[Hiring] Senior Manager, Engineering - AI Agents @Five9

Role Description

The Senior Manager, Engineering - AI Agents will lead the development and delivery of Five9’s AI Agent software platform, which provides customers with fully autonomous self-service agents for customer support, sales, and services use cases in the contact center. This is one of the hottest areas of application for AI Agent technology!

This role is responsible for building and managing a high-performing engineering team that develops scalable, reliable, and production-grade AI-powered systems used in real-time customer conversations. You will be responsible for hiring and developing engineers, improving engineering processes, and enabling strong execution across the software development lifecycle.

While this is a management role rather than an individual contributor position, the ideal candidate will bring strong technical credibility with engineers and guide architecture discussions, technical decisions, and engineering best practices. You will collaborate closely with Product, SRE, Support, and other engineering teams to deliver an enterprise-grade platform while fostering a culture of operational excellence, ownership, and customer empathy.

Key Responsibilities

• Team Leadership & Development
  • Hire, onboard, and grow a high-performing engineering team of 4-8 engineers in the United States
  • Provide coaching, mentorship, and career development for engineers
  • Establish clear ownership, accountability, and engineering rigor
  • Conduct performance management, feedback, and growth planning
  • Foster a culture of collaboration, innovation, and operational excellence
  • Mentor senior engineers and emerging technical leaders
• Delivery & Execution
  • Lead planning and enable strong execution of engineering initiatives and product roadmap
  • Ensure projects are delivered predictably and with high quality
  • Focus on customer success, ensuring quality AI agent experiences with low latency and high accuracy
  • Break down large initiatives into achievable milestones
  • Partner with Product Management to prioritize work and manage trade-offs
  • Collaborate with Forward Deployed Engineering (FDE) teams on AI agent implementations
  • Drive continuous improvement in development processes and team productivity
• Technical Leadership
  • Perform code reviews, guide software architecture and technical decisions
  • Review technical designs and ensure sound engineering practices
  • Help teams make pragmatic technology decisions balancing innovation and reliability
  • Drive the team to manage customer expectations of uptime and performance by defining and reviewing SLO/SLI's, developing metrics to measure as such and maintaining for all the services
  • Ensure systems are scalable, maintainable, and production-ready
• Operational Excellence
  • Promote strong service ownership and reliability culture
  • Ensure effective on-call practices and incident response processes
  • Drive root cause analysis and continuous reliability improvements
  • Partner with SRE teams to define SLIs, SLOs, and operational metrics
  • Handle customer escalations and issues related to AI Agent quality
  • Participate in on-call escalation rotations for provided services
• Cross-Functional Collaboration
  • Work closely with Product, UX, SRE, Forward Deployed Engineering (FDE) and Support teams
  • Align engineering execution with product strategy and customer needs
  • Communicate engineering progress, risks, and technical decisions clearly to stakeholders
• AI-Augmented Engineering Practices
  • Use of modern AI-assisted development tools to improve engineering productivity, and represent “best in class” examples of how to effectively use it
  • Help the team adopt responsible and effective use of AI in software development workflows
  • Evaluate emerging developer AI tools and incorporate them where beneficial
  • Promote experimentation and learning around AI-enabled engineering practices

Qualifications

• 3+ years experience leading or managing software engineering teams
• 8+ years professional software development experience
• Experience participating in hiring and helping grow engineering teams
• 5+ years experience developing enterprise SaaS software
• Strong background in distributed systems and modern software architectures
• Experience or exposure to GenAI / LLM-based systems
• Experience using or adopting AI-assisted software development tools
• Bachelor’s or advanced degree in Computer Science, Computer Engineering, or similar
• Strong track record in hiring outstanding software development teams, through rigorous interviewing and vetting processes

Desired Experience

• 1-2 years experience building AI Agent platforms for CX, including voicebots, chatbots and AI assistants

Technical Background

• Software Engineering
  • Strong background in Java or JVM-based backend systems
  • Experience designing distributed systems or microservices architectures
  • Familiarity with API design (REST/gRPC) and scalable service architectures
• AI / GenAI Platforms
  • Familiarity with LLM-based systems, prompt engineering, AI Agent architectures and design patterns
  • Understanding of common AI platform patterns such as embeddings, RAG pipelines, or model integration
  • Awareness of performance and reliability considerations for AI-backed systems
• Cloud & Infrastructure
  • Experience building SaaS platforms in public cloud environments (GCP preferred but not required)
  • Familiarity with microservices architectures and cloud-native systems
  • Basic understanding of networking concepts such as load balancing, service-to-service communication, and API gateways
• Operational Excellence
  • Experience operating production services in enterprise SaaS environments
  • Familiarity with observability practices (metrics, logging, tracing)
  • Experience participating in or leading incident response and root cause analysis
• Leadership & Collaboration Skills
  • Proven ability to build and develop strong engineering teams
  • Strong mentoring and coaching capabilities
  • Ability to guide engineers through technical design and problem solving
  • Excellent communication skills across engineering and product organizations
  • Ability to align teams around clear priorities and ownership

What Success Looks Like in This Role

• Hire a strong engineering team delivering reliable AI platform capabilities
• Predictable and high-quality delivery of engineering initiatives for our core AI Agent platform
• Clear engineering ownership and operational accountability
• Customer obsession resulting in customer satisfaction with AI Agent quality, latency and accuracy
• Scalable and maintainable platform architecture
• Engineers effectively leveraging AI-assisted development tools
• A culture of accountability, collaboration, and technical excellence

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.

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
• Generous employee stock purchase plan
• Paid Time Off, Company paid holidays, paid volunteer hours and 12 weeks paid parental leave

Compensation

The US base salary range for this role is $133,000 — $391,500 USD. 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.