13: Stevie Case - Press Start to Sell: From Gaming Glory to Revenue Leadership

The Winwire

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