Head of Engineering – AI Platform Transformation

About SimplifyVMS

SimplifyVMS is a leading

VMS platform , providing

cutting-edge Vendor Management System (VMS) solutions

that empower organizations to manage their

contingent workforce, direct sourcing, and total talent strategies .

We are a sophisticated multi-tenant SaaS platform built on a MEAN stack (MongoDB, Express, Angular, Node.js) with a mature microservices-based architecture. We are now entering a transformational phase — evolving from a traditional SaaS platform into a fully AI-powered system.

Our goal:

refactor and re-architect the platform to integrate generative AI capabilities (e.g., Claude, OpenAI, etc.), enable AI-assisted code generation, introduce automated debugging frameworks, and implement full CI/CD-driven regression and automated testing — within an accelerated 2–3-month timeframe.

We are seeking a hands-on, execution-driven Head of Engineering who has successfully led similar platform modernization or AI-driven refactoring initiatives.

Role Overview The Head of Engineering will: Own the end-to-end technical transformation of the platform Refactor and modernize a complex microservices MEAN stack system Architect and implement AI integrations (e.g., Claude or similar LLMs) Introduce AI-assisted development workflows Build automated testing (unit, integration, regression) Establish CI/CD automation Build and scale the engineering team to support this evolution Deliver results within an aggressive 2–3 month transformation window

This is not a maintenance role — this is a platform reinvention mandate. Mission: 90-Day Transformation Mandate

Within 2–3 months, the candidate will: Audit and deeply understand the current platform Identify architectural bottlenecks and technical debt Design a modernization and AI integration roadmap Refactor critical services to support AI augmentation Implement automated testing and regression frameworks Introduce AI-assisted development and debugging workflows Establish engineering velocity improvements Build/augment the team required to sustain the transformation

Key Responsibilities 1. Platform Audit & Refactoring Strategy Conduct comprehensive technical audit of: Microservices architecture API structures Data flows DevOps pipelines Test coverage gaps Identify refactor priorities Redesign components to be AI-compatible and modular Improve service isolation and performance 2. AI Integration & Augmented Engineering Integrate LLM tools (e.g., Claude, OpenAI, etc.) into: Code generation workflows Debugging assistance Intelligent documentation Refactoring recommendations Build AI-native services within the SaaS platform Design guardrails for AI-generated code validation Create AI-driven observability and issue detection frameworks 3. Automated Testing & Regression Framework Implement comprehensive: Unit testing Integration testing End-to-end testing Regression testing Establish automated test coverage benchmarks Embed testing into CI/CD pipeline Reduce manual QA dependency Introduce automated code quality gates 4. DevOps & CI/CD Modernization Improve build pipelines Introduce automated deployments Enable zero-downtime releases Improve observability and monitoring Reduce technical debt 5. Team Leadership & Engineering Buildout Leverage existing engineering team to accelerate ramp-up Identify skill gaps and recruit targeted hires Establish performance standards Introduce engineering best practices Build a culture of high-velocity AI-augmented development Align product and engineering roadmaps

Mandatory Experience Requirements Candidates MUST have: 12+ years of software engineering experience Experience leading microservices-based SaaS platforms Deep expertise in MEAN stack (MongoDB, Express, Angular, Node.js) Proven experience refactoring complex production systems Experience integrating LLMs or generative AI into engineering workflows Demonstrated success implementing automated testing frameworks Experience building AI-assisted development pipelines Prior experience leading rapid transformation initiatives Experience building and scaling engineering teams Candidates without hands-on transformation experience will not be considered.

Highly Preferred Experience Experience converting traditional SaaS platforms into AI-enabled platforms Experience with LLM orchestration frameworks Knowledge of prompt engineering and AI guardrails Experience with cloud-native architectures (AWS, Azure, GCP) Experience implementing observability tools (Datadog, New Relic, etc.) Experience reducing tech debt in high-growth environments

Leadership Profile We are looking for someone who is: Highly technical and hands-on Comfortable reviewing code directly Architecturally strong Fast-moving and execution-driven Calm under aggressive timelines Builder-oriented Strategic but operationally excellent Able to inspire and elevate existing teams

Key Success Metrics (First 90 Days) AI integration framework live Refactored core services 70–80% automated test coverage CI/CD fully automated Regression testing in place Measurable improvement in deployment velocity Reduced bug backlog AI-assisted debugging operational Clear roadmap for ongoing AI-first platform evolution

What This Role Is Not Not a maintenance engineering manager Not a pure architect disconnected from execution Not a legacy system caretaker This is a transformation leadership role.

Compensation Competitive executive compensation Performance-based bonus tied to transformation milestones Equity participation Executive benefits package

To Apply Please include: Summary of similar transformation you have led Description of platform complexity handled Timeline achieved AI integration experience details Team size managed Testing automation frameworks implemented