Senior Python Engineer - Playwright Browser Automation

Prestige Trucking Insurance is a US commercial trucking insurance agency, hiring in India. We've built Insure Stack: an agent uploads an intake form and it quotes major trucking carriers in seconds - by driving those carriers' web portals with Playwright.

Your job is to add new carriers to the platform, keep the existing automations running, and fix them when they break.

What you'll do:

- Add new carriers - build Playwright automations that log into a carrier's portal, navigate it, fill quoting forms, and pull back quotes. Each new carrier is a new automation you design, write, and ship.

- Keep the existing automations alive - carrier portals change their layouts, forms, and login flows without warning. You keep our automations working through those changes.

- Fix errors fast - when a quote fails, diagnose it (changed selector, new login step, timeout, portal-side change) and get quoting back up.

- Be the human in the loop - when an automation can't handle something on its own, step in, resolve it, and push the quote through.

- Make each fix permanent - when you fix a recurring failure, update the automation so it handles that case itself next time. Fewer manual interventions over time is the goal.

- Keep it fast - quoting runs in parallel under a tight time budget.

What we need:

- 4+ years of production Python.

- You have driven browsers against third-party websites you don't control, in production - Playwright, Selenium, or Puppeteer. This is the requirement that matters most.

- Real experience with what goes wrong: session expiry, timeouts, login flows, layout changes, rate limiting, bot detection.

- Async Python and concurrency.

- Retries, backoff, error handling - you build things that recover instead of just crashing.

- You've been the person on the hook when an automation broke in production.

A note on what this role is - and isn't: This is hands-on Playwright (Selenium or Puppeteer experience works too) writing real code against live third-party websites. It's not a no-code or workflow-automation role - no Zapier, Make, n8n, Power Automate, or UiPath.

It's also different from QA/test automation. Writing Playwright tests against your own application is a genuinely different discipline from driving someone else's live site in production, where the page can change without warning. Both are valuable skills - this role needs the second one. When we talk, we'll ask about the specific projects where you've done it, so it helps if you can point to that work in your application.

Strong pluses: anti-bot work (proxy rotation, CAPTCHA handling, fingerprinting, session persistence); document extraction/OCR; insurance, fintech, or logistics domain.

Working hours: Starting hours are 9:00 AM EST for the first 90 days while we walk you through the platform and the carriers, with the team available in real time. After that, there may be room to revisit the schedule.

Our hiring process - please read:

1. A technical interview: with our team.

2. A mock trial run: we give you a real problem from our platform and you work through it, so we can both see whether it's a good fit.

We're upfront about the mock trial because it's how we hire. We're less interested in how someone interviews than in what they can actually build with a real problem in front of them. If that sounds like the kind of process you'd do well in, we'd love to hear from you.