Senior Director of Enterprise AI & Architecture

Join Flywire, a leading global payments enablement and software company. As the Senior Director of Enterprise AI & Architecture, you will establish and lead a centralized Enterprise AI organization, defining the strategy, roadmap, and operating model for AI adoption across the business. This high-visibility role requires a strong technical background, experience in AI and machine learning, and a passion for driving measurable business value through technology.

• Establish and lead the centralized Enterprise AI organization, defining and owning the Enterprise AI strategy, roadmap, and operating model.
• Build and lead a high-performing team spanning architecture, AI engineering, platform, governance, and security, delivering measurable business value.
• Serve as a strategic leader for the AI Center of Excellence, representing the Enterprise AI organization to the Executive team and reporting on milestones, ROI, and risk posture.
• Familiarity with enterprise AI platform capabilities such as model access gateways, model catalogs, AI orchestration layers, policy enforcement, prompt and response controls, observability, cost monitoring, and usage governance
• Bachelor’s degree in Computer Science, Engineering, Information Systems, Data Science, or related field required
• Understanding of AI/ML model lifecycle practices, including model selection, experimentation, validation controls, performance monitoring, drift detection, feedback loops, auditability, and responsible production deployment
• Experience with Agentic AI patterns, including autonomous or semi-autonomous agents, tool/function calling, workflow orchestration, human-in-the-loop controls, guardrails, monitoring, and safe deployment practices
• Strong understanding of Generative AI concepts and implementation patterns, including LLMs, RAG pipelines, agentic AI frameworks, enterprise ML deployment patterns, SLMs, embeddings, prompt engineering, retrieval-augmented generation, vector databases, semantic search, evaluation frameworks, and enterprise knowledge integration.
• 15+ years of progressive technology leadership experience, including senior responsibility for engineering, architecture, platforms, data, infrastructure, automation, AI, digital transformation, or enterprise technology delivery, including 5+ years managing multi-disciplinary engineering or architecture teams
• Strong technical fluency across cloud platforms, APIs, microservices, data platforms, observability, automation, cybersecurity, identity, privacy, and modern engineering practices
• Familiarity with Model Context Protocol (MCP) or similar approaches for connecting AI systems to enterprise tools, data sources, APIs, and workflow actions in a secure and governed manner
• Significant hands-on leadership experience with AI, machine learning, Generative AI, automation, advanced analytics, intelligent platforms, developer productivity tools, or emerging technology capabilities, at a large Enterprise Organization
• Experience at large Enterprise, enabling enterprise adoption of AI productivity tools such as Gemini, ChatGPT, Claude, or similar platforms
• Experienced at defining and influencing organizational strategy, inclusive of board and executive level communications(written and verbal)
• Track record of partnering with executive stakeholders and translating technology strategy into business outcomes
• Strong command of compliance requirements relevant to payments (PCI-DSS, SOX).
• Strategic yet technical, with ability to dive deep into architecture, engineering, security, data, operations, and business process details
• Experience with FinOps practices and cloud cost governance for AI/ML workloads
• Demonstrated success building or leading an enterprise AI, platform engineering, or architecture function at scale
• Inspirational thought leader with passion for building and scaling AI-enabled technology and business capabilities. Pragmatic, hands-on leader with strong bias for action and measurable outcomes
• Proven experience leading Enterprise-scale technology transformation; preferably in a regulated environment, such as financial services, or another highly governed industry
• Proven ability to lead internal teams, contractors, vendors, and system integration partners in a fast-paced, high-accountability environment
• Experience at a global payments, fintech, or healthcare technology company
• Familiarity with federated delivery models and domain-led architecture teams
• Background in responsible AI, AI ethics frameworks, or model explainability
• MBA or advanced degree in Computer Science, Engineering, or related field