Enterprise sales: 7 strategies for closing complex deals

Posted April 2, 2024

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By Serena Miller

Editor, Sales Best Practices at Outreach

Every organization dreams of the opportunity to secure the largest deals — those that lead to long-lasting financial gains and a significant reputational boost. Closing a monumental contract is tangible proof of your company's success, quickly boosting brand recognition and market reach. Of course, bigger deals involve more complexity. 

Winning enterprise deals demands a deep understanding of industry dynamics, the right personnel, and a well-crafted sales strategy. But when done right, enterprise sales partnerships can foster long-term growth and position your company as an industry authority.

If your organization is interested in navigating more complex deals, read on for an in-depth guide to the unique challenges of enterprise sales and how to overcome them.

Report: Outreach gets to the heart of today’s enterprise buyer preferences

Expect more interactions, larger buying committees, and longer deal cycles. Learn how changing buying behaviors impact your enterprise sales team.

7 actionable enterprise sales strategies

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Enterprise sales strategies, involve all decision-makers in the sales process
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Successfully pursuing enterprise sales at your organization hinges on adopting and employing strategies that address the unique needs of large companies. These are seven enterprise sales best practices that can help any sales team close the most complex and valuable deals they encounter.

Consider this as a starting framework, but remember, real mastery in enterprise sales comes from hands-on experience and a deeper, ongoing engagement with each concept.

1. Focus on customer relationships

Strong customer relationships are at the core of any successful enterprise sales process. Sales personnel should adopt a consultative approach dedicated to creating personalized and informative interactions. Eighty percent of respondents in a recent Outreach survey said they would be more likely to purchase a product or service with a consultative sales experience. 

To present themselves as consultants effectively, reps should come prepared with relevant data points, be ready to answer questions in real-time, and expertly guide buyers through the intricate buying process. In turn, your company should invest in training its sales team on both the details of clients' industries and your organization’s own offerings. When implemented well, this strategy positions your sales professionals as valued advisors, building trust and fostering a sense of collaboration and partnership.

2. Provide tailored solutions

If an organization is going to spend a significant amount of their budget on your solution — and the time and effort required to adopt it — they’ll expect to receive something tailored to their needs. 

Sales reps should work to develop a deep understanding of each enterprise-level client to customize your organization’s offerings to align with their specific challenges and goals. This might translate to building new processes or incorporating custom features that cater specifically to the requirements of enterprise accounts. 

Your organization should build flexibility into product development processes so it can swiftly respond to custom requests. By accommodating custom requests and crafting solutions that address the issues faced by large organizations, businesses enhance the perceived value of their offerings and position themselves as flexible and proactive partners.

3. Identify and cultivate the right prospects

As the size of the deal grows, the pool of potential customers shrinks, so identifying and cultivating the right prospects during the enterprise sales process is critical. This relies on a comprehensive understanding of your organization’s target audience. And it also requires a sales team dedicated to nurturing relationships with individuals at those organizations that align with your buyer personas.

Enterprise buyers now commonly bring multiple decision-makers into the sales process while expecting your sales reps to provide frequent opportunities for touching base. This often leads to a more drawn out sales cycle and means that sales professionals should leverage a variety of communication channels to stay connected as leads advance through the pipeline. By investing time and resources in understanding and cultivating the right prospects through a consistent, personalized outreach strategy, organizations position themselves to successfully navigate extended sales cycles and evolving buyer preferences.

4. Involve all decision-makers in the sales process

The companies targeted during the enterprise sales process usually have multiple levels of decision-makers that sales personnel need to win over. Seventy-six percent of buyers say that their CFOs and financial teams are now more involved in the sales process, while 74% say the same about procurement. 

Connecting with multiple decision-makers, also referred to as multi-threading, requires sales teams to identify the stakeholders who have real decision-making authority and engage them throughout the sales cycle. Your organization should also involve its own executive team in the sales process when appropriate to demonstrate commitment and ensure your leadership is aligned with the client's goals.

5. Equip your sales team with compelling case studies and success stories

Closing enterprise-level deals requires persuasive evidence in the form of case studies that potential clients can relate to. Compelling case studies bolster the credibility of your company by providing tangible evidence of the value and impact of its solutions. Building and communicating these success stories is a collaborative effort between marketing and sales

These teams should regularly update case studies on the company website, incorporate them into sales presentations, and maintain internal customer reference lists for sales personnel to leverage. This approach ensures that the sales team is well-equipped to illustrate the practical benefits of your organization’s offerings in a way that resonates with potential clients.

6. Develop a successful enterprise sales team

Building a sales team equipped to close large-scale deals encompasses strategic hiring, comprehensive training, and establishing the right roles. Your company should recruit individuals with a strong understanding of the enterprise sales landscape and a proven track record of closing the largest deals. Then invest in that talent by providing training opportunities tailored to addressing the challenges posed by major clients.

Specialized roles, like enterprise sales managers, solution architects, and account executives, can also play a crucial role in navigating the complexities of large deals. As your enterprise sales endeavors progress, collect and analyze key metrics, such as win rate and customer acquisition cost (CAC), and fine-tune your sales strategies to keep your sales team on track for success at the enterprise level. 

7. Adopt a enterprise sales platform

Finally, the complexity of enterprise sales demands a platform with features that go beyond those of a traditional customer relationship management (CRM) system. Your organization should conduct thorough research to identify an enterprise sales platform that aligns with its needs and goals. 

Look for a solution that leverages the capabilities of modern AI, acts as a centralized hub for managing deals, and automates outreach, and tracks engagement across the entire sales pipeline. It should also provide sales teams with real-time analytics that make it easy for them to continually optimize their approach for each client. Ensure that the platform integrates with your organization’s existing systems and provide onboarding support for the entire sales team during the implementation process.

Watch the replay: Enterprise executive roundtable

We've assembled an all-star lineup of enterprise sales, marketing, and customer success leaders. Together, they share the insights and best practices they use to lead their organizations and what they're prioritizing in today's market.

Succeed in enterprise sales with Outreach

If your organization wants to drive revenue using enterprise sales, it first needs to empower its sales team with a platform designed to help them execute at the highest level. Outreach is a sales execution platform dedicated to unlocking seller productivity and closing the most valuable sales opportunities. 

It includes everything needed to design, measure, and improve sales workflows in a single platform, from pipeline management and sales forecasting to rep coaching and AI-powered conversation intelligence. Outreach gives every member of your sales team, from leadership on down, the tools and insights needed to increase deal velocity and close more pipeline.

Request a demo and discover how Outreach can elevate your company’s enterprise sales strategy.


Enterprise sales FAQ

What is enterprise sales?

Enterprise sales is a strategic approach to selling focused on the demands of large organizations. Also called complex sales (yes, really), it requires significant effort together with a deep understanding of the needs and internal dynamics of the target organization. 

Enterprise sales aren’t transactional: they involve real relationship-building, forging connections with key decision-makers, and aligning offerings with the client’s strategic objectives. 

Take a software company looking to secure a contract with a large organization to provide a business intelligence (BI) solution. In an enterprise sales scenario, the sales team would engage with a range of stakeholders, like members of the procurement department, with IT leaders, other department heads, and potentially C-level executives. 

The negotiation process might extend over several weeks or months, involving detailed presentations, a thorough exploration of how the software aligns with the enterprise's overarching goals, and discussions on how to customize it to better meet those objectives. This demonstrates the focus on long-term relationship-building inherent in enterprise sales, where success relies on understanding and catering to the diverse needs of multiple decision-makers.

Enterprise sales vs. self-service, SMB, and mid-market sales

Enterprise sales aren’t the be-all, end-all when it comes to driving revenue for most organizations. Most companies also rely on self-service, small and mid-sized business (SMB), and mid-market sales, all of which require different mindsets and distinct strategies.

Self-service sales

Self-service sales are characterized by high volume, quick transactions, and customers who can guide themselves through the purchasing journey. Organizations must provide customers with a streamlined and user-friendly experience that helps them navigate through the sales process independently. Products and services that rely on self-service models are typically standardized and target customers who have little need for customization.

Self-service sales are well-suited to play a complementary role within your organization’s sales strategy. By allowing customers to initiate and complete transactions independently, self-service models free up resources that can be directed toward more complex sales endeavors.

SMB and mid-market sales

Mid-market sales — also referred to as SMB sales — are positioned between the size and complexity of enterprise sales and the simplicity of self-service models, with significant variability in client requirements and organizational structures. SMB-focused sales teams must be able to customize their offerings to meet the specific needs of clients while still efficiently navigating the sales process. Mid-market sales serve as an opportunity for businesses to establish meaningful relationships with a wide range of companies, gain additional experience for their sales and fulfillment teams, and better prepare for enterprise-level sales.

Why focus on enterprise sales?

The risks and challenges that come with enterprise sales are justified by the substantial rewards these deals offer. Pursuing enterprise sales can change an organization's trajectory, providing long-term financial gains and other benefits that contribute to sustained growth and industry prominence. Enterprise-level clients have a higher lifetime value (LTV), which translates into extended and lucrative partnerships. 

These enduring relationships result in a continuous revenue stream over the course of the partnership, making the initial investment of time and resources in enterprise sales particularly rewarding over the long term. Successful enterprise sales also help businesses to tap into new, more expansive markets, broadening their customer base. In short, enterprise sales can position your company as a key player and influencer within its industry, fostering a strong network that leads to future opportunities your organization would otherwise miss out on.


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