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

Vihan Sharma is the Chief Revenue Officer of Liveramp. We delve into the high-stakes deal with Carrefour that cemented his reputation in ad tech & retail, establishing him as a daring leader while drawing on his product roots. We also talk about his unique cultural agility, "humble" leadership style, and the meeting that changed his approach to product leadership and sales.

10:15 Major deal at Carrefour

16:51 Navigating challenges, Liveramp secures Carrefour partnership.

18:42 Convincing internal team to build industry-first capability.

23:47 Developed clean room product, established retail media.

33:44 Warren helped Noel see the urgency. Executives convinced of the project's importance.

35:16 Scaling challenges in developing customer-centric capability.

41:57 Carrefour deal led to US market expansion.

51:19 Navigating cultural nuances in multinational organizations crucial.

55:58 Balancing career and family through joint decisions.

01:01:51 Important CFO challenges status quo, aids decision-making.

Michelle Zatlyn is the Co-Founder, President, and COO of Cloudflare. We cover some lesser known early stories of Cloudflare (including picking up unused servers) and the uncommon practices & principles that built a billion-dollar cybersecurity legacy. Michelle also challenges conventional narratives around work-life choice in tech, offering a candid take on building a generational company while fostering a big life outside the office.

Join us on Episode 14 of The Winwire for an engaging dive into the journey of Alex Varel, where determination and achievement go hand in hand. Alex's path from small beginnings, selling used Nintendo games in school, to securing major deals in Spanish broadcast television, demonstrates a remarkable blend of creativity and business acumen.

In this episode, Alex recounts his journey, marked by innovative strategies that scored him his first major role, through the challenges of high-stakes media sales, to his current role in shaping the future of talent development at Multiverse. He shares the crucial moments and lessons that have shaped his career, offering valuable insights into navigating the complexities of professional growth and business success.

This episode is a deep dive into the themes of perseverance, strategic leadership, and resilience. Listen as Alex Varel provides a candid look at his impressive career, offering both inspiration and pragmatic tips for those aiming to leave their own legacy. Expect a session rich with practical wisdom, entrepreneurial insights, and forward-thinking ideas.

00:00 - Intro

02:50 - Alex's Entrepreneurial Spirit: From School Hallways to Radio Sales

09:00 - Breaking Into Spanish Broadcast Television

11:00 - The Seven-Figure Airline Deal: A Career Milestone

20:00 - Transitioning to Digital and Venture-Backed Companies

22:05 - The Game-Changing MongoDB Deal

32:00 - Leadership Insights: Empathy and Adaptability

35:00 - The Importance of Recruiting, Understanding, and Developing Talent

37:00 - Five Pillars of Focus in Sales Mastery

41:00 - Empathy, Modern Challenges, Adaptability, and Resilience

50:15 - The Move to Multiverse: Addressing Talent Supply Chain Challenges

55:20 - Learning from His Biggest Mentors: Embracing Feedback and Growth

Stevie, now the CRO at Vanta, was once known for her groundbreaking achievement as the top global player in the game Quake. In this episode, she shares her remarkable transition from dropping out of college to climbing the sales ladder at powerhouse companies like Twilio and Visa.

Discover how Stevie's unique start in the gaming world shaped her innovative approach as a female leader and single mom. We explore her seminal deal at Twilio, revealing how she turned a minor opportunity into one of the company's biggest wins through relentless pursuit and strategic thinking.

Uncover the art of leveraging product-led growth in sales, the importance of building genuine relationships, and the skill of turning technical complexity into lucrative deals. Stevie's story is a testament to defying odds, embracing challenges, and finding joy in the continuous game of business and life.

This episode is not just about sales tactics; it's about a life lived with passion and determination.

00:00:00 - Introduction: Meet Stevie Case

00:01:00 - From Gamer to Sales Pro: Stevie's Unconventional Career Path

00:05:05 - Starting Out at Twilio: Taking on Enterprise from a PLG Base

00:08:10 - Cracking the USAA Account: Getting a Foot in the Door

00:11:50 - Turning $500 into $100K: Leveraging Successful Use Cases

00:18:55 - Bringing the C-Suite Along: Getting Executive Buy-In

00:23:25 - Securing That First Formal Deal: Establishing Vendor Credibility

00:26:20 - Going from 5X to 6X: Expanding Deals within the Account

00:30:05 - Pricing Misstep to Key Insight: Extracting the Real Budget

00:37:40 - Feedback Can Be Brutal But Essential: Embracing Tough Coaching

00:44:30 - Passion Fuels Persistence: The Importance of Loving Your Work

In this episode, Paul Ohls, the Chief Revenue Officer of Sprinklr, recounts an entertaining story involving a multi-million dollar sale, golf etiquette, and how his aloof Texan persona nearly cost him a career-defining deal while in Australia.

He also debunks common myths surrounding the use of champions in strategic deals – elucidating how skilled sales teams mitigate risk, empower champions, and leverage business problems to punch far above their weight.

As with most successes, Paul's was no overnight affair. In this episode, he imparts wisdom on assessing job prospects, excelling at strategic deal-making, and gleaning insights from key mentors.