What is Complex Sales? An Explainer on Enterprise Sales

Complex sales, also known as enterprise sales, refers to a type of sale that is relatively large and resource-intensive. It typically involves selling large-scale solutions to corporate customers. Customer acquisition cost is high, but the rewards are also higher.

Complex sales, or enterprise sales, can be contrasted with self-service, where customers buy without needing a salesperson at all, or transactional sales, where there is a salesperson involved, but there are likely to be relatively few touch points.

Related: Complexity Bias, Occam’s Razor & Your Sales Process

What is a Complex Sale?

I define complex sales based on three key factors:

  • Number of decision makers
  • Length of sales cycle
  • Buyer’s perceived risk

A complex sale involves multiple stakeholders, a longer sales cycle, and a high degree of perceived risk on the part of the buyer.

There are likely to be several other factors in the complex sales process.

  • The deal is likely to be business-to-business (b2b).
  • There may be a request for proposal (RFP) which means you will be competing against a number of other sellers.
  • You may have to sell a customized product designed especially for the buyer.
  • It is likely to involve a high price.

There is no dollar definition of a complex sale. The term is used for anything from $50,000 to eight-figure deals.

There is no single point where a transactional sale suddenly becomes an enterprise sale. Every sale can be measured against those three metrics, and placed somewhere along a continuum.

There may even be a separate category of extremely complex sales, for very big deals involving things such as politics, public scrutiny, cultural barriers.

The reason it’s useful to make the measurement is so you can understand the selling environment you’re operating in, and define how your sales team should handle deals.

Factors to Consider for Complex Sales Cycles

There are a number of factors you need to be aware of when launching into an enterprise sale.

1. Timeframe and resource

It takes a long time to make the first enterprise sale, and it’s typically relatively labor-intensive. In addition, these are high risk deals, so it’s probably necessary to pursue several at once.

If it could take a year or two years to make the first deals, you’ll need a sales team that’s properly resourced for that period of time. Even if in the long run it ought to pay off, you’ll need a healthy bank balance to make it work.

2. Size of the market

A key factor in success is the total market for the products you’re offering. Are there enough companies you can successfully sell to? What’s the size of the pipeline, and is it strong enough to sustain an enterprise sales team.

Because it’s likely that you’re targeting a relatively small market, you may well be dealing with a very small world, so reputation will be extremely important. Everyone is likely to know some information about you.

3. Customization and support

As mentioned above, the largest enterprise sales deals are likely to involve designing a bespoke product for your customers, which will then need significant onboarding and post-deal support.

Complex Sales Processes and Methodologies

A complex sale calls for a more granular sales process than a few stages that came pre-populated in your CRM’s drop-down list. The more complex the sales environment, the more critical the sales process – and the methodology to progress through it – becomes. Typically a complex sale involves four stages:

1. Discovery

As mentioned above, there are relatively few clients in this market. You’ve got to get deep inside their world. Learn all about them. Subscribe to industry news. And talk to the client. Work with them to understand their needs and pain points.

2. Definition

You need now to work out what your solution to the client’s problem is. That’s a job for you and your product team. Having understood their needs, how are you going to build a fantastic solution which is going to tick every box for them?

3. Development

Now you will need to co-work with the client to develop and tailor this solution. How can you add value? What can you offer that no one else can do? Where are you going to make a unique difference?

4. Delivery

The final stage is about working with the client to put the solution in place. This is an often-overlooked stage, but absolutely vital. First, getting the customer is just the start. Keeping them is vital. And second, this is the opportunity to grow your presence within their company and beyond with resales, referrals, and reputational benefits.

What Skills Do You Need For Complex Sales?

The complexity of your sales environment has far-reaching consequences for how your organization should be structured and operated.

What skills do salespeople need?

A complex sales cycle requires a different type of salesperson.

  • Salespeople must be skilled in detecting and reducing perceived risk, for everyone involved in the decision.
  • Due to the number of stakeholders, salespeople must navigate multiple relationships, and have the people-skills for building and maintaining trust.
  • Because of the length of the sales cycle, salespeople must demonstrate patience and skill in moving through the sales process, not miss important milestones or take shortcuts that jeopardize the deal or the account.
  • Because of the perceived risk to the buyer, salespeople must be skilled in detecting and reducing perceived risk, for everyone involved in the decision.

Additionally, salespeople in a complex environment often need to:

  • Have solid business acumen to understand and communicate value
  • Navigate both external as well as internal stakeholders and politics
  • Possess or be willing to learn consensus-building skills
  • Understand and communicate across a variety of cultures and belief systems
  • Be collaborative and team-oriented
  • Focus on quality rather than quantity

What skills do sales managers need?

Sales managers must possess these same skills and characteristics, but they must also be able to:

  • Measure salespeople based on the ability to build relationships, communicate (differentiated) value and progress through the sales process
  • Continually coach the salespeople and improve the sales process with best practices
  • Be willing to help salespeople build the right sort of skills
  • Master sales technology and how to measure the right leading indicators to ensure that everyone on the team will reach their targets
  • Create incentives and corrections appropriate to the complex sales process

For a complex sales team to be truly effective, their entire process and way of working must be approached as a system, and optimized for continuous improvement across the organization – very similar to how medicine and other professional fields are evolving. More structured teamwork, less individual heroism.

George Brontén is the Founder and CEO of Membrain. He is a life-long entrepreneur with 20 years of experience in the software space and a passion for sales and marketing. With the life motto “Don’t settle for mainstream”, George is always looking for new ways to achieve improved business results using innovative software, skills and processes.

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