Workana

Freelancer marketplace connecting clients with professionals

AI Web Scraping Engineer - Stealth Data Acquisition

Data EngineeringConfirmed live in the last 24 hours

Full-timeRemote in USANo salary listed

About the Job

Requirements

At least 4 years of experience building production web scraping systems at scale, including infrastructure rather than only scripts.
Hands-on experience with headless browser automation using Playwright, Puppeteer, or Selenium, including stealth plugins or patches.
Practical experience defeating or working around Cloudflare, DataDome, PerimeterX, Akamai Bot Manager, Kasada, or similar anti-bot systems.
Strong understanding of TLS fingerprinting, HTTP/2 fingerprinting, canvas/WebGL fingerprinting, and browser fingerprint spoofing.
Experience with residential, mobile, or datacenter proxy rotation and session management at scale.
Proficiency in Python and/or Node.js/TypeScript for scraping and orchestration.
Experience using LLMs or AI models for content extraction, parsing, and classification on messy or unstructured HTML.
Familiarity with CAPTCHA-solving approaches and detection-avoidance strategies.
Must be based in and authorized to work in the United States.
Must pass a standard background check before starting.
Comfort working in a fast-moving, iterative environment where target sites frequently change defenses.

Responsibilities

Design, build, and maintain stealth-based scraping pipelines that evade bot detection, fingerprinting, and rate-limiting defenses.
Reverse-engineer target sites' anti-automation measures, including TLS/JA3 fingerprinting, canvas/WebGL fingerprinting, and behavioral detection, and build countermeasures.
Architect distributed scraping infrastructure using rotating residential or mobile proxies, headless browser farms, and session/cookie management at scale.
Integrate AI/LLM-based parsing to handle dynamic, unstructured, or frequently changing page layouts without brittle selectors.
Build self-healing scrapers that detect layout/DOM changes and adapt automatically.
Monitor scraper health, success rates, and detection signals, and rapidly iterate when sites patch defenses.
Ensure data pipelines follow client-defined legal and ethical guardrails, including terms-of-service review, robots.txt handling, and rate limiting, as directed by the legal/compliance team.
Collaborate with data engineering to deliver clean, structured, deduplicated datasets to downstream systems.

Desired Qualifications

Experience with mobile app API reverse engineering in addition to web.
Background in adversarial machine learning or anti-bot research from either side.
Experience with distributed task queues such as Celery, Kafka, or SQS for scraping orchestration.
Prior work in a data-as-a-service, alternative-data, or web-intelligence company.

AI Web Scraping Engineer (Stealth Data Acquisition)

Workana · United States (Remote) · Full-time · Posted 2026-09-11

Workplace: remote

Department: Pinwheel

Description

About Our Client

Pinwheel API is a leading data infrastructure company enabling seamless access to employment and income verification data through secure APIs. The company powers payroll connectivity for fintechs, lenders, HR platforms, and financial services across the US market.

Role Overview

As an AI Web Scraping Engineer (Stealth Data Acquisition), you will be responsible for designing, building, and maintaining resilient, undetectable data collection systems at scale. This is not a "requests + BeautifulSoup" role — we need someone who has operated against modern anti-bot infrastructure (Cloudflare, PerimeterX, DataDome, Akamai, Kasada) and knows how to stay under the radar while extracting structured data reliably and continuously. You will integrate AI/LLM-based parsing to handle dynamic, unstructured, or frequently-changing page layouts and build self-healing scrapers that detect layout/DOM changes and adapt automatically.

Responsibilities

Stealth Scraping Pipeline Development – Design, build, and maintain stealth-based scraping pipelines that evade bot detection, fingerprinting, and rate-limiting defenses.
Anti-Bot Reverse Engineering – Reverse-engineer target sites' anti-automation measures (TLS/JA3 fingerprinting, canvas/WebGL fingerprinting, behavioral detection) and build countermeasures.
Distributed Infrastructure Architecture – Architect distributed scraping infrastructure using rotating residential/mobile proxies, headless browser farms, and session/cookie management at scale.
AI-Powered Parsing Integration – Integrate AI/LLM-based parsing to handle dynamic, unstructured, or frequently-changing page layouts without brittle selectors.
Self-Healing Scraper Development – Build self-healing scrapers that detect layout/DOM changes and adapt automatically.
Monitoring & Iteration – Monitor scraper health, success rates, and detection signals; rapidly iterate when sites patch defenses.
Compliance & Legal Guardrails – Ensure data pipelines are compliant with client-defined legal and ethical guardrails (ToS review, robots.txt handling, rate limiting) as directed by Pinwheel's legal/compliance team.
Data Pipeline Collaboration – Collaborate with data engineering to deliver clean, structured, deduplicated datasets into downstream systems.

Requirements

4+ years building production web scraping systems at scale (not just scripts — real infrastructure).
Deep hands-on experience with headless browser automation (Playwright, Puppeteer, Selenium) including stealth plugins/patches.
Practical experience defeating or working around Cloudflare, DataDome, PerimeterX, Akamai Bot Manager, Kasada, or similar.
Strong understanding of TLS fingerprinting, HTTP/2 fingerprinting, canvas/WebGL fingerprinting, and browser fingerprint spoofing.
Experience with residential/mobile/datacenter proxy rotation and session management at scale.
Proficiency in Python and/or Node.js/TypeScript for scraping and orchestration.
Experience using LLMs/AI models for content extraction, parsing, and classification on messy/unstructured HTML.
Familiarity with CAPTCHA-solving approaches and detection-avoidance strategies.
Must be based in and authorized to work in the United States.
Must pass a standard background check prior to start.
Comfortable working in a fast-moving, iterative environment where target sites change defenses frequently.

Nice to Have

Experience with mobile app API reverse engineering (in addition to web).
Background in adversarial ML or anti-bot research (from either side).
Experience with distributed task queues (Celery, Kafka, SQS) for scraping orchestration.
Prior work in a data-as-a-service, alt-data, or web intelligence company.

Benefits

Compensation in USD
Fully remote work
Career growth on an international company

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About the Company

Workana

Freelancer marketplace connecting clients with professionals

Workana connects businesses with independent professionals in Latin America through a freelancer marketplace. Clients post projects and hire talent across fields like IT, design, marketing, and admin support, while freelancers create profiles, showcase skills, and bid on opportunities. The platform earns commissions on completed projects and uses an escrow system to securely hold client payments until the work is finished to the client's satisfaction. It differentiates itself by focusing on the Latin American market, using freelancer rankings and tiers, and growing through regional expansion and partnerships to simplify hiring remote talent with secure transactions.

Company size: 5,001-10,000
Company stage: Series C
Total funding: $15.8M
Headquarters: Buenos Aires, Argentina
Founded: 2012

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