University of Chicago
Taught by: Craig Wortmann

Though marketing courses are legion in business schools, sales classes are hen's-teeth rare. That's one reason Craig Wortmann's class feels so refreshing.

The other reason is that Wortmann, a clinical associate professor and former CEO of two software companies, customizes material for the kind of scared and starving entrepreneur he once was. Students learn skills specific to small-business sales—for example, how to narrowly target customers ("If you are targeting Fortune 1000 companies, you are targeting no one") and how to reset expectations so customers aren't unrealistic about what you can deliver ("I once brought in a contract from Eli Lilly we couldn't handle, and it nearly killed my company"). There is a lot of role playing, as the students master the arts of walking customers through a sales conversation and overcoming objections.

Students also build tool kits, including a "sales trailer" (a simple, provocative message about the business), a "story matrix" (anecdotes about the company that can be leveraged in a pitch), and a novel forecasting tool that evaluates sales opportunities based on the market and a company's resources.

In the final weeks, teams pitch their companies—some of them real, some made up for the class—to CEOs and VCs recruited by Wortmann. "I ask the executives to beat up the students," he says. "They come up with all kinds of objections, constantly check their iPhones while the team is talking, act impatient and rude."

Wortmann's thick skin, developed over years of selling, helps him through the class's early days, when many students treat it as a necessary evil. "Ninety-nine percent come in saying, 'I don't like this, but I know I have to know it,' " says Wortmann. "At the end, they say, 'This was the most horrifying experience of my M.B.A. and one of the best.' "

Syllabus for Entrepreneurial Selling: