Vice President, Engineering and AI Innovations

Five9; United States; Hybrid; USD 233,000 - 512,000; Full time

Benefits offered by this job

Health, dental, and vision coverage

401k with employer matching

Stock purchase plan

Paid time off & holidays

Parental leave

Disability insurance

Job summary

Five9 is hiring a VP of Engineering, AI Innovations, to lead our AI Insights, Agent Assist, and GenAI Studio teams. You will own end-to-end delivery, drive architectural modernization, and scale our cloud-native SaaS products for enterprise clients in the US.

You'll partner with Product, Design, Sales Engineering, and Customer Success to define a bold long-range AI strategy, hire top leaders, and foster a culture of excellence with high velocity and reliability.

Qualifications

• 10+ years experience in engineering management.
• Experience leading Engineering delivery for Customer Experience AI products, including Agent Assistance, AI Agents, and Conversational Analytics.
• Deep understanding of modern AI architectures: LLMs, RAG systems, embeddings, vector databases, multimodal models.

Responsibilities

• Lead and mentor multiple engineering teams across backend, ML, frontend, DevOps, and SRE.
• Own end-to-end delivery from development through operations for Five9’s AI products.
• Define and drive architectural modernization to scale AI products.

Skills

Engineering management

AI/ML expertise

Java

Distributed systems

API design

CI/CD tooling

Leadership

SRE fundamentals

Education

Bachelor's degree or higher

Tools

AWS

GCP

Azure

Terraform

GitHub Actions

Jenkins

Spinnaker

Job description

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.

Required Work Experience

• 10+ years 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 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: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices. For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in office.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

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

Our total reward package also includes:

• 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.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$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.

Five9 is committed to providing reasonable accommodations for qualified individuals with disabilities throughout the application and interview process. If you need assistance or an accommodation due to a disability, please contact us at [e-mail] to request an accommodation. Requests will be handled confidentially and in accordance with applicable law.

View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.