Senior Director, Enterprise AI

Five9•Irving, TX

2d•Hybrid

About The Position

Five9 is seeking a Senior Director, AI and Innovation to lead its Enterprise AI Program. This role is responsible for identifying, building, and scaling AI-driven capabilities across the company. It operates at the intersection of strategy, engineering, and business operations, aiming to translate AI capabilities into tangible value for customers, agents, and internal teams. The position involves setting the vision and roadmap for enterprise AI initiatives, building and leading a team, collaborating with senior leaders in product, engineering, CX, and operations, and serving as the primary internal advocate and governance owner for responsible AI adoption.

Requirements

8+ years of experience in technology strategy, innovation, product management, or AI/ML program leadership.
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.
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.

Nice To Haves

MBA or advanced technical degree a plus.
Experience in the contact center, CX, or SaaS industry is a plus.

Responsibilities

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, including expanding coverage, maturing plugin authoring, testing, and deployment, and improving output quality and reliability.
Establish and own enterprise-wide governance, risk, and compliance frameworks for responsible AI use, including data privacy, model risk, and vendor evaluation.
Partner closely with Enterprise Data, Enterprise Apps, Product Development, and Infosec to connect to governed data sources, align on security controls, and ensure integration 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.

Benefits

Health, dental, and vision coverage, beginning on the first day of employment.
Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
Short & Long-Term Disability.
Basic Life Insurance.
401k saving plan with employer matching.
Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
Generous employee stock purchase plan.
Paid Time Off.
Company paid holidays.
Paid volunteer hours.
12 weeks paid parental leave.
Annual performance bonus.
Stock and/or other applicable incentive compensation plans.