"Free" pen-test

I'm looking for a bit of advice. I was tipped off that company X had minimal security for their large bundle of IP addresses running on Micro$oft servers. I got my mate Fred (!) to have a look and he reckoned they were _very_ vulnerable. So, we went to the security director and
"sold" him a free penetration test. Fred then got admin access to
their web server plus bucketloads of info about their DMZ and even their 192.168.0.x network. I went back to Mr Director thinking he'd wet himself and he said "I'm not too worried about that....just carry on if you can".

Well. Fred is keen to keep going. But I reckon that someone who is
"not worried" that his web server could have been taken down in about
4 hours is not worth wasting time on. Needless to say, the cunning plan was to sell him a pile of stuff once he was scared enough.

My question is this: how do white-hatters usually approach these things?

Grateful for any tips (and thanks for reading if you got to here)

Pete

Pete Smith
www.petesmithcomputers.com

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