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Cloaked is a consumer privacy and identity platform backed by $375M Series B funding, protecting 10M+ identities and removing 1B+ records from data brokers. The company is building AI-native privacy solutions with autonomous agents that monitor and defend users' digital footprints.
As Staff Offensive Security Engineer, you will operate as a persistent advanced threat against Cloaked's own infrastructure, moving beyond compliance-driven security toward strategic, high-impact offensive work. Your mandate is to compromise critical assets before real adversaries do, with complete autonomy to design and execute campaigns across the attack surface.
Key responsibilities include: designing custom exploit development and logical subversion strategies rather than relying on automated scanners; building complex offensive systems that test defenses at scale; ruthlessly prioritizing targets based on catastrophic business risk; partnering with product and engineering leaders to understand core business logic and identify vulnerabilities; teaching engineers to eradicate entire attack classifications at the root; and providing hands-on security guidance, architecture review, and audit support across business units.
You are expected to be a builder first—writing code to anticipate vulnerabilities before systems are deployed. You bring multi-disciplinary experience across customer support, QA, development, blue team, red team, or similar angles. You are fluent in modern cloud and SaaS architectures, including multi-cloud environments, IAM trust boundaries, tenant isolation, and API misconfigurations. You communicate complex exploits clearly to engineering teams without condescension.
Cloaked operates a hybrid model from NYC with a distributed team. The office includes amenities (gourmet cafe, cocktail bar, rooftop area, full kitchen). Compensation is above market rate with salary, bonus, and equity. Benefits include 401K, top-tier health/dental/vision, flexible work arrangements, home office stipend, competitive PTO (minimum per quarter), monthly health stipend, late-night meal stipend, and professional development opportunities.
