When is early, too early?

I’ve joined too early as a Head of Sales' more than once:

Scoutible was a psychology test delivered through a mobile game, to spot top performers. We assumed that a machine learning algorithm could recommend top candidates trained on a data set from employees at small startups.

Once I recruited our head of Data Science and Psychology, we learned that our target players should come from the likes of Wells Fargo. So our go-to-market motion had to be started from scratch. Did I mention that we didn’t have a product yet? Ouch.

Another startup’s co-founder recruited me on a promise of a done deal with a publisher (one of the three largest players in our space) that would create immediate scale for our marketplace. That partner backed out (a month after i joined) and my co-founder wouldn’t push it (a sensitive relationship). It’s a meaningfully different deal to join a startup with zero product, vs 1/2 of a marketplace fixed, at scale.

Another founder told me (a month after I joined) that our first enterprise contract (used to close Series A) was actually a friend that had to back out. As with the example above, beware of raising based on success with “friendlies”. Demo the product, don’t believe, “Done deals”.

In all 3 cases, the product was not ready (from wire frames to managed services instead of a platform) and in 2 out of 3 the founders assumed key tailwinds that never materializes. It pays to do due diligence both on the product readiness and the key go-to-market relationships required to kick-start product market fit. Run your own VC process.

Early stage is hard. Suspension of disbelief and good timing are required. Make sure you like the work and the people, because things tend to get harder before they get easier.

Otherwise get a job at Salesforce and make $500k working 5 hours a day.