he joked, “isn’t magically going to become disciplined because Salesforce now contains AI.” For Weening, the process comes


first, then technology, and finally behavior change. That sequence sounds remarkably familiar because it is. We’ve all seen technology waves come and go. CRM didn’t eliminate bad sales management. Marketing automation didn’t eliminate bad marketing. AI won’t eliminate bad processes. It may simply allow bad processes to run faster.


THE SALES ARMY Perhaps most surprising for the CEO of an AI-native technology company, Weening remains an unapologetic believer in human salespeople, re- jecting the idea that AI will eliminate complex B2B selling. Instead it will change selling. It will accelerate research. It will reshape discovery. It will help sellers identify changes inside accounts. It will automate administrative work. But when purchases are complex,


are consequential, and unfold over 12 to 36 months, people still need help navigating decisions. That’s why Weening continues to draw on Neil Rackham’s work on complex sales and the buying cycle. In simpler transac- tions, automation will devour activity. In complex transactions, AI will aug- ment judgment. That’s a very different future from the fashionable prediction of autonomous agents selling to au- tonomous agents while humans watch from the sidelines. Weening’s bet is more human. Remove the paperwork. Increase the intelligence. Give the salesperson better information. Then let the hu- man do what humans do best: Under- stand another human being making an important decision.


FIVE NOS TO A YES Near the end of our conversation, Weening returned to his first men- tor, Paul Shearstone, who taught the young salesperson a simple rule: “It


takes five nos to make a yes.” A lifetime later, you can still hear


that lesson underneath Weening’s leadership philosophy. Persistence became grit. Grit became trans- formation. Transformation became leadership. And leadership is gradually becoming mentorship. That may ultimately be the most interesting chapter of Michael Weening’s story.


Not simply salesperson to CEO but rather warrior to teacher. The


young man who once stood in front of a customer’s car door until he got the order now spends much of his time trying to remove obstacles for other people. That’s what maturation looks like when ambition evolves into leadership rather than disappears. And perhaps that’s the real differ- ence between achieving success and becoming a successful leader. One is about what you can win. The other is about how many people can win because you were there. 


Just a Few of Many CEOs Whose Careers Began in Sales


• Howard Schultz (Starbucks): Started his career as a sales rep- resentative for Xerox selling word processors before joining and leading Starbucks as CEO.


• Alex Gorsky (Johnson & Johnson): Began as a sales representa- tive for Janssen Pharmaceutica (a J&J subsidiary) in 1988 before ris- ing through the ranks to become CEO and chairman in 2012.


• Anne Mulcahy (Xerox): Joined Xerox as a field sales representative in 1976 and eventually climbed to become the company’s CEO.


• Mark Hurd (HP and Oracle): Started his career in entry-level sales at NCR Corporation, ultimately rising to become CEO of National Cash Register Company (NCR), Hewlett-Packard, and co-CEO of Oracle.


• Warren Buffett sold securities at Buffett-Falk & Company for three years in the 1950s.


• Thomas Watson Sr. joined NCR as a salesman in 1895, excelled at selling cash registers, and eventually climbed to become the general sales manager before leaving for IBM where he became the CEO.


• Mark Cuban started by selling software, which led to founding a company called MicroSolutions, grew it to $30 million, and sold it to CompuServe.


• Bill McDermott started an entry-level sales position selling copi- ers and office equipment. He eventually held major executive sales roles, including executive vice president of Worldwide Sales and Operations at Siebel Systems, before leading companies like SAP and ServiceNow as CEO.


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