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I wrote about how we did it at Intercom here: https://www.intercom.com/blog/how-intercom-got-our-first-cus...

In short it was a combination of individual customer outreach our CTO jumped on Skype (yes Skype) to help with installing, I did handholding through onboarding, I ran "webinars" to like 4 people, or less. Everything was just tiny tiny steps.



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