Head of Engineering (AI | Digital Transformation)
• *Head of Engineering**
(Digital Transformation — AI-First Platform & Global Engineering Leadership)
United States (Remote)
Full-Time
• *About YPO**
YPO is a global leadership community of 35,000+ chief executives across 142 countries, built on peer learning, shared experiences, and trusted relationships.
YPO’s digital transformation is building a platform where members discover relevant peers and events, understand why they see what they see, control their data, and trust every interaction.
• *The Opportunity**
The Head of Engineering will lead the transformation of our engineering organization and drive our global digital transformation initiative.
We’re looking for a strategic, hands-on engineering leader who has successfully built systems and teams from the ground up, with a proven track record of architecting new systems, leading technology transformations, and building high-performing teams.
This role carries dual accountability:
• Stabilizing the existing BAU environment
• Leading a greenfield AI-native redesign of YPO's global member, chapter, and network experience
• *YPO is building an AI-first engineering organization.**
Candidates are expected to actively and enthusiastically use AI tools in how they build, design, and ship.
• *Primary Responsibilities**
• *Architecture & Modernization**
• Lead evolution of legacy systems into modular, cloud-ready architecture
• Serve as architect and player-coach (designing, prototyping, coding)
• Transition to API-first, services-based architecture
• Define 3–5 year North-Star Architecture
• Build AI-native foundations (retrieval, embeddings, agentic workflows)
• Apply
• *Domain-Driven Design (DDD)**
to define service ownership and boundaries
• Implement
• *event-driven systems**
(Kafka, streaming platforms)
• Adopt
• *serverless-first patterns**
(AWS Lambda, Step Functions, EventBridge)
• *Data Architecture & Governance**
• Architect unified data platform (lakehouse, pipelines, lineage, quality)
• Implement enterprise-grade governance (RBAC, privacy, auditing, residency)
• Ensure data is trustworthy, observable, and AI-ready
• Lead
• *Snowflake**
adoption and data warehouse strategy
• Implement Elastic for search, analytics, and observability
• *AI Engineering & Intelligent Experience**
• Drive AI integration across products and operations
• Build AI-native systems (search, recommendations, agentic assistants)
• Implement LLM-powered services (RAG, embeddings, monitoring, auditability)
• *• Champion AI-first engineering culture and AI-assisted development**
• *Engineering Operations, DevOps, SRE & Security**
• Establish CI/CD, automated testing, and
• *infrastructure-as-code**
• Enforce IaC discipline (Terraform, AWS CDK — not optional)
• Design
• *multi-account**
• *AWS environments and IAM guardrails**
• Implement SRE practices (observability, incident response, on-call)
• Establish DevSecOps, security, and compliance frameworks (SOC2, GDPR, CCPA)
• *Organizational Design & Leadership**
• Recruit, develop, and mentor engineering talent
• Evolve organization to support scalable, modern engineering delivery
• Strengthen leadership across platform, data, DevOps, and product engineering
• Build AI-forward teams with active AI tool usage
• Operate dual-track model (BAU + transformation)
• Partner with Product, Design, and Business leaders
• *Vendor Strategy & Budget Ownership**
• Define build/buy/partner strategy
• Manage vendors and systems integrators
• Own engineering budgets and cost optimization
⚡
• *Required Qualifications**
• *Leadership & Experience**
• 15+ years software development; 8+ years in architecture/leadership
• Experience building and scaling engineering teams in complex environments
• Proven success leading modernization and transformation initiatives
• Experience stabilizing legacy systems while building greenfield platforms
• Track record of mentoring teams and driving engineering excellence
• *Core Technical Skills**
• Microservices, distributed systems, APIs, event-driven architecture
• Domain-Driven Design (DDD)
• Serverless (AWS Lambda, Step Functions, EventBridge)
• Infrastructure as Code (Terraform, AWS CDK — required)
• Multi-account AWS, IAM design, security architecture
• Data engineering, lakehouse architectures, Snowflake
• Elastic (search and observability)
• CI/CD, DevOps, containerization
• AI engineering (LLMs, RAG, embeddings, vector databases)
Apply Now
Apply Now
(Digital Transformation — AI-First Platform & Global Engineering Leadership)
United States (Remote)
Full-Time
• *About YPO**
YPO is a global leadership community of 35,000+ chief executives across 142 countries, built on peer learning, shared experiences, and trusted relationships.
YPO’s digital transformation is building a platform where members discover relevant peers and events, understand why they see what they see, control their data, and trust every interaction.
• *The Opportunity**
The Head of Engineering will lead the transformation of our engineering organization and drive our global digital transformation initiative.
We’re looking for a strategic, hands-on engineering leader who has successfully built systems and teams from the ground up, with a proven track record of architecting new systems, leading technology transformations, and building high-performing teams.
This role carries dual accountability:
• Stabilizing the existing BAU environment
• Leading a greenfield AI-native redesign of YPO's global member, chapter, and network experience
• *YPO is building an AI-first engineering organization.**
Candidates are expected to actively and enthusiastically use AI tools in how they build, design, and ship.
• *Primary Responsibilities**
• *Architecture & Modernization**
• Lead evolution of legacy systems into modular, cloud-ready architecture
• Serve as architect and player-coach (designing, prototyping, coding)
• Transition to API-first, services-based architecture
• Define 3–5 year North-Star Architecture
• Build AI-native foundations (retrieval, embeddings, agentic workflows)
• Apply
• *Domain-Driven Design (DDD)**
to define service ownership and boundaries
• Implement
• *event-driven systems**
(Kafka, streaming platforms)
• Adopt
• *serverless-first patterns**
(AWS Lambda, Step Functions, EventBridge)
• *Data Architecture & Governance**
• Architect unified data platform (lakehouse, pipelines, lineage, quality)
• Implement enterprise-grade governance (RBAC, privacy, auditing, residency)
• Ensure data is trustworthy, observable, and AI-ready
• Lead
• *Snowflake**
adoption and data warehouse strategy
• Implement Elastic for search, analytics, and observability
• *AI Engineering & Intelligent Experience**
• Drive AI integration across products and operations
• Build AI-native systems (search, recommendations, agentic assistants)
• Implement LLM-powered services (RAG, embeddings, monitoring, auditability)
• *• Champion AI-first engineering culture and AI-assisted development**
• *Engineering Operations, DevOps, SRE & Security**
• Establish CI/CD, automated testing, and
• *infrastructure-as-code**
• Enforce IaC discipline (Terraform, AWS CDK — not optional)
• Design
• *multi-account**
• *AWS environments and IAM guardrails**
• Implement SRE practices (observability, incident response, on-call)
• Establish DevSecOps, security, and compliance frameworks (SOC2, GDPR, CCPA)
• *Organizational Design & Leadership**
• Recruit, develop, and mentor engineering talent
• Evolve organization to support scalable, modern engineering delivery
• Strengthen leadership across platform, data, DevOps, and product engineering
• Build AI-forward teams with active AI tool usage
• Operate dual-track model (BAU + transformation)
• Partner with Product, Design, and Business leaders
• *Vendor Strategy & Budget Ownership**
• Define build/buy/partner strategy
• Manage vendors and systems integrators
• Own engineering budgets and cost optimization
⚡
• *Required Qualifications**
• *Leadership & Experience**
• 15+ years software development; 8+ years in architecture/leadership
• Experience building and scaling engineering teams in complex environments
• Proven success leading modernization and transformation initiatives
• Experience stabilizing legacy systems while building greenfield platforms
• Track record of mentoring teams and driving engineering excellence
• *Core Technical Skills**
• Microservices, distributed systems, APIs, event-driven architecture
• Domain-Driven Design (DDD)
• Serverless (AWS Lambda, Step Functions, EventBridge)
• Infrastructure as Code (Terraform, AWS CDK — required)
• Multi-account AWS, IAM design, security architecture
• Data engineering, lakehouse architectures, Snowflake
• Elastic (search and observability)
• CI/CD, DevOps, containerization
• AI engineering (LLMs, RAG, embeddings, vector databases)
Apply Now
Apply Now