Five9 · 1 day ago
Vice President, Engineering and AI Innovations
United States
Full-time
Remote
Director/Executive
$233K/yr - $512K/yr
10+ years expFive9 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.
Call CenterCustomer ServiceEnterprise SoftwareSaaSSales
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
Qualification
Required
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
Preferred
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.
Company
Five9
Five9 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.
1001-5000 employees
H1B Sponsorship
Five9 has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (13)
2024 (15)
2023 (13)
2022 (20)
2021 (15)
2020 (15)
Funding
Current Stage
Public CompanyTotal Funding
$861.6MKey Investors
Oaktree Specialty LendingSapphire VenturesAdams Street Partners
2024-02-28Post Ipo Debt· $747.5M
2014-04-04IPO
2014-03-10Debt Financing· $30M
Leadership Team
Jonathan Rosenberg
CTO and Head of AI
Jim Alexander
VP, PMO and Quality Engineering
Recent News
2025-12-19
thefly.com
2025-12-18
2025-12-17
Company data provided by crunchbase