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Everything You Need to Know about Enterprise Sales Strategy

Everything You Need to Know about Enterprise Sales Strategy

Chetna Sabharwal
Chetna Sabharwal
December 9, 2022
5 min read

Picture this: Between five customers who bring in $10 dollar profit each and a single customer who can bring in $50, which would you choose?

Eeny, meeny, miny, moe

On the face of it, they may appear to be no different. But when you think about it, you realize that dealing with multiple customers means that you incur higher overheads. It's also more work, more stress, and more frustration. You are dealing with 5 different pain points compared to the second choice. Moreover, customer retention and repeat sales are easier to implement when you are dealing with a single customer.

As your business grows, it is more profitable to turn to big buyers and go for enterprise-level deals. It lays the foundation for solid revenue and recurring profits. 

What is enterprise sales? 

Enterprise sales is defined as selling to large companies as opposed to sales made to small businesses or individuals. 

Dealing with large companies involves long-term contracts and bigger revenue impacts. It also comes with its challenges, like longer sales cycles. Salespeople need to get hold of top decision-makers. Even when you finally get through to decision-makers, you might be up against several competing bids before you close a deal. 

Catching a big fish is never easy. 

Unlike transactional sales, the enterprise sales model is fairly complex, to the point that it is also called complex sales.

Why pursue enterprise sales? 

An enterprise sales strategy helps you establish your credibility in a market because you ride on the credibility of the big players by virtue of closing deals with them and becoming their partners. The fact that you’re in business with big players makes you appear more attractive to small businesses and other potential customers.

Enterprise companies also have the potential to deliver higher revenue per deal. Moreover, deals are often signed for multiple years (or renewed with ease), which means you can often rely on recurring revenue. Additionally, if you incorporate other sales strategies with enterprise companies, like cross-selling and upselling, you are able to easily grow your revenue with comparatively fewer resources spent.  

Despite their many positives, enterprise deals represent a challenge for sales reps. Enterprise sales involves long periods of discussion and evaluation. Because the sales cycles are long-winded, there’s a tremendous opportunity for the lead to go cold. Complex sales are complex indeed. 

SourceIt’s called complex sales for a reason!

However, although enterprise sales cycles are longer, the time you spend battling the lead’s objections actually gives you a chance to build a lasting and recurring relationship. Think of it as a bond-building exercise. 

Complex sales model vs. other sales models

Does enterprise selling work for all companies? Will enterprise sales work for you? 

That’s a fair question. Whether you opt for enterprise sales or another sales model depends on your company size and the revenue it generates.

For example, if your business is small and still growing and you do not yet have the manpower to service large corporations, then SMB sales might be more suitable for you. Or you might need to approach enterprise sales with the support of channel partners. Go through our guide on channel sales to evaluate if it will work for you.

The bottom line is: Before you pursue enterprise sales, you need to ask yourself if you can do justice to the enterprise you are looking to bring on board as a customer. If not, you risk ruining your reputation. Wait till you are ready to do it right. 

Here are two types of sales models that are comparable with enterprise sales 

Enterprise sales vs. self-service sales

Use this sales strategy if: You are selling a low-cost product with low customer acquisition costs. 

Why it works: 

  • Your business sells a high volume of goods. 
  • The transaction process is faster.
  • Buyers enjoy a quick, convenient platform where they can sign-up and buy without having to talk to anyone (yes, that’s a factor for lots of people). 

It only works if: 

  • Your sales process is linear and straightforward.
  • Salespeople and the customer support team aren’t very heavily involved in ensuring a good customer experience. 
You don’t always have to reinvent the wheel

Enterprise sales vs. SMB sales

Use this sales strategy if: Your product solves a common problem in the market and caters to small or medium-sized businesses who want an immediate solution.

Why it works 

  • There are fewer gatekeepers standing between you, and the decision-maker.
  • Fewer stakeholders could lead to shorter sales cycles.

It only works if:

  • Your product is affordable to SMBs.
  • You can reach a high enough volume to meet your revenue goals.

How to create a successful enterprise sales strategy?

Understand the enterprise’s business

Sales reps also have to be great business analysts. The enterprise customer may be telling you about the pain points but might be overlooking the underlying causes. 

Delving deep into the enterprise customer’s pain points will help you deliver goal-oriented solutions that actually work. 

This guy knows the drill, and he’s totally diggin’ it!

Identify the stakeholders and vendor process 

At an enterprise level, there is often no single decision-maker for purchase approvals. In most cases, the approvals travel up the pecking order and also typically follow a prescribed process. Find out what you’re dealing with early on in the sales cycle. 

Explain your pricing and payment model

You don’t want things to fall apart after you finally obtain a positive purchase decision simply because of your pricing model. That would be a tremendous waste of your time and also the prospect’s time (which might mean they never open a door for you again). Be upfront and detailed, especially if you have complex or rigid pricing and payment models. 

Imagine you’re talking to Michael Scott.

Ask for feedback 

If the deal doesn’t go through, there are other enterprises for you to pursue. But what should you do differently? Ask for feedback so you can do better next time or maybe even turn things around in your favor this time around. For instance, maybe your point didn’t come across, and the client is still confused. Or perhaps they have doubts which should be addressed or taken up in a separate meeting. 

Send out summaries

It’s not just sales reps who need to remember the key points of a pitch discussion. You need to keep your product and the discussion fresh in the enterprise customer’s mind. They should be able to recall key points at a glance. An email after the discussion can also keep the two of you on the same page and drive progress according to plan.

Do your homework

Go over prior conversations before follow-up calls. Be sure to refresh the enterprise customer’s memory about how your product is helping them. Repeat points of agreement from your earlier interactions with them. Conversation intelligence can help you do this right.

Have your answers ready 

Decision-makers at corporations are looking at a handful of factors before signing up for your product. Go into your pitch calls and subsequent calls ready with your answers on these points. 

Here are five questions you must have answers ready for: 

What's your value proposition? 

What superpowers will your enterprise customers get after the purchase? Your value proposition should stress tangible, measurable solutions to pain points instead of product features. How is your SaaS product making their lives better?

Here’s a checklist for your value proposition:

  • It should resonate with the enterprise customer and help them achieve their goals.
  • There should be a differentiating factor that sets you apart from your competitor. 
  • Substantiate your value proposition with past clients and testimonials.

Whom do I contact for after-sales service/ what level of service will I get? 

Always have ready information about what happens after your customer comes on board. Get the contact information of colleagues who will take the baton from you once the deal is made. Some prospects might feel more confident about service if you offer to stay available to them in case of any challenges. You should be able to gauge the lead’s sentiments by this stage since you have been talking to them and negotiating with them through the sales process. If they need to feel like you’ll hold their hand through the process, offer to stay in the loop. 

Show them that you care. 

What if we're not happy with the results? 

This is a tricky one – your lead wants assurance that your solution will perform as promised, but they also want assurance that they can exit the deal if they are unhappy. 

A free demo can help your lead explore your solution’s benefits before they are tied in with a contract. You can also be flexible with your first subscription period, to allow the lead to develop trust and confidence hands-on. 

Can we speak to other enterprise customers to verify your claims? 

It’s expected for the enterprise customer to ask for references. A long list of client testimonials should be a ready part of your sales arsenal. You might not be able to bridge actual conversations with other enterprise customers since you’re dealing with busy people. However, you can drop names of happy customers, or better still – to maintain complete control – you can share client testimonials with your enterprise prospect. 

Make a big deal of every deal with Wingman 

Handling enterprise sales processes can be tricky. If you’re feeling like David before Goliath, Wingman can be your magical, giant-in-the-bag sling. 

Wingman helping you take home your enterprise-level deal

Wingman is an AI-powered conversation intelligence platform that helps sales teams win whether they are pitching to a small, medium, or large company. It gives you live, on-call cues on opportunities to cross-sell, upsell, battle competitor mentions or respond to a pain point. Metrics around call volumes and call success ratios help sales leaders to personalize coaching. Real-time at-risk deal alerts help you to save high-stakes deals in time. 

Wingman also delivers AI-powered automated notes, call recordings, summaries, and transcripts to help sales reps recap prior conversations. 

Wingman delivers convenience it integrates seamlessly with other platforms like Salesforce, Slack, CRM, and other business tools to achieve high efficiency on a sales call. 

Increase your B2B sales with Wingman. Want to learn how? Book a free demo today!

Real-time sales coaching software that helps your team win deals with confidence

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