[Context]

English is not my native language, and I think I owe a huge part of my English skills to one great teacher, who was teaching me in high school (10+ years ago).

[Idea]

I have recently managed to reach out to this particular teacher, with interest in him providing some lessons. However, after high school, I have happened to move rather far away from my hometown, so in person lessons wouldn't be possible. Hence the idea to ask him about possibility of providing some online lessons.

[The Problem]

This teacher has never provided any lessons online, and is worried that he is going to miss traditional tools, like CD audio players, videos, printouts, etc.

He is however interested in learning about the possibilities, but I honestly have no idea what sort of software to recommend, as I was never teaching personally.

Obviously Skype etc. comes to mind first, but he really stressed the point of needing it somehow augmented, in ways directed towards teaching.

[Question]

So my question is: Do you know of any software for teaching remotely I could recommend? Ideally all integrated with video conferencing, ability to easily share scanned printouts, videos, pre-recorded audio, etc.

Maybe there are any startups out here working on something alike, and looking for early testers, or even just idea feedback?

[Disclaimer]

Of course I've tried some obvious Google searches like "how to teach English online", but there is a lot of material out there, tons of it looking like some content farms more than real people, and to be honest I cannot imagine myself how good are any of the services/software available for teachers who never taught online. So I really hope someone here is experienced already in this area and could help with choosing something to start with. :) Just looking at https://angel.co/language-learning there is 500 such companies, so it seems really difficult to get through this volume of data...

EDIT: formatting