I have 5 years in insurance sales experience, how can I break into tech industry through customer Success?

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You can, I did something similar myself. The important thing is to remove the industry jargon and keep it to something they understand from a KPI standpoint. I would also recommend taking a look at InsurTech organizations where your insurance background can be rolled into your new role.

Be mindful of tech right now though, Insurance may not be sexy but there are lots and lots of layoffs in tech currently.

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