Selling to an old friend?

I noticed an old friend of mine who I haven't spoke to in around 9 years has just joined a company, in the position in which I sell into with the perfect criteria. What is everyones opinion on this or how to approach it...if at all?

👑 Sales Strategy
10
Rallier
Politicker
3
SDR Manager and Consultant
I always struggle with this too. I tend to avoid pitching them, just because I don't want to make things awkward. I might just congratulate them without trying to sell to them. 
Smithy
Politicker
3
Director of Sales
I’d reach out and have a catch up and just be up front. 

say that you were trying to speak to their predecessor and it’s a divine twist of fate that this has happened 
salesnerd
WR Officer
2
Head of Growth
Ehhh, I hate doing this. I've tried to do it in the past and lost friends because of it. They choose a different provider, they blow you off, etc. It's not worth it unless you don't care that much about the relationship.
Tres
Politicker
1
Account Executive
Reach out! What's to lose - doesn't sound like they are that close of a friend if you haven't spoken in so long, so might as well leverage the connection to try and get a sale. 
paddy
WR Officer
1
Director of Business Development
I agree. Reach out but do some research and try to find out if you can genuinely make their job easier with whatever you're pitching.
JuicyKlay
Celebrated Contributor
1
AM
Just give him a call to congratulate him. If he asks about your job bring it up. 
cw95
Politicker
1
Sales Development Lead
Shit, good answer. May have to try that one! 
JuicyKlay
Celebrated Contributor
1
AM
Just keep it cool. Think about who you’d want him to act if you were in his position. 
Blackwargreymon
Politicker
1
MDR
Reach out! What's to lose - doesn't sound like they are that close of a friend if you haven't spoken in so long, so might as well leverage the connection to try and get a sale.
Clashingsoulsspell
Politicker
1
ISR
I always struggle with this too. I tend to avoid pitching them, just because I don't want to make things awkward. I might just congratulate them without trying to sell to them. 
TheSolicitorGeneral
Politicker
0
Small Market AE
Let it come naturally, don't try and hard sell one of your old boys!! 
MR.StretchISR
Politicker
0
ISR
I always struggle with this too. I tend to avoid pitching them, just because I don't want to make things awkward. I might just congratulate them without trying to sell to them.
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