Why Signed B2B Deals Often Fail to Convert Into Liquid Capital

Shalom Ben Or, founder of the fintech firm DealSync, argues that the root of the problem lies in the reliance on human judgment and disconnected workflows to manage the 'sales-to-cash' gap. When companies move beyond simple subscription models—such as businesses using outcome-based AI or hardware-heavy contracts—standard lending models frequently fail to value these agreements. CFOs often find themselves reacting to liquidity shortages after the fact, rather than structuring deals to be financeable from the outset.

According to Atradius, 43% of credit-based B2B sales in the U.S. were overdue in 2025, a statistic reflecting the pressure placed on company cash flows. Ben Or suggests shifting the CFO’s technology stack away from manual deal desks toward what he terms a 'programmable' approach. By embedding financial judgment earlier in the sales process, firms can package complex revenue streams into assets that lenders are actually equipped to evaluate. The goal is to transform financial strategy from a reactive, administrative burden into a proactive tool for capital efficiency.