Vice President, Engineering and AI Innovations

San Ramon, CA - USA

Monthly Salary: Not Disclosed

Posted on: 2 hours ago

Vacancies: 1 Vacancy

Job Summary

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 Five9s 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. Youll 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 247 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 excellencehigh 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 Five9s 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 frameworksOKRs 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 50 mile radius of our San Ramon office. For candidates who reside within 50 miles of our San Ramon location this role is Hybrid and would require 3 days a week (M W TH) in our San Ramon 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.

$233000$512000 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 including our privacy notice to California residents here: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

Required Experience:

Exec

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 journ...