Senior AI Automation Engineer

Position Summary

HackerOne is seeking a Senior AI Automation Engineer to join our Enterprise Data & AI team. In this role, you'll operate across two complementary dimensions: building and maintaining the scalable data infrastructure that powers our AI systems, and designing and delivering AI-powered automation solutions that free Hackeronies from routine, manual work to focus on strategic, high-value outcomes.

You'll achieve success by leading with AI-first thinking, demonstrating agility through change, applying first-principles problem solving, and using data to learn and adapt along the way. Leveraging your technological expertise, domain knowledge, and dedication to business objectives, you'll drive innovation to propel HackerOne forward.

Enterprise Data & AI’s Mission & Vision

The HackerOne Enterprise Data & AI team democratizes source of truth information, transformative insights, and AI tooling and infrastructure to power enhanced decision-making, autonomous execution, and mission-aligned scale. The future is one where every Hackeronie is a catalyst for positive change, advancing data-driven, AI-powered, human-led innovation while fostering our culture of transparency, collaboration, and customer obsession.

What You Will Do

• Lead the end-to-end design and delivery of scalable, secure, and intelligent data products and AI automation solutions that support HackerOne's transformation into an AI-first organization.

• Build, optimize, and maintain data pipelines and infrastructure that serve as the foundation for AI-powered systems and agentic operations.

• Design and deploy AI-powered automation solutions that eliminate routine, manual work and unlock human capacity for strategic direction, creativity, and edge-case governance.

• Partner across business and engineering teams to identify high-leverage opportunities for automation, integration, and system modernization.

• Drive the architecture and execution of platform-level capabilities, leveraging AI and modern tooling to reduce manual effort, improve decision-making, and increase system resilience.

• Provide technical leadership to internal engineers and external development partners, ensuring design quality, operational excellence, and long-term maintainability.

• Shape and contribute to our incident and on-call response strategy, playbooks, and processes, focusing on building systems that fail gracefully and recover quickly.

• Act as a multiplier to mentor other engineers, advocate for technical excellence, and promote a culture of innovation, curiosity, and continuous improvement.

• Champion effective change management and enablement, ensuring systems are not only launched, but adopted, understood, and evolved.

Minimum Qualifications

• 6+ years of experience in a Data Engineering, AI/ML, or similar role with a proven track record of leading the design, development, and deployment of scalable data products and AI-powered solutions, preferably using Python.

• Extensive hands-on experience building and optimizing data pipelines, products, and solutions.

• Extensive experience working with data technologies and tools such as Airflow and AWS.

• Experience with infrastructure as code tools such as Terraform or Pulumi.

• Experience designing and delivering AI-powered automation solutions, translating operational needs into scalable, automated systems.

• Proven track record of successfully championing new initiatives focused on architectural enhancements.

• Proven track record of having substantial impact across the company, demonstrating your ability to drive positive change and achieve significant results.

• Passion for working backwards from the Customer and empathy for business stakeholders.

• Excellent communication skills, with the ability to present data-driven narratives in verbal, presentation, and written formats.

Preferred Qualifications

• Proven track record of having substantial impact across the company, demonstrating your ability to drive positive change, and achieve significant results.

• Passion for working backwards from the Customer and empathy for business stakeholders.

• Experience working with Model Context Protocol (MCP) for AI tooling and integration.

• Thrive on solving ambiguous problem statements in an early-stage environment.

• Excellent communication skills, and can present data-driven narratives in verbal, presentation, and written formats.

• Experience shaping strategic vision and roadmaps for AI and SaaS.

• Experience working with Agile and iterative development processes.