Ever feel like you're always a step behind in your leadership journey? Discover how belief can be the key to inspiring employees & mastering yourself. In this episode of The Winwire, we're joined by Chet Kapoor, CEO of DataStax and former CEO of Apigee. With a career spanning from NeXT Computer to leading a $625 million sale to Google, Chet brings a wealth of experience in tech leadership and innovation. Chet shares his unique philosophy on leadership, emphasizing the importance of...

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:...

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:...

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...

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...

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...

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...

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...

In Episode 11, we dive into Brian O'Kelley's extraordinary tech journey. From founding AppNexus to leading Scope3, Brian shares insights from pivotal billion-dollar deals that made companies – as CTO of Right Media, and as CEO of AppNexus. He opens up about his relentless drive for innovation and talks about how he was able to build strategic partnerships at the biggest companies in the world – without a product.

In this episode, we delve into the captivating career of Judi Hand. From her early days learning under her mother's entrepreneurial guidance to leading transformational strategies at US West and AT&T, and now at TTEC, Judi's journey is a masterclass in leadership and innovation.  Hear the stories of how she redefined business cultures & incubated new business lines with her unique blend of hands-on leadership and strategic acumen.  This episode is a treasure trove of insights for...

18 months without a sale pushed Richard Rivera to rethink his approach. He shares the stories of two of his gamechanging career deals. In the episode, we talk about Richard's new book, The Champion Sell. He shares how champion relationships, emotional connections, and certainty transformed him into a sales rockstar closing $50M+ deals. 00:00:00 - Introduction 00:04:00 - Richard's Early Struggles at BladeLogic 00:06:20 - Turning his confidence around through stories 00:08:00 - Deal #1: The...

In the early days at Snowflake, Matt Feldman grinded closing $5k deals as the self-proclaimed “$5k King.” Just a few years later, he was promoted to a key leadership role in one of the most elite organizations in software.   Hear Matt recount one unforgettable $75k deal that taught him key lessons about consensus – and not just among execs. He also shares hard-learned lessons on handling rejection, maintaining empathy amidst pressure, and balancing technical excellence with business needs.

Jordan Plater started his career at Qualtrics making $10/hour. Just 7 years later, a chance “casino night” encounter led to him closing the company's largest deal ever - a $30M agreement with AmEx. Hear the play-by-play of how Jordan strategically navigated internal politics and displaced a 10-year incumbent to land this milestone enterprise deal against all odds.

When selling to Fortune 100 companies, a single deal can make or break your year. Craig Pratt knows this well and shares his playbook in this episode. We hear how Craig recovered from an early blowout loss and went on to lead multiple eight-figure sales. Craig also explains his "validate the value" approach to proving ROI with strategic clients, and shares his biggest influences over a 30+ year sales career.

In this episode of The Winwire, we sit down with John Ernsberger, whose audacious journey led him from quitting his finance job to co-founding Stella Connect, a company eventually acquired by Medallia for a cool $100M. John recounts the early struggles, the transformative pivot(s), and the seven-figure customer partnership that set them on the path of success.  Listen in as he shares his deal stories, twists & turns, and learnings from battle scars over the last two decades.

Discover how 'the one that got away' turned into a career-defining moment for Adam Aarons – multiple times. In this episode, Adam takes us behind the scenes of three marquee deals – including one with Solectron that fizzled out – only to catalyze the win of a lifetime. He also talks about the enduring impact of influential mentors – and an unforgettable tale at PTC with Mark Cranney & Jack Lynch. This episode encapsulates the essence of resilience, the art of relationship-building, and...

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. See all episodes at https://thewinwire.com and contact us at...

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 and Bank of America. We hear how his vision, conviction, and innovative approach shaped Degreed's unique identity and future.

In the inaugural episode of "The Winwire", we chat with Kevin Haverty, a key figure in ServiceNow's impressive growth as Chief Revenue Officer. In 2012, Kevin was in his first quarter with ServiceNow on the brink of IPO – and needed to close a million-dollar gap within 48 hours. Join us as we delve into this high-stakes deal negotiation, the strategies employed, and the lessons learned. Kevin's story is a ride that showcases the grit, quick thinking, and leadership required to close...

This is The Winwire, the podcast where industry leaders share the transformative deals that defined their careers. In this "Episode 0" mini-ep, we introduce the podcast and quickly lay out what to expect from the series – including engaging tales, memorable lessons, and the strategies behind some of the biggest deals in the industry. It's not just advice – it's entertainment, insight, and inspiration. Subscribe so you don't miss our debut and future episodes in the coming weeks. Theme Music:...