True Confessions of a Sales Leader

In this episode of "True Confessions of a Sales Leader," we sit down with Ryan George, the visionary founder and CEO of Simpleview, who shares his remarkable journey of building a company that has revolutionized the destination marketing industry. From navigating the challenges of the 9/11 attacks and the 2008-2009 financial crisis to adapting to the COVID-19 pandemic and the shift to remote work, Ryan's story is one...

In this episode of True Confessions of a Sales Leader, host Scott Olsen sits down with Tom O'Keefe, a seasoned executive who shares his captivating journey from sales leader to CEO. Tom emphasizes the importance of embracing curiosity and adaptability in achieving success and offers valuable insights on continuous learning, surrounding yourself with talented people, staying adaptive to technology, and finding the right fit as ...

This episode of "True Confessions of a Sales Leader" features Joe Belenardo, CRO of Anthology, sharing invaluable insights from his extensive career in sales leadership. Drawing from over three decades of experience, Joe delves into the principles of servant leadership, trust, empowerment, and the significance of personal growth for building high-performing teams. His journey from the early days at IBM to leading sales at...

In this episode of “True Confessions of a Sales Leader,” we explore how to create a successful sales team and scale it to grow and perform within the company. 

We’re excited with this episode’s guest, Henry Schuck co-founder, CEO, and Chairman of the Board of ZoomInfo. Henry joins Scott Olsen, founder of the Olsen Group, and Gary Brashear, managing partner of the Olsen Group. 

If you don’t know the story behind Zo...

In our first episode of the new season, we tackle a growing problem not only facing sales organizations but entire companies—keeping your team intact.

Our guest is Scott Campbell, Senior VP at Sales at Docker, who has been responsible for ramping up a new sales team in 2021. Scott joins (our own) Scott Olsen, founder of the Olsen Group, and Gary Brashear, managing partner of the Olsen Group. 

You’ve read the headlines about the mass ...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our seventh segment focuses on how buyers are going through a period of change, and sales people need to adapt to this change. Now more then ever, circumstances are ofte...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our sixth segment focuses on the power of listening in the sales process. The best sales people talk less, and spend time trying to understand the customer's proble...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our fifth segment focuses on what it means to sell "value". Selling isn't about pitching products, it's about you and the customer finding a shared v...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our fourth segment focuses on why focusing on your salesperson's strengths are the perfect gateway to  coaching their deficiencies. By providing compliments and ack...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our third segment focuses on why you should be careful when providing negative feedback or direct coaching tips to your sales team. Naturally it seems to make sense to j...

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our second segment focuses on why you shouldn't be vague when you coach your sales team. Instead of using generic statements like "you should be selling value....

Welcome to our new segment, Sales Leader Q&A with Dr. Ruff. 

These are short, 5 to 10 minutes segments with our sales coaching expert, Dr. Richard Ruff, where we provide quick and actionable tips that you can take and implement with your sales team right away.

Our first segment focuses on why you shouldn't be comparing your sales team members when coaching your team, but instead, focus on always coaching ...

In this episode of “True Confessions of a Sales Leader,” we look at how being vulnerable and building self-awareness can make better sales leaders and ultimately sales teams with our guest, Mike Porter, chief sales officer at NAVEX Global. 

Here are four key takeaways:

1. Bring your experience as a salesperson 

Many great sales leaders were also great salespeople but all not great salespeople  make great sales leaders. When they move ...

We’re excited to welcome back to “True Confessions of a Sales Leader,” Dr. Richard Ruff and John Hoskins, respected experts in sales coaching, founders of The Level Five Selling Coaching System, and authors of a new book, “Level Five Sales Leader: Field-Tested Strategies to Close the Quota Gap! (The Level Five Selling Trilogy”).

They join Scott Olsen, founder of The Olsen Group, and Gary Brashear, managing partner of the O...

We don’t have to tell you the challenges of managing a sales team during a pandemic. An even bigger challenge is bringing on new sales reps to your team without a physical location. How do you assimilate them into your unique culture? How do you train them? Keep them engaged? 

Listen in as our guest, Tom Whalen, director of inside sales at McKesson, provides a first-hand experience of how his team is accomplishing this. Tom joins Sc...

Organizational changes are hard enough. Add Covid, a dispersed staff, then figuring out how to get everyone on the same page— and keep them there. And if you’re a sales organization, how can you do this seamlessly without client disruption? 

In this episode of “True Confessions of a Sales Leader,” we explore how organizations can successfully pivot to change their own culture but also meet client demands and expectations. ...

Part 2 of our dual episode of “True Confessions of a Sales Leader” continues with a discussion with Dr. Richard “Dick” Ruff and John Hoskins, respected experts in sales coaching, founders of The Level Five Selling Coaching System, and authors of the book,  Level Five Selling: The Anatomy Of A Quality Sales Call Revealed. 

In this episode, we’ll share insights and some real-world tactics on how you can get started on a sales coaching...