Senior Software Engineer, AI

Cloaked https://www.cloaked.com 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.

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

WHAT WE OFFER

Cloaked is a well-funded Series B startup based out of NYC.

Although we are a distributed team, the NYC team operates with a hybrid model. The office building is home to several amenities, including a gourmet cafe, cocktail bar, and a rooftop work area.

We have a fully built out kitchen packed with drinks and snacks. The Cloaked team has diverse interests and so we frequently embark on team outings and go out for socials!

COMPENSATION AND BENEFITS

We offer above market rate pay and equity based off of the market’s best commercially available data. Your compensation will be a combination of salary, bonus and equity.

Cloaked employees have 401K, as well as top of the line Health, Dental, and Vision benefits.

We offer flexible work arrangements and the ability to work remotely as needed. Cloaked provides a home office stipend in addition to a new company laptop (and other tech depending on the role).

PERKS

🌴 Competitive PTO: We encourage employees to take a minimum # of vacation per quarter. We see PTO as a preventative burnout measure and are committed to changing the industry standard.

🤸 Monthly health stipend: Used for any kind of physical, mental or emotional care you’d like to take for yourself, be it a gym membership, a meditation app, or time with a personal trainer.

🥗 Late Night Meals: We understand that sometimes work can get in the way of meal prep. In response to that, we offer employees a monthly meal stipend to be used when they don’t have time to get a home cooked meal going!

🧠 Professional Growth: Opportunities for career development and personal growth are provided to all employees who seek to further their knowledge and capabilities through an unlimited professional development fund. Additionally team members are encouraged to regularly attend conferences and industry events.

We are really excited about having you join our mission-driven team and help us build the future of online privacy!