Sales · · 10 min read

The Only Enterprise Sales Guide You Need Bookmarked

With scale comes complexity. To succeed in enterprise sales, you need to develop unique systems, understand risks, and follow best practices.

enterprise sales

Enterprise sales are where ideas meet analysis, capital, and execution. The best part is you get to sell these ideas to players in the big league.

Stakes are high, and rightfully so. One good sale can strap a rocket to your business to get you to infinity and beyond.

But, before aiming for the stars, you need to stay grounded, lay the foundations, and navigate the complex ebbs and flows of the market.

In this article, we’ll be running through enterprise sales 101:

  • The basics of enterprise sales.
  • Why enterprise sales are important.
  • Common challenges and how to overcome them.
  • Understanding risks.
  • How to succeed in enterprise sales.
  • Best practices.

The Basics of Enterprise Sales

Enterprise is more than just demonstrating value. It’s about scaling and the complexities that go with it. Expect longer cycles, multi-year contracts, and sales emails to several stakeholders.

The emphasis won’t be on the product because any sale can be enterprise if it’s big enough or needs more complex integration.

It’s a massive investment for both you and your customers. Before closing a sale, you’ll be pitted against competitors through several rounds of bidding.

Multiple departments get a say in the choice. Decision makers, end-users, and executives all share their thoughts. That means your sales pitch needs to be flexible.

The Importance of Enterprise Sales

If you want to scale your business, go for smaller fish but get them en masse. Or go for the bluefin tunas of sales—enterprise. Choosing the latter provides you with:

Better Credibility

Landing a deal with clients like HP, Dell, or Netflix puts you on the map. Optics, or how the industry perceives your business plays a huge role in your future success.

It’s like getting the blue Twitter verification check (pre-Elon, of course). But that doesn’t mean you need to go for the big dogs and the Fortune 500s.

There are tons of emerging businesses in tech, finance, and even supply chain management to consider. Strategize which leads to go for and prepare a solid sales or marketing campaign.

Better Customer-base

Quality over quantity is the name of the game. For example, bidding for a contract in a Fortune 500 company might take months or even a year to close.

With a large enough sales team, you could probably go for a few more leads. But, you don’t want to spread yourselves too thin and go for a hundred other accounts.

Once you’ve managed to land a deal in enterprise, your business opens itself to an entirely new market. Converting a few cold sales into a closed deal a year still gets you high-value recurring revenue.

Recurring Revenue

Remember, sales cycles last longer in enterprise sales. Landing a deal means you’re product’s been vetted by major decision-makers. This translates to your product staying for the long haul.

But, your product or services need to provide critical solutions that are essential to the success of a large company. This could be anything from new blockchain technology to email solutions.

Common Challenges of Enterprise Sales

enterprise sales challenges

Enterprise sales demand more complex sales processes. You’d need more touchpoints, better strategies, and tighter execution.

It’ll be a long and winding road. And throughout the enterprise sales journey, you’d often face the following hurdles:

Longer Sales Cycles

Enterprise sales include critical business-defining transactions. There’s a direct correlation between the length of the cycle and the complexity and price of the solution you’re offering.

These longer cycles tend to overlap, which could result in foggy forecasting. Monthly or even quarterly quotas become harder to predict and manage.

But, once a deal is closed, it could be the start of a solid partnership. This is when nurturing comes in. We’d be playing the long game, but it’ll be the one generating the highest revenue.

Custom Solutions

If you’re in SaaS, you’ve noticed that most pricing tiers include a basic plan for small businesses, premium plans for those wanting to scale, and enterprise plans with no pricing.

That’s because most enterprise customers would need custom solutions to unique problems. Products have to be flexible enough to provide these solutions at scale.

This is where most start-ups face their first hurdle. Thriving in this industry requires solid technical skills, ingenuity, and understanding of a customer’s needs and getting it for them.

Multiple Shareholders

Too many cooks can spoil the broth. In enterprise sales, there are going to be a lot of cooks—in this case, decision-makers and stakeholders.

A company can have multiple tech experts, financial officers, managers, and of course, end users. It’ll come down to a multitude of opinions coming from all directions.

Each stakeholder has their own metrics or buying criteria. This ultimately slows down the sales process, but it ensures you’re product or services are vetted for successful deliveries.

Complicated Contracts

Unfortunately, closing an enterprise sales deal isn’t as simple as a handshake. Contracts are extremely detailed and dense. The larger the deal, the more complicated the contracts.

In most cases, an experienced sales lead is required to navigate these papers. However, the best-case scenario is to have an experienced lawyer help with the contract.

This way, you won’t have to spend unnecessary time going through countless pages. The important thing is understanding what the customers want and what your business wants.

Higher Risks

The bigger the risk, the larger the payouts. But you’re running a business—not gambling. What you need to do is take calculated and intentional risks throughout the sales process.

A single misstep or miscommunication can cause months of work to go down the drain. To close the deal, businesses need their products to be solid, integrations have to be airtight, and the sales team needs to be trained in all the technicalities that come with the product.

Understanding Risks

Even after landing a deal with revenue coming in, there are still potential risks that can lead to a death spiral. You don’t want to go unprepared.

Luckily, most of these risks are avoidable through data-driven strategies. Here are the top five risks enterprise sales teams need to consider, assess, and prepare for:

Delayed Revenue

Long sales cycles ultimately mean delayed revenue. It can take a toll on your sales team’s mental. Make sure the working environment stays positive and optimistic. Trust the process.

On the same note, delayed revenues mean managers need to assess cash flow. Your business needs to stay afloat between deals.

Are there other sources of revenue? How will your businesses pay for overhead? These are just some of the questions you need to answer if you’re in the enterprise industry.

Sales Underperformance

Missing quotas is common in the world of sales. Forbes says more than half of the people in the industry miss annual quotas. With delayed revenue between deals, your business needs life.

The common issue is sales personnel being unaware of potential customers or opportunities that can build cash flow during downtimes.

But, focusing too much on finding alternative revenue streams can spread you too thin. That’s why you’d need streamlined strategies like email marketing or social media to help find revenue.

Unoptimized Sales Process

Enterprise sales are complex as it is. Without an optimized sales process supporting it, you’re not doing anyone any favors.

Every step of the cycle needs to be airtight. In Enterprise sales, everything’s scaled up to eleven. Hundreds of salespeople are fighting for the same contract.

When stepping inside the ring, make sure you’ve got all the tools needed to make the process smooth. This could be the deciding factor that separates you from the competition.

Heated Negotiations

Things would be easier if you were just talking to a single decision-maker. This won’t be the case for enterprise sales. It’ll take multiple touchpoints, several email nurtures, and calls.

There will be cases where parties don’t find a good compromise. You can easily find yourself talking to people who’ve made million-dollar purchases.

Your leads can walk away at any time because of any reason. Saying enterprise sales is a difficult negotiating environment would be an understatement.

As always, keep a level head. If you’ve got a system, stick with it.


One of the biggest issues of working with a longer sales cycle is being consistent. Things could be sailing smoothly, then all of a sudden, hit a storm in the middle of the sea.

Being in an enterprise means being in an industry where negotiations are easily swayed by the tides of the market.

There are so many variables to keep track of and unpredictable events. It’s important to stay calm and logical.

How to Build A System to Succeed in Enterprise Sales

enterprise sales startegy

You want to be able to ride the waves of the market. But, what you don’t want is to be swallowed whole by these waves. This can easily happen without a system in place for your sales funnels.

Having a system or sales strategy can help your business weather any storm. And the foundations of most systems or strategies revolve around four basic principles:


The first principle is all about gathering information. Understand your business and product’s strengths and weaknesses and assess how it fares with competition in the market.

Then, look into your prospects. Before even sending cold emails, gather as much information as possible to make your outreach campaigns as personalized as they can be.

These go beyond your typical “pain points”. Each lead has its own specific set of issues. The best way to understand them is through a combination of communication and research.


After doing your due diligence with research, you’d need to have consistent communication with your leads to truly understand their problems.

This is where email nurturing and lead qualifications come in. As mentioned earlier, you need to talk to several decision-makers in a company before your product is even considered.

Higher-ups probably want to hear about how your product can help reduce costs and increase revenue. End-users might care more about how it can streamline and optimize their work.


With consistent communication, you can work with your customer to create truly tailor-fitted solutions for their problems on a larger scale.

There might be cases where your product needs to be integrated into a company’s existing software. Security should also be enterprise-level and compliant with the company’s policies.

Here, you might want to have your development team and sales team work together to deliver the best solution to your customer.


The result of any enterprise sales will be the culmination of ideas, analysis, and execution to deliver the end product to your customer.

After working closely with your customer and developing tailored solutions to their unique pain points, it’s time for implementation and closing the deal.

This doesn’t mean we’re done and dusted. After closing a sale, one of the most important things to consider is aftercare. Great customer support is a big factor in securing recurring sales.

Enterprise Sales Best Practices

With a system in place, you’ve laid the foundations to help you traverse the world of enterprise sales. But, to ensure consistency in your system, you’d need the following best practices:

Define Objective

Before sending your cold sales emails, talk with your team about your objectives. Create outlines of what you want to achieve and set up ways to track them.

For example, during lead generation through email outreach campaigns, use an email tool with intuitive analytics. Compare campaigns, and see what works and what doesn’t.

If you’re not sure what to go for in terms of goal setting, you can try using the SMART method. It helps you identify goals that are specific, measurable, achievable, relevant, and time-bound.

Identify Key Decision Makers

An enterprise company has a lot of moving parts. Each one would have its own head honcho. These are the people you want to find. Do in-depth research and create strategies for each.

An email with a pitch for the head of operations won’t be that effective for the head of finance. But, you wouldn’t want to create every email manually. This could take hours.

What you want is a set of email templates for each key player that you can personalize. It will still take time to perfect each draft. On the upside, you’d still have a great outline to work with.

Qualify and Verify Leads

Lead qualification is important in any type of sales, and it’s only further emphasized in enterprise sales. You’ll be reaching out to large companies, each being a sizable payday if a deal closes.

But, enterprise sales isn’t a sprint. It’s a marathon. The starting line starts with how you source and qualify your leads. Research and personalization go deep in enterprise, and you don’t want to waste time and resources on leads that aren’t qualified.

More importantly, you need to email validation to ensure that you’re sending emails to an actual person. Without verifying, you could get stuck sending emails to an invalid address.

Create a Structured Sales Process

Having a structured sales process provides you with a repeatable and measurable system. If you’ve laid a solid foundation for your system, then all you have to do is “trust the process.”

But, this doesn’t mean that it’s plug-and-play for every customer. You should always stay dynamic and respond to unexpected events, such as objections.

To help you in creating your own structured sales process, here are seven steps you should consider including in your cycle:

  • Prospecting
  • Preparation
  • Approach
  • Presentation
  • Handling objections
  • Closing
  • Follow-up

Studies from TAS Group suggest that 70% of companies following a structured sales process are high sales performers. Those who follow the process also have a 28% boost in revenue.

Ensure Clear and Consistent Communication

Stay consistent in every step of the sales process (and there are a lot of steps). Strategize the next steps you should take and forecast how you’ll follow up. This will be easier with the help of a structured sales process.

To make things easier for both you and the customer, ask what their preferred method of communication would be. Some prefer communicating through Slack; others might want a Zoom meeting or a simple email.

As a rule of thumb, avoid being too focused on making a sale. These meetings should be about building relationships. People in enterprises are already used to hundreds of sales pitches. Take the meetings as an opportunity to talk about things they find interesting that aren’t about work.

Key Takeaways

If you want to scale operations, enterprise sales is where you’d want to be. The risks are high, but the rewards are even higher. You gain access to better-quality customers, have higher recurring revenue and a single closed deal from a big name puts you on the map. But, to ensure success in this competitive landscape, remember the following:

  • The fundamentals of any solid enterprise sales system include discovery, diagnosis, development, and delivery.
  • Risks such as delayed revenue, sales underperformance, unoptimized sales processes, and heated negotiations are common in enterprise sales.
  • The best way to find quality leads in enterprise sales is through enterprise-ready CRM and marketing tools.

If you want to connect your business with the right people, you need an enterprise-ready email marketing tool like Instantly to streamline and optimize the process. Start for free now!

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