Do you want to learn to program? Or do you enjoy the higher level design ideas? Penetration testing will be closer to what you are doing now from a sysadmin level but you will learn security models and largely write scripts to test systems. I would not be fearful of this role, you can do it.
The architecture role will be design oriented. Do you understand what Azure/cloud offers your business? Things to consider: how will you do identity management, backups, security models (VPN etc..), etc... You're goal here will be more at the business level and how you "scale" your IT processes with respect to achieving those goals (and reduce COGs).. Azure is effectively infrastructure as code, which reduces the demand for system administrators since your physical machines are now virtualized. An architect will probably not code very much, penetration tester will write basic scripts to do much of the work... Architect is more about consensus building/collaboration/project management, penetration testing is more of an individual contributor role. These are of course basic descriptions of the roles.. they may vary in implementation wherever you go.
Going from help desk to system admin is a bigger leap than sysadmin to pen tester in my opinion. Fear not! If you meet like 50-70% of the reqs you're qualified.
The architecture role will be design oriented. Do you understand what Azure/cloud offers your business? Things to consider: how will you do identity management, backups, security models (VPN etc..), etc... You're goal here will be more at the business level and how you "scale" your IT processes with respect to achieving those goals (and reduce COGs).. Azure is effectively infrastructure as code, which reduces the demand for system administrators since your physical machines are now virtualized. An architect will probably not code very much, penetration tester will write basic scripts to do much of the work... Architect is more about consensus building/collaboration/project management, penetration testing is more of an individual contributor role. These are of course basic descriptions of the roles.. they may vary in implementation wherever you go.
Going from help desk to system admin is a bigger leap than sysadmin to pen tester in my opinion. Fear not! If you meet like 50-70% of the reqs you're qualified.