Engineering Leader: AI-Driven, Scalable Software Systems

Jobtailor; Illinois; On-site; USD 150,000 - 190,000; Full time

Job summary

Jobtailor is seeking an experienced engineering leader to mentor teams, drive scalable software architecture, and align technical roadmaps with business goals. You will champion DevOps, AI-assisted development tools, and modern deployment strategies across distributed systems.

You will collaborate with Product Management, UX, Architecture, and Engineering to deliver customer-centric solutions, manage performance, and ensure platform reliability in enterprise environments.

Qualifications

• Bachelor's degree or equivalent work experience.
• Six to eight years of relevant technical experience.
• Five or more years of leading a software engineering team.
• Proven experience leading geographically distributed teams through coaching and performance management.
• Strong expertise in software architecture, system design, and building scalable enterprise apps.
• Hands-on experience with Java, Spring Boot, RESTful APIs, microservices, and backend engineering best practices.
• Deep understanding of performance, resiliency, observability, security, and integration across distributed systems.
• Experience partnering with Product Management, UX/Design, Architecture, and Engineering to deliver customer-centric solutions.
• Strong knowledge of CI/CD pipelines, DevOps, automated testing, and modern deployment strategies.
• Proven ability to align technical roadmaps with business strategy.

Responsibilities

• Lead, mentor, and develop software engineers through coaching, performance management, and career development.
• Drive design, development, and delivery of scalable, secure, high-performing software solutions.
• Partner with Product Management, Architecture, UX, and Engineering to define technical roadmaps and deliver customer-focused solutions.
• Oversee application architecture, API design, system integrations, and platform reliability across complex environments.
• Establish and enforce engineering best practices for code quality, security, testing, observability, and operational excellence.
• Lead Agile delivery teams, ensuring predictable execution and continuous improvement of processes.
• Champion DevOps and CI/CD practices for automation and deployment efficiency.
• Collaborate with senior leadership to align engineering strategy with business priorities and drive innovation using AI-assisted tools.

Skills

Engineering leadership

Software architecture

Java

Spring Boot

CI/CD

Agile delivery

Stakeholder management

Communication

Mentoring

Coaching

Collaboration

Distributed systems

Security

Observability

System design

Education

Bachelor's degree, or equivalent work experience

Tools

CI/CD pipelines

AI-Assisted development tools

Automation platforms

Performance management tools

Job description

Jobtailor is seeking an experienced engineering leader to mentor teams, drive scalable software architecture, and align technical roadmaps with business goals. You will champion DevOps, AI-assisted development tools, and modern deployment strategies across distributed systems.

You will collaborate with Product Management, UX, Architecture, and Engineering to deliver customer-centric solutions, manage performance, and ensure platform reliability in enterprise environments.