Senior Director, Enterprise AI

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.
Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.
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
Work Location: This role is hybrid. 3 days a week (T, W, TH) in our Dallas office is required.
As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.
Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.
Our total reward package also includes:
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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.
All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.
The US base salary range for this role is below.
$175,900—$281,500 USD
Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer.
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Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.