Breaking into enterprise sales: how to close $100k+ deals

Posted August 20, 2019

By Audrey Weber

Associate Content Editor at Outreach

Barbara Weaver Smith is a modern-day Captain Ahab, but instead of hunting sea mammals, she trains thousands of people from small and midsize companies to scout, hunt, and harvest whale-sized sales deals. After more than a decade of experience, Barbara knows that the enterprise sales process is an entirely different beast when compared to SMB.

Enterprise sales — or complex sales — involves intricate sales cycles and comparatively large deal sizes, typically ranging north of $50,000. Deals that are 10x to 20x the size of your current average deal size are called whales, and pursuing these deals is known as whale hunting.

It's not easy, but it can be done. Based on current literature as well as on our experience at Outreach and those of our customers and partners, here is what you need to know about enterprise sales - plus some tips and tricks - so you can be like Barbara.

Enterprise Sales: The Basics

Enterprise sales refers to a type of selling environment with the following key characteristics:

  1. Target customers are large organizations.
  2. Purchases, contracts, or subscriptions depend on multiple decision makers, usually in excess of six business leaders with different priorities, inhibitions, and personalities.
  3. Sales cycles (from initial contact to contract signing) take longer to complete, sometimes involving more than 12 months of strategic nurturing. In contrast, B2C sales and selling to SMBs can come to a conclusion within a matter of days.
  4. Average deal size is large, with six-figure deals being fairly common.
  5. Sophisticated and well-informed, enterprise buyers control the dynamic and usually send RFPs (requests for proposals) to several competing vendors.
  6. Products and services need to have adequate flexibility for hyper customizations to meet unique customer needs and preferences.

What Makes an Effective Enterprise Sales Rep

As expected, complex sales calls for sellers with particular skills.

The products and services they sell require substantial investment — as well as risk — on the part of corporate buyers. A hole in such an investment (e.g., failure to achieve expected ROI or transformational change) will send shockwaves of disappointment and mistrust across both buyer and seller.

To prevent a serious mismatch between solution and customer, enterprise sellers shed their role as conventional salespeople and genuinely assume the functions of a trusted adviser instead. Doing so entails domain mastery, business acumen, empathy, and relationship-building skills.

Enterprise sellers seek a full understanding of customers’ pain points, buying process, and growth potential. Because they know which solutions will actually solve a client's problems, successful enterprise sellers will rarely sell their product to a prospect that has little need of it — even when the company is willing to buy. On the other hand, excellent enterprise sales professionals will negotiate strongly on behalf of their company — refraining from granting too many concessions — when there’s an excellent product-fit.

Because they expect to engage multiple influencers per target account, complex sales professionals also adopt different approaches and messaging for each decision maker. They appreciate the priorities of each influencer and drive tailored conversations around those priorities. When engaging CFOs for example, enterprise sellers will likely highlight the features of the solution that improve P/L, or the elements that make up an attractive ROI. Engaging a CTO on the other hand, they may discuss third-party integrations, security, and regulatory compliance.

Finally, keeping all decision makers on one page requires collaboration and consensus building. And because complex sales involves longer sales cycles, enterprise sellers need patience and time management skills to successfully nurture prospects over long periods of time.

How To Close Those $100K+ Deals

Enterprise sales delivers the biggest deals. But it also requires the most powerful playbooks. In enterprise selling, you shape your process, product, and people according to the buyer’s needs and aspirations, not the other way around. From sales development to customer success, each stage of the enterprise sales process needs to be calibrated and continually optimized over time.

However, everything starts with the right attitude. As entrepreneur and sales veteran Amy Volas wrote, your mindset matters. That’s because enterprise selling takes much longer to close and entails higher-quality touchpoints with multiple decision makers. Making things even more difficult, there’s always the chance that, at the end of the line, it just might not be a good fit after all.

Just imagine how you would feel if the prospect company declined your proposal after 10 months of careful nurturing and endless hours of tailoring your approach for eight stakeholders with diverse personalities and expectations. Without the right mindset and patience, such an episode could discourage your reps from attempting selling to an enterprise again.

High performers across industries will tell you that there’s a system to success. Sure, talent and training are important. But data, metrics, and testing also play crucial roles in driving business outcomes. By streamlining your workflows and using the right tech, you allow science to automate complex sales, making success easier to achieve.

In today’s tech landscape, that translates to allowing automation, machine learning, natural language processing, and other forms of artificial intelligence to do the heavy lifting so your team can provide authentic human touches at points of engagement where empathy and personalization make a huge difference.

Here are some tactical tips that can help you close high-value deals faster:
  • Accurately define your ideal enterprise customer. Mold your prospecting and sales development process around that profile.
  • Treat prospects as as a market of one. Enterprise-scale customers respond best to the ABS (account-based selling) treatment because of their sheer size and lifecycle value. That means equipping your account executives (AEs) with best-in-class insight, resources, and tools for engaging this elite segment of the B2B market.
  • Embrace technology to augment human talent. In addition to CRMs and marketing automation, Sales Engagement Platforms (SEPs) such as Outreach can help sales teams spur more meaningful conversations and book more meetings.
  • Document the setbacks and successes of your customers as they deploy your solutions. Create and curate cases studies not only to help with product development and improvement, but also to showcase success stories. Connect prospects with relevant case studies that involve pain points and situations that are very similar to their own.
  • Enter the sales floor as an adviser, not as a seller. Stop thinking about making the sale. Instead, focus on making the customer happy. Prioritize customer success, not quota attainment.

Outreach customers can also build effective sequences for enterprise executives. These sequences involve:

  • More touchpoints than SMB (10 to 18 steps over the course of 60 days)
  • Omnichannel coverage (email, phone calls, social messaging, SMS texts, events, etc.)
  • A high degree of personalization

It takes a lot to succeed in enterprise sales, but when you do, the effort is well worth it. While customer acquisition costs might be steep in terms of time and resources, the returns are compelling over the long run. After all, enterprises account for the heftiest contracts in your portfolio. Which means more enterprise sales will propel your revenue performance even further.

The most important thing to remember, however, is that enterprise sales functions primarily on relationships. Build trust and everything else follows. The more enterprises trust you, the more willing they are to keep you in business.


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