I had to brute force it, at least the second time at EchoSign.
When we launched we had a small but decent number of sign-ups, and once we had a paid product in a few months, a small number of reasonably happy paying customers. Not many. But at least a few that were happy. Enough to say “push on”.
But it wasn’t enough. We only got to about $200k in ARR by the end of the first year, and were running low on cash. We had something for sure — but not enough, and not growing fast enough, for true product-market fit.
In the end, we had to go more enterprise, and have a richer product, and develop more critical integrations (Salesforce, etc.) to find true product-market fit for real, which in the end took probably 18 months from Day 1. At that time, there wasn’t a big enough market for the simple, horizontal product we launched with.
But we didn’t know. We weren’t in agreement if going up-market was a good one. We weren’t in agreement on how aggressively to push our API, or our freemium vector, or different expressions of our product. We weren’t in agreement on our target verticals and markets.
In the end, we tried everything. We closed big customers like Dell, BT, GE, Comcast, etc. in Year 1. We did every integration. We took the customer feedback we did have, and kept adding as many features they’d pay for as we could. We tried leading tradeshows in different verticals. And in the end, it probably took 3.5 years to have the product it would have been nice to have on Day 1.
Sometimes you know. But sometimes, you get 10 customers however you can, then 15, then 20, then 100, then 200, etc. And you sort of brute-force it. Because, sometimes it may take until 100+ customers and $500k in ARR before you really know.
Your initial ideas as founders in terms of what the market wants are often directionally correct, but specifically wrong.