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Enterprise Sales Prospecting: What Does It Take To Ace It?

7 min
Executives examine opportunities to boost ROI.

Everybody remembers closing their first “big one.” They remember the huge commission received, and the feeling of victory after arduous weeks or even months of work. The key to successfully bagging an enterprise client lies in understanding the scale, being patient, and being consistent.  

Enterprises are large-scale companies in terms of both size and revenue. Typically, an enterprise consists of over 2,000 employees and $1 billion in revenue. Enterprises could have the same problem as SMBs but selling to them is a whole different game.  

Imagine you are selling POS software to a local restaurant v/s Olive Garden. On paper, both are similar businesses with similar problems, but if you juxtapose both, you would be able to see the difference in scale and complexities between them. 

What is Enterprise Prospecting?  

Enterprise sales prospecting is the process of evaluating large companies as potential buyers who can be a good fit for your product offering.

Enterprise prospecting differs from SMB prospecting principally in scale, size, and notably the contract value. Essentially, everything gets dialed up to 11.

Prospecting these large companies, unsurprisingly, takes a lot more time as more people are involved in the decision-making process. The lack of brevity when dealing with enterprises extends beyond just prospecting.  

The Difference Between Prospecting Enterprises and SMBs


Big ticket
Long sales cycle
More objections
5+ decision-makers

Small ticket
Short sales cycle
Fewer objections
1 to 2 decision-makers

Multiple factors such as the nature of the organization, the goals, the ACV, the modus operandi, etc., distinguish enterprises from SMBs. While Gartner’s definition of SMBs revolves around size and scale, the sales processes followed by SMBs and enterprises differ greatly as well. 

As a result, their sales prospecting strategies, too, are different. 

Let’s understand the three key challenges that are unique to enterprise sales prospecting.

#1 Longer sales cycles demand more patience 

Expect a significantly longer sales cycle compared to SMBs. On average, closing a deal with a small to medium business takes about 1 to 2 months, terms for the contract last about 1 year, and there are 1 to 2 decision-makers involved.

In complete contrast to SMBs, enterprises sign a 6-figure deal but take 6 or more months to complete it. This lengthy period consists of a great deal of due diligence done by both sides of the party; an extensive number of hours are spent climbing the web of gatekeepers, influencers, and blockers to reach the multitudes of decision-makers.

#2 Multiple decision-makers are involved 

In an enterprise deal, a product is sometimes meant to be used across departments. In that case, the number of decision-makers involved exponentially rises. Around 6 to 10 decision-makers are often involved, more if the deal is cross-departmental.  

The list of decision-makers can consist of specialized department heads, regional managers, and the entire C-suite.  

The decision-making process for enterprises is extremely slow, not just because of the sheer number of people and the hierarchy involved but also the distance between every decision-maker. For a multinational enterprise, decision-makers can be found spread across time zones and continents. At the scale at which an enterprise operates, these individuals are incredibly occupied within their work hours, and coordinating a time to synchronize between all the decision-makers can be a challenge. 

Additionally, in an enterprise setting, unanimous agreements and final approvals are necessary to move things forward within the sales process. Every objection raised by a decision-maker acts as a veto until resolved. 

#3 Sales objections keep rising at every stage 

Objections raised within an enterprise context revolve around the long-term viability of your product to be the solution. It is to test the agility of your product to blend in with its own technologies and functions. 

Objections will demand answers regarding the time taken for integration, availability to develop custom features by your tech team that meets the PO needs of the company, the timeframe of when they will be able to see the results, and pricing. Figuring out pricing for an enterprise-level business is a long-winded and complicated process.

Due to the scale of an enterprise, the number of decision-makers is high, thus there will be more objections raised, at multiple levels of approval. Objection handling can take up the most amount of time within the sales cycle as the objections coming in from C-suite executives of various departments will concern the same number of departments. The best way to handle these objections is to support your business case with numbers and facts. Show testimonials of how you have resolved this exact issue for other companies within the same industry or sector, offer free trials, and be willing to wait.

5 Tips to Ace Enterprise Prospecting 

Enterprise prospecting is not easy by any stretch of the imagination due to two major reasons:  

  1. You will be facing tough competition from your competitors trying to pitch their product to the enterprise at the same time.  
  2. You will need to keep track of the countless touch points and people involved in the prospecting process  

To cut through this clutter and help you make your shots count, here is what you must do when prospecting an enterprise: 

#1 Think like an enterprise  

When enterprises go shopping for a solution, they are looking for a product that provides the solution for a well-defined issue. An AE must be able to pierce into the depths of those issues and understand them completely, pitching their product holistically around that very problem.

Deviating from the core of what issue the enterprise is facing would cause the buying company to lose interest as they exactly know what they want and will know that they are not getting it.

On the enterprise scale, companies look for solutions that can fit into their highly customized and specific processes. These rigid processes are often unwelcoming to change, so it is a clever idea to position your product with adaptability to an enterprise’s existing technology stack.  

#2 Planning your outreach 

First things first, you need to create a map of the hierarchy and the people within the company. You will uncover the stakeholders, decision-makers, and their decision-making power in accordance with their ranks. Taking the bottom-up approach will be a good starting point to begin your outreach.

An enterprise’s middle management is usually the stakeholder. Stakeholders may have lower decision-making power, but they are more in numbers and have the ability to connect you further.

Connecting and pitching to stakeholders about the features of your product and how it relates to their problems is relatively easy compared to pitching to C-suites. Additionally, having stakeholders endorse and advocate your product from within is a huge boost to your appeal.

While there is only one Director of Sales, there may be 30 or more SDRs that can be your avenues to reach this person.

Starting from the bottom up allows you to cast a wider net and experiment with your outreach messaging, as the consequence of a mistake at this stage is low. Going through the levels of hierarchy, you will refine your communication until it is apt for the C-suite. 

#3 How to create a winning sales pitch for the C-suite 

The members in the C-suite are not so readily accessible as there are several gatekeepers between you and them. This is applicable universally, but at the enterprise scale, getting access and time with the C-suite executives is substantially more difficult.

Therefore, you must find the right opening for your pitch. One that will highlight the value of your product and engage the prospect. In order to grab and hold the attention of the prospect, your pitch should be airtight, short, and condensed with valuable information. Use the internal endorsements from tip #2, support your pitch with realistic timelines, and use quantitative data to make your case.

Focus on your ‘one-shot.’

On the enterprise scale, there is not going to be more than one single opportunity to pitch your product given the logistical complexity of scheduling meetings in a large company.

A good sales pitch needs a deck that is just as powerful. Creating a pitch deck that focuses on the enterprise’s specific needs, coupled with just the relevant statistics and benefits of your product is the answer to increasing the shareability and lifetime of your pitch.

The executives may want to look at your pitch on their own individually, hence, having your deck do the pitching in your absence can be incredibly beneficial. 

#4 Relationship building   

Here’s a new acronym for your sales vocabulary – 

DABS – Don’t always be selling.

An ineffective salesperson is constantly trying to sell to the prospective buyer, never truly building a relationship with the prospect outside of the sale. If the sale falters through (given the persistent pitching, it most likely will), any recall of the salesperson or their product is completely lost in the prospect’s mind. Communication will completely halt and the effort the salesperson put in will amount to nothing.

Enterprises are long-term opportunities. It is improbable that a salesperson will close the sale within the very first interaction they may have with the company. Building a relationship with the prospect is the first goal. You can build a relationship with empathy, by engaging in conversations where you are not pitching your product but by letting the prospect lead and talk about themselves.

Relationships, especially with enterprises, go a long way. Even if an opportunity does not go in your favor, establishing and maintaining a good relationship with the company can eventually land you that contract.    

#5 Post closure efforts 

Closing an enterprise deal can open opportunities for further 6-figure deals, so the work does not end once the deal is done. Follow tip #4 and maintain that relationship beyond the deal. Putting in consistent efforts after the deal creates a moat around the contract between your company and the enterprise, protecting it from competitors and ensuring renewals.

There is always a possibility that the enterprise may want to expand its purchase of your product to different departments and regions if they see the benefits. Hence, it is good to be present in the loop by keeping a healthy relationship.

Keeping a good relationship will help you get referrals to other enterprises; referrals are a terrific way to begin cold outreach to another company. It builds credibility when you approach a new large company with another enterprise vouching for you. 

6sense and Enterprise Prospecting

Enterprise prospecting demands multiple levels of research. Finding leads, mapping the organization, and measuring the compatibility of your product against their needs. 6sense can help you check all these boxes, and more, on a single platform.

6sense enables you to go after enterprise deals by filtering companies based on their size. It arms you with buyer intent data, uncovering the accounts that are actively looking for your product, so you can invest resources towards deals that have higher chances of success.

6sense gives you access to technographic data of the company. You can customize your pitch to adapt the product with their technologies and speed up your sales cycle by using firmographic data to enrich your sales intelligence

So, We’re Saying 

Enterprise prospecting comprises many variables a salesperson needs to account for. 6sense aligns those variables in a way that ensures that you are not flying blind when prospecting.

6sense tells you which account is the right prospect at the right time, and how to reach that account. Give it a try! 

The 6sense Team

6sense helps B2B organizations achieve predictable revenue growth by putting the power of AI, big data, and machine learning behind every member of the revenue team.

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