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 experience levels, 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.

  • Time: Small businesses are more likely to close deals within a few weeks, with a more transactional sales model. An enterprise company may take several months or even up to a year to close a deal.
  • Money: Marketing and selling to enterprise companies requires an investment on your part. Since enterprise sales cycles are longer, you’ll be paying for your reps to spend more time with these potential customers. Plus, customer success teams will spend more time onboarding and helping these customers become successful with your product.
  • Complexity: A small business is likely to be happy with an out-of-the-box solution on a standard pricing plan with basic customer support. The deals close quickly, with little internal fuss. An enterprise customer, on the other hand, needs customized touchpoints at every step of the buyer journey. They’ll be required to complete due diligence, run contracts past their legal team, and more. Once the deal is done, enterprise customers will likely require deep customization to fit your solution into their workflow and team. Both the sales team and customer success team will need to work out custom onboarding, training, integrations, and more.

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.

Curious minds, this way! Learn all about challenger selling and its impact.

What Does a Typical Enterprise Sales Cycle Look Like?

Of course, no two enterprises are exactly alike, meaning the way you sell to them may be completely different. That said, In a typical B2B sales setting, this is what an enterprise sales cycle might look like:

Prospecting and Discovery

Like any other sales cycle, you need to discover new sales opportunities and decide whether these businesses are a good fit for your sales.

A sales or business development team may do this before the deal is qualified and passed to an account executive.

Multiple Meetings with Internal Champions and Stakeholders

Internal champions are essential to closing deals, and they can help you get on the good side of stakeholders and decision-makers within the company.

In this stage of the enterprise sales cycle, the goal is to build customer relationships that could last a long time. Sales professionals working on enterprise deals need to understand very clearly the pain points and problems that their prospect is looking to solve and have a very clear answer to how their product solves that problem.

Under the direction of a sales leader or sales director, the sales team will craft a customized sales pitch that might be delivered multiple times in different meetings with stakeholders. They’ll also assemble a product demonstration or any other materials that might be needed to show they’re ready to close this deal successfully.


The negotiation stage can be brutal in enterprise sales since there are often too many cooks in the kitchen and no shortage of opinions being thrown out.

Sales reps working on enterprise deals need to know how to keep the deal moving forward and may enlist the help of a sales executive from their company to do so.

Proposal and Contract Delivery

This stage will also last longer for enterprise deals than in a traditional B2B sales process. First, the sales team will need to put together a proposal or contract. Then, stakeholders will review it and likely revise it. Your team will need to approve the revisions and send the document back again.

Using online documentation tools will help smooth out this process, but it will still take some time.

Review with the Customer’s Legal and Technical Teams

Multiple rounds of reviews may be necessary to keep all the teams happy. For example, tech teams inside your prospect’s company may need to see specific technical requirements of your product to fit it into the current setup. The legal team may want to adjust some of the wording in your contract.

To speed things up, you may try using a mutual action plan early on in the deal, and get everyone on the same page with the tasks that need to be done, and who is in charge of completing them.

Final Close and Onboarding

Once the deal is finally closed, your work isn’t over. The account executive working with this customer now needs to help with onboarding and settling them with the customer success team. This is a vitally important part of the deal because the customer's first steps in your product will make or break that relationship moving forward.

Why are Enterprise Deals so Important?

Enterprise deals can do a lot for a company—starting with the large 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 populate second- and third-level connections. This will help you generate even more qualified leads, especially if you interview your contacts 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, your enterprise sales representatives and account executives must be your most skilled. This team should deeply understand your product, its capabilities and limitations, and a realistic vision of what it can deliver for an enterprise client.

Whether your sales management plan involves putting existing salespeople 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 and recreation industry).

Seek out your personal connections and research new connections in your ideal industries. Talk to them about their thoughts on your product to gain insight. LinkedIn can be a great source for enterprise leads.

‎Remember, the enterprise sales cycle is longer than SMB, so spend more time ensuring your target leads fit your brand well. 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 speak with an executive or the prospect considers their options internally.

Because of these factors, having multiple sales in the works is essential. This will keep you (or your reps) active at all times and 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.

Pro tip: In Close, you can create an automated email workflow to keep in touch with leads while providing a more natural experience.



3. Identify Key Stakeholders & Decision Makers

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 and horizontally.

The CEO might love your product and sign off on buying it. Still, 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 who 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 essential 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 that 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. 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 in mind is essential. We only have so much short-term memory, so regular check-ins, a good email series, and strategically timed touchpoints should be built into your sales methodology.

A good CRM system can automate many 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 customers sound ready to convert, you’ll want to follow up with them regularly. If you were in the early stages of the sales process, you might want to spread your follow-up messages 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 prospects everything your platform can do for them.

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

If sales continually fall through, however, it might be time to revisit your ideal customer persona or schedule 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 celebrating it can be a great way to reward the hard work 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, and 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 an 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 occasionally. 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 extra guidance every now and then can help your clients take full advantage of your platform and keep them from looking elsewhere.

Staying in touch also adds the 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 are many 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 starting to break into Enterprise deals, you can still win at this type of sale.

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

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

Table of Contents
Share this article