The job board, previously a reliable revenue stream generating 15-20 new job postings a month, saw postings collapse in 2023.

“That fell off massively in 2023.”

Jimmy initially treated it as a conversion-rate problem and tweaked copy and buttons, but concluded the real cause was a drop in macro demand for content hiring that no amount of landing-page optimization could fix.

“The macro demand was way down and there wasn't anything I could really do to boost job board revenue.”

In summer 2023, Superpath split into three tiers (free, an unnamed paid Slack plan, and Superpath Pro), which confused prospective members about which plan to buy.

“This all made sense to me, but it created a ton of confusion for potential members.”

The middle, paid-Slack-only tier had no name of its own, so support requests piled up from people unsure which plan fit them.

“the middle tier didn't have a name”

The freelancer marketplace (vetting and matching content freelancers, handling payroll/1099s) had happy customers but was hard to sell because of its pricing structure.

“it's too hard to sell”

The pricing combined a flat platform fee, a content-spend cap, invoiced overage, and a percentage fee waived only for ACH payment, and Jimmy judged the resulting structure too confusing for prospects to say yes to.

“It's way too confusing.”