---
title: 'Senior Director, Enterprise AI at Five9'
canonical: 'https://feeny.ai/job/senior-director-enterprise-ai-five9-irving-j7bsdh55zf0f'
type: 'job'
last_seen: '2026-09-09'
---

# Senior Director, Enterprise AI at Five9

- **Company:** Five9
- **Location:** Irving, TX
- **Compensation:** $176k–$282k
- **Work type:** hybrid
- **Posted:** 2026-09-09
- **Last confirmed live:** 2026-09-09
- **Apply:** https://www.five9.com/about/careers/job-detail?gh_jid=6185777004

## Job description

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.

View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

## About Five9

## Company Overview
- **One-liner**: Five9 provides a leading cloud contact center platform (CCaaS) that enables organizations to deliver digital engagement, analytics, workforce optimization, and AI-powered customer experiences.
- **Entity Type**: Public (NASDAQ: FIVN)
- **Headquarters**: San Ramon, California, USA (with additional offices in San Francisco, Toronto, London, Munich, Porto, Madrid, São Paulo, and Mandaluyong City)
- **Founded**: 2001
- **Founders**: Not publicly available

## Core Business
- **Primary industry/industries**: Cloud Contact Center as a Service (CCaaS), Customer Experience (CX) software, AI & Automation, Workforce Optimization
- **Target customers**: Enterprise, mid-market, and SMB organizations across all verticals (B2B/B2C)
- **Mission or purpose statement**: “Our vision is to make customer service a more human experience.” [five9.com](https://www.five9.com/about)

## Products & Services
- **Five9 Cloud Contact Center Platform**: Core omnichannel contact center solution (voice, email, chat, SMS, social) with intelligent routing and IVR.
- **Digital Engagement**: Integrated digital channels including SMS, web chat, email, and social messaging.
- **Five9 Analytics**: Real-time and historical reporting, speech analytics, and sentiment analysis to improve agent performance and customer outcomes.
- **Workforce Optimization (WFO)**: Workforce management, quality management, and recording (acquired Virtual Observer in 2021).
- **AI & Automation Suite**:
  - **Intelligent Virtual Agent (IVA)**: Conversational AI chatbot and voice bot for self-service (acquired Inference Solutions in 2021).
  - **Agent Assist 2.0**: AI-powered real-time agent guidance and summarization (using OpenAI).
  - **Voice AI Agents**: Generative AI agents for automated customer interactions.
- **Professional Services**: Implementation, integration, and consulting services.
- **Aceyus VUE**: Data and reporting integration platform (acquired in 2022).

## Market Standing
- **Valuation/Market Cap**: Publicly traded; specific metrics not provided in available sources.
- **Key Metric**: Over 3,000 customers worldwide; 350,000+ agents using the platform; 2,600+ employees; 1,450+ technology and channel partners. [five9.com](https://www.five9.com/about)
- **Notable Investors/Partners**: BT (expanded partnership for cloud adoption), MCM Telecom, XTT Mexico; partners include global SIs and technology vendors. Acquisitions: Acqueon, Aceyus VUE, Inference Solutions, Virtual Observer.
- **Growth Signals**: Named a Leader in the 2025 Gartner® Magic Quadrant™ for CCaaS (8th time); opened new European engineering hub in Porto, Portugal; expanded LATAM partnerships; introduced Agent Assist 2.0 with AI Summary; won Glassdoor Employees’ Choice Award for Best Places to Work (2022). [five9.com](https://www.five9.com/about)

## Competitive Advantages
- **Cloud-native heritage**: Born in the cloud in 2001, with 20+ years of CCaaS experience.
- **Analyst recognition**: Consistently named a Leader in Gartner Magic Quadrant, Forrester Wave, IDC MarketScape, and Aragon Research Globe.
- **High customer satisfaction**: 86 Net Promoter Score (NPS) for professional services.
- **Comprehensive AI portfolio**: Integrated IVA, Agent Assist, and Voice AI Agents differentiate from competitors.
- **Scale and reliability**: Manages billions of call minutes annually across 2,600+ concurrent agent seats (average).

## Strategic Focus
- **AI-first innovation**: Continued investment in generative AI and conversational AI to automate and enhance customer interactions.
- **Global expansion**: Strengthening presence in LATAM (new partnerships), EMEA (engineering hub in Portugal), and APAC.
- **Platform depth**: Integrating acquisitions (Acqueon, Aceyus, Inference Solutions) to provide end-to-end CX and WFO capabilities.
- **Partner ecosystem**: Deepening relationships with systems integrators and telcos (e.g., BT) to accelerate cloud migration.

## Why Work Here
- **Culture**: Fast-paced, start-up-like environment with established enterprise customers; values include honesty, respect, inclusion, transparency, ownership, and customer focus. [five9.com](https://www.five9.com/about/careers)
- **Diversity & Inclusion**: Committed to a diverse and inclusive culture where employees are empowered and heard. [five9.com](https://www.five9.com/about/careers/jobs)
- **Remote/Hybrid Policy**: Not explicitly stated; offices in multiple locations suggest hybrid/office model.
- **Benefits** (US full-time): 100% employer-paid health insurance (choice of 4 medical plans), dental, vision, life/disability insurance, 401(k), FSA, employee assistance program, commuter discounts, company equity, accrued PTO + paid holidays, company events. [five9.com](https://www.five9.com/about/careers)
- **Recognition**: Received Glassdoor Employees’ Choice Award for Best Places to Work (2022). [five9.com](https://www.five9.com/about)
- **Growth opportunities**: Internship program with impactful work and exposure to executives; career paths across development, customer success, sales, marketing, finance, and professional services.

## Sources
1. [Five9 About Page](https://www.five9.com/about)
2. [Five9 Careers Overview](https://www.five9.com/about/careers)
3. [Five9 Fact Sheet](https://www.five9.com/resources/five9-company-fact-sheet)
4. [Five9 Careers – Job Listings](https://www.five9.com/about/careers/jobs)

## Other roles at Five9

- [Finance Applications Administrator](https://feeny.ai/job/finance-applications-administrator-five9-manila-g1zhvwgaaw15) — Manila, Philippines
- [HR Applications Administrator](https://feeny.ai/job/hr-applications-administrator-five9-manila-014n35t6fc5f) — Manila, Philippines
- [Director, IT Operations](https://feeny.ai/job/director-it-operations-five9-manila-qk7s284stw6r) — Manila, Philippines
- [Sr Network DevOps Engineer - Operations](https://feeny.ai/job/sr-network-devops-engineer-operations-five9-bengaluru-nhe14xmsq4ah) — Bengaluru, India
- [Sr Network DevOps Engineer - Operations](https://feeny.ai/job/sr-network-devops-engineer-operations-five9-chennai-d91zwg0p8f45) — Chennai, India
- [Sr DevOps Engineer](https://feeny.ai/job/sr-devops-engineer-five9-bengaluru-gh185fs0zvk1) — Bengaluru, India
- [Sr. DevOps Network Engineer- Operations](https://feeny.ai/job/sr-devops-network-engineer-operations-five9-chennai-70ncd3d7985e) — Chennai, India
- [Sr. DevOps Network Engineer- Operations](https://feeny.ai/job/sr-devops-network-engineer-operations-five9-bengaluru-z1x6290h2rfq) — Bengaluru, India
- [Senior Software Engineer in AI - FrontEnd React/Redux, Java](https://feeny.ai/job/senior-software-engineer-in-ai-frontend-react-redux-java-five9-bengaluru-2qptgjcc9zv0) — Bengaluru, India
- [Telecom Engineer - Voice Deployment](https://feeny.ai/job/telecom-engineer-voice-deployment-five9-porto-016w6k014rqv) — Porto, Portugal