Vice President, Engineering and AI Innovations

Five9

11d • Hybrid

About The Position

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. As VP of Engineering, AI Innovations, you will lead the our team of talented software developers that are responsible for Five9’s AI Insights, Agent Assist and GenAI Studio products. These products are in widespread usage today. You will be responsible for directing the next phase of the evolution of these products, significantly expanding their feature sets, improving their capabilities with the latest and greatest in AI technologies, and expanding their reach to more customers with better scale and enterprise capability. You’ll take end-to-end ownership, from development through operations.

Requirements

• 10+ years experience in engineering management.
• Experience leading Engineering delivery for Customer Experience AI products, including Agent Assistance, AI Agents, and Conversational Analytics.
• AI / ML / GenAI Expertise
• Deep understanding of modern AI architectures: LLMs, RAG systems, embeddings, vector databases, multimodal models.
• Practical experience integrating LLMs into production systems, including prompt orchestration, function calling, structured outputs, and multi-agent workflows.
• Familiarity with model evaluation, A/B testing, safety techniques, latency/throughput trade-offs, and observability for AI systems.
• Understanding of fine-tuning, distillation, and model optimization (quantization, pruning, MoE, etc.).
• Experience with applied ML for NLP, ASR/TTS, NLU, and agent-assist use cases preferred.
• Expert-level proficiency in Java and JVM-based ecosystems.
• Strong command of modern distributed systems design: microservices, event-driven architectures, concurrency, and fault tolerance.
• Experience in development and operations of software in public cloud (AWS, GCP, Azure). Nice-to-have: experience with Google Cloud Platform (GCP)
• Experience building highly scalable, low-latency systems for enterprise SaaS.
• Strong understanding of API design (REST, gRPC), SDKs, and integrations with enterprise systems.
• Proficiency with CI/CD (GitHub Actions, Jenkins, Spinnaker, etc.) and Infrastructure as Code (Terraform).
• Deep knowledge of SRE principles: SLIs/SLOs, incident management, error budgets.
• Experience running 24×7 production systems at scale, ideally in multi-region global deployments.
• Expertise in security, privacy, and compliance relevant to CCaaS environments (SOC2, GDPR, HIPAA, FedRAMP preferred).
• Solid grasp of network fundamentals (TCP/IP, HTTP/2/3, WebRTC basics, load balancing).
• Proven ability to lead, mentor, and grow high-performing engineering teams across multiple disciplines (backend, ML, frontend, DevOps, SRE).
• Track record of hiring top-tier engineering leaders and technologists.
• Ability to create a culture of excellence—high velocity, high quality, and accountability.
• Strong conflict-resolution skills; able to navigate ambiguity and align cross-functional teams.
• Exceptional written and verbal communication skills; able to clearly articulate vision, architecture, and trade-offs to both technical and non-technical audiences.
• Comfortable partnering with Product, Design, Sales Engineering, Customer Success, and Executive Leadership.
• Ability to inspire teams with a compelling technical vision and roadmap.
• Deep empathy for customers and agents using Five9’s AI products.
• Experience engaging customers directly to gather insights and validate direction.
• Ability to translate customer problems into clear technical strategies and roadmaps.
• Ability to define and execute the long-range engineering strategy.
• Strong understanding of the AI competitive landscape; able to guide build-vs-buy decisions and partner evaluations.
• Experience driving architectural modernization initiatives to scale AI products.
• Mastery of engineering execution frameworks—OKRs, agile methodologies, metrics-driven management.
• Ability to balance innovation with reliability, velocity, and long-term maintainability.
• Skilled in managing large, multi-quarter programs and cross-org dependencies.
• Proficiency with capacity planning, headcount allocation, staffing strategy, and forecasting infrastructure costs.
• Experience negotiating vendor contracts, including AI model providers and cloud services.
• Ability to lead through rapid growth, shifts in technology, and organizational restructuring.
• Experience merging teams, establishing new engineering sites, and building distributed engineering organizations.

Nice To Haves

• Experience with applied ML for NLP, ASR/TTS, NLU, and agent-assist use cases preferred.
• Nice-to-have: experience with Google Cloud Platform (GCP)
• Expertise in security, privacy, and compliance relevant to CCaaS environments (SOC2, GDPR, HIPAA, FedRAMP preferred).

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. 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees