Head Of Engineering

POSITION PURPOSE

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.

You must be detail-oriented, possess exceptional relationship-building skills, and thrive in a highly iterative, agile, and fast-paced environment. The ideal candidate maintains a strong growth mindset, stays current with emerging technologies and engineering best practices, and has experience building exceptional solutions that meet standards of excellence.

This role carries dual accountability: stabilizing the existing BAU environment while leading a greenfield AI-native redesign of YPO's global member, chapter, and network experience.

AI-First Technology Organization: YPO is building an AI-first engineering organization. Candidates are expected to actively and enthusiastically use AI tools in their daily work and leverage AI into how they build, design, and ship.

PRIMARY RESPONSIBILITIES

• Lead the evolution of YPO's tightly coupled legacy stack into modern, modular, cloud-ready systems

• Serve as both architect and player-coach: designing systems, prototyping solutions, and writing code while guiding teams

• Lead the structured transformation of current state architecture into an API-first, services-based architecture with minimal disruption to 37,000 global members

• Define the 3–5-year North-Star Architecture for YPO, including platform boundaries, technology choices, and standards for scalability, extensibility, and resiliency

• Establish the engineering foundation required for next-generation AI-native experiences including retrieval architectures, vector stores, embedding pipelines, event-driven patterns, and agentic workflow orchestration

• Apply Domain-Driven Design (DDD) principles to decompose bounded contexts, define service ownership, and establish clean API contracts across platform domains

• Design and implement event-driven architecture using Kafka and streaming platforms to enable real-time data flows, decoupled services, and event sourcing patterns across the platform

• Adopt serverless-first patterns (AWS Lambda, Step Functions, EventBridge) where appropriate to reduce operational overhead, improve cost efficiency, and accelerate delivery

• Architect a unified data platform, replacing today's fragmented data landscape with a modern data lakehouse, governed pipelines, lineage, metadata, and quality controls

• Implement enterprise-grade data governance including RBAC, role scoping, privacy-by-design, auditing, data residency, and consistent definitions of member and chapter data

• Ensure data is trustworthy, reconciled, observable, and usable for analytics, personalization, AI, and operational intelligence

• Lead adoption of Snowflake as the cloud data warehouse of record — including data modeling, virtual warehouse governance, cost controls, data sharing, and Snowpark-based transformations

• Implement and manage Elastic (Elasticsearch / OpenSearch) for full-text search, log analytics, observability pipelines, and member experience search surfaces

• Drive AI integration strategy and implementation to enhance products and operations

• Architect AI-native systems including intelligent search, personalized events, agentic assistants, recommendations, and automated operational workflows

• Implement LLM-powered services with safety, governance, and monitoring (RAG, embeddings, retrieval scoring, prompt management, auditability)

• Champion an AI-first engineering culture: every engineer, product manager, and designer is expected to actively use AI-assisted development (Copilot, Cursor, Claude, etc.) as a core part of their workflow — not experimentally, but operationally

• Introduce modern engineering practices including agile delivery, CI/CD, automated testing, and infrastructure-as-code

• Establish Infrastructure as Code discipline — Terraform and AWS CDK are the primary tools (not optional). All infrastructure should be versioned, peer-reviewed, and deployed through automated pipelines rather than manual console deployments in production

• Design and enforce IAM boundary design — least-privilege access policies, cross-account role assumptions, service control policies (SCPs), and permission boundaries across all AWS workloads and environments

• Implement a multi-account AWS strategy using AWS Organizations — separating workloads by environment (dev/staging/prod), domain, and security posture, with centralized logging, billing, and guardrails

• Implement SRE and observability standards (metrics, logging, tracing, alerting), on-call rotations, incident response, and blameless post-mortems

• Implement and maintain security, compliance, and governance frameworks across all engineering initiatives

• Establish a DevSecOps culture including vulnerability management, secure-by-design practices, platform hardening, dependency management, and continuous compliance (SOC2, GDPR, CCPA)

• Recruit, develop, and mentor engineering talent while fostering a collaborative, growth-oriented culture

• Partner with existing engineering teams to evolve the organization in support of future platform innovation and scalable delivery

• Strengthen leadership across engineering disciplines including platform, data, DevOps, mobile, frontend, backend, QA, and security

• Demonstrated experience building, scaling, and leading engineering teams in complex environments

• Experience guiding engineering organizations through transformation and modernization while helping teams adopt contemporary engineering practices

• Build and prioritize hiring for AI-forward roles — engineers, UI developers, product managers, QA professionals, and data specialists should demonstrate active, current use of AI tools within their work. Ideally, candidates are energized by AI and already incorporating it into their day-to-day practice, as this aligns closely with the direction YPO is moving toward

• Define the dual-track operating model: (1) BAU stabilization and support, and (2) greenfield transformation delivery

• Collaborate with Product, Design, and Business leaders to ensure technical decisions align with strategy

• Drive technical rigor through code reviews, architecture reviews, and engineering excellence initiatives

• Define build/buy/partner strategy for all major platform components

• Evaluate, negotiate, and manage engineering vendors, contractors, and systems integrators to ensure alignment with engineering standards and modernization goals

• Manage engineering budgets, vendor spend, total cost of ownership, and cost-performance optimization across cloud, data, and application platforms

Required Qualifications

• 15+ years of software development experience with 8+ years in architecture and solution design

• Demonstrated experience building, scaling, and leading engineering teams in complex environments

• Proven success leading large-scale modernization efforts and agile transformations in enterprise environments

• Experience transforming engineering teams into modern, high-performing organizations and optimizing team structure, processes, and capabilities

• Experience stabilizing legacy systems while building greenfield platforms simultaneously

• Track record of mentoring engineers and leaders while fostering a culture of technical excellence and best practices

• Experience building solutions that meet global standards including internationalization, localization, multi-region deployments, and compliance requirements

• Strong learning mindset with demonstrated commitment to staying current with emerging technologies, industry trends, and best practices

• Python, SQL, JavaScript/TypeScript, GCP, Azure Cloud, Dart/Flutter, C#/.NET, Kubernetes

• Microservices architecture and distributed systems design

• Domain-Driven Design (DDD) — bounded contexts, ubiquitous language, aggregate design, and service decomposition patterns

• Event-driven architecture — Kafka, Confluent, AWS Kinesis, or equivalent streaming platforms; event sourcing, CQRS, and pub/sub patterns

• Serverless architecture — AWS Lambda, Step Functions, EventBridge, API Gateway; cost modelling and cold-start mitigation

• Infrastructure as Code (mandatory) Terraform and AWS CDK required; GitOps workflows, module design, state management, and policy-as-code (OPA/Sentinel)

• Multi-account AWS strategy — AWS Organizations, Control Tower, SCPs, account vending, centralized logging (CloudTrail, Security Hub, GuardDuty)

• IAM boundary design — least-privilege role architecture, permission boundaries, cross-account trust policies, OIDC federation, and Just-In-Time access patterns

• Data engineering, ETL processes, and data lakehouse architectures

• Snowflake — data modeling, virtual warehouses, Snowpipe, Snowpark, data sharing, governance and cost management

• Elastic Stack (Elasticsearch / OpenSearch) — cluster design, index lifecycle management, full-text search relevance tuning, ingest pipelines, and Kibana/observability dashboards

• CI/CD pipelines, DevOps, and containerization (Docker/Kubernetes)

• APIs, RESTful services, and event-driven architectures

• Global architecture patterns including multi-region deployments, data residency, and scalability for international users

• Modern observability, incident response, SRE, and platform reliability engineering

• AI engineering: LLM integration, RAG, embeddings, vector databases, inference orchestration, agent frameworks

• Security best practices: secure coding, authentication/authorization, encryption, vulnerability management

• Cloud security and compliance standards: SOC 2, GDPR, CCPA, HIPAA, or similar frameworks

• DevSecOps, RBAC, auditing, and governance of access and identity across platforms and vendor systems

• IAM and identity governance — design of trust boundaries, privilege escalation controls, and zero-trust network access patterns

• Hands-on experience implementing AI/ML solutions in production environments

• Knowledge of LLMs, generative AI, and machine learning frameworks

• Experience integrating AI APIs (OpenAI, Azure AI, Anthropic) into enterprise applications

• Understanding of prompt engineering, fine-tuning, RAG, and responsible AI principles

• Active AI practitioner — uses AI coding assistants (GitHub Copilot, Cursor, Claude, etc.) daily; enthusiastic about the trajectory of AI and can articulate how it changes engineering practice. This is a mandatory attribute, not a nice-to-have

• Proven ability to recruit, mentor, and develop high-performing engineers

• Strong leadership, coalition-building, and communication skills across technical and business stakeholders

• Demonstrated experience transforming a support-oriented engineering culture into a modern, product-centric, engineering-driven organization

• Experience driving technical rigor while maintaining team velocity and morale

• Excellent relationship management skills; possesses gravitas while remaining humble and approachable

• Demonstrated commitment to continuous learning and professional development

• Active engagement with the technology community through conferences, publications, or open-source contributions

• AI-first hiring philosophy — has a track record of building teams where AI tool adoption is a cultural norm, not an afterthought; can assess AI readiness in candidates and lead by example

Success in 12 Months

Within a year, The Head of Engineering will have:

• Stabilized the existing BAU systems while launching the foundation of YPO's new AI-native platform

• Established the foundation for both a modern technical platform and a high-performing engineering organization

• Legacy systems evolving into modular, cloud-ready services built on Azure and AWS

• Kafka-based event streaming backbone operational, decoupling key services and enabling real-time data flows

• Domain-driven service boundaries defined and enforced across the platform — clear ownership, clean contracts

• Multi-account AWS strategy implemented with full IaC coverage (Terraform/CDK) and IAM guardrails in place

• A modern data lakehouse with Snowflake as the warehouse of record, trusted data pipelines, and unified data models in place

• Elastic-powered search and observability surfaces live and deliver measurable member experience improvements

• A Center of Excellence operational, driving engineering standards and best practices

• Security, compliance, and governance frameworks embedded into all engineering processes

• Agile and DevOps practices are institutionalized through CI/CD pipelines and SRE operations

• AI capabilities integrated into key workflows with measurable value delivered

• An AI-first engineering culture firmly established — every engineer, PM, designer, and QA professional is actively using AI tools in their daily workflow; AI adoption metrics are tracked and celebrated

• A lean, high-performing engineering team delivering faster, with higher reliability and accountability

EDUCATION / TRAINING

Bachelor’s degree in computer science, Engineering, Information Systems, or equivalent professional experience.

PHYSICAL REQUIREMENTS

Ability to collaborate across global time zones as needed.
Willingness to travel domestically and internationally (~10–15% annually).

EOE

YPO is an Equal Opportunity Employer and is committed to fostering a diverse and inclusive workplace. We do not discriminate on the basis of race, color, religion, creed, gender, gender identity or expression, sexual orientation, national origin, age, marital status, veteran status, disability, genetic information, or any other characteristic protected by applicable law.

EOE

YPO is an Equal Opportunity Employer. YPO takes pride in supporting a diverse workforce and demonstrates this through its policies and practices. YPO does not discriminate in recruiting, hiring, training, promotion, or other employment practices for reasons of race, color, religion, gender, national origin, age, sexual orientation, marital or veteran status, disability, or any other legally protected status.