The Winwire Podcast
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.
Welcome to The Winwire
Behind every great founder or executive is a deal that defined them.
Join us on ’The Winwire’ as we uncover the transformative deals that launched careers and companies. Learn from the best in business, and apply their strategies to your own success journey – whether you’re an executive or are just starting your career.
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All Episodes
A single deal can make or break your year. Craig Pratt knows this well and shares his playbook in this episode - sharing how a key loss set the stage for his ascent, and discussing a win that defined his 30+ year career.
John Ersnberger, the Co-Founder of Stella Connect (acq. Medallia, $100M) and now Co-Founder of Jump takes us through his bold journey through many pivots – and the deal that changed Stella forever.
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Discover how 'the one that got away' turned into a career-defining moment for Adam Aarons – multiple times. Adam takes through multiple deals that he rescued from the brink – and how his mentors helped him get there.
What if a deal you close ends up opening doors you'd never expected? This is exactly what happened to John Sapone, our guest in Episode 3 of "The Winwire" and SVP of Sales at Snowflake. Listen as he recounts the deal that brought him into contact with industry titans like David Schneider and Frank Slootman, and set him on his eventual path to ServiceNow & Snowflake amidst significant personal changes at home.
What kind of deal does it take to save your company from near collapse, get your family out of credit debt … and change the face of lifelong learning in global organizations? In this episode of The Winwire, we talk to David Blake, co-founder & CEO of Degreed – about his “miracle” deal, hearing how his vision, conviction, and innovative approach shaped Degreed's unique identity and future.
Join us in our premiere episode as Kevin Haverty, former CRO of ServiceNow, recounts a high-stakes, 48-hour negotiation that cleared ServiceNow's path to IPO. Learn how strategy, quick-thinking, and decisive leadership transformed a million-dollar deal into a defining moment in Haverty's career and ServiceNow's journey.