Key skills
JavaAIMLNLPGenAIAnalyticsgRPCAWSAzureGCPGoogle CloudTerraformJenkinsGitHub ActionsGitHubLoad BalancingSaaSAgileCI/CDLeadershipOKRsA/B TestingCommunicationCustomer SuccessSales
About this role
Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. As VP of Engineering, AI Innovations, you will lead a team responsible for advancing Five9’s AI products, enhancing their features, and expanding their capabilities using cutting-edge AI technologies.
Responsibilities:
- Lead the team of talented software developers responsible for Five9’s AI Insights, Agent Assist and GenAI Studio products
- Direct the next phase of the evolution of these products, significantly expanding their feature sets
- Improve their capabilities with the latest and greatest in AI technologies
- Expand their reach to more customers with better scale and enterprise capability
- 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.)
- 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)
- 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
- 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
- Experience with applied ML for NLP, ASR/TTS, NLU, and agent-assist use cases
- Nice-to-have: experience with Google Cloud Platform (GCP)
- Expertise in security, privacy, and compliance relevant to CCaaS environments (SOC2, GDPR, HIPAA, FedRAMP preferred)