How to Win Bigger Sales Deals 

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Table of Contents

Every sales rep and manager wants to land bigger deals. With all of the effort, decision-making, skill, and energy that goes into winning a deal – why not win a big one? Working a complex deal can be a daunting task. But, with the right tools, roadmap, and persistence, you can start closing bigger deals.

What it takes to win bigger deals

There are a different set of nuances, strategy, and a higher level of patience that goes into winning a big deal. Typically, the larger the deal size, the longer it will take to close. Also, bigger deals mean that your prospect will have to make a bigger decision for his or her company. Most likely they will need to bring in others on the deal and/or get approval from different departments.

You’ll have to do additional discovery and fact-finding, analyzing customer pain points, and proving the value of your solution to multiple stakeholders in your prospect’s company. This can lead to several perceived problems, slowdowns, or setbacks along the way that you’ll need to address before you win the deal.

The strategies that will lead to larger customers

If you don’t build a solid foundation from the beginning, large deals will slip through your fingers. You have to make sure that you’re targeting the right accounts and speaking to quality prospects. 

Big deals don’t always start with large contract values. You must also understand how to grow a deal once you’ve penetrated an account. Lastly, you’ll want to understand the value that you and your company can bring to the table and how to show that value to your prospect.

Are You Targeting the Right Customer?

There are so many different types of customers, and anyone who has created customer profiles knows this to be true. So how do you know if you are targeting the right customer? What makes the “right” customer?

Loyal customers spend 67% more, on average than new customers. Why does this matter? It indicates that the “right” customer, the one you should be targeting with your marketing strategy, is the loyal customer. 

New customers are important to your business, sure, but if you are focusing too heavily on acquiring new customers you will miss out on quality customers who can bring your company more profits. 

Customer quality is vitally important

Now, that doesn’t mean you should only focus on the loyal customers you already have. You still have to acquire new customers but the key is to acquire better quality customers who will become loyal.

What is a quality prospect? 

First, you need to figure out what a quality prospect is. Think about a current customer that brings your company value. Consider what it is about that customer that makes them valuable to your business, whether it’s the demographic information or other characteristics that enhance their appeal.

Quality is going to be defined as something different to each business which is why it’s important that you consider the unique nuances of your business when building this profile.

Having a quality target customer in mind will help you allocate resources to that type of customer and create messaging that caters to their needs. Remember that what counts is loyalty so in the end the quality prospect that you are appealing to should be one that remains loyal and one that comes back time and time again spending more money than their counterparts.

These loyal customers expect to be rewarded with the same level of service every time they return but they also expect to be rewarded for simply returning in the first place and that can mean loyalty points, loyalty programs, discounts on products, punch cards that give them something free after every 10 purchases, or other extras.

How to find them

So how do you find them now that you know what they look like? Market research and in-depth quantitative information can go a long way. You can do things as quickly and as easily as sending surveys to existing customers, looking at US Census Bureau information about your target audience, or researching data from third-party firms.

Your market research might require interviews with current customers and perhaps qualitative studies on how your quality customers in that target demographic feel about your current business as well as your products and services.

Key strategies:

Referral. If you can get a referral, it will tremendously increase your chances of a meeting

Research. Due your diligence researching about the prospect before you make your initial contact.

Introduction. Try to get introduced before you make a business approach.

Connect. Once the initial contact has been made, leverage a social platform such as LinkedIn or Twitter to establish a deeper connection.

During all this, you might find that certain products or services appeal to one group and not another. This is why it’s important to segment your market based on things like buying habits, ethnographic, psychographics, and demographics.

How to Boost Deal Size 

With the right customers in mind, it’s time to start selling. After making eight or more touches to get an initial meeting, and several more touch-points to create a qualified opportunity, sellers may get impatient once they get to the proposal phase.

However, during the proposal phase sales reps need to take their time especially when it comes to bigger contracts.

Offer Something Unique

If you want to boost your deal size, you need to focus on creating obvious upsells. You didn’t go through all that work to figure out your quality target customer and use market research to better understand what it is they love for nothing. This is the point at which you use that information to introduce a product that you know they’ll love, add some sort of complimentary service that you know will offer value.

Remember that you need to be flexible here. Offer your client something that’s customized for what they will find most appealing and most rewarding because there is no single product that’s going to work as the perfect upsell for everyone. You might need to offer a full-service solution, an extra product, or premium (exclusive) content.

Move Beyond Low Priced Packages 

In many cases, smart customers will try to hedge their bets by investing in your lowest tier product. This reduces any risk if they aren’t satisfied or they don’t end up using your solution. They can explore how your products or services work without committing to a large contract.

This logic can cause a problem if your solution provides higher value through a network effect or if the customer would benefit from economies of scale.

Consider a scenario in the telecommunications industry. If your reps are trying to sell to a company and one person says they’ll consider licensing the lowest tier products, right out of the gate this could negatively impact the results they see because your communications tool might work better if everyone in the organization is using it and not just a few people.

In situations like these, team plans or higher tier plans will give the customer better opportunities to gain more value from your product. This is what you want to emphasize and explain during the proposal stage.

You also want to explain that as time moves on prices will most likely increase but if customers want a long-term commitment now, maybe something for 2 years or longer, they can get preferred rates and protection against future price hikes. You might even make this slightly more appealing by giving them one or two months for free if they agree to a long term commitment.

Give Extras

Don’t forget defined areas where you can add values in the form of strategic discounts. Throwing in something like a free subscription to a webinar service or premium training courses that help them use your platform or even offering an extended warranty can be the icing on your customer’s cake.

Try to avoid slashing your prices when closing the sale and instead offering extras that give value to the prospect but still close a larger sized deal.

4 Ways to Land the Big Fish

With all the tools at your disposal, quality prospects in mind, and the right steps to boosting the size of your deal – now you need a handful of ways to land that big fish. 

1. Start by emphasizing stoicism, control over emotions, and the knowledge of when to walk away from a deal. This seems counterintuitive in a sales role but it might be in your best interest in certain cases to accept a “no” from a potential client that was somewhat hesitant and walk away.

If you do this calmly and effectively, it might trigger a callback and a deal because you weren’t desperately seeking their approval and trying to give them anything and everything they wanted.

2. Remember that every customer is different so not every solution, product, extra feature, or free trial is going to fit the same people. Every company and individual will have its own framework, its own strategy, and its own needs which is why you have to be creative in combining different packages with unique values and prices.

Have several options on the table before you start pitching.

3. Large clients are not the experts in your industry. Even though they might be an authority in their field, you are the authority in your field and those companies are looking to you as someone who can quite literally diagnose their problem and give them a prescription.

They don’t want to hear you preaching about how amazing the product is or how outstanding your service is and how their company will completely fall apart if you don’t use it. They want someone who will attentively listen to their problem, diagnose their issue, and give them the solution.

Integrating the “we” more often than “you” or “I” will go a long way toward making them feel like you were in this together.

4. While it might be impossible for you to offer a product or service that’s completely different than anything else on the market that doesn’t mean your company can’t still be unique. You can differentiate your company by controlling your approach to the sales process:

Offer a sample before someone has engaged in multiple discussions with sales staff. 

Give them a month of your platform for free before they’ve even given you excuses as to why they’re hesitant. 

If you’re trying to sell to a CEO, catch a flight and meet them in person. You’d be surprised what this in-person communication can do in a world where people are accustomed to declining phone calls and ignoring emails on a daily basis.


In the end, winning bigger deals starts with the same level of groundwork as any other deal. You must talk with your team internally and examine current customers that add value to your business and what it is specifically about them that creates value.

From there, it’s your responsibility to find ways to add more value to your current customers while also focusing your attention targeting new prospects that share the same qualities and making an effort to engage them in a sales conversation.

As you get closer to the finish line with prospects, always look for ways that you can add even more value and incentives to build and close larger deals.