The Winwire Podcast

ex-CRO, Salesloft
18: Steve Goldberg - From Salesforce to Salesloft: Lessons from a Career of Closing Transformative Deals

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

Chief Revenue Officer
December 14, 2023
12: Paul Ohls, CRO of Sprinklr - Golf Course Gaffes & Career-Defining Wins

Join us as Paul Ohls shares tales of big time golf mishaps, major deals, and building champions in sales. Discover how quick thinking and resilience can turn blunders into business victories.

CEO & Co-Founder
November 30, 2023
11: Brian O'Kelley - Forging Billion-Dollar Companies with Unlikely Allies

Brian O'Kelley shares his journey from building to Right Media to founding AppNexus to leading today at Scope3 – revealing key deals that sparked 9 and 10 figure exits with tech behemoths.

Chief Revenue Officer
November 16, 2023
10: Judi Hand - The Small Business Comeback that Sparked a Career

Explore Judi Hand's journey from a budding entrepreneur's daughter to a corporate trailblazer at TTEC. Hear stories about her transformative leadership, strategic insights, and the power of mentorship in reshaping businesses.

Experienced CRO & Author of "The Champion Sell"
November 2, 2023
9: Richard Rivera - The Art of Building Champions

With 18 months and no sales, Richard Rivera had to rethink his approach. He shares the stories behind two gamechanging career deals that cemented him as a sales rockstar closing $50M+ contracts. We discuss his book "The Champion Sell" and how champion relationships, emotional connections, and certainty fueled his success.

VP of Sales - Tech, Media, and Telco
October 5, 2023
8: Matt Feldman - How $5K Deals Shaped a Snowflake Leader

Hear Snowflake sales VP Matt Feldman recount his rise from $5k deal “king” to leader, and tune in for the memorable deal that sticks in his mind until this day. Matt also shares lessons on resilience, empathy amidst pressure, and blending technical excellence with business alignment.

Head of Sales, Emerging Markets
September 20, 2023
7: Jordan Plater - From $10/hr to a $30M Relationship Masterclass

Jordan started at Qualtrics making just $10/hr. 7 years later, a chance casino night encounter sparks a $30M deal with AmEx - Qualtrics' largest ever. Hear how Jordan outmaneuvered a 10-year incumbent through hustle and strategic networking to pull off this career-defining enterprise sale.