Vice President Engineering AI Innovations

About Five9

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.

Role Overview

As VP of Engineering, AI Innovations, you will lead our team of talented software developers 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.

Required Work Experience

• 10+ years of experience in engineering management.
• Experience leading Engineering delivery for Customer Experience AI products, including Agent Assistance, AI Agents, and Conversational Analytics.

Required Skills

Technical Skills

• 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 is preferred.
• Software Engineering Foundations: 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).
• Operational Excellence: Deep knowledge of SRE principles (SLIs/SLOs, incident management, error budgets). Experience running 24x7 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).

People & Leadership Skills

• Engineering Leadership: 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.
• Collaboration & Communication: 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.
• Customer-Centric Mindset: 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.

Organizational & Strategic Skills

• Vision and Strategy: 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.
• Execution & Delivery: 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.
• Budgeting and Resource Planning: Proficiency with capacity planning, headcount allocation, staffing strategy, and forecasting infrastructure costs. Experience negotiating vendor contracts, including AI model providers and cloud services.
• Change Management: Ability to lead through rapid growth, shifts in technology, and organizational restructuring. Experience merging teams, establishing new engineering sites, and building distributed engineering organizations.

Work Location & Compensation

This role is fully remote for candidates residing outside the 50-mile radius of our San Ramon office. For candidates within 50 miles of San Ramon, this role is Hybrid (3 days a week: Monday, Wednesday, Thursday in the office). Five9 supports pay transparency. Actual compensation is based on skill set, experience, certifications, and work location. The displayed range reflects the target for new hire salaries across the US. Your recruiter can share more details. The total compensation package may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Total Rewards Package

• Health, dental, and vision coverage from day one. Five9 covers 100% of employee premiums and a high portion of dependent costs.
• Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
• Access to an innovative mental health support platform.
• 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 plan documents and agreements. US Base Salary Range: $233,000—$512,000 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 here: https://www.five9.com/pt-pt/legal. Note: Five9 will never request that an applicant send money as a prerequisite for employment.

Key skills/competency

AI/ML, GenAI, LLMs, Software Engineering Management, Distributed Systems, Cloud Computing, SRE, Engineering Leadership, Product Development, Customer Experience AI