The Winwire

12: Paul Ohls, CRO of Sprinklr - Golf Course Gaffes & Career-Defining Wins

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.

11: Brian O’Kelley - Forging Billion-Dollar Companies with Unlikely Allies

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.

10: Judi Hand - The Small Business Comeback that Sparked a Career

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

9: Richard Rivera - The Art of Building Champions

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

8: Matt Feldman - How $5K Deals Shaped a Snowflake Leader

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.

7: Jordan Plater - From $10/hr to a $30M Relationship Masterclass

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.

6: Craig Pratt - Turning Early Losses into Career-Defining Wins

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.

5: John Ernsberger - Leaps of Faith, Pivots, and a $100M Payoff

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.