<![CDATA[THE OLSEN GROUP - Blog]]>Sun, 30 Nov 2025 18:59:49 -0800Weebly<![CDATA[Unlocking B2B Sales Success]]>Mon, 15 Jul 2024 07:00:00 GMThttps://www.olsengroup.net/blog/unlocking-b2b-sales-successPicture
In the latest episode of "True Confessions of a Sales Leader," I had the privilege of hosting two distinguished guests from IntroHive, a leading company in the customer intelligence space. Lee Blakemore, CEO, and Justin Picciano, Vice President of Sales and Customer Success, shared their valuable insights and experiences navigating the complex world of B2B sales.
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Our conversation delved into several critical aspects of sales leadership, starting with the importance of consistently hitting sales forecasts. Lee's perspective on this topic was particularly enlightening, emphasizing how forecast accuracy not only demonstrates a deep understanding of the business and market but also builds trust within the organization and the board of directors. This is a challenge that many sales leaders have grappled with, and Lee's insights offered a fresh and practical approach.
Another standout moment from the discussion was the concept of sales teams as "market scouts." Justin and Lee elaborated on the strategic role that sales teams can play in gathering market intelligence and driving innovation. This idea resonated strongly with me, as it highlights the untapped potential of sales teams to shape product development and drive organizational success.

The conversation also touched on the perennial challenge of gaining access to decision-makers in today's B2B landscape. Lee and Justin's thoughts on the matter, particularly their emphasis on the power of relationships and the need to balance data-driven insights with human intuition, provided a valuable framework for addressing this issue.
Throughout the episode, I was impressed by the depth and practicality of Lee and Justin's insights. They tackled complex topics with clarity and offered actionable advice that sales leaders can implement in their own organizations. Their willingness to share their own challenges and lessons learned added an extra layer of authenticity and value to the conversation.

Key takeaways from this episode:
  • Consistently hitting sales forecasts is crucial for building trust and demonstrating a deep understanding of the business and market.
  • Sales teams have significant potential as "market scouts," and empowering them to take on this strategic role can drive innovation and organizational success.
  • Building strong relationships is essential for gaining access to decision-makers in the B2B landscape, alongside leveraging data and technology.
  • Effective collaboration across functions is vital for sales success, and proactively addressing cross-functional challenges can drive better outcomes.

The most successful sales leaders are able to balance data-driven insights with human intuition, leveraging both to make informed decisions.

I highly recommend this episode to any sales leader looking for practical insights and fresh perspectives on the challenges and opportunities in B2B sales. Lee and Justin's expertise and candor make for a truly valuable and engaging listen.

You can find this episode and all our previous conversations on Spotify and Apple Podcast. If you found this discussion informative and valuable, please consider leaving a review and sharing your thoughts. Your feedback helps us continue to improve and bring you the best content possible.

Thank you for tuning in, and I look forward to sharing more insightful conversations with you in the future.
]]><![CDATA[Lessons in Adaptability and Success]]>Sun, 09 Jun 2024 07:00:00 GMThttps://www.olsengroup.net/blog/lessons-in-adaptability-and-successPicture
​In this compelling episode of "True Confessions of a Sales Leader," we gain valuable insights from Ryan George, the founder and CEO of Simpleview, a company that has transformed the destination marketing industry with its innovative CRM, CMS, website design, and digital marketing solutions. Throughout the conversation, Ryan shares his wealth of experience and lessons learned on adaptability and success during his entrepreneurial journey.

Ryan discusses the importance of building a team with complementary skill sets, maintaining open communication, and fostering trust among partners and employees. He also highlights the significance of staying focused and strategic as the company grows, while being prepared to pivot and adjust strategies in the face of market challenges and industry shifts.

One of the most impressive aspects of Simpleview's success is their 99% customer retention rate, which Ryan attributes to their commitment to customer happiness and success. He shares how they maintain a consistent employee-to-customer ratio, surround accounts with subject matter experts, and separate the roles of account management and sales to ensure customers receive the dedicated support they need.
As the world becomes increasingly data-driven, Ryan emphasizes the importance of developing a data mindset within the organization. He encourages leaders to invest in training and education to empower their teams to leverage data for better decision-making. Additionally, he stresses the need to stay open to technological advancements, such as AI, and integrate them into products and processes to remain competitive.
Ryan also touches on the significance of adapting to the needs and preferences of different generations, particularly in light of the shift towards remote work. He advises leaders to embrace flexibility and find ways to maintain strong connections among team members to successfully navigate the challenges posed by the changing workforce dynamics.

Three key takeaways for sales leaders:
  1. Foster a culture of adaptability: Be prepared to pivot and adjust strategies in the face of market challenges and industry shifts.
  2. Embrace a data mindset: Encourage your team to stay curious, develop a data-driven approach, and leverage technological advancements to make informed decisions.
  3. Cultivate collaboration and balance: Promote collaboration and balance among various departments, align incentives and metrics, and encourage open communication to create a harmonious and productive work environment.

Ryan's journey serves as an inspiration for sales leaders looking to build resilient, adaptable organizations that can thrive in the face of change. By fostering a culture of adaptability, embracing a data mindset, and cultivating collaboration and balance, sales teams can navigate the ever-evolving business landscape and achieve long-term success.
Be sure to listen to the full episode to gain more valuable insights from Ryan's inspiring journey. And don't forget to subscribe to "True Confessions of a Sales Leader" on Spotify or Apple Podcast for more thought-provoking conversations with sales leaders from across the industry.
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P.S. In the episode, Ryan mentions an insightful book on organizational tension and design that has influenced his approach to aligning sales, marketing, and other departments. The book he was referring to is "Designing Organizations to Create Value: From Strategy to Structure" by Jim Brickley, Clifford Smith, Jerry Zimmerman, and Janice Willett.
This book explores the critical link between an organization's strategy and its design, providing valuable insights on how to structure a company to minimize conflicts and maximize value creation. While the book is currently out of print and may be difficult to find, it's worth seeking out at used bookstores or your local library. You can also check online marketplaces like Amazon, where a few copies may be available: https://www.amazon.com/Designing-Organizations-Create-Value-Structure/dp/0071393927
If you manage to get your hands on a copy, you'll likely find the book's lessons on organizational design and alignment valuable as you navigate the challenges of building and scaling your own organization.
]]><![CDATA[Embracing Curiosity and Adaptability: Going from Sales Leader to CEO]]>Wed, 24 Apr 2024 07:00:00 GMThttps://www.olsengroup.net/blog/embracing-curiosity-and-adaptability-going-from-sales-leader-to-ceoPictureTom O'Keefe and Scott Olsen
In this inspiring episode of "True Confessions of a Sales Leader," we explore the captivating journey of Thomas O'Keefe, a seasoned executive who has successfully navigated the path from sales to the C-suite. Tom shares invaluable insights and experiences, emphasizing the importance of curiosity and adaptability in achieving success as a sales leader.

Throughout the conversation, Tom highlights the power of continuous learning and growth. He stresses the significance of stepping outside one's comfort zone and taking on new challenges, even if it means facing rejection or failure. As he recounts his early days in sales at ADP, Tom shares how his persistence and willingness to learn from his mistakes laid the foundation for his future success.
Listen in to discover the four key takeaways from Tom's journey:

  1. Embrace Continuous Learning and Growth
  2. Surround Yourself with Talented People
  3. Stay Curious and Adaptable in the Face of Technology
  4. Focus on Finding the Right Fit as a Leader

One of the most valuable pieces of advice Tom shares is the importance of gaining board experience, especially for those aspiring to become CEOs. He recommends volunteering for non-profit organizations and joining their boards to understand governance structures and gain exposure to leadership roles. Tom emphasizes that this experience can provide invaluable insights into how leaders operate in different domains and help individuals develop the skills necessary to succeed as a CEO.

As the conversation delves into the role of technology in sales, Tom showcases his passion for leveraging cutting-edge tools to drive results. He discusses how AI and natural language processing are revolutionizing the way sales teams operate, from analyzing customer interactions to predicting churn. Tom's insights serve as a reminder that sales leaders must stay curious and adaptable in the face of technological advancements to remain competitive.

Perhaps the most striking aspect of Tom's journey is his transition from sales leadership to the CEO role. He candidly shares the challenges and fears that come with taking on such a responsibility, emphasizing the importance of self-awareness and introspection. Tom advises aspiring CEOs to focus on finding the right fit, where their skills and passions align with the needs of the company and its stakeholders.

For sales professionals and leaders looking to grow in their careers, Tom's story is a roadmap for success. By embracing curiosity, seeking out new challenges, and surrounding themselves with supportive mentors and colleagues, individuals can navigate the path to leadership with confidence. Tom's journey also serves as a reminder that adaptability is key in an ever-evolving business landscape, particularly as technology continues to shape the future of sales.

Be sure to listen to the full episode to gain more valuable insights from Tom's inspiring journey. And don't forget to subscribe to "True Confessions of a Sales Leader" for more thought-provoking conversations with sales leaders from across the industry.
]]><![CDATA[Principles of Effective Sales Leadership]]>Tue, 05 Mar 2024 08:00:00 GMThttps://www.olsengroup.net/blog/principles-of-effective-sales-leadershipIn this episode of "True Confessions of a Sales Leader," we dive into the world of higher education technology and explore what it takes to lead sales teams with a servant leadership approach in this rapidly evolving industry.
Our guest is Joe Belenardo, Chief Revenue Officer at Anthology Inc, a leading provider of educational technology solutions for colleges and universities worldwide. With over 30 years of experience in sales and leadership, including 28 years in Ed Tech, Joe brings a wealth of insights to the conversation.
Listen to the full episode on Apple Podcast or Spotify.
Key Takeaways from the Episode
  • ​Embrace servant leadership Joe believes in flipping the traditional "command and control" leadership model. Servant leaders prioritize the needs and interests of their team members, focusing on empowering and developing them. By serving his people and helping them succeed, Joe enables them to deliver great results for clients.
  • Build strong, trusting relationships in the tight knit higher ed tech community, relationships and trust are paramount. Joe encourages his team to develop deep, multi-threaded relationships with clients. When you consistently provide value and earn trust, you gain loyal advocates who will spread positive word-of-mouth.
  • Navigate the "turbulence" with empathy and adaptability Like any industry, ed tech goes through ups and downs. Leaders must balance empathy for their team's challenges with driving organizational goals. Joe emphasizes the importance of listening, reading situations carefully, and adapting your approach to resonate with different client and employee personas.
  • Inspire your team to "be bold" At Anthology's 2024 sales kickoff, Joe rallied his 400-person customer-facing organization around the theme "be bold." Through enablement, team-building, and generating genuine excitement, he aimed to invigorate the team to embrace a bold mindset in their work. Some key principles: be prepared, be successful, be confident, be appreciative, and believe in what you're doing.
For more wisdom from Joe – including his take on how AI is shaping higher ed tech, what makes a great (or terrible) sales experience, and why he loves the "energy, change and fluctuation" of leading sales – check out the full episode.
Subscribe to "True Confessions of a Sales Leader" on your favorite podcast platform, and please take a moment to leave a review!
]]><![CDATA[Scaling a Successful Sales Team from the Ground Up]]>Mon, 15 Nov 2021 08:00:00 GMThttps://www.olsengroup.net/blog/scaling-a-successful-sales-team-from-the-ground-upIn 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.

Listen to this episode on Apple Podcasts or Spotify.

Key Highlights from the Podcast

Here are four key takeaways if you prefer reading: 

1. Define success
In ZoomInfo’s early days, they hired salespeople, had an onsite onboard program in place, provided the sales team with a book written by the founders, and personally coached each member. After some time it was realized some of the sales team weren’t a good fit (it happens). They then defined the characteristics needed for someone to be successful, their coach-ability, work ethic, and ability to learn. This metric now lets them articulate and be more objective in what to look for in a salesperson. 

2. Know your customers
Yes, this may sound obvious but one “trick” (Henry’s air quotes) he says works well is simply ensuring your team visits a potential customer’s website before meeting with them. Look for information that connects their business value proposition or needs, with your product. Have your sales team know what prospect’s interests are before picking up the phone or meeting with them. This is a great way to consistently get a conversation going and build trust quickly. 

3. Never stop learning … or coaching
Constant learning and improvement and looking for ways to get better should not only be the salesperson’s goal but the sales leaders as well. If you’re a sales leader, make yourself available, bring yourself in early in the process and use your company’s proven, strong fundamentals to get back to the basics, which will ultimately allow for more growth. 

4. In the early days, find the common characteristic of success
In the early days, before you have a strong sales onboarding and process in place, you’ll need to find the common characteristic of your successful sales people. Once you have it, test for that ability and only hire those who fit the criteria. After you have grown and are able to put adequate resources into training and coaching, you can open up your hiring standards. 

Be sure to listen —and subscribe here. And please take a moment to leave a review.

Here is a snippet where Henry describes how he used a data-driven approach to select the right sales talent to drive ZoomInfo's growth during the early years. 
]]><![CDATA[Hiring and Retaining the Right Sales Team]]>Sun, 31 Oct 2021 07:00:00 GMThttps://www.olsengroup.net/blog/hiring-and-retaining-the-right-sales-teamWelcome to Episode 13 of  “True Confessions of a Sales Leader.” 

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.
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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 are 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 high performing sales professionals.

Listen to this episode on Apple Podcasts or Spotify.

Key Highlights from the Podcast

Here are four key takeaways if you prefer reading: 

1. First steps

For starters, the brand matters. Docker has a well-established brand name, has been in business for over a decade, but also recently rebooted with a different market focus. Though this allowed them to re-fire up their efforts to hire, there were still challenges. One way to overcome this is to look for “raw talent” for junior roles, train them and provide the opportunity for them to succeed, even if they’re outside of your industry. 

2. Build a culture of success

In typical sales organizations, there might be individual objectives, making it difficult to get your sales team to operate as a cohesive team. One thing to communicate is that the company’s success is your team’s success and vice versa and you are 100% there to support them. This is important to communicate since you can’t be on every sales call, Zoom meeting, or hallway meeting. Provide the resources they need to help them grow to build a strong team culture. 

3. The search is on 

If you’re searching for new sales members (and let’s assume we all are these days), cast a wide net, use recruiters and prepare to bring in some new talent even outside of your industry. Yes, it’s a big challenge and there’s not a clear path, however, success can come from your first or second hires. As a sales leader, if you can prove you can bring on someone new with a lack of experience and they’re successful and add value quickly, you can overcome the bias in hiring inexperienced and out-of-your industry salespeople. 

4. Focus on their journey, not sales numbers

Avoid the “can I make my numbers next quarter?” or “what’s my 2022 quota going to be?” language by setting expectations. This can take a lot of the emotion out of the room in some tough situations as well. Of course, sales numbers matter but to maintain a sales team and keep them from bolting, celebrate what they’ve accomplished, and help them better understand what they’re trying to accomplish with quantifiable achievements via a summary statement.

Be sure to listen —and subscribe here. And please take a moment to leave a review.

Here's a snippet of our interview where Scott Campbell shares his thoughts on what characteristic is likely to lead to success in sales.
]]><![CDATA[Sale Leader Q & A with Dr. Richard Ruff - "Getting Better at Selling - It's About Persuading Not Informing"]]>Sun, 18 Jul 2021 07:00:00 GMThttps://www.olsengroup.net/blog/sale-leader-q-a-with-dr-richard-ruff-getting-better-at-selling-its-about-persuading-not-informingAre your sales people persuading or informing? Listen to our behind the scenes interview with Dr. Ruff below to understand what sales professionals can learn and do to join the ranks of sales professionals that have mastered the art and science of persuasion.
  1. Listen to "How to Sell Value"
  2. Listen to "Sell More by Talking Less"
  3. Listen to "Consequences of Inaction"
The above podcast episodes are based on Dr. Ruff's article ​"Getting Better at Selling - It's About Persuading Not Informing". 
getting-better-at-selling---its-about-persuading-not-informing_7-13-2021.pdf
File Size: 55 kb
File Type: pdf
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]]><![CDATA[Sales Leader Q & A with Dr. Ruff - "Poor Self Assessment Leads to Poor Sales Coaching"]]>Mon, 14 Jun 2021 19:05:32 GMThttps://www.olsengroup.net/blog/sales-leader-q-a-with-dr-ruff-the-pitfalls-of-comparing-your-salespeople-with-each-otherWelcome to our new segment, Sales Leader Q&A with Dr. Richard Ruff. 

These are short, 5-minute 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 series takes a deeper look into Dr. Richard Ruff's article titled "Poor Self Assessment Leads to Poor Sales Coaches." Here are four ideas Dr. Ruff has picked up over the years by watching sales managers that integrate a "let's get the self-assessment right before we begin" step into their sales coaching efforts.
  1. Listen to "The Pitfalls of Comparing Your Sales Team with Each Other" 
  2. Listen to "Using Clarity to Improve Your Sales Team"
  3. Listen to "Providing Effective Feedback to Your Sales Team"
  4. Listen to "Coaching to Your Salesperson's Strengths"
The above podcast episodes are based on Dr. Richard Ruff's article, ​"Poor Self Assessment Leads to Poor Sales Coaching".
poor-self-assessment-leads-to-poor-sales-coaching.pdf
File Size: 40 kb
File Type: pdf
Download File
]]><![CDATA[Episode 12: Building Stronger Sales Teams through Self-Awareness]]>Thu, 27 May 2021 22:29:54 GMThttps://www.olsengroup.net/blog/building-stronger-sales-teams-through-self-awareness​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. Our guest is Mike Porter, chief sales officer at NAVEX Global. Mike joins me and Gary Brashear, managing partner of The Olsen Group. 

As Covid starts to wind down (we hope) how will your sales teams work? Will there be travel involved? Back to offices? And, more importantly, as a sales leader, where is your team’s head space right now? What are the next steps to coaching them and helping them— and yourself—grow to meet today’s unique selling challenges? 

Listen on Apple Podcast

Key Highlights from the Podcast

Here are four key takeaways if you prefer reading: 

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 enhance specific capabilities needed for each sales person to achieve their goals ( e.g., coach them on questioning,  handling objections, prospecting, etc.). 

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 forces us to look at our own challenges but also teaches how to improve ourselves.

3- You can’t avoid the (in)famous flight risk
You’re one of the few sales leaders who provide consistent high quality  coaching. You’ve built a great team but now some of them have defected to a better role elsewhere. Coaching people to build 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, plus you’ll attract sales people who want to learn and excel as well.

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 sales managers write their own 80/20 document, too. It helps provide self awareness and a way to teach team members how to treat you—and vice versa.

Interested in creating your own 80/20 document, click here for a template.

Here's a snippet where Mike Porter discusses how leaders can minimize their blind spots. 
]]><![CDATA[Episode 11: The Art of Sales Coaching]]>Sun, 28 Mar 2021 07:00:00 GMThttps://www.olsengroup.net/blog/11-the-art-of-sales-coachingWe’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”).

Richard and John join Gary Brashear, managing partner of The Olsen Group, and myself 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.

Here are four key highlights from the podcast episode.

1. Find time for coaching
According to their new book,  if you have 50% of your salespeople hitting their sales targets, you can increase that by 30% with regular effective sales coaching. So, what’s the issue? Time. Many sales leaders struggle to carve out the time to coach. Yes, coaching takes a lot of time, energy, and patience. Senior sales leaders need to work with frontline sales teams to determine what factors are interfering with them to find the time to coach. 

2. Keep coaching simple and immediate—for now
Picture this: a sales manager goes on a sales call with a rep and offers many levels of feedback like “you need to develop a trust premise,” or “you didn’t ask any questions,” or “your closing was too soft.” It’s good feedback but if you’re that rep that’s an overwhelming amount of feedback in one sitting. Focus on one behavior at a time, prioritize, and agree on what you’re going to work on. Keep it simple. 
Here's a 56-second snippet on Dr. Richard Ruff's approach to keeping sales coaching simple.

3. Ride-alongs are still effective
Ride-alongs have always helped improve how sales leaders can coach. And for the time being, “ZOOM-alongs” are taking their place and can actually be a better vehicle to coach. Sales leaders can be available at a moment’s notice and can jump on a sales call the same day and provide immediate feedback.

4. Learn from past mistakes
When launching a sales initiative, ask your company or organization about how previous initiatives failed or stalled. Have that conversation up front so you can understand some of the barriers you might encounter as you implement your own initiative, then develop a plan to battle those barriers.

Be sure to listen —and subscribe here. And please take a moment to leave a review.

Here's a snippet with Dr. Ruff on keeping coaching simple.
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