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Move to start up job from big company?

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Oct 6, 2019
I've been at a large software company for 21 years. Been a great run, made great money, and lots of friends. Still have another 8 years of working to go, which I could continue to do pretty well here.

I came across a pre-IPO company who is building products to grow in the Cloud space where I have deep expertise. I'm currently in a very senior IC role at the large company, I am being offered a position in the pre-IPO company at a Senior level (VP of Cloud Sales). This is a brand new org, where the idea will be to convert current customers to the cloud offering as well as win net new.

The big bet is an IPO, which has been filed for S1 but there is no timeline to go IPO. The other benefit is to gain the experience of building out a new cloud practice at the VP level.

Annual pay and comp plan is about the same for on target. In the big company its predictable that I will land between 90% and 110%, however in the pre-IPO company its a brand new product so who knows... I plan to negotiate in a fixed bonus for 24 months until the product matures.

Anyways, I'm really considering leaving the job security and comfort of the big company. To go big and shoot for the moon. I have a deep network in the big company, so there's a good chance I can land back there if the pre-IPO company didnt work out.

Anybody made a similar move? TIA

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