What makes a complex deal complex? What even is a complex deal?

These are questions you probably asked yourself when you read the title, and that's understandable. After all, the world of B2B never stops evolving. New concepts are being developed daily.

If you want to start selling your product to large enterprises beyond the small-and-medium-business (SMB) bracket, you need to get familiar with complex deals and the mechanisms behind them.

This is precisely what we’re here to help you with. Keep reading this article to get everything you need to know about complex selling, in simple terms.

What is a complex sale?

In B2B, a complex sale (also called an enterprise sale) is a transaction with a longer sales cycle and purchase price. Complex sales are usually perceived as being a higher-risk transaction. As you could have guessed, these types of sales usually require a different approach from a classic sales one to successfully close the deal.

Key elements of a complex sale

A few critical elements differentiate a complex sale from a regular sale. Having an understanding of these differences is necessary for an SDR to be able to navigate a complex sales process.

The elements are…

✅ More than one decision-maker is involved

Other than the chief decision-maker, more parties will be involved in making the final purchasing decision. Usually, those decision-makers will perform different tasks in the sales process.

Some of the other parties that salespeople work with during a complex sale are…

  • The chief decision-maker’s gatekeeper
  • A team leader or head of the department who will use the product
  • Members of the company legal team
  • A financial department representative such as a CFO
  • The tech team responsible for setting up and maintaining your product

✅ The sales cycle is longer

When there are several decision-makers involved, they naturally take more time to communicate and make a final decision.

During a complex sales process, you usually speak to different people at different times, rather than on one call with all of the decision-makers. Every one of the people you speak to has to form their own purchasing opinion. Only after that will they decide whether any other people need to get involved.

The whole sales process takes longer as a result.

14 strategies to shorten your sales cycle with CRM
Find out what a sales cycle is, why you need to keep it short, and how to minimise the length of each stage of it in CRM!

✅ The decision is perceived as a higher risk by the prospective company

Since the purchasing price during complex sales sits at $50,000 or above, your product purchase is considered a high-risk investment.

The decision-makers involved in the purchasing process have a higher degree of pressure to make the right decision.

As we said in our article on decision-makers, they often have a sense of responsibility before their company and teams. The prospective company will scrutinise your sales pitch and product. Mistakes on the sales representative's part have dire consequences compared to a regular sale.

How complex sales work

Due to complex sales in B2B environments, the chief decision-maker is usually an executive with authority over the relevant sphere. The CEO, CMO or CTO are all positions that could be the chief decision-makers during an enterprise sale. However, any person in charge of purchasing operations could be the primary decision-maker.

All those parties must be convinced that making this purchase is the right decision. Disagreement or power struggles between parties leads to a stall in the progress of the sale, potentially leading to a sales rep not being able to win the deal.

An example of how a complex sale works can be found in real estate.

Imagine you’re trying to sell a house to a family. A house is a significant financial investment for almost anyone. You must convince the entire family of the house's worth. Both spouses must agree on the worth of purchasing this specific house, and the kids need to enjoy the house. Power struggles or disagreements between the family members hinder the progress of the sale or fail it altogether.

How do complex sales impact businesses?

Complex sales also require specific skills from sales representatives. There is also an impact on how sales methodologies and processes are handled, with new factors to consider when approaching difficult sales.

Impact on salespeople

Complex sales are more complex than SMB sales. Still, SDRs assigned to complex sales also need the right tools and skills to win deals. Without them a sales representative is lost in a whirlwind of tasks and processes that need undertaking.

One such process is the need to navigate multiple relationships simultaneously. A sales representative will most likely speak to the decision-makers involved in the sale separately. But that doesn’t necessarily mean that these separate conversations will all be happening in an orderly fashion.

You could have multiple calls, email chains and LinkedIn messages to respond to every day. Of course, it's needless to say that all of these conversations differ. The sales representative working on the deal must keep track of all the conversations.

  • With the help of a CRM system, sales representatives can make easy work of this by using the following features…
  • The feed in the customer card, any documents, transcripts of messages and emails exchanged with the prospect can be stored in a single place.
  • CRM systems like NetHunt CRM offer integrations with the other tools in a sales team’s tech stack.
  • Implementing a CRM system can also help sales representatives make the most of their soft skills during an enterprise sale and keep informational intelligence.

The conversation details can easily be recorded, making building trust significantly easier.

Patience is also of paramount interest for sales representatives during enterprise sales. Missing an important milestone or taking a shortcut devastates sales and forfeits time and effort.

The sales representative must utilise value-based selling to win a complex sale.

Decision-makers have the company's best interests at heart. They won’t consider purchasing a product unless they believe that it will provide value to them.

Impact on sales processes

There are several factors affecting the sales process that you should be aware of when going into a complex sale.

It takes significant time to close an enterprise sale; it’s very labour-intensive.

Therefore, it’s wise to have multiple in progress simultaneously. You need a resourceful and motivated sales team and a detailed onboarding process to prepare new hires for such work.

Depending on the size of the market in which you operate, companies you reach out to will be familiar with your company or your other clients. You must work at maintaining your reputation.

Enterprise deals often involve a high degree of customisation. They usually involve your company offering a bespoke product that can be tailored to your client's needs.

More work must be done once the deal has been won. Providing your clients with an in-depth onboarding process and further product support is crucial. You must be as interested in your clients achieving success as you are in selling to them.

The five stages of a complex sales cycle [+ tips]

An enterprise sale also has a few more stages than you might see in an SMB sale.

A company that executes both types of sales would need to set up multiple pipelines for their enterprise and small-medium business clients in their CRM.

The handling of those stages is also slightly different from what you usually see during sales.

These are the stages of an enterprise sale cycle…

Stage 1: Discovery

Your clients will expect in-depth knowledge of their industry from you.

During the discovery stage of the sales process, subscribe to news outlets that cover news from that industry and familiarise yourself with the industry's market conditions.

Stage 2: Qualification

Sales qualification, also known as lead qualification, is the process by which your sales representatives determine whether the prospect is a good fit for your products or services.

The tools you need during the qualification stage are…

  • A lead qualification framework which contains the criteria by which you will decide whether your prospect meets your qualification standards.
  • A fleshed-out Ideal Customer Profile (ICP) which helps you understand how well your prospects match an ideal customer for your business.

Even if a prospect doesn’t match your ICP, you should still try to engage them. An ICP is just an estimate, not a set of criteria.

Stage 3: Proposal

This stage is where you state your offer to a prospective client, describing the benefits that purchasing your product provides.

Don’t make the common mistake of just stating the key features of your product. This isn’t enough to engage an enterprise client.

Instead, utilise value-based selling to make decision-makers see how your product helps them achieve their goals.

➡️ Check out our guide to writing sales proposals that work. ️

Stage 4: Closing

If the sales representative has done well during the sales process, they arrive at the closing stage organically.

This doesn’t mean that the deal is won just yet.

Prospects frequently need a little extra push to complete the deal.

Can you blame them? Nobody likes saying goodbye to their hard-earned money, not even large companies.

Pay attention to certain cues indicating that the prospect favours purchasing your product.

They usually ask questions about implementation, pricing, and other agreement details once they want to purchase a product. Also, prospects ask more questions during successful calls that go successfully than unsuccessful ones.

Stage 5: Delivery

The delivery stage could take on various forms in a complex deal.

If you’re a SaaS provider, delivering your product might involve help with the implementation of the product, alongside in-depth onboarding for new clients. However, for an industry that sells physical products, the process varies largely based on the conditions agreed upon in the contract.

Either way, you should ensure your clients receive their products and services promptly.


Now you know the formula to how to close complex deals.

However time-consuming and labour-intensive they may be, if you follow the right process and use the right tools, you should start finding enterprise clients soon.

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