One, you have to get Zen. You cannot force 9 month sales cycles into 9 days. You cannot force Fortune 500 companies to buy six and seven figure deals in the same way SMBs buy a $10/month product. In the first 2 years, this will create a lot of stress. But later, you won’t care as much. You’ll have enough deals in the pipeline, that they “hatch” in various orders, and you’ll get predictability around it. This is why “pipeline” doesn’t make any sense to start-ups, not really, but makes total sense for BigCo sales executives.
Two, get help that has closed similar sized deals. Great enterprise sales executives and VPs know how to shorten sales cycles to as short as practical. You can’t bring a 9 months deal in, in just 9 weeks or 9 hours. But you probably can shorten it to 6 months, or even 4 months. A great VP of Sales knows that one of the best ways to hit her number is to short sales cycles to the maximum practical. Any more than that, and you take a revenue hit. Crazy discounting and high pressure sales tactics don’t work on long sales cycle deals. They just lead to a smaller deal, no faster.
Junior and inexperienced sales reps can often do OK with small deals, with good guidance and training. But they can’t bring a $750k deal with Aetna in faster.
But a great, experienced VP of Sales can.