Senior Software Engineer, Agentic Systems

About the role

We are building an autonomous, black-box web application penetration tester. This role involves turning the team's offensive expertise into reliable, scalable, and unattended autonomous pentesting capability.

Responsibilities

• Build and evolve the agent harness and orchestration that turns an LLM into a reliable autonomous pentester.
• Design the tools and tool-shaped feedback the agent uses to probe and exploit, and the structured-output and validation layers that keep it reliable.
• Translate the team's offensive expertise into repeatable agent capabilities, partnering directly with our attackers to encode how they think into something the agent can do consistently.
• Own and grow our evaluation infrastructure: benchmark suites, a failure-mode taxonomy across the pipeline, and regression detection.
• Manage LLM inference in production: model selection, prompt and context engineering, and keeping cost and latency under control.
• Ensure production-safety and no-false-positives: every finding the agent reports must be real and reproducible.

Requirements

• 5+ years building production software, with strong Python.
• Hands-on experience building LLM-powered applications or agents, tool use / function calling, structured outputs, multi-step orchestration, and the glue that makes it all hold together.
• Real experience with evaluation: you've built or owned the harness that tells you whether a model or agent change is an improvement.
• Strong instincts for prompt and context engineering, and the judgment to keep the model's job small and well-scoped.
• Ownership mentality, comfortable owning a critical, fast-moving subsystem end to end.

Competencies/Qualifications

• Experience with web application security, broken access control, IDOR/BOLA, SQLi, XSS, SSRF, SSTI, enough to collaborate fluently with offensive engineers.
• Experience building eval harnesses or benchmarks specifically for agents (synthetic environments, CVE-based test targets, capture-the-flag-style scoring).
• Experience with agent frameworks, and strong opinions about when not to reach for one.
• Familiarity with graph data models (e.g., Neo4j) for representing application state and attack context.

Benefits

• Inclusive Team: We value diversity and promote an inclusive culture where everyone can thrive.
• Growth Opportunities: Be part of a dynamic and growing team with numerous career development opportunities.
• Innovative Culture: Work in a collaborative environment that encourages creativity and out-of-the-box thinking.
• Hybrid & Remote Work: We embrace a mix of remote and hybrid work models depending on role and location, including our Chicago office, where some roles require regular in-office presence.
• Competitive Compensation: We offer competitive salary, equity, and benefits. Our benefits include health, vision & dental insurance for you and your family, a flexible vacation policy, and generous parental leave.

Pay

Base salary range: $169,000 - $208,000 annually. The exact salary will be determined based on the selected candidate’s location, qualifications, experience, and relevant skills.

Schedule

Full-time, remote position.