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 "moving the human heart" and believing in ideas earlier than anyone else. He discusses how this approach has shaped his career and led to significant wins, including a pivotal $10 million deal with AT&T. We also dive into Chet's strategies for balancing optimism with realism, managing self-doubt, and the art of presenting half-baked ideas. Plus, learn about his personal habits for effective self-leadership and decision-making. Ready to transform your leadership style and become a true visionary? Listen now and discover how to believe early, inspire deeply, and execute flawlessly in your business endeavors.   Follow Michael Katz on LinkedIn: https://www.linkedin.com/in/michaelnkatz/ Follow Chet Kapoor on LinkedIn: https://www.linkedin.com/in/chetkapoor/   Check out Flowsend.ai for growth-optimized timestamps, descriptions, and more.

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.

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 anyone looking to navigate the corporate world with resilience and creativity. 00:00:00: Introduction and Guest Background 00:01:48: Judi's Transformative Strategy Win at US West  00:09:31: How she droves bottoms-up change 00:13:00: Pivotal Deal Win: Incubating a New Business at TTEC 00:18:14: Origination vs. The Engine  00:22:42: The Power of Storytelling 00:26:04: Why TTEC’s Mission Motivates Her  00:28:23: Judi’s Mentors and Inspiration

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 deal that turned it around (the Aha deal) 00:18:20 - Building champions at Dell 00:23:00 - The big negotiation & close 00:29:30 - Gaining Certainty Through Visualization 00:34:30 - Deal #2: AT&T - The record setting $50M deal 00:42:26 - Last Minute Deal Drama 00:45:00 - Game theory in Sales 00:50:50 - Why people should care about The Champion Sell 00:57:35 - Richard's mentors and what they taught him

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 the transformative power of mentorship amidst adversity.

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 winwirepodcast@gmail.com

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 transformative deals. Tune in for an inside look at the deal that catapulted Kevin & ServiceNow into the top rungs of leadership. More episodes in your podcast player and at thewinwire.com.   Contact us at - Email: winwirepodcast@gmail.com Twitter: @MiguelKatz or @KawinHQ LinkedIn: https://www.linkedin.com/in/michaelnkatz/