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About This Role
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.
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
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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
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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
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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!
Compensation Range: $180K \- $250K
Salary Context
This $180K-$250K range is above the median for AI Software Engineer roles in our dataset (median: $183K across 194 roles with salary data).
Role Details
About This Role
AI Software Engineers build the applications and systems that AI models run inside. They own the API layers, data pipelines, frontend integrations, and infrastructure that turn a model into a product users interact with. Every AI company needs engineers who can build the software around the AI.
The challenge is building reliable systems around inherently unreliable components. Models are probabilistic. They'll give different answers to the same question. They hallucinate. They're slow. They're expensive. Your job is to build an application layer that handles all of this gracefully while delivering a product that users trust and enjoy.
Across the 3,708 AI roles we're tracking, AI Software Engineer positions make up 7% of the market. At Cloaked, this role fits into their broader AI and engineering organization.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
What the Work Looks Like
A typical week includes: building API endpoints that serve model inference with caching and fallback logic, designing the data pipeline that feeds context to a RAG system, implementing streaming responses in the frontend, debugging a race condition in the async inference pipeline, and optimizing database queries for the vector search layer. It's full-stack engineering with AI at the center.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
Skills Required
Full-stack engineering skills with AI integration experience. Python and TypeScript are the most common requirements. You'll need to understand API design, database architecture, and how to build reliable systems around probabilistic outputs. Experience with streaming, async processing, and caching patterns is increasingly important as real-time AI applications proliferate.
Knowledge of vector databases, embedding APIs, and LLM integration patterns (function calling, structured outputs, retry logic) differentiates AI software engineers from general software engineers. Understanding cost optimization (caching strategies, model routing, batched inference) is valuable since inference costs can dominate application economics.
Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
Compensation Benchmarks
AI Software Engineer roles pay a median of $219,250 based on 424 positions with disclosed compensation. Senior-level AI roles across all categories have a median of $230,000. Disclosed range: $180K to $250K.
Across all AI roles, the market median is $217,500. Top-quartile compensation starts at $272,100. The 90th percentile reaches $325,000. For comparison, the highest-paying categories include AI Safety ($300,000) and Research Engineer ($280,000). By seniority level: Entry: $120,000; Mid: $200,000; Senior: $230,000; Director: $272,150; VP: $250,000.
Cloaked AI Hiring
Cloaked has 1 open AI role right now. They're hiring across AI Software Engineer. Based in New York, NY, US. Compensation range: $250K - $250K.
Location Context
AI roles in New York pay a median of $220,000 across 1,045 tracked positions.
Career Path
Common paths into AI Software Engineer roles include Software Engineer, Full-Stack Developer, Backend Engineer.
From here, career progression typically leads toward Staff Engineer, AI Architect, Engineering Manager.
If you're a software engineer, you're already 80% there. Learn the AI integration patterns: RAG, streaming inference, function calling, structured outputs. Build a project that demonstrates you can wrap an AI model in a production-quality application with proper error handling, caching, and user experience. That's the portfolio piece that gets you hired.
What to Expect in Interviews
Technical screens look like standard software engineering interviews with an AI twist. Expect system design questions about building reliable applications around probabilistic models: handling streaming responses, implementing retry logic for API failures, and designing caching strategies for LLM outputs. Coding rounds test standard algorithms plus practical integration patterns like async processing and rate limiting.
When evaluating opportunities: Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
AI Hiring Overview
The AI job market has 3,708 open positions tracked in our dataset. By seniority: 102 entry-level, 1,705 mid-level, 1,469 senior, and 432 leadership roles (Director, VP, C-Level). Remote roles make up 14% of the market (508 positions). The remaining 3,180 roles require on-site or hybrid attendance.
The market median for AI roles is $217,500. Top-quartile compensation starts at $272,100. The 90th percentile reaches $325,000. Highest-paying categories: AI Safety ($300,000 median, 21 roles); Research Engineer ($280,000 median, 147 roles); AI Architect ($254,798 median, 67 roles).
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
The AI Job Market Today
The AI job market spans 3,708 open positions across 16 role categories. The largest categories by volume: AI/ML Engineer (2,605), Data Scientist (310), AI Software Engineer (259). These three account for the majority of open positions, though smaller categories often have higher per-role compensation because of specialized skill requirements.
The seniority mix tells a story about where AI teams are in their maturity. Entry-level roles (102) are outnumbered by mid-level (1,705) and senior (1,469) positions, reflecting that most companies are past the 'build a team from scratch' phase and need experienced engineers who can ship production systems. Leadership roles (Director, VP, C-Level) total 432 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 14% of all AI roles (508 positions), with 3,180 requiring on-site or hybrid attendance. The remote share has stabilized after the post-pandemic correction. Senior and specialized roles (Research Scientist, ML Architect) are more likely to be remote-eligible than entry-level positions, partly because experienced hires have more negotiating power and partly because these roles require less hands-on mentorship.
AI compensation is structured in clear tiers. The market median sits at $217,500. Top-quartile roles start at $272,100, and the 90th percentile reaches $325,000. These figures include base salary with disclosed compensation. Total compensation (including equity, bonuses, and sign-on) runs 20-40% higher at companies that offer those components.
Category matters for compensation. AI Safety roles lead at $300,000 median, while Prompt Engineer roles sit at $140,000. The spread between highest and lowest-paying categories reflects the premium on specialized technical skills versus broader analytical roles.
The most in-demand skills across all AI postings: Python (1,890 postings), Aws (1,103 postings), Azure (877 postings), Rag (855 postings), Gcp (631 postings), Prompt Engineering (560 postings), Pytorch (545 postings), Claude (498 postings). Python dominates, appearing in the vast majority of role descriptions regardless of category. Cloud platform experience (AWS, GCP, Azure) is the second most common requirement. The newer entrants to the top skills list (RAG, vector databases, LLM APIs) reflect the shift from traditional ML toward generative AI applications.
Frequently Asked Questions
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