Senior Manager, Engineering - AI Agents

Five9 • San Ramon, CA

21h • Hybrid

About The Position

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.
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.

Requirements

• 3+ years experience leading or managing software engineering teams
• 8+ years professional software development experience
• Experience participatingin 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 recordin hiring outstanding software development teams, through rigorous interviewing and vetting processes – either as the hiring manager or as part of interview panels

Nice To Haves

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

Responsibilities

• Team Leadership & Development
• Hire, onboard, and grow a high-performing engineering teamof 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 andtechnical 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 measuring as such and maintainingfor 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 wherebeneficial
• Promote experimentation and learning around AI-enabled engineering practices

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager