A Look Over the Leadership Fence

Discovering the Discovery

Welcome to today’s episode! We’ve got something special lined up—a real-world look at what makes a discovery call successful. Joining us is Craig Witmer, CTO of Kern Medical, who steps in to simulate a live discovery meeting and share the do’s and don’ts every Account Executive should know. To make it even more engaging, Miles Lowry, Senior Cybersecurity Consultant and long-time colleague of Anthony, plays the role of the Account Executive in this role-play. Craig even shares one of his worst sales call experiences—a true horror story you’ll want to hear. After the role-play, we break it all down and get candid insights straight from the decision-makers Account Executives are trying to win over. This episode is packed with practical tips, real-world perspective, and stories you won’t forget. Let’s dive in!

Teamwork makes the Dream Work

It’s a dynamic day of conversation—touching on Jay-Z, healthcare, and the art of building relationships that lead to trust. Ryan Sheldon, former SE partner to Anthony Schubert, joins the discussion to share stories from their time together at Nutanix and Rubrik. Their experiences naturally steer the conversation toward the importance of building a reliable internal team—people you connect with early, invest in deeply, and trust to perform with excellence. When challenges arise, it’s those relationships that make the difference. You want a crew that not only knows their role but is ready to grab an extra oar when the waters get rough. Leadership often coins the phrase “never lose alone,” but Ryan and Anthony explore how that idea was put into practice—and how it led to real success.

A Look Over the Leadership Fence

Today’s episode is a special one. I’m joined by Jason Heinrich, VP of Enterprise Sales at Infoblox — a former boss, mentor, and someone I deeply respect as a leader. We dive into what it means to approach enterprise sales from both the first-line and second-line leadership perspectives. This conversation is all about helping sellers better understand how to position themselves within their sales organizations while staying true to the fundamentals that drive long-term success. Jason shares what he considers “good” in modern sales, how he guides sellers through today’s complex selling landscape, and his philosophy on balancing the needs of the business with the growth of the individual. It’s insightful, practical, and packed with wisdom from someone who’s been in the trenches. Come on in!

Building Rapport in a Remote World

On today's episode, Anthony welcomes in long-time friend and former colleague, Patrick Phillips, to discuss how the post-pandemic shift to work from home has impacted the ability to create relationships that have the same staying power as when we in person. We'll discuss what changed when we moved to remote work, the continued importance of creating personal connections and how we can find new ways to develop deep bonds with our clients in this new landscape. We will highlight the current challenges and explore some suggestions on how to overcome them in this brand new world. So grab a cup and listen in!

Embracing the Friction

In today’s episode, we’re joined by a good friend and former colleague, Prem Neelay. Prem currently serves as a Majors Account Manager at Palo Alto Networks, bringing with him a wealth of experience from previous roles at Nutanix and on the customer side at TiVo. Beyond his day-to-day responsibilities, Prem is deeply committed to mentoring new sellers at Palo Alto, helping them navigate the complex world of IT sales and avoid common pitfalls along the way. Our conversation today centers around a powerful idea: friction in sales isn’t something to fear—it’s something to embrace. Friction signals the start of a real opportunity. When sellers lean into it rather than shy away, they build trust, unlock larger deals, and forge long-term customer relationships.