Enterprise Sales Guide: Process, Sales Cycle, Strategies & More

Enterprise Sales Guide: Process, Sales Cycle, Strategies & More

Selling enterprise-level, high-value contracts can take months of negotiation. Unless you’re very lucky, your sales team likely has varying levels of experience, and some may lack the complex sales expertise necessary to close the deal.

Still, even if your business is still in startup mode, it’s more than possible to aim for the big fish—and this guide will show you how.

What is Enterprise Sales?

Enterprise sales refers to the sales process used to sell products or services to large companies. It typically involves large contracts, long sales cycles, and multiple decision makers.

In enterprise sales, a salesperson will often arrange product demos for different stakeholders within the prospect company, interview decision makers to understand their pain points, and develop solutions in a more consultative role.

The unique strategies and requirements of enterprise sales mean larger investment from the seller, and therefore represent a higher risk than standard sales–but also a higher reward when large contracts are signed.

The Difference Between SMB Sales and the Enterprise Sales Process

The core differences between small- to mid-size business (SMB) sales and enterprise sales can be simplified into three main points: time, money, and complexity. Enterprise sales requires more time and money than SMB sales and involves more complex offerings.

For example, a small business may sign up for Microsoft 365 and work with a sales rep to arrange onboarding and training with their six employees over a week or so. They are more likely to be satisfied with the standard out-of-the-box product and standard support offering.

Enterprise solutions typically require implementation across an entire department or organization. Let’s say Disney decides to move their email platform to Microsoft 365. They can’t just sign up on the website and launch the new platform.

They might need to integrate new security measures such as single sign-on (SSO), adjust the settings to fit their needs, and then roll out proper training before launching the new platform. It’s a complicated process that requires a hands-on approach and additional support.

SMB sales vs enterprise sales process

The standard prospect requires less research and due diligence compared to a complex product that will impact an entire organization. SMB sales tends to be more transactional and requires significantly less rapport than more strategic sales at the enterprise level. This is because the investment is much greater, the salesperson will handle more questions, sales objections, and custom details.

Why are Enterprise Deals So Important?

Enterprise deals can do a lot for a company—starting with the large amounts of revenue they generate per transaction. So, what other benefits do enterprise deals get your company? Lots.

Build Custom Features Other Customer Will Love (and Pay For)

Enterprise sales often involves custom integrations or features. You may find yourself with one client paying for the development of a new feature for your product. That’s a win!

Create a Repeatable Sales Process

Once you’ve gone through the enterprise sales process once, you’ll develop a roadmap you can follow with similar enterprise clients. You’ve also built some brand credibility with world-class clients.

Remember the example of the Disney email migration above? Once you’ve closed the deal and completed implementation for them, you can use that information to sell your SaaS email services to Netflix. Another win!

Grow Your Network

You’ll meet several people during the enterprise sales process. Connect with them on LinkedIn and allow social network algorithms to start populating second- and third-level connections. This will help you generate even more qualified leads—especially if you interview your contact and tag them in a case study on the success of your product implementation.

9 Sales Strategy Tips for Enterprise Sales

Due to the size of the deals, it’s essential that your enterprise sales representatives and account executives be your most skilled. This team should have a deep understanding of your product, its capabilities and limitations, and a realistic vision of what it can deliver for an enterprise client.

Whether your sales management plan is to take existing salespeople and put them into enterprise sales roles or onboarding experienced enterprise salespeople from outside your organization, your enterprise sales team should have a deep understanding of these fundamentals.

1. Find the Right Prospects

Your product or service isn’t right for everyone—but it is right for some people. To find your ideal customers, you have to know where to look.

If your company hasn’t already developed an ideal customer profile for potential customers, do that first. Decide if your product is best-fit for wide scale use (like Microsoft Office), or if it’s more of a niche product (like managing pavilion rentals in the Parks & Recreation industry). Seek out your personal connections and do research for new connections in your ideal industries, and talk to them about their thoughts on your product to get insight. LinkedIn can be a great source for enterprise leads.

Remember, the enterprise sales cycle is longer than SMB, so make sure you spend more time ensuring the leads you target are a good fit for your brand. While not every lead will convert, focusing on qualifying leads can improve your chances.

2. Expect Long Sales Cycles

Enterprise sales can take 6 to 18 months to close. During these longer sales cycles, you’ll want to remember two things:

  • There will be periods of intense work on the project where it feels like you’re working 40+ hours a week on one deal.
  • There will be periods when your work on the deal is minimal, for example while you wait to get in touch with an executive or the prospect considers their options internally.

Because of these factors, it’s important to have multiple sales in the works. This will keep you (or your reps) active at all times, and will keep deals coming in throughout the year, rather than one or two large deals once or twice a year.

Due to the long sales cycle, it's also important to follow up and keep the deal moving forward. In Close, you can create an automated email sequence to keep in touch with leads while providing a more natural experience.

3. Identify Key Stakeholders & Decision Makers

Identify Key Stakeholders & Decision Makers in Enterprise Sales

As we shared in our 7 Essential Startup Rules for Successful Enterprise Sales list, “No matter how high up the person you're selling to, you need to sell to different groups of people within the enterprise, up and down the hierarchy, vertically as well as horizontally.”

The CEO might love your product and sign off on buying it, but if you’re not working with the IT department on implementation, the end users who will need to understand the ins and outs of day-to-day use, managers who will want to learn how to use reporting features, financial analysts who will want to see the return on investment figures, etc., you may lose the customer.

Establish good rapport with these corporate influencers within the company and when appropriate, connect people at your company to people at your prospects that share similar job titles. Having your CIO contact their CIO allows for important networking and helps establish trust a little faster.

4. Look for Problems You Can Solve

As companies grow, their problems grow, too. The pain points a smaller company experiences are important, because the company is doing its best to establish a secure foundation and stand out among their competition. But once an organization becomes a big name in its industry, it likely begins facing much bigger issues.

So, how do you help? The good news is your prospects likely know their problems, and are willing to share that information in the hopes that you have a solution. And you do— so sell it to them!

As a good sales representative, you know clients buy solutions. Frame your pitch around outcomes and tell stories about how their product solved other companies’ similar issues. Keep your conversations focused on the many ways your product will overcome their obstacles and make them more successful.

Looking for problems to solve doesn’t end after you close the deal. Make sure to follow up with your contact over the next few months or even years to see if they need additional solutions. You might sell them an upgraded package—or start developing a new solution all your customers will love.

5. Follow Up (Even More Than Normal)

From initial contact to onboarding, keeping your brand top of mind is important. We only have so much short-term memory, so regular check-ins, a good email series, and strategically timed touch points should be built into your sales methodology.

A good CRM system can automate much of these processes, and help schedule check-in phone calls or alert you when it’s time to send a handwritten note, so you can stand out from what everyone else is doing.

How often should you follow up with an enterprise customer? It depends on your past interactions. If your customer sounded ready to convert, then you’ll want to follow up with them pretty regularly. If you were in the early stages of the sales process, you might want to spread your follow up messages out a bit more.

7. Don’t Get Discouraged if a Deal Doesn’t Happen

Enterprise sales is hard work, and lost deals can seem crushing. But don’t let it get you down. You can only control your own actions—and a prospect’s decision to “go in a different direction” or change their mind isn’t in your hands.

Stay resolute and optimistic, knowing that you’ve asked the right questions and done your best to show your prospect everything your platform can do for them.

Don’t Get Discouraged if an Enterprise Deal Doesn’t Happen

This optimism can actually help you. It’ll motivate you to stay in touch every six months or so, just checking in with your prospect to hear how their chosen solution is working out. Be happy for them, but be present in case their solution falls through. You may just get that sale yet!

If sales continually fall through, however, it might be time to revisit your ideal customer persona or schedule a sales training to brush up on your skills.

8. Celebrate Key Milestones With New Enterprise Customers

Enterprise client onboarding is certainly a huge milestone for you and your company, and having a celebration can be a great way to reward all the hard work that everyone put into the process.

Involving the client can have big benefits, too. You want enterprise client executives to become advocates for your company, refer you to others, provide a glowing testimonial or case study–so include them in the celebrations. This can serve as the start of establishing a long-term relationship that results in mutual benefits.

Keep building that relationship by celebrating milestones with your solution, such as reaching 80 percent adoption rate, reaching a specific revenue, or meeting some other goal you’ve helped them reach.

9. Monitor Client Success With Regular Touch Points

Your work isn’t over once you’ve sold the deal and onboarded your client. Now comes the client success part of the job.

Some organizations transition clients to an account manager to oversee client success, but it’s still helpful for the original sales rep to check in every once in a while. After all, you’ve built so much rapport throughout the sales process, don’t let it all go now!

Monitoring client success is as important as any other aspect of the enterprise deal. It allows you to check in, find out what solutions they need help implementing, and share features they may not be taking advantage of. Providing a little extra guidance every now and then can help your client take full advantage of your platform, and keep them from looking elsewhere.

Monitor Enterprise Client Success With Regular Touch Points

Staying in touch also has the added benefit of uncovering fantastic success stories you can use as social proof in your next enterprise sale.

Grow Your Business by Breaking into Enterprise Deals

The enterprise sales process is long. There’s a lot of touchpoints, communicating with various stakeholders, presentations showing different aspects of your product–and so many client end goals to keep track of.

But even if you're just starting to break into the world of Enterprise deals, you can still win at this type of sale.

And when you do, it'll help grow your business faster than you might expect.

Want to learn more about breaking into enterprise? Get our exclusive guide to enterprise sales: