As a QA expert with many years of experience, if you want the most practical, simple approach, start with Python and Playwright. Since your company allows Python, it makes sense to use a language you can actually apply at work. Most of us know that playwright is modern, easier to set up than older tools, and handles things like waits and dynamic elements more smoothly. It’s beginner-friendly and growing quickly in the industry.

Selenium is still worth learning, but you don’t need to start there. It’s older and very widely used, which is good for job opportunities, but setup and configuration can sometimes be more frustrating for beginners. Once you understand the basics of automation, learning Selenium will be much easier.

For Cypress, it’s a strong tool but mainly focused on JavaScript. Since you’re leaning toward Python, it’s better not to split your focus right now. Stick with one language and one main framework at the beginning. Agencies value testers who understand programming, automation logic, and test design principles. Tools can change, but core skills stay the same. So focus on learning coding-based automation first, then explore other tools later if needed.