Lead Software Engineer – Enterprise Observability

Jobtailor; Town of Florida (NY); On-site; USD 150,000 - 210,000; Full time

Job summary

Jobtailor is seeking a Senior Observability Engineer in the New York area to architect and optimize scalable observability systems. You will lead cross-functional teams, build automation for instrumentation, and drive AI-native tooling for proactive issue detection and resolution.

With 7+ years in software/infrastructure engineering focused on observability, you will influence architecture, CI/CD integration, and data monitoring across cloud-native environments.

Qualifications

• 7+ years in software/infrastructure engineering with observability focus.
• Associate degree in CS/Engineering or related field.
• Strong foundation in operating systems, networking, algorithms, and distributed systems.
• Expertise in programming (Python, .Net, Java, Go, Node.js), System architecture and AI Ops, CI/CD, IaC, Cloud-native development, API design (REST/gRPC).
• Proven leadership and mentoring experience.
• Agile delivery experience and observability maturity strategy.

Responsibilities

• Architect and optimize observability environments using software engineering best practices.
• Build automation scripts and tools to streamline observability instrumentation and deployment.
• Integrate observability into CI/CD pipelines using IaC and configuration management tools.
• Conduct observability code reviews and implement automated validation checks.
• Build AI-native tools for autonomous issue detection and resolution.
• Lead the design of distributed systems focused on reliability, scalability, and performance.
• Manage data routing, transformation, and endpoint monitoring integrations.
• Mentor junior engineers and foster a culture of continuous improvement.
• Collaborate across teams to align observability strategies with business goals.
• Communicate technical insights and recommendations to leadership.

Skills

Observability engineering

Distributed systems

Leadership

Mentoring

CI/CD

Infrastructure as Code

Cloud-native development

Python

Java

Go

Communication

Education

Associate degree in Computer Science, Engineering, or related field

Tools

Terraform

Ansible

GitHub Actions

Azure DevOps

AWS

Azure

GCP

Job description

Responsibilities

• Architect and optimize observability environments through software engineering best practices
• Build automation scripts and tools to streamline observability instrumentation and deployment
• Integrate observability into CI/CD pipelines using infrastructure-as-code (IaC) and configuration management tools
• Conduct observability code reviews and implement automated validation checks
• Build AI-native tools for autonomous issue detection and resolution
• Lead the design of distributed systems focused on reliability, scalability, and performance
• Manage data routing, transformation, and endpoint monitoring integrations
• Mentor junior engineers and foster a culture of continuous improvement
• Collaborate across teams to align observability strategies with business goals
• Communicate technical insights and recommendations to leadership

Requirements

• Associate degree in Computer Science, Engineering, or related field
• 7+ years in software/infrastructure engineering with observability/logging focus
• Strong foundation in operating systems, networking, algorithms, and distributed systems
• Expertise in: Programming (eg. Python, .Net, Java, Go, Node.js), System architecture and AI Ops, CI/CD (eg. GitHub Actions, Azure DevOps), Infrastructure as Code (eg. Terraform, Ansible), Cloud-native development (eg. Azure, AWS, GCP), API design (eg. REST, gRPC)
• Proven leadership and mentoring experience
• Agile delivery experience and strategic thinking around observability maturity