The sales process varies greatly depending on the purchase. If you’re selling a cup of coffee, the options are relatively simple. You choose a price based on size, add any extras, and send your customers on their way.
But what happens when the purchase isn’t as straightforward? Take buying a CRM, for example. You can’t just pick it off a menu. You need to evaluate pricing, implementation, features, integrations, and ongoing support. It’s a decision that requires research, deliberation, and often, multiple stakeholders.
This is the nature of complex sales—they demand strategy, patience, and the right tools to navigate the process effectively.
In this article, we’ll explore the challenges of complex sales and the strategies your team can use to close deals more efficiently.
What is considered a complex sale?
Complex sales typically involve high-value products or services, which are often highly customizable. Sometimes called enterprise sales, complex sales generally have a longer sales cycle involving multiple stakeholders and decision-makers.
Complex sales examples
Complex sales are common in SaaS, B2B, and service industries, such as with the following:
- Software with customizations, options, or add-ons
- Financial or consultative services
- Selling products or services to large organizations
What’s the difference between complex and transactional sales?
Because of the hefty price tag, complex sales lead to a longer sales cycle than transactional sales.
Transactional sales typically involve minimal customer relationship development and focus on brief, individual purchases—like movie tickets or coffee.
Complex sales cycle stages
The lengthier sales cycle for complex sales is a direct result of higher costs and greater decision-maker involvement.
Here is an overview of the sales process for complex sales:
- Discovery/needs analysis: Understanding your customers’ needs and challenges is key to demonstrating how your product or service can help. This step is usually a discovery call where a sales rep asks questions to gain more information about the customer’s specific needs. You can also gain more information on their budget and how soon they are looking to implement a solution. Sales pros will also do some market and competitive research at this stage. This stage can involve multiple meetings and additional stakeholders.
- Identifying product/customer fit: Once you’ve learned more about your prospect’s goals, challenges, budget, and timeline, you can use this information to decide if they’re a good fit for your business. This stage is sometimes called qualification and can include different sales frameworks like BANT (Budget, Authority, Need, Timeline) or MEDDIC (Metrics, Economic Buyer, Decision Criteria).
- Customize the solution: You know your prospects’ needs, so now it’s time to put together a package that will work for their needs and budget. This involves tailoring your offer. Product demos, proof of concept (POC), or pilot programs can be helpful to show customers exactly what your product or service can do for them.
- Build relationships: Be available to your prospect and any decision-makers. Answer questions, provide resources, and be available for ongoing communication.
- Objection handling: Customers may have concerns about pricing, competitors, or implementation. Sales reps can address these concerns using data, product comparisons, and customer testimonials.
- Create your sales proposal: Take all the information you have gleaned and draft a sales proposal that outlines the terms and conditions and pricing. This stage often involves legal review and procurement discussions.
- Closing the deal: If the decision-makers accept your proposal, you can finalize the agreement. This can include negotiations, compliance checks, and/or deciding on a timeline for implementation with your customer.
Closing the deal is just one step; ensuring customer success and fostering long-term relationships requires ongoing work.
This includes:
- Regular check-ins and performance reviews to help ensure customer satisfaction.
- Identifying upsell and cross-sell opportunities to drive continued revenue growth.
- Customer advocacy efforts, such as case studies and referrals, to further support business growth.
Complex sales challenges
Complex sales processes present unique challenges due to product/service intricacy, team involvement, and procedural complexities.
Let’s look at the most common challenges sales teams encounter.
Longer sales cycles and multiple stakeholders
Complex sales involve high-priced, tailored solutions with multiple decision-makers.
This leads to a longer sales cycle where prospects must understand the product features and need approval from other members of the organization. This requires patience, persistence, and resources from the sales team to ensure prospects have the information they need to make a decision or communicate with the appropriate team members.
“Hands down, the hardest part of the complex sales process is managing multiple stakeholders,” Katy Drury, Head of Revenue Enablement at Pandadoc, says. “Each individual has their own perspective about what is important to them and goals they want to achieve. This means you will be working with a technical buyer who will handle the implementation, a financial buyer who wants to only know contracting details and the why, and an end user who only cares about the how. In order to really understand a business, you need to understand all of the different lenses of the employees and cater your conversations accordingly.”
Relationship building
Transactional sales may not require extensive communication with customers. But for complex products like software tools, there are many touchpoints along the sales journey. From initial questions and discovery calls to follow-ups and demo calls, sales teams must address buyers’ questions and objections and continue to show how a solution solves problems or adds value.
“Complex sales come with a lengthy sales cycle that stretches over months,” Lev Tretyakov, CEO and head of Sales at Fortador, says. “No matter how long it takes, you need to maintain the prospect’s interest and trust, which is honestly hard. Most sales teams give their best effort only in the beginning, and they lose momentum the longer they wait. Buyers sense this drop in energy, and they start doubting the commitment or value of your solution.
“Keep engaging the prospect. Be their reliable partner more than you are a persistent seller by sharing information that adds value at different touchpoints. Show that you are invested in their success more than you want to close a deal.”
Risk assessment
Because complex sales involve high-priced products that can also affect performance and ROI, buyers can be hesitant to act fast and make a decision.
Salespeople can address this concern by sharing success stories and demonstrating a product’s or service’s return on investment.
Competitor options
Chances are your sales prospect is comparing multiple options. Sales teams must be well-versed in competitor features and how their product compares to similar options or solutions.
Managing complex sales processes
As you can see, there are more steps and intricacies involved in navigating the complex sales process. Luckily, there are various tools teams can use, like CRM platforms and Configure Price Quote (CPQ) software to make this easier and more efficient.
Using a CRM for complex sales
A customer relationship management platform (CRM) helps organizations centralize customer data. This means reps have access to customer contact info, profiles, transaction information and history, and more in a single platform.
Easy data access saves reps time spent searching in multiple locations. They’re also armed with up-to-date information whenever they speak with a prospect, enabling them to provide the best experience and customer service.
How can CPQ software help manage complex sales processes?
CPQ software helps sales teams generate fast, accurate quotes for complex products and services. It helps to automate the quote-building process to eliminate manual work and reduce human error.
CPQ software helps streamline and centralize the quote creation process. You can define pricing rules to help sales reps automatically apply discounts and bundle pricing, a process that can be lengthy and confusing when done manually.
“Fact-checking is the hardest part of all of this,” Katie says. “You have to make sure your math is right on all the line items with discounts and the various pricing models taken into account. When creating enterprise contracts, I have sat down for upwards of 45 minutes just double-checking the math on the many line items. Then, you need to make sure that the numbers are correct and that they follow the rules of your organization. This means it needs to follow the discount policy, have the right approvals, and be compliant with what billing needs to invoice correctly. All of this documentation could live in many, many different places.”
Tools like PandaDoc CPQ offer a number of features to help reps create accurate quotes and get fast approvals to close deals faster.
Key features of CPQ software for complex sales
- Guided selling tools walk reps through the configuration process, taking the guesswork out and helping them select the best products and services for customers’ needs.
- Product configuration allows teams to create bundles and predefined rules to help reps create accurate quotes with options and add-ons.
- Approval workflows allow teams to create rules to trigger the review process, helping to eliminate bottlenecks and stalled deals.
- CRM integration means reps can access customer data without switching platforms. PandaDoc is the only CPQ that offers two-way CRM integration with platforms like HubSpot and Salesforce.
- Reporting and analytics to measure performance and track recipient behavior once a quote is delivered. Analytics tools also help you create dashboards and visuals to demonstrate the ROI of your CPQ tool.
Industries that benefit from CPQ in complex sales
CPQ software is a must-have for any organization that deals with complex, customizable products and services. Because CPQ empowers reps to create error-free quotes regardless of various options or add-ons, CPQ tools are helpful for multiple industries, including:
- Tech/SaaS: Accelerates sales cycles by automating pricing, bundling, and subscription management for software solutions.
- Healthcare: Ensures accurate pricing and compliance with regulations for complex medical equipment and service contracts.
- B2B eCommerce: Streamlines custom pricing and bulk order configurations, improving speed and accuracy in online transactions.
- Financial services: Automates pricing and proposal generation for financial products, reducing errors and enhancing customer trust.
- Manufacturing: Simplifies complex product configurations, ensuring accurate quotes and reducing production delays.
- Supply chain: Improves pricing transparency and contract management, helping businesses optimize costs and supplier relationships.
- Construction: Speeds up bid generation with precise pricing and customization options, reducing errors and project delays.
Winning at complex sales
Complex sales require a different approach than traditional transactional sales. With longer sales cycles, multiple decision-makers, and higher stakes, these deals demand a strategic combination of deep buyer understanding, skilled communication, and the right technology to drive success.
To navigate these challenges effectively, sales teams must focus on relationship-building, patience, and problem-solving rather than just product pitching. Organizations can optimize the sales process and improve win rates by understanding buyer motivations, addressing objections, and using tools like CPQ, CRM, and proposal management software.
Ready to see how PandaDoc can help you win more complex deals? Start your free 14-day trial today!
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