“the cheapest version of marketing automation was like $400 a month when we started trip and it was obvious it didn't need to be $400 a month it was that much because their margins were huge and their sales model mod was very time intensive and we were like if we build self- serve I know we can charge less and make it self- serve”

Use sales-model differentiation as a wedge against painful incumbents

Drip beat Infusionsoft / Marketo / SilverPop on sales model, not features. The incumbents required mandatory sales calls and demo-gated pricing — customers hated it but had no self-serve alternative. Look for categories where users are forced through a pain point (hidden pricing, mandatory demos, multi-week sales cycles) and offer instant self-serve at half the price. The friction itself is the wedge.