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The Art of Enterprise Selling: A Different Motion and Mindset

  • Writer: Michael L. Nash
    Michael L. Nash
  • Dec 23, 2018
  • 6 min read

Updated: Jun 13, 2025

Personally, I have spent the majority of my sales career selling and managing sales teams focused on large account sales, also known as enterprise sales. Although the sales cycles tend to be a bit longer and the risks higher I always loved the challenge of working with the largest and most iconic companies in the world. Over the years my team's have closed hundreds of six, seven, and eight figure deals at companies such as: Microsoft, General Electric, Amazon, Walmart, Wells Fargo Bank, Federal Express, Coca Cola, Comcast, Time Warner Cable, Verizon, Salesforce, 3M and many more. It's through that direct experience I have learned, in order to be successful selling to these super large and complex organizations, you have to match your solutions to their buying process. This segment of the market has some unique buying characteristics and if you decide to go after it, you must have the right selling motion.


I have shared many times that selling B2B SaaS solutions has become increasingly challenging for multiple reasons. One of the main culprits driving this challenge has to do with the sheer increase in the number of buyers or stakeholders involved in a typical B2B SaaS purchase. Recent industry research shows the number to be in the 6-10 range and growing for global five thousand (G5K) size accounts. Regardless of the number of buyers involved in the decision process, we know three outputs to be true:

  1. With each additional decision maker the complexity and risk of the opportunity increases

  2. With each additional decision maker the deal cycle lengthens

  3. With each additional decision maker the close rate decreases

This is pretty obvious stuff and does not take a rocket scientist or Elon Musk to figure out. However, to successfully navigate this new buying dynamic there a few key changes we need to make as professional sellers.


AMP UP YOUR DEAL QUALIFICATION


First, we must be hyper disciplined in our "deal qualification" process. We cannot run the risk of becoming either single or double threaded on a few key decision makers and believe we have a qualified deal worth pursuing. Navigating the "who" part of the decision process is even more critical as the number of decision makers increases. One mis-step or missed person in the process can, at best, slow down a deal and, at worst, blow it up. I know because I have been there and it's not a place I want you or any of my friends to go. Part of what I teach and coach sales people on is how to have the conversational intelligence and inspire the buyer to share all the key people involved in the buying process early in the sales cycle. I truly believe it's the sales person's responsibility to ask the buyer questions the buyer has not asked themselves to identify all the potential people involved in the buying process. For example, if the buyer does not say the CFO needs to "sign off" of a potential deal, it's your responsibility to bring that person/role up and ask "I noticed you did not mention that your CFO needs to sign off...you are probably right but my experience with other customer's making this level of investment that is that is usually not the case." Have the seller confirm but keep asking and verifying.


PERSONALIZE AND HAVE A COLLECTIVE VALUE VISION THAT SPANS ACROSS THE DECISION MAKING TEAM


Secondly, I have learned over the years, from thousands of transactions, that people buy for their reasons and not the seller's. It's imperative that we figure out what those reasons are and then have the business acumen to articulate how our solution maps back to those reasons so much so that the buyer is motivated to discover how your solution can deliver them a better future. When you are dealing with one or two decision maker's it's not very difficult to figure our each person's reason(s) for potentially investing in your solution. As such, qualifying their needs and crafting your solution(s) to address those need(s) is fairly simple. For this reason, segments such as smb or mid-market typically have shorter cycle times and higher close rates. They also tend to have higher churn rates but that a different story for another day.


However, as the decision team increases in size, with the tipping point around six (6), how you sell must change because how these "buying teams" make decisions and purchase is different. There are books written on this that go back twenty five plus years but let me try to net out a couple of critical nuggets. Although buyers still buy for their personal reasons, when they are part of a larger buying group, their personal reasons need to collectively integrate with the others involved the decision. In other words, how do you get a VP of Service, CIO, Director of IT, Legal, Procurement, and the CFO all on the same page? After all, they all represent different parts of the business, may have cultural differences, and likely have different buying criteria. In fact, some of them may not even like one another. You can see this why this is really tough for sellers to navigate, especially when we are outside the company looking to influence within. I will share two critical selling success factors that will increase your odds of closing the deal and putting you closer to the enviable status of "trusted advisor":

  1. Identify, develop, and support your champion through the buying process. You will need someone on the inside who has the will and skill required to navigate internally and drive the group's decision. This person is not easy to find is not always obvious by title or rank. Brent Adamson and Matthew Dixon, authors of The Challenger Customer, do a thorough job of qualifying how to find and support this person.

  2. Create an overarching theme to the value/change your solution will provide that everyone on the buying team can support and rally behind. Again, each person on the buying team will have their own personal reasons for saying "yes", but to sell effectively to a buying group, we must create a collective reason.


Let me provide a real world example. A few years back, while I was leading Service Cloud sales at Salesforce, we working with a company called Univar, the country's largest distributor of industrials chemicals. Think of them as the Fedex of B2B chemical distribution. They are a one stop shop than enables world class quality chemical suppliers to sell and distribute their products to companies within industries such as oil and gas, agriculture, aerospace, energy, mining, pharma, water treatment, etc. We were working with a decision making team across sales, service, IT, marketing, finance and procurement. Multiple people from each line of business, approximately 12-15 total, were involved in the decision, and each had their own personal reasons for potentially wanting to buy Salesforce to replace their legacy applications. Fortunately, we were able to navigate the buying process and find a person we would develop as our champion and change agent. He happened to be the CIO and had the will, skill, and political moxie to navigate the broader organization towards a decision. Through learning the challenges of the overall business and the impact to the Univar's customers, we collectively came up with a vision of bringing "Amazon like B2C Service" to Univar's B2B business. That evolved into the collective value vision the CIO utilized to get the other decision makers on board. It summarized, for everyone at Univar, what they were trying to achieve as a business, regardless each person's specific role or place on the org chart. Soon there after, we were able to successfully negotiate a very large multi-year agreement that was a win for both parties.


So let's quickly quickly review what's critical when selling to the enterprise;


  1. You must be hyper disciplined on your deal qualification process and insure you know who all the key decision makers and influencers early in the sales cycle. They must all be qualified properly.

  2. Identify and support your champion. This must be the right person. Picking the wrong horse here will certainly quell your chances for a deal.

  3. Come up with a collective value vision that spans across the entire decision making team




 
 
 

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