# Madison-Davis, LLC — Vice President of Engineering

- Generated: 2026-08-25 06:38:37 PM EDT
- Original/canonical posting: https://jobright.ai/jobs/info/6a7b3559ecf5194164fbc891
- Jobright source: https://jobright.ai/jobs/info/6a7b3559ecf5194164fbc891
- Posted: 2026-08-25 10:56:58 AM EDT
- Valid through: 2026-09-25 10:56:58 AM EDT
- Applicants: Not disclosed
- Work model/location: Remote, United States
- Employment type: FULL_TIME
- Compensation: $250,000-$300,000
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 74%

## Direct-match strengths

Enterprise modernization, AI-assisted engineering, agentic workflows, cloud-native platforms, APIs, microservices, distributed systems, DevOps, CI/CD, and engineering transformation are strong.

## Hard or material gaps

Hard required-technology gap: the posting requires a strong background in Java-based enterprise development, which is not supported by Keith's source record. The unnamed end employer also limits organization-scope verification.

## Evidence map

1. Enterprise modernization — 3/3: Direct cloud, SaaS, and legacy-data modernization.
2. AI-assisted engineering — 3/3: Direct Codex and agentic engineering.
3. Cloud-native distributed platforms — 3/3: Direct AWS, APIs, microservices, and distributed systems.
4. Engineering transformation — 3/3: Direct teams, delivery systems, and standards.
5. Global large-scale organization — 2/3: Global enablement plus teams up to 25, but exact employer scope is unknown.
6. Java enterprise development — 0/3: Mandatory and unsupported.

## Full normalized job description

Note: The job is a remote job and is open to candidates in USA. Madison-Davis, LLC is recruiting an executive technology leader for a major enterprise platform modernization initiative. The Vice President of Engineering will accelerate the transition to cloud-native architectures and build an AI-first engineering organization using Generative AI, intelligent automation, and agentic workflows to improve productivity, quality, and delivery speed.
Responsibilities
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
Skills
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
Company Overview
Madison-Davis is a staffing and recruiting company offering financial services. It was founded in 1982, and is headquartered in Tarrytown, New York, USA, with a workforce of 51-200 employees. Its website is http://tmdg.com.
Company H1B Sponsorship
Madison-Davis, LLC has a track record of offering H1B sponsorships, with 3 in 2026, 22 in 2025, 15 in 2024, 8 in 2023, 3 in 2022, 1 in 2021. Please note that this does not guarantee sponsorship for this specific role.

## Artifact metadata

- Resume and cover letter: Not generated under the fit gate.
- Google Drive used: No