Staff Security Engineer

We’re looking for a Staff Security Engineer to lead the security of the cloud applications and AI systems we build and ship for clients. This role is ideal for an experienced engineer who can define security architecture and standards, own the hardest security problems end-to-end, and provide technical leadership across teams.

In this role, you will work as a key technical leader on a cross-functional team, defining security architecture across cloud infrastructure, application code, and AI/LLM workloads. You’ll lead threat modeling and security reviews, mentor more junior engineers, partner closely with engineering and leadership, and ensure the systems we ship are secure, reliable, and built to last.

Why This Role Matters

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate.

Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on.

What You’ll Do

Craft & Delivery

• Define security architecture and engineering standards across web, API, and cloud-native systems, leading the hardening of complex services
• Lead threat modeling and security design reviews across applications and AI systems, setting how risk is identified and prioritized
• Architect cloud security controls across identity, network, and data layers, owning IAM strategy, secrets management, and encryption
• Lead the integration of security automation into CI/CD pipelines, driving shift-left detection and policy-as-code across teams
• Lead detection engineering, logging, and incident response practices across production systems
• Own the security of AI and LLM-powered applications in production, defining defenses against prompt injection, data leakage, model abuse, and agentic-AI threats
• Lead the design and integration of AI services into production security workflows, including LLM APIs, tool and function calling, and multi-step agent flows for detection and triage
• Bring an AI-forward mindset to your daily work, using tools like Claude, Cursor, and other modern AI assistants to ship higher-quality work at pace

Collaboration & Communication

• Partner with product, engineering, and leadership to shape security strategy and align technical direction with business outcomes
• Translate complex security tradeoffs, risks, and opportunities into clear narratives that drive decision-making across technical and non-technical stakeholders
• Lead security reviews and technical discussions, raising the bar for engineering rigor and constructive challenge across the team
• Engage closely with engineering, data, and client teams to align security work with broader business priorities and measurable outcomes

Leadership & Influence

• Define security architecture and engineering standards, bringing depth on tradeoffs, long-term implications, and responsible AI practices
• Mentor and grow junior and mid-level engineers, multiplying impact through coaching, code reviews, and pairing on hard problems
• Take ownership of the most ambiguous and highest-stakes pieces of work, driving them through to production with care for reliability, cost, and safety

What You’ll Bring

• 7+ years of professional security or software engineering experience, with at least 3 years leading application and cloud security initiatives
• Deep expertise in application security, secure coding practices, and the OWASP Top 10
• Strong experience with threat modeling, penetration testing, vulnerability management, and secure code review
• Deep cloud security expertise across identity, network, and data layers
• Strong experience embedding security automation and policy-as-code into CI/CD pipelines
• Strong experience with detection engineering, logging, and incident response at scale
• Strong experience securing AI and LLM-powered applications, including prompt injection, data leakage, model abuse, and agentic-AI threats
• Experience with security, compliance, and governance frameworks
• Demonstrated leadership and technical mentoring experience across a team or organization
• Strong stakeholder communication skills, with the ability to translate technical depth across audiences
• Demonstrable, day-to-day usage and expert knowledge of AI-forward tools such as Claude and Cursor
• Excellent problem-solving skills and the ability to navigate highly ambiguous technical and business challenges with sound judgment

You’ll Do Well Here if You Are

• A doer. You see something broken and fix it. You’d rather move on clarity than wait for certainty.
• A fast learner who knows you don’t know everything. The AI landscape changes weekly. You’re senior enough to know better and curious enough to keep learning anyway.
• Direct in a way that makes the work better. You give honest feedback. You’d rather have the hard conversation than blow smoke.
• Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don’t put your name on work you wouldn’t stand behind.
• Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
• All in. You treat clients’ businesses like your own. You take the work seriously without taking yourself seriously.
• Resourceful when the budget, timeline, or team is tight. Constraints don’t slow you down. They sharpen you.
• Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.