[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.

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

Skills

• 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)

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.
• Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Company Overview

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