Complex Sales

Complex Sales

What is Complex Sales?

Complex sales, also called enterprise sales, refers to the long, intricate B2B sales process that takes place when corporate businesses purchase high-value products or services from another company.

Complex sales processes have a few defining characteristics:

  • Multiple decision-makers
  • Longer sales cycles
  • High value and high risk
  • Customized solutions
  • Educational selling
  • Relationship building
  • Post-sale support

Understanding and navigating the complexities of this selling process is crucial for success in selling high-value products or services to large organizations. It requires a strategic approach, patience, and a skill set that includes excellent communication, negotiation, and problem-solving abilities.


  • Complex sales process
  • Complex selling
  • Enterprise sales

Complex Sales Business Challenges

Collaborating With More Decision Makers

In standard sales, an individual or a small team makes decisions. On average, a B2B sale involves 6 to 10 different decision-makers, each with their own priorities and concerns. This group always includes senior and C-suite executives, technical experts, procurement professionals, and end-users.

Each stakeholder comes from a different background and has different levels of influence, which adds difficulty from the salesperson’s point of view. Credibility isn’t built overnight; sales professionals need to play to each decision-maker’s individual needs and wants.

They also have to provide personalized and targeted content for each decision-maker. For instance, an IT or systems manager will need you to speak more to the product’s functionalities and integration capabilities, while a CEO would care more about its potential ROI and how it aligns with their business goals.

Building Relationships with C-Level Decision-Makers

When it comes to the C-suite, their time is extremely limited. So, it’s difficult to secure meetings or discussions with them.

They also deal with issues at a strategic level, which is quite different from operational or tactical concerns. In fact, there’s a good chance they’re unaware of specific operational details like budget limitations and technical challenges.

Anyone who wants to build a relationship with them needs to understand and speak to their specific high-level concerns effectively. This means having a solid grasp of best practices within the company, current trends, and the competitive landscape. Generally, it also means finding an advocate within the company who will vouch for your product to them.

Educating Customers About Complex Products and Services

Solution selling is a big part of complex sales. Even if the product is something your customer is familiar with (e.g., a CRM or ERP system), connecting with the customer and addressing their unique needs requires you to:

  • Ask open-ended questions
  • Uncover the buyer’s specific goals and challenges
  • Establish common ground, so you can lead into your pitch

Normally, sellers use a sales qualification framework like SPICED or MEDDPICC to guide them through these conversations. That way, they can ask the right questions to uncover key influencers in the decision process and map out the decision timeline.

Longer Sales Cycle

The B2B sales cycle range from several months to over a year. On average, it takes 102 days to close a typical deal. More complicated enterprise deals take 6 to 12 months to close.

Despite advances in sales automation technology, it’s only getting harder to move deals across the finish line efficiently. According to the 2023 GTM Survey by Tomasz Tunguz of Theory Ventures, the average enterprise sales org saw a 36% increase in cycle length from 2022 to 2023.

The time needed for discussions, negotiations, approvals, and decision-making processes within the buying organization makes complex sales a lot harder to close. Plus, conflicting viewpoints and agendas add to the complexity of reaching a consensus.

Higher Perceived Risks

The more expensive the product or service is, the higher the stakes. Enterprise deals are frequently six or seven figures in value, so buyers will need to be convinced of its value and ROI before committing.

Potential risks of investing in new business software or switching to a different provider include:

  • Business disruption
  • Potential for technical difficulties or incompatibility with existing systems
  • Upfront costs and long-term expenses
  • Low user adoption rates
  • Loss of data or security breaches
  • Lower-than-promised ROI

These risks make buyers more cautious and require sales professionals to provide solid evidence of the product’s capabilities, track record, and potential impact on the organization. It also means they’ll have to test and prove the product’s value before committing to anything long-term.

Plus, from a sales standpoint, there’s an opportunity cost for every hour of work that goes into the sales process. A complex sale takes a lot more time and effort than standard B2B selling. And since most enterprise sales require a custom solution, it means your team invests significant time and resources into one specific deal instead of working multiple at once.

Requires More Resources

Enterprise software is always resource-intesive to implement. Let’s say you’re switching CRMs. Your immediate resources would be:

  • Downtime for implementation
  • Custom software and features
  • System integration and API development
  • Migration costs (importing data from your old CRM)
  • IT support to get things set up and running
  • Employee onboarding and training

But that’s just the tip of the iceberg. On an ongoing basis, there are maintenance fees, software upgrades, and user support to consider. 

A Trend Toward Self-Service

Arguably the biggest challenge in an enterprise selling environment is the fact that sellers have very little time with their prospects.

In spite of the effort they put forth in each deal, buyers are up to 70% of the way through the entire decision process by the time they talk to a sales rep. Given that the average prospect evaluates 3 to 5 vendors, your sales team has ~5% of the total sales cycle time to influence the buyer in their favor. 

In that time, though? 72% of buyers say they don’t want to talk to a seller at all. So, it’s up to your marketing team to create the content and experiences that nurture them throughout every stage of the sales funnel, from Awareness to Decision. And it’s up to your sales managers to implement sales enablement tools that help your reps share that content throughout the process.

Complex Sales Cycle Stages

1. Discovery

During the discovery stage, you’ll get the lay of the land — everything from their business structure and target market to their current system, pain points, and expectations of a new solution.

This is also the stage where you’ll learn everything you can about internal stakeholders, their motivations, and who has the final say in buying decisions.

  • Will you be speaking to an IT team that troubleshoot the software?
  • Does a procurement team handle negotiations and contracts?
  • Who uses the product every day who could vouch for its value?
  • Who has the power to veto everything (even am otherwise-unanimous decision)?

All this information helps you map out the purchasing process, which makes it easy to guide the sale along. It also helps you tailor yoursales conversations and product demos to different members of the company (and ultimately drive home the benefits that’ll convince them to say “Yes”).

2. Needs Analysis

Once you’re past the discovery phase, you can move on to qualification and diagnosis. This is where you’ll figure out if they’re truly a qualified lead or if you’ll need to pursue other opportunities.

You should already have some insight into their pain points and goals from discovery. Now, it’s time to dive deeper with targeted questions that help you:

  • Understand their current processes and workflows
  • Identify any roadblocks or bottlenecks that prevent them from achieving their goals
  • Uncover specific metrics and indicators they use to measure success
  • Determine which features, services, and integrations are “must-haves” for them (based on their non-negotiables and current system limitations)

Once you know all this, you can put the pieces together. You can pinpoint ways to position your product as the solution to their roadblocks and bottlenecks. The idea here is, if you can get your prospect on board with the idea that failure to act will compromise them in the future, they’ll be more than eager to hear you out.

3. Solution Presentation

At this point, you’re ready to do a full walk-through of your product or service. You can show them how it works and what makes it unique and valuable.

In a B2B selling environment, complex sales demos are generally carried out by a top sales executive or AE.

If you’ve done everything right up until now (asking the right questions, uncovering critical information, figuring out what matters to everyone on the call), you should have no problem giving a demo that hits all the right points.

4. Proposal

This is where you present your initial offer. You might use a generic template, but complex sales generally require more customization and personalization.

The proposal should include:

  • A summary of the prospect’s needs and goals
  • A detailed breakdown of the proposed solution (including costs)
  • Case studies or customer success stories that demonstrate how your product has solved similar problems for other companies in their industry
  • A timeline for implementation and expected results

Depending on the nature of your product or service, you may also include a proof-of-concept or pilot program here to further demonstrate its value and effectiveness.

After a fair deal of negotiation and approvals, the proposal process will eventually end with the key decision-maker signing the dotted line.

5. Product Development

For complex, bespoke, or tailored products, the process will require you to retrofit your product to the client’s needs. You’ll keep the core UI elements and functionality, but you’ll need to change the underlying code to fit with the client’s tech stack and feature requirements.

This includes:

  • Coding and programming
  • Designing custom features
  • Implementing specific integrations
  • User testing and feedback

Depending on the level of customization required, this stage can take anywhere from a few weeks to several months.

6. Implementation

Implementation is the final stage before the sale is complete. It’s where you put your plan into action and get everything set up for your client.

This is also where you’ll be working closely with their IT team, providing support and training to ensure a smooth transition between systems. You’ll need to:

  • Migrate data from old systems
  • Set up all the integrations
  • Train employees on how to use the new product
  • Address any issues or roadblocks that arise

This is a critical stage because if implementation isn’t done correctly, it can negatively impact the client’s experience and perception of your product.

Once the system is fully integrated, post-sale support is passed off to the customer success and service teams.

How CPQ Simplifies Complex Sales

Configure, price, quote (CPQ) software is a sales technology that streamlines the quote-to-cash process by:

  • Automating approval workflows
  • Generating accurate quotes in a few minutes
  • Ensuring pricing consistency across sales channels
  • Using product rules to ensure all configurations are compatible
  • Centralizing proposal/contract, editing, signature, and storage
  • Creating a consistent flow of customer and sales pipeline data with CRM integration

Some CPQ systems even have additional features designed for lengthy, intricate enterprise deals. DealHub CPQ, for instance, has a digital sales room feature called DealRoom, which serves as a virtual meeting and collaboration space for all stakeholders involved in the complex sales process.


What are examples of complex sales?

Here’s a real-wold example of a complex sale:

Let’s say ACME Corp, an enterprise SaaS company, looking for a comprehensive CRM solution to enhance its global sales and customer service operations. ACME Corp’s decision-making process involves multiple departments, including IT, sales, and customer service, each with its own set of requirements for selecting a new system.

They connect with 3 different vendors, who put together custom proposals and give demos tailored to ACME Corp’s specific needs. After several weeks of negotiation and evaluation, ACME Corp ultimately chooses Salesforce because its product aligns best with the company’s goals and offers competitive pricing.

Salesforce goes on to implement the new CRM system for ACME Corp, providing training and support throughout the process to ensure a smooth transition.

What is a simple vs. complex sale?

A simple sale involves a straightforward transaction between a buyer and a seller, usually involving a low-priced product or service. The decision-making process is typically short (if not immediate) and doesn’t require much customization or negotiation.

Complex sales involve multiple stakeholders, lengthy decision-making processes, and high-priced products or services that require customization to fit the buyer’s specific needs. It often involves multiple meetings, negotiation, and approval processes before reaching a final agreement.

CPQ Integrations