Should I approach my boss from my previous company for a LOR for my Master’s in Computer Science (From USA)? I graduated in 2018 (in computer science) and worked in an education startup (Sept'18-Feb'19), as a co-founder of sorts, and later joined a well-known company in Mar'19 and have been working there ever since. My main role at the startup was as an educational instructor (a fact which I feel can help my candidature) and doing sales in the part-time. Will obtaining a Letter of Recommendation (LoR) from the main founder help my candidature? While I can obtain two LORs from my current workplace, I felt that my experience at that startup would help demonstrate my commitment towards making education accessible.
I have obtained an academic LOR. This is specifically focusing on whether I need to obtain another Academic LOR or no.
It is likely that your application will be reviewed by a faculty committee. It is likely that some, at least, of them will want to see some prediction of academic success in your letters. If you were applying for other industrial jobs it would be different, but I suggest that at least one of your letters come from someone who knows you well and can make a fair assessment that you will succeed in an academic setting.
A head of a startup or others in industrial positions have a different focus and their letters probably can't properly attest to your academic qualities. It is impossible to judge how much they can help you, not knowing the details, but it sounds like a risky move.
Direct your letters toward the needs of the program you want to join, not the workplace you have been in.