Senior Software Engineer at Five9 – United States | Jobyssey

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.

Five9 is seeking a Senior Software Engineer to rapidly modernize our internal platform tooling and drive full-stack engineering maturity. This is primarily a hands-on developer role — you will own the transformation of existing internal tools to be 12-factor compliant, building polished front-end interfaces alongside robust back-end services, and embedding world-class telemetry (Grafana, Prometheus, Loki) throughout the platform.

You will also provide architectural direction for software supporting our Infrastructure-as-a-Service (IaaS) platforms, orchestration systems, and platform engineering initiatives. You will champion modern 12-factor application design, transition legacy pipelines into Kubernetes-native GitOps workflows, and mentor mid-tier developers — all while keeping shipping velocity high.

This is a private cloud/on-premise infrastructure position. We build and manage our own bare-metal and virtualized data center footprint. Do not apply if your experience is exclusively in public cloud environments (AWS, GCP, or Azure). Candidates must have hands-on, practical experience with physical/on-premise hardware orchestration, hypervisors, and managing Kubernetes on bare-metal/private-cloud layers.

Key Responsibilities

12-Factor Application Modernization (Primary Focus)
- Rapidly audit and refactor existing internal tools and services to strictly comply with 12-factor application principles — configuration via environment, stateless processes, explicit dependency declarations, disposability, and dev/prod parity.
- Own end-to-end delivery of modernized services: back-end APIs (Go/Python) paired with clean, functional front-end interfaces (React or Vue) that surface platform data and controls to internal users.
- Decompose monolithic or ad-hoc scripts into properly structured, independently deployable services with clearly defined interfaces.
Full-Stack Development
- Build and maintain internal web UIs using modern front-end frameworks (React or Vue) — dashboards, tooling consoles, and operational interfaces that teams actually want to use.
- Design and develop robust REST/gRPC back-end APIs in Go and Python following clean architecture patterns.
- Ensure front-end and back-end components are instrumented end-to-end with traces, metrics, and structured logs from day one.
Observability & Telemetry
- Own the platform observability stack: design, implement, and continuously improve our Grafana, Prometheus, and Loki deployment for all internal services.
- Define and enforce instrumentation standards — every new or refactored service must ship with meaningful RED metrics, structured JSON logs forwarded to Loki, and distributed traces.
- Build and maintain Grafana dashboards and alerting rules that provide actionable signal for on-call engineers; define and manage SLIs/SLOs across critical platform services.
- Implement Prometheus exporters for custom internal services and integrate alerting with PagerDuty or equivalent.
- Drive log aggregation strategy with Loki — label taxonomy, retention policies, and LogQL query libraries for common operational queries.
Architecture & API Development
- Design, develop, and support robust APIs and automation services from scratch using Go and Python.
- Conduct architecture reviews and enforce design standards across the platform engineering team.
- Drive the modernization of legacy platform components with a bias toward simplicity and operational transparency.
CI/CD & GitOps Transformation
- Lead the refactoring of existing deployment pipelines to be fully Kubernetes-native.
- Define and implement disciplined software release cycles using GitLab CI/CD and ArgoCD for GitOps-driven deployments.
- Establish automated testing gates (unit, integration, contract) as hard requirements in the pipeline.
Technical Leadership & Mentorship
- Mentor mid-tier developers, establish coding standards, enforce peer reviews, and reduce technical debt.
- Improve engineering maturity across the team — instill a culture of instrumentation-first development where observability is never an afterthought.
- Maintain and overhaul technical documentation; make it easy for new engineers to onboard and contribute.
Infrastructure as Code (IaC)
- Drive enterprise-grade infrastructure automation and orchestration using Ansible, AWX, and Terraform.
- Oversee the secure and highly available architecture of core lifecycle services such as Harbor and GitLab.

Required Qualifications

8+ years of software engineering with proven technical leadership and architectural design experience.
Full-Stack Development: Strong front-end skills (React or Vue) alongside deep back-end experience — you are comfortable owning the full request lifecycle from UI click to database.
Observability Expertise: Deep, hands-on expertise with Grafana, Prometheus, and Loki — not just deploying them, but designing dashboards, writing PromQL/LogQL, building exporters, and enforcing instrumentation standards across a team.
12-Factor Mastery: Demonstrated experience auditing and refactoring real applications to be 12-factor compliant in a production environment.
Programming: Deep expertise in Python and Go (Golang) for building distributed systems and enterprise APIs.
Kubernetes Certification: CKA or CKAD strictly required (CNCF). Hands-on experience with on-premise clusters, preferably Rancher.
Cloud & Infrastructure: Strong experience with OpenStack, private cloud environments, and foundational infrastructure networking.
Automation & Tooling: Extensive experience with Ansible, AWX/Tower, Harbor, and GitLab.
Modern Delivery: Proven expertise in SDLC practices, code refactoring, automated testing, and GitOps (ArgoCD).

Preferred Qualifications

Experience designing and shipping internal developer portals or operational tooling used by platform and SRE teams.
Hands-on experience with distributed tracing (Jaeger, Tempo, or OpenTelemetry) to complement the Grafana/Prometheus/Loki stack.
Deep practical experience implementing SRE principles at large-scale enterprise.
Familiarity with Bare Metal as a Service (BMaaS) provisioning and integration.
Experience navigating ITIL change management processes within highly automated CI/CD frameworks.
Experience establishing engineering standards and driving a culture of accountability and continuous improvement.

Work Location: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices. For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in 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.

$90,700—$252,200 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: .

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

Explore more jobs