Senior Director, Enterprise AI & Architecture

Flywire•Boston, MA

23h•Hybrid

About The Position

Flywire is building a centralized Enterprise AI organization to govern, scale, and accelerate AI adoption across the business. The Sr. Director, Enterprise AI & Architecture will found and lead this function, establishing the enterprise-wide standards, governance model, shared platform strategy, and talent infrastructure needed to deliver measurable business value. This is a high-visibility role at the intersection of strategy, technology, and compliance in the highly regulated sectors.

Requirements

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.
Experience at large Enterprise, enabling enterprise adoption of AI productivity tools such as Gemini, ChatGPT, Claude, or similar platforms.
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.
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.
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.
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.
Understanding of AI/ML model lifecycle practices, including model selection, experimentation, validation controls, performance monitoring, drift detection, feedback loops, auditability, and responsible production deployment.
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.
Strong technical fluency across cloud platforms, APIs, microservices, data platforms, observability, automation, cybersecurity, identity, privacy, and modern engineering practices.
Bachelor’s degree in Computer Science, Engineering, Information Systems, Data Science, or related field required.
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.
Strategic yet technical, with ability to dive deep into architecture, engineering, security, data, operations, and business process details.
Proven experience leading Enterprise-scale technology transformation; preferably in a regulated environment, such as financial services, or another highly governed industry.
Track record of partnering with executive stakeholders and translating technology strategy into business outcomes.
Experienced at defining and influencing organizational strategy, inclusive of board and executive level communications(written and verbal).
Demonstrated success building or leading an enterprise AI, platform engineering, or architecture function at scale.
Proven ability to lead internal teams, contractors, vendors, and system integration partners in a fast-paced, high-accountability environment.
Strong command of compliance requirements relevant to payments (PCI-DSS, SOX).
Experience with FinOps practices and cloud cost governance for AI/ML workloads.

Nice To Haves

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.

Responsibilities

Define and own the Enterprise AI strategy, roadmap, and operating model in alignment with company OKRs.
Build and lead team spanning architecture, AI engineering, platform, governance, and security.
Leading the strategy and delivery of foundational AI platform capabilities that support secure, scalable, and reusable AI-enabled applications.
Serve as strategic leader for the AI Center of Excellence; represent the Enterprise AI org to the Executive team reporting on milestones, ROI, and risk posture.
Define architecture patterns for AI-First applications, copilots, intelligent workflows, automation agents, enterprise knowledge solutions, and reusable AI components.
Oversee a risk-tiered governance and architecture review process; own the technology exception process.
Guide platform capabilities such as model access, retrieval frameworks, vector databases, enterprise knowledge integration, prompt and response controls, observability, and governance guardrails.
Partnering to define standards for AI-assisted software engineering practices across the SDLC, including coding, testing, documentation, requirements analysis, code review, and engineering workflow automation.
Partner with Applications, Engineering, Infrastructure, Operations, Architecture, Security, and Data teams to pilot, refine, and scale AI-enabled practices over time.
Establish and maintain enterprise AI/ML standards, frameworks, playbooks, and reference architectures.
Driving adoption of a centralized AI platform including LLM gateway, model registry, agent frameworks, and shared APIs.
Evaluate emerging AI vendors and technologies; run pilot programs and proofs-of-concept.
Prevent shadow AI proliferation by providing self-service resources and pre-approved patterns that make governance easy.
Partner with engineering, operations, finance, customer service, and other business functions to identify and deliver high-value AI-enabled process improvements.
Lead the development of AI capabilities such as decision support, workflow automation, document intelligence, knowledge assistance, summarization, triage, productivity tools, and service quality improvements.
Help business teams move from AI ideas to practical use cases with clear outcomes, adoption plans, controls, and value measures.
Lead enterprise enablement of AI productivity tools such as Gemini, ChatGPT, Claude, and related assistants, including standards, training, adoption practices, and usage guardrails.
Build reusable playbooks, enablement models, and communities of practice that raise AI fluency across IT and the broader organization.
Embed security, privacy, responsible AI, sensitive data handling, human oversight, vendor risk, and production readiness into AI platforms, business use cases, engineering practices, operations, and employee tools.
Partner with Security, Legal, Risk, Compliance, Data, Architecture, and business teams to define and operationalize enterprise AI governance.
Create governance models that support responsible experimentation while protecting customers, employees, business partners, and enterprise data.
Partner with Finance to implement FinOps guardrails, cost allocation models, and real-time AI spend dashboards.
Embed responsible AI principles — PCI-DSS, SOX compliance, ethics, and explainability — into every initiative.
Build and lead a small, high-performing AI-First organization with strong architecture, engineering, automation, platform, and delivery capabilities.
Lead from the front with a hands-on, roll-up-the-sleeves leadership style and strong ownership of outcomes.
Owning delivery across scope, schedule, budget, quality, risk, dependencies, adoption, and business value.
Develop talent and create a culture of curiosity, accountability, disciplined experimentation, continuous learning, and measurable outcomes.