How do you make the shift from selling to small/mid sized businesses to enterprise? And vice versa, how do you manage the adjustment from enterprise sales to SMB?

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Senior Enterprise Sales Executive in Softwarea month ago
There are a lot of if this then that you can weave in here, but something I learned during my time in SMB is you really have to work the top faster and you need to get your prospects in and out the funnel faster.  The most successful person I worked with in the SMB segment that was methodical about their funnel, they followed a very specific process, they made 1 or 2 attempts at moving them through and if they couldn't they'd move on - no chasing, but they did have a process of going back to all those deals and either starting them from scratch or trying to get them past the original step they were on. Your juggling multiple accounts at the same time (assuming a much large territory) so process is everything. Going from SMB to Enterprise you need to be able to do deep work (ex. dig into a company, understand their business and have a observation/point of view that will inform your outreach), there are definitely going to be more players so finding the common thread that connects all their individual wins is going to be critical and conversely you're going to need to utilize and understand how best to utilize more people inside your own organization. You still need a very good process, but you're more likely than not only handling a few deals at any given time simultaneously. 
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Founder in IT Services22 days ago
Enterprise sales are about deeper relationships, deeper customer knowledge, and more specialization. Whether you're in sales or customer success, you need to build a consultative skill set. This involves bringing in-depth experience and people who can help you understand the customer's business and what value means to them. On the other hand, small and mid-sized businesses (SMBs) require a more scalable approach. This means systematizing processes and leveraging technology to operate at scale. While you still need to have conversations with customers, it's more about process and technology optimization.

If you're moving from enterprise to SMB, you need to become more process-centric and focus on enabling technologies and standardization. Conversely, moving from SMB to enterprise requires a deeper dive into the human side of things, understanding the customer's business and industry.

From a customer success perspective, the larger the customer, the less likely you can use a cookie-cutter approach. For example, if you're selling software for a few thousand dollars a year, you need a product that works the same way every time. However, if you're selling for millions of dollars a year, the customer expects a level of value that likely won't come out of the box. You need to invest in understanding what value means to the customer and bring a more consultative experience. This applies both post-sale and during the sales cycle, where a personalized process is crucial.

With SMBs, there's often more ambiguity, whereas with enterprise clients, you need to establish deep relationships to avoid getting lost. Data becomes increasingly important as well. When you have tens or twenties of customers, you can be well plugged into what's going on with them. But when you have hundreds or thousands of prospects, you need to identify buying signals and other indicators from the data to manage effectively.

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CEO in Services (non-Government)21 days ago
Knowing your buyer is always step one in making  a shift in your market.  How your solution impacts  your buyer and their personas is important.  In different size organizations, different roles may have the authority to make buying decisions. 

One key way to do this is to research and create dynamic buyer personas to teach and train your revenue professionals how to engage and add value.   As you move from SMB to Enterprise, the buying complexity increases - primarily because more and more people are involved in making any decision.  This reality requires new skills and tools to navigate the decision team and create a positive outcome.
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