[Originally posted as an essay on Medium]
My previous startup had a sales cycle problem. We sold an enterprise product targeted at agencies and big consumer brands, and — while we could clearly articulate benefits — we could only point to an opaque, fuzzy ROI for the buyer during the sales process. As a result our sales cycle (including delightful hurdles like vendor approval that consumer web startups should thank their lucky stars they never have to deal with) could stretch for months.
“Never again,” I said to myself, and I set a goal: my next product would have a two week sales cycle. If I couldn’t get a user to convert from free to paid in fourteen days I’d move on and test if retention emails and down-the-road product upgrade notices would entice them back.Continue Reading..