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A strong, high-performance sales team is critical to a successful business. But what makes a sales team successful, and what strategies can leaders use to create one that’s highly successful? To address these questions, we're talking to CROs and sales executives about "How To Turn a Good Sales Team into a Great One." As a part of this series, I had the pleasure of interviewing Brian Will.

Brian Will

Brian Will

Brian Will is a Serial Entrepreneur and an industry-leading Business and Sales Management Consultant. During his career, Brian has created or co-created seven very successful companies in four different industries. These companies were worth over half a billion dollars at their peak. Brian is also the Author of the Wall Street Journal Bestselling book ‘The Dropout Multimillionaire.’

Thank you for doing this with us! Before we begin, our readers would like to learn a bit more about you. Can you tell us what brought you to this career path? 

That story goes back to my childhood. I grew up in an abusive home and failed high school in my junior year. I managed to graduate but was an angry young man with a giant chip on my shoulder. Because of my issues with authority, I kept getting fired and struggled to hold a job. At the age of 21, I finally decided that my best shot would be starting my own business.

The first company I started was a landscaping company. I didn’t have any idea what I was doing but I figured anybody could mow grass and plant bushes. Since then, I have done four more startups in insurance and technology and now restaurants and real estate. I sold two companies to venture capitalists and one to a private equity company.

Can you share an interesting or amusing story that has occurred to you in your career so far? What lesson was learned?

Twice, after my companies were acquired, I was told that I wasn’t qualified to run them anymore because I didn’t have a college degree. I was good enough to build it and sell it, but not good enough to run it after the sale. I always found that quite humorous. The first time it hurt my feelings, the second time I laughed it off. I took the money and went and built another company and sold it again to a different venture capitalist.

Are you working on any exciting new projects now? How will it help people?

I wrote the book 'The Dropout Multimillionaire' last year. It hit the Wall Street Journal best-selling list right after the launch. The book is about building a business, growing a business, or selling your business. It tells real-world stories about what it takes to succeed, and includes a lot of lessons on what not to do. 

With that in mind, I have recently launched a media and consulting company to work with business owners. I want to take all this experience and knowledge of 35 years of success and failure and help these entrepreneurs beat the odds and succeed in their business ventures. 

None of us can achieve success without some help along the way. Is there a particular person whom you are grateful for who helped get you to where you are?

My first mentor was Steve, my senior partner in an internet marketing company we owned. We launched in 2003, and after 9 months, we hadn’t generated any sales and had spent over half a million dollars. Steve came into my office and said he wanted to invest another $66,000 to buy some servers. I told him that we were losing money and that I didn’t want to invest in servers for a business not doing any sales. 

Now Steve was significantly more successful and experienced than I was at the time. He had made millions of dollars and I hadn’t made much of anything. I remember him looking at me and saying, “Brian, you can give me your equity back right now and you don’t owe any of the money. We will walk away friends with no hard feelings. But I want an answer right now.” I sat there staring at Steve for what seemed like an eternity. I wanted out, but Steve was worth millions and had done this before. I finally looked at Steve and said, “Ok Steve, I’m in” He said, “Good, now I never want to hear that again.”

Thirty days later our first deal took off and 18 months later we sold the company to a private equity firm for 60 million dollars. It still scares me today to think about what my life would be like if I had said “I’m out.” 

Sometimes you need to trust the person who has been there and done that… and not yourself. This is why I am so adamant about entrepreneurs getting a mentor or a coach. 

For the benefit of our readers, can you tell us a bit about your experience leading sales teams? How many years of experience do you have, and what size?

In the last 20 years, I have taught sales training to around a thousand people. Most of this is direct to consumer sales through call centers. The training and techniques, however, are universal between phone sales and face-to-face sales. Sales are sales.

As an example, in 2012-2013, we built a call center in Chicago to sell Medicare policies. After a complete overhaul of the call center, my sales teams and training sold over one billion dollars in annual policy sales that year. In 2014 I took a position as an interim CEO of a publicly traded insurance company sales center in Portland. After overhauling that center, we increased our sales from $50 million to $150 million in annual sales run rate in just over 6 months.

What do you think makes a sales team great? What strengths or characteristics do you try to cultivate?

The key to an effective sales team or sales center is what I call bottom-up P&L (profit & loss) management. We never look at an organization from the top down. Revenue is a misleading number. Overall profit doesn’t tell the story of productivity and potential. Each person must have an individual P&L. This allows us to identify the strong from the weak. This then allows us to either coach up… or coach out the low performers. Just because someone sells the most, does not mean they are the most profitable. Top performers come in all shapes and sizes. I often say I can’t tell you who is going to be one of the best, but I can usually tell you who isn’t going to make it. 

As with any department, there can be a lot of different strengths, weaknesses, and personalities. How do you manage such diversity on an individual basis?

This is a tricky question and gets into human nature and motivation. Most people think salespeople are motivated by money. I would tell you that most salespeople are motivated by laziness.

Most salespeople will only work hard enough to pay their bills. They will only work up to the level of their internal self-worth. After that, they will slack off the rest of the week or month until the next pay period starts. This is human nature. Take a look at your sales commission data to see if this holds true at your organization.

As a manager of a sales team, you need to understand that not everyone will be a killer closer. We use the 10%-70%-20% rule. 10% of your team will be super closers. 70% of your team will be average. 10% of your team will need to be replaced. Your organization will run on the 70% average closer. Your 10% super closers are the icing on the cake. This becomes even more pronounced the bigger you get. The key is to keep your 70% happy and constantly replace the bottom 10%.

What strategies have you tried to increase motivation, engagement, and productivity? We want to hear it all.

This gets back to the laziness motivation factor mentioned above. If we know our people will slack off after they hit whatever goal they have to pay their bills, then we have to motivate them in a different way to get them to keep going. 

This is why companies have contests or recognition awards. It is an attempt to push the sales team past their basic lifestyle and money needs, to achieve something special. It could be your name on the wall, or it could be a trip to the Bahamas. In some cases, we would do a Starbucks run for the top salespeople by ten o’clock. 

You would be surprised how a cup of coffee becomes a badge of honor and is more important than the commission from the sale. This is a key management trick.

Of all the strategies you've tried, which did you find to be most effective? Did this have a direct correlation to sales? 

I mentioned to bottom-up P&L above. This is both an effective tool for management to see who is profitable and who isn’t, but it is also an effective tool to share with each individual. If I show you where you rank among your peers, it creates personal pressure. Nobody wants to be last. If they don’t care they don’t need to be here. If I show you that you are unprofitable and I show you exactly why (based on the metrics we track)… you have the option of fixing those exact metrics, or you know that your job is in jeopardy. There is no mystery to anyone where they stand. Self-motivation of a salesperson is a very effective motivator. 

Can you tell us about a time that your sales team outperformed their targets? How high over did they go, and what was that like for everyone involved? 

I was brought in to consult for a company’s sales division up in Minneapolis that was losing a million dollars a month on the P&L. This was a small division of a publicly traded company. Because they were very corporate and set in their ways, they struggled to adapt to what I was telling them. It took just over a year to get everything in place. Once we had all the pieces there, that division went from losing a million dollars a month, to the most profitable division in the company. 

Just because companies are publicly traded, or worth billions of dollars does not mean they know what they are doing all the time. Companies are run by people. People can be arrogant and clueless at the same time. In this case, I had to ease them into small changes one at a time, to get them where they needed to go.

Great things often take time. What do you think is a realistic timeline to take a sales team from good to great? 

If you have the right sales trainer and the right manager, it can happen very quickly. I like to take my low performers off the sales floor in the morning and do a 30-minute refresher course. I have seen sales turn around immediately. It’s usually a matter of not following the training or scripts. These are easily corrected if the salesperson is willing to listen and learn. If they aren’t, they don’t need to be there anyway.

Amazing, let's get to the meat of it. What are your five strategies that will help turn a good sales team into a great one?

  1. Build a bottom-up P&L for every salesperson on the team. This is critical to everything else.
  2. Build a P&L for every lead source. This is the second most critical piece.
  3. Build a P&L for each product sold based on the two P&Ls above. Some products aren’t worth selling.
  4. Know your numbers. Automate all these and study all of them daily. You would be surprised how fast the numbers can change.
  5. Know your numbers. Know your numbers. Know your numbers.

Lastly, you're a person of great influence. If you could inspire a movement that would bring a great amount of good to many people, what would that be?

The concept of giving back is important to me. We are all out here trying to be more successful and have more money and more things. There's nothing wrong with that—I chased business and money for many years. After I had sold my second company, I was out in Park City skiing and visiting a friend who was much more successful than I was and he asked me “What are you passionate about, and what are you doing to give back?”

I told him I had no idea. I had been so busy building companies that I had never thought about it. I remember him looking at me and saying “Brian, you are never going to be truly happy until you find a passion and give back to the world that provided you with the opportunity to have what you have.”

It took me a couple of years to figure that out. I eventually found my passion in writing and working with and helping entrepreneurs. I also got involved in local politics and was elected to City Council. This also allows me to improve my hometown and make it a better place for my friends and neighbors to live and raise their families.

So, my answer is this: no matter where you are in the journey, find a passion and a way to give something back. Even if it’s small today, start working on your legacy.

How can our readers further follow your work online? 

My website is You can find my podcast episodes there, as well as my book, 'The Dropout Multimillionaire - 37 business lessons in how to succeed with No Money – No Education and No Clue.' 

The podcast is also online at Thedropoutmm on Apple, Spotify, and YouTube.  

Phil Gray
By Phil Gray

Philip Gray is the COO of Black and White Zebra and Founding Editor of The RevOps Team. A business renaissance man with his hands in many departmental pies, he is an advocate of centralized data management, holistic planning, and process automation. It's this love for data and all things revenue operations landed him the role as resident big brain for The RevOps Team.

With 10+ years of experience in leadership and operations in industries that include biotechnology, healthcare, logistics, and SaaS, he applies a considerable broad scope of experience in business that lets him see the big picture. An unapologetic buzzword apologist, you can often find him double clicking, drilling down, and unpacking all the things.