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