If you’re a B2B company in today’s crowded and ultra-competitive landscape, you’ll know just how challenging it can be to win small and medium clients. Their budget constraints and lack of resources can often become huge hurdles that seem almost impossible to overcome.

Prospecting to large businesses presents an opportunity, as these organizations typically have a clear internal structure and more substantial budgets. Closing deals with them should be more straightforward.
Unfortunately, it isn’t. The enterprise sales cycle is definitely not a walk in the park, but there are ways to become a master at it. Keep reading our guide to find out more.

What is enterprise sales?

Let’s begin with clarifying what “enterprise sales” means. When we talk about the enterprise sales model, we refer to all those processes involved in prospecting and selling products or services to the high-stake and potentially very lucrative world of large, often international, businesses.

Beginning a business partnership with a company like this can mean dealing with complex sales processes and, sometimes, extensive contracts, transactions, and other types of interactions that not all businesses are used to.

This complexity, therefore, also demands a certain level of investment in the right communication channels, sales platforms, staff, and legal expertise.

This is one of the reasons why enterprise sales can become so complicated, especially for smaller businesses.

Nonetheless, when done properly, embracing an enterprise sales model can be a goldmine of opportunities. Some of the benefits that you can expect to gain from a well-thought-out enterprise sales strategy include:

  • Increased profits
  • Enhanced brand image and reputation
  • Profitable long-term relationships with high-profile accounts
  • A sharper competitive edge
  • Boosted industry expertise, credibility, and leadership

7 of the best strategies to nail enterprise sales

With the concept of enterprise sales clarified, let’s take a look at some of the best strategies to master this sales approach.

1. Assemble and train a top-notch team

Before you start targeting your first enterprise account, it’s important to put together an excellent team. Carefully select the best people from a range of different departments and with an array of skills that you know will be crucial throughout the whole process, such as:

  • Sales manager
  • Marketing manager or CMO
  • Service or product designer, depending on the nature of your business
  • PR expert
  • Account manager

Each of these professionals should have some experience with successfully handling larger clients or, at the very minimum, show leadership, communication, and proactive-thinking skills.

Once you’ve assembled your best people, don’t just assume that they’ll automatically do a great job.

Keep mentoring them, training them, and checking in with them to ensure that things are progressing as they should and to answer any questions or clarify any doubts that they may have.

2. Zoom in on your ideal enterprise customers

You know you want to get started with enterprise sales, but you should be crystal clear on who you should be targeting. If not, then this is the right time to sit down and reflect on your ideal enterprise customer.

Just as you’ve probably already done with a smaller-size customer type, you’ll want to create an ideal customer persona (ICP). Only this time, you’ll need to think about the type of business you want to prospect to, not the individual client.

The process is quite similar. Begin by gathering information about your current customers and analyzing what your competitors are doing. Identify which large companies they are forming partnerships with and examine their promotional strategies. By leveraging these insights and learnings, you can tailor them to enhance your offerings and meet your sales goals.

Similarly, you can also benefit from writing down a list of your services and trying to tease out the specific benefits that potential customers could gain from them. Remember to always use the most up-to-date data and try to make your ideal customer profiles as detailed as possible.

3. Identify key stakeholders

Once you know which companies to talk to, it’s time to work out who the right person to approach is. Platforms like LinkedIn offer a great starting point to help you find out the key stakeholders, as do their own websites.

Be aware that there are likely to be multiple stakeholders. For instance, if you’re a SaaS company offering marketing solutions, you’ll need to know who to talk to in marketing and IT.

Once you’ve found the key people to speak to, start making the first contact with them. Don’t begin with a sales pitch straight away.

Instead, try to be as personable as possible and, if they seem interested, offer to arrange a quick video call whenever it’s most convenient for them to go through things in more detail.

Keep track of all your contacts by saving them to your CRM so that you have a secure place to go back to whenever you want to check your progress.

4. Be patient and keep communicating

One of the most challenging aspects of enterprise sales is the amount of time it can often take before you finally close that hard-won deal.

Smaller businesses can have things done in a matter of weeks, but with enterprises, it can take months. Don’t let this put you off, though; see it just as part and parcel of playing the long game with a client who could potentially stick around for many years to come and lift your profits, too.

While you’ll want to keep track of how things are progressing, don’t harass them with daily or even weekly emails or messages.

Check in with the key people every couple of weeks, and keep your communications short and sweet. Remember, you’re likely dealing with extremely busy people whose time is often limited.

5. Leverage best-in-class enterprise sales tools

Enterprise sales require enterprise-grade tools to be handled in the best possible way. So, once you’ve started the process, it’s worth taking a look at your current tech stack and finding out whether the tools you’re using are up to scratch.

At the very minimum, you’ll want to use the following:

If you can’t afford every single one of these, focus on the CRM and a communications platform to start with.

These solutions are vital to helping your sales team manage and monitor all customer-related and sales-related activities by providing a safe, reliable, and easily accessible way to get the information they need when they need it.

6. Fine-tune interactions to meet expectations

Finally, you’ve reached the stage you’d been working toward for so long; you’ve scheduled a meeting with a key person at one of the enterprise accounts that you’ve been targeting for months. It all sounds promising, but this isn’t the time to rest on your laurels.

Instead, focus on fine-tuning your interactions with those stakeholders in order to make the right impression and win that sought-after account.

Leverage the customer data in your CRM to work out, for example, the most productive time and channel to contact one of the key stakeholders that you’re communicating with.

Make sure you understand exactly what problem your target has that your offering can solve—the more specific answers you can provide as to why they should choose you, the better. You may even want to offer custom solutions tailored to each enterprise client.

7. Keep tracking, measuring, and reviewing

Just as you’ll be doing with your CPM (corporate performance management), you should be keeping a close eye on the progress you’re making with your enterprise sales process.

Establish a few sales metrics and key performance indicators, such as client retention, win rate, and deal progress speed, to figure out how your enterprise sales team is doing.

Whenever you spot anything that’s not working as well as you’d like, take the time to point it out to the relevant people and, if needed, run some ad-hoc training sessions.

When your team successfully closes a deal more efficiently than anticipated, it is important to analyze the entire sales process in detail. Identify the elements that contributed to that success and determine which practices can be replicated in the future. Recognize the team members who demonstrated exceptional skills during the project and consider how the lessons learned can be integrated into the overall process.

Wrapping up

Boosting productivity and revenue by following an enterprise sales model is possible, but you need a well-thought-out plan to achieve that.

By following the steps outlined in this guide, you’ll be well on your way to mastering the often long and tricky game that is the enterprise sales cycle.

FAQs

What does “enterprise sales” mean?

Enterprise sales is a sales approach that involves prospecting and, ultimately, selling to large accounts. An enterprise is a business that has a large workforce, multiple departments, and significant resources. They often, but not always, operate internationally.

What are the best enterprise sales strategies?

Some of the best strategies to master enterprise sales include assembling a great team, leveraging the right technology, fine-tuning your communications, assessing your performance regularly, and understanding who your ideal enterprise customers are.

It’s important to play the long game, as enterprise sales deals often take months, if not years, to be sealed.

Originally published Aug 18, 2025