Web Automation Engineer

Description

You'll keep the company connected to the open web. Every product we ship depends on reliably accessing pages at web scale, and the modern web actively resists automation with detection systems, challenge flows, and fingerprinting that evolve weekly. This role is equal parts research and engineering: understand how those systems work at the deepest level, then turn that understanding into infrastructure that keeps our scraping fast, reliable, and resilient. If you like taking apart obfuscated JavaScript on a Tuesday and shipping the fix to production on Wednesday, this is for you.

 

Salary Range: $235,000–$260,000 USD/year (SF) / $217,000–$233,000 CAD/year (Toronto)

Equity Range: Competitive equity. Details shared during the process.

Location: San Francisco, CA (SF HQ) or Toronto, ON (Toronto Hub). Hybrid, onsite 3+ days a week.

Job Type: Full-Time

Experience: 3+ years building browser automation, web infrastructure, or systems-level software

Work Authorization: Must be authorized to work in the United States or Canada. We're not able to sponsor US visas right now. For Canada, we'll consider sponsorship on a case-by-case basis through our Toronto Hub.

About the company

The company is the easiest way to turn the web into data AI agents can use. One API call converts any URL into clean, LLM-ready markdown or structured data. It's the boring-hard problem everyone building with LLMs eventually hits, solved.

We hit 8 figures in ARR in year one and more than doubled it in year two. Growth like this is rare, and we're just getting started.

We're a small team punching far above our weight. Everyone here owns a real piece of the product and company, end to end, and runs it themselves. No hiding behind process or headcount.

This is a place for people who want to work at the frontier: an AI company building the infrastructure other AI companies run on, not one bolting AI onto an existing product. We move fast, go deep, and are building the tools superintelligence will rely on to gather data from the web. That library is called Alexandria, and it starts now.

Responsibilities

• Reverse engineer detection: Research how modern websites detect and challenge automated traffic, and take apart those mechanisms and challenge flows
• Find the signals: Identify the browser, device, network, and behavioral signals that separate automated access from human traffic
• Replicate and harden: Reproduce those signals synthetically in authorized test environments to validate and harden our approaches
• Turn research into production: Build the automation, diagnostic, and monitoring tools that keep scrape reliability high as the web shifts
• Own scrape success rate: Measure it, explain regressions, and ship the fixes
• Ship fleet-wide: Work with platform engineers to roll improvements out across the crawling fleet at scale

Requirements

• Languages: Strong JavaScript/TypeScript and/or Python, and comfortable picking up whatever a problem demands
• Browser internals: Real understanding of rendering, JS engines, headless automation (CDP, Playwright, Puppeteer), and where automated browsers differ from real ones
• Network fundamentals: Solid grasp of HTTP/TLS, proxies, and browser and device fingerprinting
• Reverse-engineering instincts: You can read minified, obfuscated code and figure out what it's actually checking
• Research with a shipping habit: You go deep on how something works, then land the fix in production, not just a writeup
• Nice to have: Deobfuscating JavaScript and VM-based obfuscation, network-level fingerprinting (TLS/HTTP2 signatures, JA3/JA4), running large browser or proxy fleets in production, or prior work at a scraping, web data, security research, or automation company
• What We're NOT Looking For
• Needs a spec: Someone who needs a fully specced ticket to start
• Narrow lane: Someone who wants to specialize narrowly and hand off everything else
• Process first: Someone who optimizes for process over shipping
• A Note On Pace
• We operate at an absurd level of urgency because the window for what we're building won't stay open forever. If that excites you, keep reading. If it doesn't, no hard feelings, but this role probably isn't for you.

Benefits

• Available to all employees
• Salary that makes sense: $235,000–$260,000 USD/year (SF) / $217,000–$233,000 CAD/year (Toronto), based on impact, not tenure
• Own a piece: Gain competitive equity in what you're helping build
• Generous PTO: 15 days mandatory, anything after 24 days, just ask (holidays excluded). Take the time you need to recharge
• Parental leave: 12 weeks fully paid, for all parents
• Wellness stipend: $100 USD/month for the gym, therapy, massages, or whatever keeps you human
• Learning & Development: Expense up to $1,000 USD/year toward anything that helps you grow professionally
• Team offsites: A change of scenery, minus the trust falls
• Sabbatical: 3 paid months off after 4 years, do something fun and new
• Available to US-based full-time employees
• Full coverage, no red tape: Medical, dental, and vision (100% for employees, 50% for partner and kids). No weird loopholes, just care that works
• Life & Disability insurance: Employer-paid basic life and AD&D, short-term disability, and long-term disability. Coverage for life's curveballs
• Virtual care and a health guide: Teladoc for the couch doctor visit, plus Rightway to answer coverage questions and fight billing errors for you
• Mental health: Talkspace, therapy and psychiatry on your schedule
• Fertility and family building: Carrot, covering you and your partner
• EAP: Free confidential counseling, legal and financial consults, and online will prep through Guardian
• 401(k) plan: Retirement might be a ways off, but future-you will thank you
• Pre-tax benefits: HSA, FSA, and commuter benefits to help your wallet out a bit
• Supplemental options: Extra life and AD&D, accident, critical illness, hospital indemnity, plus pet, legal, and identity protection through MetLife
• Available to Canada-based full-time employees
• Full coverage, no red tape: Extended health, dental, and vision through Manulife (Diamond, the top tier), 100% employer-paid for you, your partner, and your kids
• Life & Disability insurance: Employer-paid life, AD&D, short-term disability, and long-term disability. Coverage for life's curveballs
• Virtual care: Dialogue Premium, so you can see a doctor or nurse from your couch, any hour
• Mental health: Talkspace Elite, therapy and psychiatry on your schedule
• Fertility and family building: Carrot, covering you and your partner
• Retirement: Group RRSP through Wealthsimple, so future-you can thank you
• Available to SF-based employees
• SF HQ perks: Snacks, drinks, team lunches, intense ping pong, and peak startup energy
• E-Bike transportation: A loaner electric bike to get you around the city, on us
• Available to Toronto-based employees
• Toronto Hub perks: Snacks, drinks, team lunches, glass-walled views down University Avenue, and a home base steps from Union Station
• Transit, covered: A PRESTO card loaded for GO Transit, subway, and streetcar, plus station parking if you drive to the train. Winter-proof, on us
• Interview Process
• Application Review: Send us your work and a quick note on why this excites you. Show us what you've taken apart: automation you've built, detection systems you've analyzed, gnarly debugging stories. We care about what you've shipped, not where you went to school.
• Intro Chat (~25 min): A quick conversation to get to know each other before we go deep. What you've been working on, what drew you to the company, and what you're looking for in your next role. Time for your questions too.
• Technical Chat (~45 min): We'll dig into a real problem from our world: why a page loads in a real browser but fails under automation, how a challenge flow decides what it's talking to, or debugging a sudden drop in scrape success. Come ready to think out loud. We care how you reason, not whether you memorized the answer.
• Founder Chat (~25 min): Culture, pace, ownership, and how you like to work. Time for your questions too.
• Paid Work Trial (~40 Hours): Work with the team on a real, scoped piece of the product, paid at a contractor rate. It's the truest signal for both sides: you see what building at the company actually feels like, and we see how you ship. Remote-friendly, and we'll flex around your current commitments.
• Decision: We move fast after the trial.
• If you want to understand the web more deeply than the people trying to keep you out of it, you should join us.
• Apply now.
• Experience: Any (new grads ok)
• Visa: US citizen/visa only