Senior Software Engineer, AI

About the role

We're looking for a Senior Software Engineer, AI to lead the development and strategic direction of Cloaked's AI Agents - autonomous agents that act on a user's behalf to monitor, manage, and enforce their privacy across their entire digital footprint. They find where your data is exposed, take action to remove it, and continuously defend your privacy in the background - turning what's always been a manual, reactive chore into something automated and continuous. 1B+ records removed to date, and now we're automating the entire fight. You'll own the technical roadmap end-to-end: agent architecture and orchestration, tool-use and integrations across third-party services, reliability and guardrails for non-deterministic systems, adversarial robustness against hostile web content, and the cloud infrastructure underneath. Long-term, this role grows beyond Agents. You'll contribute across Cloaked's engineering org and help shape how we build AI-native consumer products at scale. WHAT WILL YOU DO? Lead the technical roadmap and architecture for Cloaked's AI agent platform Design and build production agents that monitor, manage, and enforce users' privacy across their digital footprint autonomously Build agents that take real action on users' behalf - submitting data-removal requests, navigating opt-out flows, and adjusting privacy settings across hundreds of services Build defenses for adversarial environments, including prompt injection, untrusted web content, and hostile data sources Integrate and evaluate frontier models (LLMs, agent frameworks, tool-use) for production use Own the orchestration layer, integrations, and the cloud infrastructure the agents run on Collaborate with design, mobile, and product teams to ship agent experiences that feel effortless to end users Serve as the AI agents domain expert on the team, raising the engineering bar through code reviews, architecture discussions, and mentorship Help the team ship features faster and with fewer bugs by setting the technical standard for the product Actively leverage AI tools in day-to-day engineering work Contribute across engineering teams beyond Agents as the business scales WHAT SKILLS AND EXPERIENCES WILL HELP YOU? Strong software engineering fundamentals - production systems, distributed systems, real-time infrastructure Hands-on experience building agentic or LLM-powered products in production Proficiency with modern agent stacks: LLM orchestration and agent frameworks (LangGraph, LangChain, LlamaIndex, or similar), tool-use/function calling, and RAG Deep familiarity with LLMs, evals, and prompt engineering in production environments Experience building reliability and guardrails into non-deterministic systems Proficiency in Python and/or Go, with a track record of building scalable backend systems Experience designing and deploying secure, production-grade APIs Strong understanding of cloud infrastructure (AWS, GCP) and containerized deployments Track record shipping consumer products at scale Active daily use of AI coding tools (Cursor, Claude, Codex) with strong prompt judgment and tool selection instincts WHAT'S NICE TO HAVE? Experience with browser automation, headless automation, or web scraping at scale Background in agent observability, eval frameworks, or LLMOps Familiarity with adversarial ML, AI safety, prompt-injection defense, or anti-fraud system design PII handling and sensitive data awareness Prior exposure to consumer privacy or security-focused products Experience with workflow orchestration and job scheduling at scale WHAT DO WE LIKE? Passion for security, privacy, and internet ethics Curiosity and constant learning at the frontier of agentic AI and applied ML Strong analytical thinking with proactive problem-solving abilities Ownership mentality - comfortable holding the pen on technical direction Effective team player in high-velocity environments Comfortable mentoring and knowledge sharing across teams Experience in startups or growth-stage companies Interest in data tracking, analytics, and product instrumentation

Benefits

Additional Information

Cloaked is a consumer privacy and identity platform on a mission to give people back control of their personal data. We let anyone generate unlimited identities - masked emails, phone numbers, and payment cards - scrub their information off data-broker sites, and shield themselves from spam, scams, and breaches, all from one app. Backed by a $375M Series B, we've protected 10M+ identities and removed 1B+ records from the data brokers who profit off personal information. Now we're building the AI-native future of privacy: autonomous agents that monitor, manage, and defend your digital footprint for you.

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