Five9 is looking for a Senior Director, AI and Innovation to lead our Enterprise AI Program — the cross-functional effort to identify, build, and scale AI-driven capabilities across the company. This role sits at the intersection of strategy, engineering, and business operations, translating emerging AI capabilities into measurable value for Five9's customers, agents, and internal teams. You will set the vision and own the roadmap for enterprise AI initiatives, build and lead a team executing against it, partner with product, engineering, CX, and operations leaders at the VP and executive level, and act as the primary internal evangelist and governance owner for responsible AI adoption at scale.

What You'll Do

• Define and drive the enterprise-wide AI strategy and roadmap, aligning initiatives with Five9's broader business and goals
• Identify high-impact opportunities to apply AI (including generative AI, machine learning, and automation) across contact center operations, customer experience, and internal enterprise functions
• Own the technical roadmap for Claude & Gemini Enterprise plugin framework, a growing library of role-based skills and agents that surface AI capabilities to employees in the context of their specific roles. This includes expanding coverage across more roles and use cases, maturing the way plugins are securely authored, tested, and deployed, and continuously improving the quality and reliability of each plugin's outputs.
• Establish and own enterprise-wide governance, risk, and compliance frameworks for responsible AI use, including data privacy, model risk, and vendor evaluation, setting policy that other leaders across the company adopt
• Partner closely with Enterprise Data, Enterprise Apps, Product Development, and Infosec to connect to governed data sources, align on security controls, and ensure every integration is built on architectural standards
• Build and defend the business case for AI investments at the portfolio level quantifying ROI, prioritizing initiatives, and owning progress reporting to executive leadership
• Own strategic relationships with external AI vendors, technology partners, and research organizations, including negotiating terms and setting partnership strategy
• Champion AI literacy and adoption company-wide through training, communication, and change management programs, and build the organizational structure to sustain it
• Track emerging AI trends and technologies, assessing their relevance and readiness for enterprise deployment at Five9, and shape long-term technology bets accordingly
• Hire, mentor, and manage a team of AI engineers, managers, and technical leads

What You'll Bring

• 8+ years of experience in technology strategy, innovation, product management, or AI/ML program leadership, including 3+ years in a people- or program-management capacity
• Demonstrated experience leading enterprise-scale AI or digital transformation initiatives from concept through production
• Strong understanding of AI/ML fundamentals, generative AI, and enterprise data platforms, enough to evaluate technical trade-offs and partner credibly with engineering teams
• Experience building AI governance frameworks (data privacy, model risk, responsible AI) in a regulated or enterprise SaaS environment
• Proven ability to influence senior stakeholders and drive cross-functional alignment without direct authority
• Strong business acumen, able to translate AI capabilities into ROI-driven business cases
• Excellent communication skills, with experience presenting to executive leadership
• Bachelor's degree in Computer Science, Engineering, Business, or related field; MBA or advanced technical degree a plus
• Experience in the contact center, CX, or SaaS industry is a plus