[Remote] Vice President, Engineering and AI Innovations

Note: The job is a remote job and is open to candidates in USA. 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.ResponsibilitiesLead the team of talented software developers responsible for Five9’s AI Insights, Agent Assist and GenAI Studio productsDirect the next phase of the evolution of these products, significantly expanding their feature setsImprove their capabilities with the latest and greatest in AI technologiesExpand their reach to more customers with better scale and enterprise capabilityTake end-to-end ownership, from development through operationsSkills10+ years experience in engineering managementExperience leading Engineering delivery for Customer Experience AI products, including Agent Assistance, AI Agents, and Conversational AnalyticsAI / ML / GenAI ExpertiseDeep understanding of modern AI architectures: LLMs, RAG systems, embeddings, vector databases, multimodal modelsPractical experience integrating LLMs into production systems, including prompt orchestration, function calling, structured outputs, and multi-agent workflowsFamiliarity with model evaluation, A/B testing, safety techniques, latency/throughput trade-offs, and observability for AI systemsUnderstanding of fine-tuning, distillation, and model optimization (quantization, pruning, MoE, etc.)Expert-level proficiency in Java and JVM-based ecosystemsStrong command of modern distributed systems design: microservices, event-driven architectures, concurrency, and fault toleranceExperience in development and operations of software in public cloud (AWS, GCP, Azure)Experience building highly scalable, low-latency systems for enterprise SaaSStrong understanding of API design (REST, gRPC), SDKs, and integrations with enterprise systemsProficiency with CI/CD (GitHub Actions, Jenkins, Spinnaker, etc.) and Infrastructure as Code (Terraform)Deep knowledge of SRE principles: SLIs/SLOs, incident management, error budgetsExperience running 24×7 production systems at scale, ideally in multi-region global deploymentsSolid 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 technologistsAbility to create a culture of excellence—high velocity, high quality, and accountabilityStrong conflict-resolution skills; able to navigate ambiguity and align cross-functional teamsExceptional written and verbal communication skills; able to clearly articulate vision, architecture, and trade-offs to both technical and non-technical audiencesComfortable partnering with Product, Design, Sales Engineering, Customer Success, and Executive LeadershipAbility to inspire teams with a compelling technical vision and roadmapDeep empathy for customers and agents using Five9's AI productsExperience engaging customers directly to gather insights and validate directionAbility to translate customer problems into clear technical strategies and roadmapsAbility to define and execute the long-range engineering strategyStrong understanding of the AI competitive landscape; able to guide build-vs-buy decisions and partner evaluationsExperience driving architectural modernization initiatives to scale AI productsMastery of engineering execution frameworks—OKRs, agile methodologies, metrics-driven managementAbility to balance innovation with reliability, velocity, and long-term maintainabilitySkilled in managing large, multi-quarter programs and cross-org dependenciesProficiency with capacity planning, headcount allocation, staffing strategy, and forecasting infrastructure costsExperience negotiating vendor contracts, including AI model providers and cloud servicesAbility to lead through rapid growth, shifts in technology, and organizational restructuringExperience merging teams, establishing new engineering sites, and building distributed engineering organizationsExperience with applied ML for NLP, ASR/TTS, NLU, and agent-assist use casesNice-to-have: experience with Google Cloud Platform (GCP)Expertise in security, privacy, and compliance relevant to CCaaS environments (SOC2, GDPR, HIPAA, FedRAMP preferred)BenefitsHealth, 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.Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.Company OverviewFive9 is a cloud-based call center software company that specializes in sales, marketing, and customer service. It is a sub-organization of Five Rivers Solutions. It was founded in 2001, and is headquartered in San Ramon, California, USA, with a workforce of 1001-5000 employees. Its website is http://www.five9.com.Company H1B SponsorshipFive9 has a track record of offering H1B sponsorships, with 4 in 2026, 13 in 2025, 15 in 2024, 13 in 2023, 20 in 2022, 15 in 2021, 15 in 2020. Please note that this does not guarantee sponsorship for this specific role.