VP of Engineering - AI-Driven Platform Modernization

Madison-Davis, LLC

New York (NY)

On-site

USD 320,000 - 520,000

Full time

14 days+

Application generator

Don’t send a generic resume — generate a resume and cover letter tailored to this exact role.

Get past ATS filters

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.