Five9

Vice President, Engineering – AI Innovations

Five9

full-time

Posted on:

Location Type: Hybrid

Location: 🇺🇸 United States

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Salary

💰 $233,000 - $512,000 per year

Job Level

Lead

Tech Stack

AWSAzureCloudDistributed SystemsGoogle Cloud PlatformGRPCJavaJenkinsMicroservicesSpinnakerTCP/IPTerraform

About the role

  • 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 in AI technologies, and expand their reach to more customers.
  • Take end-to-end ownership, from development through operations.

Requirements

  • 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.
  • 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.
  • 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.
  • 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).
  • 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.
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.
  • 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.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
AI technologiesLLMsRAG systemsembeddingsvector databasesmultimodal modelsJavamicroservicesAPI designCI/CD
Soft skills
leadershipmentoringconflict-resolutioncommunicationcustomer empathystrategic thinkinginnovationprogram managementcross-functional collaborationteam inspiration
Certifications
SOC2GDPRHIPAAFedRAMP