity, quality, and speed.

You will shape an AI-first culture while guiding API-first, microservices-based architectures and regulated enterprise-scale programs. The role demands executive leadership, deep Java and Python expertise, cloud-native

Qualifications

• Executive-level software engineering leadership experience required.
• Proven success leading enterprise application modernization initiatives.
• Strong background in Java-based enterprise software development.
• Experience with Python and modern software engineering ecosystems.
• Deep expertise designing cloud-native platforms and distributed systems.
• Experience building API-first and microservices-based architectures.
• Demonstrated success implementing AI capabilities within software engineering organizations.
• Experience leading large-scale engineering and organizational transformations.
• Strong understanding of Agile delivery, DevOps, CI/CD, platform engineering, and software lifecycle management.
• Excellent executive communication and stakeholder management skills.

Responsibilities

• Define and execute the long-term modernization strategy for a large-scale enterprise platform.
• Lead transformation of legacy apps to cloud-native architectures.
• Drive AI-assisted software engineering and agentic AI capabilities adoption.
• Modernize architecture with APIs, microservices, and scalable distributed systems.
• Build an AI-first organization focused on automation and developer productivity.
• Improve delivery through Agile, DevOps, CI/CD, and SDLC practices.
• Align technology investments with long-term business strategy with executives.
• Lead organizational transformation across teams, processes, and operating models.
• Mentor engineering leaders and foster a culture of innovation and ownership.
• Establish best practices around architecture, quality, reliability, and performance.

Skills

Executive leadership

Enterprise modernization

Java development

Python

Cloud-native

APIs & microservices

AI in software engineering

Agile/DevOps

Stakeholder management

Distributed teams

Tools

CI/CD

Platform engineering

Job description

A well-established enterprise technology organization is seeking a transformational Vice President of Engineering to lead one of its largest technology modernization initiatives.

The organization is undertaking a multi-year transformation of a highly complex, business-critical platform that has supported core enterprise operations for decades. Significant investments have already been made toward a next-generation platform, and the organization is now looking for an executive leader who can accelerate modernization while redefining how software engineering is delivered.

This role extends beyond platform modernization. The long-term vision is to build an AI-first engineering organization that embeds Generative AI, intelligent automation, and agentic workflows throughout the software development lifecycle to improve engineering productivity, software quality, and delivery speed.

What You'll Lead:

• Define and execute the long-term engineering modernization strategy for a large-scale enterprise platform.
• Lead the transformation of legacy applications into modern cloud-native architectures.
• Drive enterprise adoption of AI-assisted software engineering and emerging agentic AI capabilities.
• Modernize application architecture through APIs, microservices, and scalable distributed systems.
• Build an AI-first engineering organization focused on automation, developer productivity, and engineering excellence.
• Improve software delivery through Agile, DevOps, CI/CD, platform engineering, and modern SDLC practices.
• Partner with executive leadership to align technology investments with long-term business strategy.
• Lead organizational transformation across engineering teams, processes, and operating models.
• Mentor engineering leaders while building a culture of innovation, ownership, and continuous improvement.
• Establish best practices around architecture, software quality, platform reliability, and engineering performance.

What You Bring:

• Extensive executive-level software engineering leadership experience.
• Proven success leading enterprise application modernization initiatives.
• Strong background in Java-based enterprise software development.
• Experience with Python and modern software engineering ecosystems.
• Deep expertise designing cloud-native platforms and distributed systems.
• Experience building API-first and microservices-based architectures.
• Demonstrated success implementing AI capabilities within software engineering organizations.
• Experience leading large-scale engineering and organizational transformations.
• Strong understanding of Agile delivery, DevOps, CI/CD, platform engineering, and software lifecycle management.
• Excellent executive communication and stakeholder management skills.
• Experience implementing AI-assisted development workflows and agentic AI concepts.
• Experience within regulated, enterprise-scale technology environments is highly preferred.
• Experience leading globally distributed engineering organizations and enterprise cloud modernization initiatives is a plus.