The art of selling a $1 million software contract to an organization is a completely different ball game from selling a $120 annual subscription to one person.
Known as enterprise software sales, or complex sales, the selling cycle can last months. It involves building relationships with prospects and tailoring solutions to address their specific problems and needs.
While it’s not as quick as selling a lower-priced personal subscription, the benefits can be huge. High-value deals with large organizations let your company lock in multiple-year contracts, larger deal size and higher revenue.
In this article, we’ll answer what enterprise software sales is, how it’s sold and how it’s different from traditional sales.
Key takeaways from enterprise software sales
Enterprise software sales involves long deal cycles with multiple decision-makers and tailored solutions, setting it apart from self-service or transactional sales.
The same four-step playbook holds across most enterprise deals: target realistic buyers, reach the actual decision-maker, prove value at scale, and close with onboarding that protects the contract.
Choose a sales methodology that fits the prospect: SPIN works for consultative discovery, Challenger for entrenched thinking, and Consultative for relationship-led repeat business.
A sales-first CRM gives enterprise reps the structure to manage long cycles, multiple stakeholders and confident forecasting.
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What is enterprise sales (and how do sales processes differ)?
Enterprise sales refers to the sale of a high-value product or service to an organization, often involving customization and tailored onboarding.
In enterprise software sales, this typically includes software as a service (SaaS) tools designed to streamline workflows, integrate with existing tech stacks and scale to meet the needs of large teams or entire organizations.
The enterprise sales process is usually long, taking weeks or months across multiple decision-makers, and reps spend much of that time working to build relationships with each enterprise account. Mid-market deals follow a similar shape on a smaller timeline.
The selling process is quite different from small business sales or B2C transactions. It can also be riskier because if the deal falls through, sales representatives have potentially put weeks of effort into a deal without any reward.
However, the upside for enterprise sales is that B2B sales organizations can close large, lucrative contracts with clients and feel more secure with annual and multi-year contracts.
The key difference in enterprise sales is complexity
Buying a personal subscription is usually simple: you select your plan, enter your details and get instant access.
Compared to software aimed at a single person or small to medium-sized businesses (SMB), enterprise software is often more complex. Usually, this is because it must be customized to suit a company’s unique needs.
At this level, prospects usually need extra support and persuasion to close the deal. Therefore, software sales are often managed by sales executives (sometimes account executives) who know the product inside and out (especially with technical products).
Software sales usually happen in one of three ways: self-service, transactional or enterprise sales. Here’s how each works:
Software sales model | How it works |
Self-service model | When a customer completes the sale on their own, they’re following the self-service model. They pick a product or plan that suits them, pay for it using the payment platform and onboard themselves using knowledge bases, tutorials and product documentation. |
Transactional sales model | When a prospect self-selects a tool but still requires some help from sales or customer support with implementation and onboarding, it’s called transactional sales. This type of sale usually happens when products have a higher price point or can’t be used straight out of the box. |
Enterprise sales model | Enterprise sales requires a more hands-on approach for the sale and organization-wide adoption to be successful. The company buying the product will need more training and help in integrating it into their existing tech stack. |
As Gartner highlights, the enterprise sales process involves several steps, like live demos, ROI calculations, vendor onboarding and customized deal structure, before a contract is signed.
This complexity sets enterprise sales deals apart from the rest, but it’s also what makes them the most profitable.
How enterprise sales can be used to close more OEM deals
In enterprise sales, software isn’t always sold to the end-user. Other software companies might also be prospects.
OEM, or original equipment manufacturer software, is when a software company licenses its product to another company so it can embed it in its application.
For example, software companies building a CRM platform might want to include functionality that isn’t feasible to build from scratch, such as document creation or one-touch video call integration.
If that technology already exists in the market, the CRM software company might consider licensing it instead.
The end-user can then benefit from having all their needs met in one tool, even though some of those needs are met by another technology company.
OEM deals are just as complex as a standard B2B enterprise deal, so the closing process is just as high-stakes.
What is enterprise software?
Enterprise software refers to a category of computer applications specifically designed to meet the complex needs of large organizations or enterprises.
It typically encompasses a range of integrated software solutions that facilitate various business processes and operations, such as:
Customer relationship management (CRM) – e.g., sales software
Enterprise resource planning (ERP)
Supply chain management (SCM)
Human resources management (HRM)
Enterprise software is known for its scalability, robustness and ability to handle high volumes of data and transactions.
It is typically tailored to meet the specific requirements and workflows of an organization, helping to streamline operations and enable better decision-making.
For example, some enterprises will choose cloud-based sales software for its flexibility, while others prefer on-site infrastructure to meet specific industry regulations.
How to sell enterprise software in 4 steps
Enterprise deals are complex, but your sales professionals can navigate the sales cycle much better with a well-thought-out sales strategy in place.
Follow these four steps to start selling at the enterprise level.
1. Find realistic buyers in your targeting pool
Because salespeople might dedicate weeks or months to a sale, it’s worth nailing down the basics. Help each one of your reps use their time as wisely as possible by targeting the most realistic buyers.
Gartner outlines the “Enterprise persona”, which focuses on four key areas: firmographics, demand drivers, technology environment and the decision process.
The firmographics are organization basics, such as the size of their company and the industry they’re in. This is important because startups with investors can view purchase decisions differently from public companies, for example.
The demand drivers are the forces driving change in software, like shifting regulations or competitive pressures.
The technology environment involves getting an overview of their current technology landscape, including legacy technology and preferred vendors.
The decision process involves identifying the key decision-makers are in the organization and whether it needs to go through several people before getting the green light.
To pinpoint your sales efforts, identify these details about your ideal customers and match your prospecting list to this buyer persona accordingly. This is key to improving your win rate, but also helps long-term customer success – it’s how you’ll grow retention.
Then you’ll need to dig into the needs and buying process of enterprise buyers. Try to uncover as much information as you can about the following to get a deep understanding:
Their drive. How will your software help the prospect meet their technology goals? Is the prospect driven by business goals or a desire to improve their tech stack?
Their buying cycle. Are they ready to buy now? How long does the company normally take to make a buying decision? How do they budget and plan for new software implementation?
Their motivation. Why do they want to buy your product? What is their need to purchase new technology? Is their current software outdated? How will your product help them?
After asking these questions, you should have a good idea about what a realistic enterprise customer looks like.
For example, a prospect looking to update their existing tech stack may do so because they feel pressure to keep up with competitors. However, it might be because it will help them win new business opportunities.
Identifying the driving force behind your target’s buying decisions is valuable for both sales and marketing.
Once you know what your target enterprise customer looks like and you understand their motivations, it’s time to find them.
You can start by searching sites where ideal prospects hang out, like LinkedIn (over 62% of B2B buyers respond to sales reps that reach out with relevant insights and opportunities).
Alternatively, try a prospecting tool to narrow down the right people to talk to.
Pipedrive’s Prospector, part of the four-piece LeadBooster add-on, collects high-quality data that matches your ideal customer parameters, such as job title, company size, location and industry.
With this information, your sales reps can plan outreach to potential customers around the drivers from your enterprise persona research, using sales tools that keep teams on track to hit targets.
2. Target the decision-maker
Don’t just reach out to anyone at the company you’re targeting. Contact someone who makes these types of decisions and has access to company funds.
Targeting decision-makers early in the selling process can save you time talking to gatekeepers and others who don’t have any say in the company’s tools and software.
Employing the MEDDIC lead qualification methodology can help here. The methodology encourages sales reps to take an upfront approach to prospects and ask qualifying questions like:
“How does your organization typically make buying decisions?”
“Is anyone else involved in the buying process?”
“What’s your role in the decision-making process?”
The answers to these questions will tell you if you’re talking to the right person or if you need to escalate the conversation to a decision-maker.
Once you’ve started a conversation with the decision-maker, it’s time to take them down the customer journey that convinces them to invest.
Keeping every stakeholder visible in your sales pipeline stops deals from stalling between handoffs.
3. Nail the enterprise customer journey
Enterprise customers are harder to close than others because enterprise software is usually a big investment.
Changing software can require budget, time, resources and external support, like change management professionals who support tech adoption.
To win the deal, you’ll need to convince the decision-maker that it’s worth it.
On this, CEO and founder of GoodData, Roman Stanek, explained:
So, what does it take to address an enterprise prospect’s concerns?
First, approach them with a value proposition that you believe will significantly help their company.
Starting a meaningful conversation with an enterprise prospect hinges on their understanding exactly what your product will do and how much it’ll help their organization in daily work life, like productivity, profitability or another benefit.
Once you’ve communicated your product’s value, focus on three actions:
1. Give examples of value-added scenarios | Show the prospect how your product has benefited similar customers and explain how it’ll help them achieve their goals if they use it. Give them real-life examples that show how your software solved a specific problem or helped an existing customer grow. |
2. Prove that your software is enterprise material | Enterprise companies are often looking for ways to expand and scale. Show your prospect that your enterprise software can grow with their existing tech stack and is secure and reliable enough to handle enterprise-level pressure (e.g., high volumes or multinational data sets). |
3. Play the long game | Enterprise deals aren’t closed overnight, so don’t try to force it or you’ll risk losing your prospect. Get comfortable with the long sales cycle at the enterprise level and pencil in regular (but not too regular) follow-ups. |
When your prospect is ready to take the plunge and buy your product, the final step is closing the deal.
4. Close the deal
Closing an enterprise software sale involves more than signing a contract and releasing login details.
It’s crucial that every new enterprise customer feels supported during the onboarding and deployment phase after the deal is done.
Enterprise software can take several weeks to implement, so it’s important that your company supports the new customer at every step.
If you don’t, users might struggle to understand your software or use it regularly. They might even decide not to continue your deal in the future, especially if they never get it off the ground.
When the ink on your new customer’s contract is signed, that doesn’t mean your work is over. Enterprise customers pay top dollar for customized products and experiences, and during the closing phase of the deal, that value needs to be delivered.
Note: Pipedrive offers personalized onboarding resources across all pricing plans, with dedicated implementation and phone support on higher tiers.
Sales strategies to use on enterprise deals
You don’t have to reinvent the wheel to be successful at enterprise software sales.
Here are three sales strategies to use when trying to close bigger deals.
1. SPIN Selling
SPIN selling is a strategy in which sales reps build a relationship with a prospect to tailor a solution that matches the prospect's problem.
The methodology centers on a four-part questioning framework:
Situation. Asking about a prospect’s processes, tools, objectives and responsibilities, so sales reps can learn about their goals.
Problem. Asking about the prospect’s challenges to build a solution around individual needs.
Implication. Asking about the problems uncovered in the previous step to help understand how they negatively affect their company. These questions reframe the size of the problem and increase the sense of urgency in solving it.
Need. Asking about potential solutions your prospect has already come across and introducing your company’s enterprise software solution.
Reps should ask situational “SPIN” questions to guide their prospects through the sales funnel rather than following a rigid script, making it a good strategy for individual enterprise prospects.
You should choose the sales strategy that best suits your enterprise prospects and your sales team. Here are some pros and cons to consider about the SPIN method:
Want to know more? Read more about how SPIN Selling can be used .
2. Challenger selling
The Challenger sales model is a sales process that focuses on taking control of the sales experience by addressing a prospect’s individual problems.
This method empowers sales reps to intentionally dispute their prospect’s way of thinking and forces them to contemplate a new perspective.
When the sales rep creates tension, it opens the door to a casual debate with the prospect, encouraging them to consider new opportunities and an alternative way forward.
Once that alternative way forward has been created, sales reps can introduce their company’s enterprise software as a uniquely positioned solution to solve the prospect’s problem.
Here are some pros and cons to consider about the Challenger selling strategy:
Want to know more? Read about how Challenger selling can be used in more detail.
3. Consultative selling
Consultative selling is when sales reps put the customer relationship above their desire to promote or sell a product.
This may seem counterintuitive, but poor customer relationships are among the biggest drivers of churn. Companies are at risk of joining this statistic if they only focus on closing deals and not solving a prospect’s problem.
The consultative selling approach focuses on your customer, their needs and their biggest pain points before you even think about offering up a product or service as a solution.
Taking the time to build trust with your customers helps you close deals and win repeat business, even if it might take a little longer than other sales methods.
Unlike other sales strategies, Consultative selling encourages enterprise customers to look past your product’s price tag and focus on its value-add.
Here are some differences between product-based selling and Consultative selling:
The right approach depends on your prospect, but in enterprise sales, leading with value almost always wins.
How enterprise software is changing the way we sell
Enterprise sales reps now have technology like AI at their fingertips to empower their selling process.
AI is especially impactful in SaaS enterprise sales, where predictive analytics and automation tools can help identify prospects’ pain points and provide personalized recommendations in real time.
This new technology has the potential to identify whether a prospect is interested, assess emotions and changes in speech patterns and determine whether a sales pitch is hitting home with the decision-makers in the room.
As venture capitalist Asheem Chandna explains in Forbes, this kind of enterprise tech sales advancement could soon be used to analyze whether a selling strategy is persuasive enough, even when sales reps are pitching over video.
“Using predictive algorithms, a sales team could access insights in real-time, allowing them to adjust their arguments on the fly or recognize more quickly when a sale can’t be closed,” he says.
"Technology could be developed to identify the ‘champion’ in the virtual room along with the skeptic – letting the salesperson focus their argument on the right person on a multi-person conference call.”
AI is now also helping mentor sales reps.
For example, Pipedrive’s Notifications analyzes a rep's past sales performance and suggests new ways to improve results.
It also uses an algorithm to scan what activities and actions each sales rep spends their time on and looks at whether or not they’re focusing on working on low-value deals while more valuable ones go untouched.
Free enterprise software trials are also helping us learn about our target audience and teaching us how to sell better.
In the past, customers had to sign lengthy deals to test out complex enterprise products. Not anymore.More software vendors are now offering free enterprise trials to prospects so they can try before they buy.
Trials provide companies with valuable information about what tools enterprise customers prefer, how easy the software is to use for new users and if it lacks certain features they require.
This shifts the burden away from what was traditionally required of sales reps.
In the past, sales reps would outline the benefits of enterprise software in a live demo to a prospect, but they could not try it out themselves until they signed a hefty contract.
Now, potential customers can try out the software, and during their trial, sales reps can jump in, communicate directly with them and resolve any issues to increase their likelihood of purchasing the software once their trial period is over.
By replacing in-person demos and visits with free software trials, enterprise sellers are getting the best of both worlds: showing prospects how great their product is while simultaneously collecting data worth its weight in gold.
Final thoughts
Enterprise software sales isn’t like other types of sales. It’s riskier, it requires your sales reps to put in more time and effort and your team needs to be in it for the long haul to be successful.
The rewards can be huge. By customizing your sales techniques to solve each prospect’s problems and building meaningful relationships with them, enterprise software sales can be incredibly lucrative for any software company.
Ready to manage complex deals with more confidence? Try Pipedrive free for 14 days and see how it handles long cycles, multiple stakeholders and enterprise-level forecasting.
