Skyrocket Your Enterprise Sales In 2021
With Our 9 Step Roadmap
Discover all our strategies to close your next enteprise deal
Discover all our strategies to close your next enteprise deal
When I joined the wonderful Merchandise Essentials team I saw a young, hungry and extremely motivated sales team and I was expecting them to talk to smaller local companies and startups.
I was surprised to see how many enterprise level companies they were talking to.
They were talking to enterprises like Sony Music, Google, Mastercard, and a lot of other big companies!
During the past few months we have been talking about this a lot because we believe that a lot of companies would like to learn how we sell to enterprises.
That’s exactly why we made this step-by-step guide to show you how you can start selling to enterprises.
In this comprehensive guide to enterprise sales you'll learn:
- How to prospect on enterprise clients
- How to identify enterprise sales opportunities in 2021 and beyond
- How to leverage your first deal to generate more deals
Let's dig in.
The 9 step roadmap
The reason that we are closing enterprise clients on a regular basis is because we have a proven roadmap. We know exactly what steps we need to take to close these big whales!
In this ultimate guide we will show you our exact steps and will guide you through the process of closing your very first enterprise deal. Of course we will not leave you hanging with just this guide. We also created some downloadables that will help you reach your goals!
These are the 9 steps that define our roadmap:
- Research your target company/niche
- How to prospect on enterprise clients
- Nurturing your enterprise champions
- How to close the first deal
- Onboarding your dream client
- Continuous improvement through the feedback loop
- Customer success management 101
- How to build long term relationships with your clients
- How to expand your company with predictability
How do we define enterprises?
It’s easy to talk about “enterprises” but how do we define enterprises?
Below there’s a small table regarding the amount of companies that are “small”, “medium”, “large” or an “enterprise”.
Besides that, we’ll show the average employees and annual sales that these types of companies are getting. This will make it easier to know what category your prospect is in.
Small | Medium | Large | Enterprise | |
---|---|---|---|---|
# of companies | 6.000.000 | 44.000 | 9.000 | 11.000 |
# of employees | Less than 250 | 250-500 | 501-1.000 | More than 1.000 |
Average annual sales | €1.6 million | €41 million | €159 million | €2.7 billion |
Advantages of enterprise sales
Of course there are a lot of advantages when it comes to enterprise sales.
Here are some of the biggest advantages:
- Bigger deals: more revenue with less deals (yay!)
- Stability: enterprises don’t like to change their suppliers. This guarantees long term deals when you provide a great service
- Marketing/branding value: if an enterprise (for example Google) works with you, other companies will be convinced that your service is amazing.
Challenges of enterprise sales
Of course it's not all roses and unicorns, otherwise everyone would be working with enterprises!
Here are some challenges of working with enterprises:
- Much longer sales cycle: because enterprise level deals are so complex, the sales cycle is typically much longer. These deals may take 6–18 months to close.
- More demanding sales process: enterprise level deals will require a great deal of time and attention from your sales and support teams.
- Chicken & egg dilemma: many enterprise level customers want to know that you’re already working with and able to support other enterprise-level clients. This makes it extra tough to land your very first enterprise deal without any social proof to rely on.

Conclusion
As you can see there are a lot of pros and cons when it comes to enterprise sales. For us the choice was simple, we would take these “disadvantages” any day to be able to work with amazing enterprises!
Download our free enterprise sales starterkit below.
Free resource
Free Enterprise Sales Starterkit
Fill out the form to access this free starterkit.
Take your enterprise sales to the next level
The 9 steps of closing & working with enterprises
The absolute key in enterprise sales is a complete custom and made to measure approach for every single client. And put in the work.
Enterprises buy solutions, not things! What is the difference between transactional and solution sales?
Transactional selling, in short, is a sales strategy where the main goal is a quick sale that results in a quick transaction. The value lies in your product and price is the main selection criteria. Solution sales or consultative sales focuses on unearthing the pain points of the client and offering a solution.
This is a much more holistic approach, as the salesperson needs to build a relationship with the prospect, map their needs and present a tailor-made solution for them.
Things that are important:
- Safety - guarantees - solidity (no risk in reputation damage)
- Amazing service - god tier
- Thoroughly understanding their business and building solutions that actually help them: you can’t trick an enterprise client into sales
- Control budget, not price!
- Open communication
- Letting them have the win
- It’s working with people, not the company
- They expect tailormade solutions: put in the work and be open to change
Step 1: Research your target company/niche
Centralized vs decentralized enterprises
Every enterprise is different. Every company has its own way of working, some enterprises are centralized and others are decentralized.
Centralized enterprises make the majority of the “big” decisions in their HQ.
Decentralized enterprises have a lot of decision power and thus have the ability to choose their own partners, employees,...
It’s really important to know in which category your prospect falls.
This will determine if you should contact a satellite office or the HQ!
Doing research on enterprises can be really time consuming but luckily we have a lot of tools that can help you automate this tedious process:
- LinkedIn Pro
- Crunchbase
- Snovio
- Lushia
- Hunter.io
- Albacross
- Prospect.io
- And of course - Google!
As you can see there are a ton of tools that you can use to do some in-depth research on your prospects.
Tools to use
>> The Enterprise Sales Tools List will make your life so much easier when prospecting on enterprises (download here)
>> A well thought-out Enterprise Sales Starterkit that guides you through every step of the enterprise sales process (claim here)
Decision makers
Solo decision maker
The first one is the solo decision maker. This person makes the final decision. Period. This person is usually the CEO, president, or division president, but they could also be a department head or special projects director depending on the company’s organizational structure. This is typical in both large and enterprise-sized companies.
Solo decision maker
The second is the sole decision maker who requires board approval. Once you get a commitment, you will need to wait for the next board meeting or business cycle, and depending on other priorities, you may have to wait multiple cycles. This is particularly apparent in compliance-heavy businesses such as banking and insurance, or in cyclical businesses like plant products.
Multiple decision makers
The third is multiple decision makers. Even though there may be one person who approves the final decision, this person relies heavily on the decisions made by a team, or in some cases, group consensus.
Oftentimes enterprise deals will require sales touch points with many different prospects. In fact, six people are involved in a decision purchase, on average. Remember that each prospect may need a personalized sales approach, including a unique value proposition.

Step 2: Prospecting on enterprise clients
The best tip you can get here is to make it personal!
Imagine you being the marketing director for Coca Cola or Google, how many prospecting requests do you expect to get on a daily basis?
Although we can’t define the number of requests, we can all agree that it’s a quite high number.
Because of that, you can’t do the same prospecting like everyone else, you have to aim higher than the “average prospecting techniques”.
If you’re average, you will get average sized clients.
Of course we’re not leaving you hanging, we have some easy pointers to help you while prospecting:
- Do your research and bring real value to your prospects
- Make their efforts as small as possible. Don’t schedule tons of meetings and video calls
- Make the conversation friendly and fun, don’t be the boring salesperson like they’re used to communicating with
- When they ask for references, give them relevant information and case studies
Send some cool swag! - Although we love automating things, don’t automate the sales process with enterprises, please.
Here below you can see some examples of cool prospect conversations that we had.

Step 3: Nurturing your enterprise champions
Nurturing your enterprise champions comes down to 1 main thing: bring value, all the time!
Below we have some small tips & tricks to nurture your enterprise champions:
- Respect their time - don’t overwhelm them with video calls
- Have casual conversations with them that are non-work related
- Engage with them on social media, they love that!
- Send them valuable content like blogs & case studies
- At all times - show a clear ROI
Nurturing these champions will make it a lot easier for your company to grow.
Why? Because we all know that it’s so much easier to sell to someone that genuinely likes us.
Free resource
Free Enterprise Sales Starterkit
Fill out the form to access this free starterkit.
Take your enterprise sales to the next level
Step 4: Closing the first deal
This is where the fun part starts. After you gained enough interest from your targeted enterprise and you presented your unique solution.
Now you must put in a crazy amount of effort, don’t be lazy now or you will lose their interest forever. When we say forever, we mean literally forever. Enterprises won’t ever consider working with you anymore if you fail to impress them!
Because they’re so used to getting the boring, generic, non-personalized presentations, it’s “easy” to impress them but you need to think about it, a lot.
By now, you should know exactly what they are having issues with and you should create a solution roadmap from A-Z. Make sure that everything is perfectly documented and double checked by multiple people. This is not a situation where you want to make a dumb mathematical mistake.

It’s important to make the presentation in-depth so they know you’re an expert. It’s equally important to make the presentation as simple as possible.
Now you’re probably thinking “huh?”, let me explain:
The people to whom you presented will need to re-present your presentation to their team members and/or managers so it’s vital to make the presentation simple enough for them to present it successfully.
You basically need to help them sell your solution to their decision makers without needing to do research themselves.
A pro tip here would be to research all the possible objections they will receive from the decision makers and prepare answers for all of them.
You need to make it as simple as possible to sell your solution and the only way to do so is by doing amazing research!
One thing that is really important when it comes to enterprise sales is to manage the timeframe and roadmap in a non-pushy manner. Be sure that everything fits in the roadmap from start to finish.
You want to give the prospect as much time as needed but you also want to limit the timeframe as much as possible, otherwise a deal cycle will take forever to complete.
Tools to use
>> A well thought-out Enterprise Sales Starterkit that guides you through every step of the enterprise sales process (claim here)
Step 5: Onboarding your dream client
Now that you closed your dream client, it’s time for something even more important…
Closing your client is 1 thing but making sure that they effectively use your solution is even more important, otherwise you will lose the client.
You want to make sure that your client knows exactly how to implement your solution and you do this by having an onboarding plan for your enterprise client.
During the sales process you mapped all the users and when they would migrate to your solution.
Following through on this planning and taking it in your hands together with the champion and decision makers show them you are a reliable partner.
Take the effort to learn everybody to work properly with your solution, because use rate determines renewal rate of your collaboration.

Step 6: Continuous improvement through the feedback loop
If you’re looking to stay in business for a very long time, then this might be the most important step for your company. A lot of people focus really hard on securing the deal but are not focused on improving their offer and products.
That’s one of the reasons why a lot of people go out of business.
Of course we’re not here to scare you but to help you!
It’s really easy to improve your business/product following these 4 simple steps:
- Determine what you need feedback on
- Plan meetings every month or quarter to discuss all the positive and negative things regarding your solution
- Take action based on the feedback you got from your clients
- Connect back to your enterprise client with specific action points that you will take.
After implementing some feedback and improving your product you should give credit to the people that came up with the idea. Help those champions boost their careers in front of their managers.

Step 7: Customer success management
Now that the enterprise is using your solution it’s important to help them achieve the best possible results. This is called customer success management.
Enterprise clients expect a personal, high-touch and proactive approach to customer success. You are the expert, so you should tell them how to use your solution and how to increase their results.
There are 5 “facts” that you need to know if you’re working with enterprise customers:
- If you’re not growing, you’re shrinking. In high-touch accounts, the status quo is not sustainable. You need to constantly be planning how to get more strategic and larger in the account—or you will be engineered out.
- Your large clients want you to own the outcome for their business. A senior exec’s job is on the hook. But, chances are, everyone at your company has forgotten what the client really wants. The objectives discussed in pre-sales are buried in a salesperson’s notepad. Your CSM is so tied up in standing meetings that it’s easy to lose sight of the bigger picture.
- Your single large client is actually many little clients internally. You’ve probably sold multiple products to them, across multiple business units, with some units engaged in services engagements and others not. This might seem like high-touch CSM at the surface, but your real-life “accounts to CSM” ratio is actually very high.
- You’re dealing with lots of political complexity. You’ve got potentially dozens of senior stakeholders who tend not to see eye-to-eye. You’re herding cats. If you haven’t addressed stakeholder engagement in a methodical way, you’re lost in the jungle.
- You can’t afford to mess up. Investors expect renewal rates north of 95% in this segment. That means every single renewal needs to come in. If you lose a 6-figure or 7-figure account, it could ruin your quarter. And there isn't much room for downsell. Every single at-risk account presents a major issue. And by the way: Your high-touch clients. Notice. Every. Detail.
It’s also a very good idea to reward the most engaged users of your solution with company merchandise.
These are:
- People you communicate most with at the enterprise
- People who use your solution most (power users)
- People who give you most honest feedback about your sol
As you can see, customer success is insanely important and will be the make or break of your business. If you’re not 100% all-in when working with enterprises, you will not stay in business.
So - keep improving your product/solution and make sure that your customers are successful with it!
If your solution is “great” but the client doesn’t get results, he’ll leave anyway so you need to make sure that nothing can go wrong, their success is your success.
Tools to use
The Enterprise Sales Tools List will make your life so much easier when prospecting on enterprises (download here)
>> A well thought-out Enterprise Sales Starterkit that guides you through every step of the enterprise sales process (claim here)
Step 8: Build long term relationships
The hard part is done by now. You successfully prospected, closed and onboarded your first (of many) enterprise clients!
Now it’s time for the fun part - now you get to build a relationship with the people you are working with.
1 thing you need to know is that you do not only build a relationship with the “contact person” but you try to build a relationship with everyone inside the company. By doing so you ensure that everyone “likes” you and together you can write a successful story.
Here are some ideas to improve your relationship with your clients:
- Send them relevant (!) blog posts and/or content
- Engage with them on social media
- Add their birthday to your CRM and send them birthday gifts (did you know you can automate this with Merchbot?)
- Invite them to events that are not only business related
- Send them a company baby bib when they get a baby
- Grow their career by introducing them to colleagues
- TL;DR - show them you really care about them
While this looks like a lot of things to remember, you should also understand that there are a lot of “pros” to this!
- You can ask for referrals due to your positive relationship with them
- They will come back to you for more projects
- It’s fun to engage with your clients!

As we mentioned above, enterprise-size companies have multiple decision-makers. That’s why your relationship-building shouldn’t be limited to just one person. In the end, you need to work your way into the minds and hearts of all those involved in the buying process.
This network of supporters within the company will be invaluable to you later on, when you want to do bigger projects at the enterprise.
Oh and when your contacts switch to a new enterprise: you’ve just landed your second enterprise.
Important note
A lot of enterprises have mandatory job switches every couple of months or years. It’s very important to get to know as many people as possible in the company or you risk losing your contact to a promotion.
If you can keep them close, they will likely land you more projects at the new enterprise they are going to work for!
Looks like a win-win to me.
Tools to use
The Enterprise Sales Tools List will make your life so much easier when prospecting on enterprises (download here)
>> A well thought-out Enterprise Sales Starterkit that guides you through every step of the enterprise sales process (claim here)
Step 9: Expanding
Closing your first enterprise deal is a huge milestone, we know, but it should not be the end goal!
Now you have some experience and key learnings through working with your first enterprise it’s time to scale to the moon.
You should be looking to expand in any way shape or form!
You can expand by closing more enterprises or you can expand by selling more to the same enterprise. It’s completely up to you what you do but we suggest this:
Sell more to the same client and expand by selling to new enterprises.
The last thing that you want is just having 1 client because when you lose this client, you’re in massive trouble.
So long story short - keep repeating this process to scale your company to the next level!
If you’re looking for an Enterprise Sales Starterkit, you will want to fill in the form below.