Steve Goldberg is a veteran sales leader who has closed some of the most significant deals in the history of Salesforce and Salesloft - most recently serving as CRO at the latter. Steve takes us behind the scenes of his biggest wins and toughest losses, sharing hard-won lessons on what it takes to succeed in enterprise sales and navigate the Fortune 500. He also opens up about the personal sacrifices he's made along the way and the mentors who have shaped his approach to leadership.

00:00: Introduction to the podcast and guest Steve Goldberg

02:05: Steve's early career, psychology background, and transition to sales

10:01: The shift to cloud computing and Steve's move to Salesforce

13:14: The importance of caring about the customer and the product

14:36: The pivotal moment with Salesforce and Dell

27:07: Steve's personal sacrifices and the impact of big deals on his career

32:28: The emotional and financial stakes of the AT&T deal

37:55: The balance between personal sacrifice and career success

39:26: The emotional rollercoaster of closing big deals

40:31: Common reasons deals fall through and how to navigate them

43:48: The importance of relationships and finding a path to success

46:52: Setbacks in Steve's career

49:19: The importance of running towards something, not away

50:18: Career mistakes and the value of learning from them

56:22: The longevity of a career and finding enjoyment in the work

57:44: Specific lessons from mentors and their influence

01:00:56: Establishing a love for the process and longevity in a career

01:03:12: Balancing work with personal life and having an outlet