Your Buyer Is Stuck With the Bill. Plan Like It. | Steve Dickerman

Revenue Problem Solvers · Oct 23, 2026 · 45m

When a seller loses, they lose a deal. When a buyer loses, they’re stuck with the bill, and their name is on it.

Steve Dickerman planned for a 60-day close selling into higher ed. He got an 18-month cycle. So he stopped accepting “things just take a while,” asked buyers what a while actually meant, and built the timeline with them, step by step: who does what, and by when. The cycle came down to 12 months.

Steve started as an SDR at Okta and left at 128% of quota with three President’s Club trips. He built the enterprise motion at IFTTT, where he closed YouTube, founded Sangria in 2021, and…