Why Enterprise Deals Stall (And the Plan That Cut 6 Months) | Steve Dickerman

A 30-minute task sat for 90 days. Nobody was lazy. The calendar was the problem. Steve Dickerman mapped every approval against it and cut an 18-month sales cycle to 12. Steve started as an SDR at Okta, stayed almost six years, and left at 128% of quota with three President’s Club trips. He built the enterprise motion at IFTTT, where he closed YouTube. In 2021 he founded Sangria, a platform built around one shared plan for buyer and seller. Today, through Unicrn, he runs sales for early-stage companies and often closes their very first deal. If your enterprise deals drag, your buyers keep saying “this takes a while,” or your executives get contracts with zero context, this conversation shows how to build the close plan with the buyer, in detail, before anyone signs. Connect with Steve Dickerman on LinkedIn. If you’re in Chicago, he’s up for coffee. Key Takeaways When a buyer says “this takes a while,” ask what a while means. The answer is usually a calendar constraint, like no staging environment while students are in session, not the size of the task. In one AI company’s deal data, deals closed 80 days faster on average when the seller aligned with an executive buyer in the first 15 days. Build the plan around earning that hour. Keep functional, commercial and technical reviewers in separate lanes. The person reviewing your security posture doesn’t get a vote on ROI. Write every step. “Review contract” becomes commercial review, then their legal, then redlines back to yours, with a turnaround time for each side. Balance give and get. Ask the buyer for six things in a row and they stop following the plan. This one is for AEs, sales leaders and founders running long enterprise or public-sector deals with big buying committees. Steve’s point about executives signing off with zero context applies to inbound too. Docket’s agent talks to website visitors in real time, qualifies them in the conversation, and books meetings with the full context attached. Visit Docket.io and mention the show for a special rate. TIMESTAMPS 00:00 He planned a 60-day close. It took 18 months. 06:09 “Things just take a while.” So what does a while mean? 10:48 80 days faster: get the exec in the first 15 days 15:03 How to align a buying committee that keeps changing 20:26 Functional, commercial, technical: keep the lanes separate 25:52 Lead with overwhelming detail 30:39 The banned dinner question sellers ask every day 35:26 You lose a deal. The buyer is stuck with the bill. 40:03 The deal that died after one bad quarter 42:38 The Monday move: write your own plan first #RevenueProblemSolversPodcast #EnterpriseSales #SalesLeadership #MutualActionPlans