One of the most common questions I get from cloud partners is about how to build an effective strategy to maximize their sales in the cloud. This week, I would like to explore some best practices on this topic. To help me formulate an answer to this question, I turned to Charlie Gilbert from Perspicuity, who is an absolute selling machine and all-around charming guy. In fact, Charlie started out selling Office 365 at the age of 17, and in the last three years has sold Office 365 to more than 1,500 small and medium business customers himself. Credible? I think so.
So what is his secret to success? It comes down to five principles:
  1. Have a value add: The cloud is rapidly changing, and new partners and competitors are emerging every day. To ensure you stand out from the competition, it is extremely important that you develop a unique value proposition. Charlie said, “You don’t have to be the cheapest, but you need to have something unique to offer your customers.” Brent Combest recently published a blog on this and recommends going vertical.

  2. Train your sellers on question-based selling: Perspicuity subscribes to the Sandler Sales methodology of question-based selling and makes an investment in training all of their sellers on this methodology. The strategy is to start by learning about the company you are talking to and focusing on gathering information that will help you build the case for the product you are selling. When selling Office 365, Charlie’s approach is to ask the prospect about their current environment to determine what the customer’s pains might be. Charlie warns against what he calls “show up and throw up,” which is starting a call by immediately trying to sell the customer on the solution. Not only is this not well received by prospects, it can also lead to selling the wrong solution to a customer.

    “Rather than show up and throw up, we try to find out more about that organization. We ask things like, ‘What are you currently doing with email?’ Once we find out what they are on, we can almost certainly get the pain they are facing. For example, if the customer is on POP, we know the pain will be that their email doesn’t sync on devices, so we can say, ‘Being on POP, how does your sales team deal with this challenge?’ We ask the right questions to lead the customer to acknowledge a problem we can help solve.” – Charlie Gilbert, Perspicuity

  3. Invest in training your sales team: In addition to getting trained on question-based selling, all new sales people at Perspicuity are trained extensively on Office 365. As a part of the process, they are also required to manage the Office 365 migrations they sell using SkyKick. This is a critical element of their success because it helps the sales people better understand the technical aspects of Office 365 so they can better sell the solution, address customer questions, and establish credibility with customers.

  4. Find the “No”: As a business major in college, I read the famous book Getting to Yes, so when Charlie talked about his strategy of “finding the no,” I was intrigued. He explained that in order to drive a high volume of sales, you need to use question-based selling to identify the reasons why a customer or lead should be disqualified as rapidly as possible (for example, a broadband issue). According to Charlie, “the quicker you can disqualify a customer, the quicker you can get to the next win.”

  5. Build and follow a process: Perspicuity has built a solid process to sell, migrate and deploy customers on to Office 365. They leverage SkyKick, a 3rd party tool to help them speed up the process of deploying and migrating customers to Office 365. Additionally, they make sure each step of the process is well documented and consistent. According to Charlie, the only deals that fail are those in which the sales person didn’t sell Office 365 correctly and follow the process.
I’d like to extend my thanks to Charlie Gilbert for our chat. If you want to hear more about Charlie’s success, I encourage you to sign up for the #Winning Loads of New Cloud Customers session which is part of the Partner Profitability track at the Worldwide Partner Conference.
Please feel free to reach out to me directly with your thoughts and burning questions related to Partner Profitability. I can be reached at, on Twitter, and on LinkedIn.
Until next time,
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