Thanks and I look forward to your contributions.

If you don't mind sharing, what is your current job title and where do you hope to be in 5 years?

Don

Welcome, dropper!

Welcome aboard.

If I were you, I'd try to get at least 2-3 years of experience as a (web, I assume) developer before trying to get into penetration testing. Pen testing really draws on a lot of previous experience and deep understanding of systems, networks, and/or applications. I think the "lucky" individuals who skip working in administration, engineering, development, etc. roles and get right into security actually put themselves at a disadvantage and really struggle to make up for that gap in knowledge.

You should definitely pursue a masters because that always looks good, but I wouldn't expect that to make an enormous difference in terms of obtaining a penetration testing position. I can't recall any advertised position asking for more than a four-year degree, and myself and many others I know had these types of positions while not possessing any degrees at the time. From what I've seen, experience is typically the most important factor. Pepper in a few certs to compliment your four-year degree, and I think you'd be in pretty good shape after getting a couple of years of work experience.