How to Successfully Transition into Enterprise Sales

There are different dynamics between selling to SMBs and selling to mid-sized and enterprise companies. Although the skills you’ve gained selling to SMBs will help you make the transition to enterprise sales, there are new skills you must acquire.

Enterprise deal cycles are significantly longer, require approval from multiple stakeholders, and are more complex from start to finish. Large enterprises require consensus from multiple parties and an ironclad business case to go forward. When selling to an enterprise, you can expect to convince stakeholders from different areas of the business that your solution is the right fit.

Here are six ways to successfully make the transition to enterprise sales:

1) Prioritize depth over breadth in the prospecting process.

Finding prospects who have decision-making authority is a better use of time than generating a long list of people with little or no authority.

Selling to SMBs is, to some extent, a numbers game. Experienced sales representatives know that if they can reach out to enough prospects who fit the buyer profile, they’ll get some bites. Finding a decision-maker is usually straightforward.

But generating a long list of prospects doesn’t work for enterprise sales. For enterprises, you’ll need to conduct in-depth research for every prospect on your list. You want to understand the prospect’s current situation and company structure before reaching out to anyone. Fortunately, more information is available on large companies, from 10k statements to press coverage. Make sure you leverage what is available to you! When you do reach out to a prospect, select your point of contact carefully.

You want to reach a decision-maker quickly, or at least someone who can connect you to a decision-maker. Finding these people can require a little digging but the effort is worth the time.

2) Understand the different priorities of enterprises as compared to SMBs.

SMB processes tend to be straightforward, efficient, and replicable. They’re looking for more transactional tools to fix certain pain points in the business.

Large companies, on the other hand, have shareholders. They want to keep shareholders happy by demonstrating consistent profitability and steady growth. Reducing the budget is always a priority. Enterprises also want to remain competitive for top talent. They have hundreds of employees (or more) to keep satisfied.

This means that enterprises are more likely to be averse to risk. Nobody wants to be put in the position of having to explain lackluster growth to shareholders. This shapes the sales process. Enterprise buyers need more data and will tend to be more critical of any claims made by salespeople. It’s more likely that they are in contact with your competitors, so it’s particularly important to show why your product is the best choice for their priorities.

3) Mentally prepare yourself for a longer sales cycle.

One of the advantages of selling to SMBs is that successful salespeople get frequent wins. That’s not so when the average deal takes months to years.

To deal with this, you need to develop patience and resilience. Start being okay with the fact that you are not going to close a sale every week and try to find validation through other actions. When your supervisor says you’re doing a great job or you clear one hurdle in the sales process, accept the win even if it’s not the high of a done deal.

Remember: When you do finally close an enterprise deal it will be that much sweeter.

4) Become comfortable talking to multiple stakeholders from a variety of departments

Multiple people are involved with purchase decisions at enterprises, and every stakeholder will require a different approach. As you work on multiple deals, you’ll become familiar with the different kinds of stakeholders involved in the purchase. For example, if you’re selling an HR product you might have to address both the VP of HR and the payroll manager. They will have a very different set of concerns, and you want to make sure that you’re pitching them appropriately. Most of the decision-makers you talk to will be seasoned experts, and you need to provide something of value in each conversation.

You can use a discussion with one stakeholder to subtly gather information about another. Even something as small as saying, “so-and-so said you’re a big football fan” can help establish rapport.

However, it is critical to treat everyone you talk to like an important decision-maker. No one wants to feel like they’re just a stepping stone to a conversation with someone else. Assume that stakeholders talk to each other.

5) Learn how to utilize different content such as case studies and white papers effectively at varying stages of the buying process.

Marketing content tends to be more important for enterprises. SMBs usually put more weight on recommendations from peers in their network. But you can expect that enterprise stakeholders will carefully review case studies, white papers, and other marketing materials that you provide, looking for similar enterprises that have had success with your solution. Case studies and other content that can demonstrate ROI and are from the same industry are particularly important.

You should be strategic in when you send content. Some content works better early on in the sales process, while other pieces of content are more relevant to stakeholders who are in the final stages of deliberation. Consult with the marketing team to find out what content is best for different stages of the sales cycle.

6) Develop an understanding of the procurement process.

The process of approving a purchase is incredibly complex at a large enterprise. Although the details may vary a little between companies, there are several distinct stages. First, a department identifies a need. They submit a request for procurement and are assigned a budget. Then, the process of selecting a solution begins. At every stage of the process, all the way through to signing the contract, multiple parties must approve the purchase.

The procurement or finance team must provide approval before a deal goes through and you’ll often times be negotiating with procurement rather than the end users of your solution. This means that you need to establish value outside of the experience those directly using your solution will recognize and you must be able to articulate the impact to the wider business. If you are providing pricing and terms that align with the outcomes of your solution you will have to explain this in language that procurement will understand. For example, procurement may not care about ease of use of your solution, but they will care about the time you are saving employees (through ease of use!) because that contributes to efficiency and dollar savings on labor. Be prepared to build multiple business cases throughout the sale!

Enterprise sales can be challenging, but by learning how the process works you can lay the foundation for a successful and rewarding transition.