Learning to be a software tester is hard work and beginning your career in a startup adds an extra layer of difficulty. Applying skills you have recently acquired while continuously studying your craft and learning about your business poses questions that have to be addressed. What information is important? How can you give feedback the quickest? When should you address test automation? And most importantly: how do you communicate testing concerns with PMs, devs, and the CEO? Through this talk I will present an experience report on my journey as new software tester and what I encountered and learned through how I approach testing, delivery, automation, and communication.