True Confessions of a Sales Leader

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 a leader. Listeners will gain inspiration and discover practical takeaways to apply to their own careers in sales and beyond.

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 Anthology highlights the importance of adaptability and building strong relationships within teams and with clients. Joe's real-world examples and strategies offer a roadmap for sales leaders looking to navigate the complexities of modern sales environments and drive their teams to success.

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 ZoomInfo, it’s a great success story. Henry co-founded the company (formerly DiscoverOrg) in 2007 in his law school dorm and has been growing the successful company ever since. Last summer, ZoomInfo became a Nasdaq-listed company and is one of the dominant players in the sales enablement technology space.Listen in to find out how Henry got on the path to build his sales teams and how he continues to do so today. 

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 exodus of employees or perhaps you’re struggling to keep or attract a talented sales team. Hired just over a year ago, Scott has been responsible for building a new sales team —90% of the team are new hires. So, how do you attract new talent like this? Listen in as we discuss what Scott has accomplished and how to implement your own changes to recruit sales rock stars. 

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 from an individual contributing role to a leading role, many leaders tend to go back to what made them successful, like being a solid dealmaker. Bring your skills, of course, but also tune into what your team brings and how to get the most out of them from your background. Coach them on confidence, on closing a deal, or even prospecting. All things you excelled at. 2. Use self-awareness to grow You may think (and rightfully so!) you’ve built a solid team, have motivated them, helped them understand cross-group coordination. However, one day, feedback, whether it’s negative or positive, from a team member might prove otherwise. It’s important to keep having those ah-ha moments. For example, maybe you’re intense, focused on the numbers. Add some levity and make sure you come across as approachable. Self-awareness exists in every single one of us and forces us to look at our own challenges but also teaches how to improve ourselves. 3. You can’t avoid the (in)famous flight riskYou’re an amazing sales coach. You’ve built a great team but now some of them have defected to the competition or a better role elsewhere. Coaching people because they need it or because they have career aspirations, then building their skills, and then having them leave can happen. It’s hard to lose a top performer to that next step in their career. The benefit? Most of your team wants to stay because you’ve built credibility and you’re helping them grow. That matters, too. 4. Develop an 80/20 document This is a great tool and can be as simple as a one-pager. Communicate 80% of the document on how you work with a sales team, what excites you, things you’re passionate about, your strengths, or even what triggers you. The other 20%? There will be time to work that out, time spent working together will reveal that. Don’t make your team members guess how to work with you. Have new team members do their own 80/20 document, too. It helps provide self awareness and a way to teach new team members how to treat you—and vice versa.

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 Olsen Group, to discuss not only their new book but just how sales coaching is an art, and how critical it is for successful sales leaders to be great sales coaches. 

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 Scott Olsen, founder of the Olsen Group and Gary Brashear, managing partner of the Olsen Group. Listen in!

In this episode of “True Confessions of a Sales Leader,” we explore the steps of creating a successful strategic partnership. Our guest is Geoff Curless, Chief Revenue Officer at Rehearsal, he helps walk us through what those steps might look like.  Join  us as we discuss how we successfully partnered with Rehearsal and what steps you can take to be successful in your own partnerships. 

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. Our guest is Blackboard vice president Dave McLaren. Dave joins Scott Olsen, founder of the Olsen Group, and Gary Brashear, managing partner of the Olsen Group. 

In this episode, we are joined by Jim Benton, CEO of Chorus, a Conversation Intelligence platform. Listen in as we discuss how Chorus and artificial Intelligence (AI) technology are helping capture and record sales conversations, make real connections, and allow sales leaders to train like never before. 

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 plan for your organization immediately. 

Welcome to part one of our special two-part episode of “True Confessions of a Sales Leader.” We are honored to have on two guests: 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.  Listen in as this virtual table of sales experts discuss why sales coaching is so important to an organization, especially in these times. In this first part of our two part discussion we will discuss:What is sales coaching?Settng milestones for coaching Coaching in a virtual environmentDeciding if your orginization needs coaching

In this episode of “True Confessions of a Sales Leader” we discuss ways sales leaders can transform their inside sales organizations. Picture this: You’re new to a sales organization and have been hired to transform it. The reasons for this needed transformation can be many, one of the most common being that the market has changed, forcing the business strategy to also change. How do you start organizing your new team to meet this transformation? John Belle, global head of inside sales at PayPal joins Scott Olsen, founder of the Olsen Group and Gary Brashear, managing partner of the Olsen Group, as they discuss the path to take.  

Have you ever had a sales mentor? Have you ever been a sales mentor? Looking for ways to integrate a mentorship program into your own sales organization but don't know how to start? In this episode of “True Confessions of a Sales Leader” we discuss the power of mentorship in sales orgs and teams and how successful companies can use mentorship to ramp up sales, build confidence, and create success. 

Managing a sales team during the pandemic? You’ll want to listen to our new episode of “True Confessions of a Sales Leader,” The Olsen Group’s podcast where sales leaders share their secrets of success, insight, and guidance.For this crucial episode, we interviewed our own Gary Brashear, Managing Partner, The Olsen Group, and Matt Greene, head of sales for Fetch (https://www.fetchpackage.com/), a company that offers direct-to-door package delivery for apartment and multi-family buildings. Gary and Matt share how they are coping with the disruption, how they are motivating their sales team, and what they see on the horizon. 

Let’s say you’ve hired a new sales team leader. They bring the chops, the energy, and the enthusiasm. But, what if they don’t have the experience your organization needs?  They might be new to your organization, maybe they’ve recently been promoted or have moved over into that role from another one. Our three experts— Scott Olsen, founder of the Olsen Group, Gary Brashear of the Olsen Group, and Tony Esposito, a chief revenue officer and VP of sales—offer crucial advice on how to coach, make the right decisions, and ensure your new sales manager is embedded into your organizations’ DNA. 

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 often out of a salesperson's control that cause a deal not to close. But sometimes having inaction during these times is the cause, and should be remedied by having a explicit conversation with the client on customer at the right time, before it's too late.

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 problems and issues first. It's important that sales people and the customer have the same vision of the problem before jumping in with any type of dialogue about a solution.

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 vision for what the value of the product is for the customer. In this segment, Dr. Ruff discusses two ways that help you and your customer find this shared vision.

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 acknowledging the persons strengths, it makes critical remarks palatable, and more importantly increases the chances that the coaching direction is actually heard and implemented by your salespeople.