Shellye Archambeau, one of Silicon Valley's first female African American CEOs, shares her journey from a challenging childhood to tech industry trailblazer. In our conversation, she reveals the power of intentional risk-taking, reframing adversity, and strengthening your strengths to achieve unprecedented success. Archambeau offers contrarian career advice, including why everyone should do a stint in sales, and how to navigate uncertainty in today's business landscape.

00:00:00: Introduction and Shellye's Perspective on Risk

00:00:39: Welcome and Shellye's Background

00:02:18: Shellye's Childhood and Early Influences

00:04:22: High School and Setting the CEO Goal

00:06:38: Handling Emotional Responses and Reframing

00:09:34: The Importance of Saying Yes to Yourself

00:12:11: Learning from Mistakes and Business Failures

00:14:27: Trade-offs and Sacrifices in Career

00:17:45: Embracing Discomfort and Growth

00:19:42: The Value of Sales Experience

00:21:18: Memorable Customer Interactions

00:24:21: Taking Risks at IBM

00:27:23: Risk and Reward in Business

00:29:46: Building a Great Career in Uncertain Times

00:31:14: Evaluating Career Moves

00:33:04: Challenging Conventional Wisdom

00:35:21: Feedback and Controversy on Ambition

00:37:42: Mentors and Their Impact

00:41:10: Closing Remarks and Book Recommendation

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

Eric Stine is the CEO of Elemica. Eric shares his transformative journey from aspiring politician to tech industry leader. We talk about a pivotal career moment at SAP reshaped his approach to sales and customer engagement, leading to a groundbreaking deal that redefined industry standards. Eric also reveals his philosophy of "aggressive humility", the power of admitting "I don't know" as a pathway to success, and the routines and tactics that have been key to his growth.

00:00:00 - From Law to Tech: Eric Stine's Unexpected Path 00:08:08 - The Art of Customer Preparation & Eric’s Core Values 00:13:53 - Navigating Career Transitions 00:15:05 - The Inflection Point: Eric’s Pivotal Career Deal 00:33:00 - Adding Humility to His Core Values 00:36:16 - How Eric deciphers and actions on feedback 00:40:51 - Learning from Mistakes and Missed Opportunities 00:42:15 - The Power of Reflection in Leadership 00:42:29 - The Importance of Considering Others' Perspectives 00:45:35 - How Running has impacted Eric’s Clarity and Decision-Making 00:50:02 - An unexpected lesson on friendship and coming out