My history is 3x 7->8 and 1x 8->9, 3 with VC, 1 with no VC...we definitely found it easier to go 6->7 in all four as the “early adopter” set all talked to each

My history is 3x 7->8 and 1x 8->9, 3 with VC, 1 with no VC...we definitely found it easier to go 6->7 in all four as the “early adopter” set all talked to each other and that was enough to get momentum and small enough that bigger players take no notice. 7->8 you start to get noticed which is both good and bad. Convincing enough buyers to “cross the chasm” and not go to a competitor is an entirely different org challenge. Also the expectations of the larger buyers adds cost and complexity (ie channel sales vs outbound vs inbound) If you are in SF area happy to host 7->8 beers/coffee meetup!