Sr. Engineering Tools & Automation Lead

five9; United States; Remote; USD 140,000 - 180,000; Full time

Job summary

Hidden Jobs is seeking a senior technical leader within our Product Engineering and Technical Program Management organization to own tools, integrations, and automation to boost engineering productivity. You will drive Jira/Confluence/Jellyfish tooling, build AI-assisted SDLC capabilities, mentor a junior developer, and transform data into executive-ready metrics while aligning with cross-functional teams.

A strong background in Python, REST APIs, and practical LLM usage, plus excellent written

Qualifications

• Bachelor's degree in Computer Science or related field, or equivalent experience.
• 4+ years in engineering operations, tooling, integrations, or process management.
• Proficient in Python and REST API integration patterns (authentication, pagination, rate limits, retries).
• Experience using an LLM as a working tool and awareness of its failure modes.
• Strong written communication and ability to mentor less experienced team members.
• Self-starter with high attention to detail and comfort operating without a fixed answer.

Responsibilities

• Own roadmap and architecture for Jira, Confluence, Jellyfish, and related engineering tools, pushing automation and self-service.
• Build integrations between engineering systems using REST APIs, webhooks, and scripting; evaluate AI-assisted SDLC work.
• Serve as technical lead and mentor a junior developer focused on integrations and AI SDLC.
• Turn Jira and Jellyfish data into executive-ready metrics and reporting with roadmap-to-delivery mapping.
• Support program and release management with tooling, data, and process guidance across the SDLC.
• Partner with engineering and product leadership to reduce friction in day-to-day workflows for engineers.

Skills

Python

REST APIs

Git & PR workflows

Leadership & mentoring

Analytical skills

Education

Bachelor's degree in Computer Science or related field

Tools

Jira

Confluence

Jellyfish

Git

Job description

Hidden Jobs is seeking a senior technical leader within our Product Engineering and Technical Program Management organization to own tools, integrations, and automation to boost engineering productivity. You will drive Jira/Confluence/Jellyfish tooling, build AI-assisted SDLC capabilities, mentor a junior developer, and transform data into executive-ready metrics while aligning with cross-functional teams.

A strong background in Python, REST APIs, and practical LLM usage, plus excellent written