This article was originally published on the Knowlarity blog.

Its tempting isnt it? The thought of closing a deal with an enterprise customer?

You earn substantial revenues, which might run into millions of dollars. You also add a well-known company to your customer list and this reputation makes it easier for you to close other deals.

However, selling to enterprises is extremely complex and far more difficult than winning deals with mid-sized companies or startups.

What Makes Enterprise Sales Tougher?

Here are just a few challenges of enterprise sales:

You dont just sell to one or two people. An enterprise deal will have several decision makers. Additionally there will be several people who you might never meet, but who will have considerable influence over the decision.

You will have to speak to a dozen or more people from different departments, attend several meetings and deliver multiple presentations.

And all this will take time. It usually takes at least 3 months to close an enterprise deal and might even take a year sometimes longer!

How can you successfully navigate all these complexities of the enterprise sale, and win the business?

Asking the Worlds Leading Authorities on Sales

To find out, we asked 47 of the worlds best known sales experts about their advice on how to win at enterprise selling.

Who are these experts?

Most of them are consultants, trainers and coaches who Fortune 500 companies go to, when they want to learn about sales.

Many of these experts have been recognized by Forbes, TopSalesWorld and Salesforce as the worlds leading authorities in sales.

Many are bestselling authors in the field of sales

Some of them are in executive roles in Training Industrys Top Sales Training Companies of 2017.

Others are CEOs and senior leaders of companies who have had years and even decades of experience in selling to enterprises.

What these Experts told Us

Our experts gave us several tips of the multiple aspects of enterprise sales

1. How to accurately identify the prospect companys needs, even if they dont explicitly tell you.

2. How to identify companies that would be most likely to buy

3. How to identify the right decision makers within a company to approach

4. How to build relationships with the decision makers

5. How to position your offering for maximum impact

6. How to know who you are competing with for the deal

7. How to do better than your competitors

8. How to objectively assess if the deal is going in your favor or not

9. How to manage a sales team focused on enterprise prospects

Here are our featured experts (in alphabetical order of last names)

Enterprise Sales Tips from 47 Top Sales Experts

Steve Andersen

Performance Methods business is primarily focused on helping our clients become more strategic to their most important customers, and so our work brings us into contact with many organizations that are trying to advance and close difficult sales with large, complex and demanding customers. When we take score and separate the winners from the losers, several factors repeatedly stand tall again and again. The most successful salespeople and account managers that we work with always seem to:

o Develop sponsors and supporters up and down the customers organization before the sale (these sponsors and supporters understand the sellers unique value and are willing to talk about it).

o Align their objectives with the objectives of the customer during the sale (which requires doing your homework, exploring possibilities and visioning success with the customer).

o Stick around after the sale to ensure that value is realized by the customer and that their relationship is expanding (activities that frequently point them in the direction of their next sale).

I recommend that contemporary salespeople consider taking this longer-term view when engaging and selling to large, complex organizations. Sure, it requires an investment of time, but the ROI will be a much higher win rate, and more repeat business within these accounts.

Bob Apollo

Selling to large enterprises is inherently more complex than selling to start-ups, scale-ups or the mid-market. There are more stakeholders involved (some of them may be invisible to you), and their procurement and approval processes often derail otherwise promising opportunities. In many cases, your most significant competition is not other vendors, but the convoluted and often opaque decision making process itself. This can be particularly challenging when you have limited sales resources.

Before investing large amounts of time and effort on such projects, you need to carefully assess not just whether you have a good solution fit, but also company fit whether the organisation has a track record of buying from vendors with similar profiles to your own. Its too easy to be seduced by the allure of winning a big brand without taking into account your realistic chances of actually doing business with them.

Naomi Assaraf

CMO and Co-Founder, CloudHQ

For larger enterprise deals, my advice would be 3 tips, in order:

1. Make sure theres a need and a budget.

2. Understand the process and track your time goals.

3. Dont waste time building relationships with anyone whos not the decision maker.

Irene Becker

Chief Success Officer, JustCoachIt

The most important tip I can offer is understanding the arena in which you will be playing and the players involved.

Enterprise buyers tend to be more risk adverse and will be looking for what is tried and true, for results that have been achieved with other enterprise clients. The average decision maker in enterprise-level organizations would want to minimize failure. Therefore, if you do not have a list of other enterprise customers, you would encounter difficulty in convincing them that you are the right fit for them.

While you might not be able to compete with other vendors in terms of an enterprise customer list, there are other things that you could do, to make a more convincing case:

o Stress how working with a smaller company like your yours can have benefits that a larger company cannot offer such as better service levels, faster deployment, access to your top management, etc.

o Rather than send a younger person to a sales meeting, send your senior leadership. That will make the decision makers feel important. Your senior leaders will also be able to have far more convincing sales conversations.

o Try to build rapport with the decision makers at a personal level. Relationships and credibility go hand in hand.

Butch Bellah

National Sales Manager, Bulls Eye Brands Inc.

"When selling to larger organizations there are a few things to remember in your sales process. For example, the wheels may turn a bit slower than in a smaller company and it may take a bit more time for each step of your sales process the prospect controls. For example, if you are waiting for the prospect to respond with data or information, it tends to take them longer to gather it and clear it for release. Understand it just takes a little more time and red tape to clear on your way to the sale. However, one thing Ive found is while you may think every one of your competitors is calling on the Big Fish or the major players in your category thats not always the case. Ive seen many times where competitors either were intimidated, didnt want to go through the extra work a large account required or simply thought there was no way they could earn the business. Its like the old story about the prettiest girl in school. Every guy thinks she has a date Friday nightand she sits home alone because no one called."

Steve Benson

Founder and CEO, Badger Maps

"Selling to enterprises involves sales cycles which are far longer than selling to small or mid-sized organizations. Deals usually take a minimum of three months to close and might take up to a year or more, depending on the nature of the industry and your product. Therefore, one of the biggest challenges of enterprise selling is to assess the performance of your sales activities. A far longer sales cycle makes it necessary for you to apply completely different benchmarks to determine how well you are doing.

These revised benchmarks are important for both the sales manager as well as the sales reps.

Sales reps would want to determine how well things are going. They would accordingly modify their approach, do more research to understand the company better, connect with other decision makers within the organization or adapt the offering to suit the organizations needs better.

Similarly, the sales manager would want to keep track of the status every single of of his/her opportunities. How is a particular opportunity progressing compared to other opportunities in the pipeline? If its not going so well, how can things be improved?

How are the sales reps performing? Do they need any coaching on how to address a specific situation? Do they need any help from other departments like the product team to understand how to position the offering?

Is a particular opportunity worth pursuing, or would it be a better idea to invest time and resources on others that look more promising. Having the right metrics and benchmarks in place make it far easier for you to answer these questions.

You companys sales leaders should determine what the ideal metrics and benchmarks should be, based on past experience, industry standards and inputs from the sales reps. You should also define the different stages of the sales cycle and make them easy to identify. These stages should ideally be reflected in your CRM and should not necessarily be the stages that you have defined for opportunities with smaller organizations.

You should also clearly define the indicators of progress from one stage to another. You can define an advancement in terms of events such as a meeting with a key decision maker, a demo, an integration test with their engineering team, etc.

Make sure that these definitions are adhered to when you determine your progress. Its extremely important to be honest with yourself about how the deal is progressing and not be overly optimistic because of a gut feeling. The more accurate your assessment is about the opportunity, the more easily you will be able to take a decision to invest more or less resources behind it, and therefore increase your overall conversion rates."

Kirsten Boileau

Head of Regional Engagement and Social Selling, SAP

"At SAP, we have discovered that social selling can play a vital role in winning enterprise accounts. Social selling has several aspects to it. Lets talk about how one of these aspects, social listening, can be used to get enterprise deals.

Successful salespeople know the importance of listening very carefully to what their buyers say. Social listening is the contemporary version of paying attention to your buyers so that you can understand them better. It can be used to gather invaluable insights about the current issues a particular company is facing and what sort of solutions they are looking for. Going through social media accounts of the key decision makers of a company will help you understand what matters to them professionally and personally. You can use this information to frame your pitches in the context of issues that are topmost on their mind and in sync with their beliefs and expectations.

Here are a couple of examples in which social listening can be used to gather valuable information, position your offering and build key relationships.

In one instance, our salespeople used social media to identify the decision makers in a target account. They found out that one of the key decision makers was unfavorably disposed towards SAP. However, they also discovered that this person was a huge sports fan. They knew that they would need to win him over to get the deal. They decided to include a lot of sports analogies in their sales presentations in order to build rapport and help him relate better with the offering. That certainly had the intended impact and they were able to win the account.

In another instance, Freddie Borsellino, one of our Success Factors account executives, used social selling to win a significantly large deal. He used LinkedIn Sales Navigator to build a relationship with the HR managers at a certain company. Through social listening, he was able to learn that they were looking for another solution in addition to what SAP was pitching to them, and that they were already evaluating vendors for that solution. That solution also happened to be something that SAP offers. Freddie took the opportunity and approached them with a proposition to evaluate the SAP solution as well. He was able to close the deal and increase the value of the combined deal size by 50%. Without social listening, he would not even have been aware that they were looking for a solution.

Social selling has played a key role in our enterprise selling at SAP. We have trained more than 7,500 sales and marketing professionals in social selling techniques across the company. We have developed a training program internally and have more than 200 trainers who are certified in the SAP approach to social sales. It works, and therefore, we continue to invest in it!"

Jeb Brooks

President & CEO, The Brooks Group

"To win in todays complex sales environment, your salespeople must shift their mindset and approach from tactical to strategic. Real success goes beyond making a one-time sale, to developing a long-term partnership and business strategy with your clients and prospects. Its about selling far beyond the initial order.

To become a strategic resource capable of driving change, salespeople need the skills to position themselves as experts. They need the in-depth knowledge of your customers organizations, buying process, industry, and the concerns of individual stakeholders within the organization.

Sure, buying committees are larger than ever before. Procurement is playing a more strategic role. And, because buyers can easily get the information they think they need on their own, its harder for salespeople to share relevant information with prospective customers.

Therefore, in order to drive change inside of your customers business, your salespeople must position themselves as expert consultants. Its about going beyond product knowledge to convincing prospects with industry news, research, and subject matter expertise. Its about demonstrating business acumen so clients trust the solutions they recommend. Its about providing thought leadership that stimulates conversation and improves credibility. Its about presenting value to effectively differentiate your solution from the competition.

Oh! And thats only the beginning!"

Bill Carmody

"Over the past two decades, the major shift in selling to large enterprise companies is the migration from 1 or 2 decision makers to as many as 8. On average, 5.4 people are involved in todays B2B purchase decisions according to CEB. The biggest mistake most sales people make is targeting only one of those decision makers. Today, you need to be at least moderately versed at social selling in order to identify all the key decision makers. LinkedIn is the obvious choice for the US market, and so I interviewed Mike Derezin, VP of LinkedIn Sales Solutions to see what tips he had to give. (Hey, why not go to the source, right?)

You can read the output of my interviews in the following two Inc articles on the subject: LinkedIn on the 3 Best Ways to Attract Your Ideal Customer and 4 Ways to Boost Your Social Selling Profile (Courtesy of LinkedIn). While there are several free ways to to leverage LinkedIn, the pros eventually break down and purchase a monthly subscription to Sales Navigator. Thats because LinkedIn does all the sleuthing for you. You put in the name of a company and title youre after and it will build you a list of the 5 to 8 likely decision makers you need to connect with.

Rather than sending a bulk generic invitation to all of them, you need to spend time on their profiles. Everything you need to know about how to sell to them is right there for the taking if you just take the time to do a little homework. Most people will not only share their career path, but also keen interests. As a bonus, head on over the Facebook and do some Google searches to see what else you can find out about each of your prospects. Youre looking for a common connection that will help you build an authentic connection. You dont start with the hard sale that turns everyone off. Instead, look for common ground such as youre both into coaching a particular sport or are part of the same group on LinkedIn. From there, look for ways to add value first. GIVE before you ever ask for something. I know you feel the sales pressure, but that smell of desperation will repel the very people youre trying to attract. Instead, look for authentic ways you can be helpful and just do it. Thats the best way to connect and being a real relationship. Large Enterprise sales take time. If you think youre going to close in 30 days, think again. The average sales cycle is between 3 to 6 months. This sales process is a marathon, not a sprint, so be prepared to invest heavily to land the business. If youre not prepared to do that, stick to smaller companies until you have enough income to support an investment in a larger enterprise."

Jim Cathcart

Remember there is no such thing as selling to an organization. ALL sales are to individuals within the enterprise. They must see you as a more appealing solution source than others. A big part of this will be in showing how much you understand them and what matters to them. Know their systems too, discover how they make decisions like this. Be easy to say Yes to.

The person who drives the decision to buy from you is your champion within the enterprise. Care for that person well, and keep in mind that career paths change and so does corporate leadership. If you are seen as only that persons solution source then you may lose the account if the decision leader changes. Connect well with as many people as you can, not just one clique or team.

Kevin F. Davis

"When responding to a lead of some kind, you dont know what step of the buying process your prospect is in. So an important question to ask is, What steps have you taken thus far in regards to making this decision? Are you the first supplier this prospect is talking to, or the third? It makes a huge difference.

If youre the first, you have a chance to influence the buying criteria in your favor. If youre the third, you know they are in the comparison stage. Acknowledge that, and ask about the earlier stages of their buying process. What problems do you have that you are trying to solve? And then, Other customer have also told us about an additional issue such as this. Your goal here is to identify at least one additional customer need that they dont currently recognize they have. Thats the best way to go from worst position to first position, late in the buying cycle."

Craig Elias

"I have three tips for selling into large enterprises:

1. Start locally by developing a relationship with the nearest regional or district manager and reduce the risk they take on buying something from you by selling something them small that compliments what they have instead of trying to replace something they already use.

2. Make sure that sale delivers real results and then upsell that person while you cross sell to other locations of the same division. Once you have multiple locations as customers work your way to a national contact for a national contract. Only then can you take your track record to sell to other divisions or other countries.

3. All of what I just said goes out the window if there is a change in the national decision maker. Now go straight to them AND do it as soon after they get the job as possible. Heres why:

According to a DiscoverOrg report, 80% of decision makers who are new in their job make decisions about the big changes/purchases they are going to make within their first 90 days. The same report also says that they spend $1 million+ on to new initiatives within this period.

Essentially, people who are newly appointed to a role and are dissatisfied with the status quo have the highest likelihood of making a purchase. Conversely, the data also shows that if you try to approach a decision maker beyond this window, your likelihood of closing the deal falls dramatically. Therefore, look for trigger events like new appointments and approach them as soon as possible."

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47 Top Sales Experts Share their Best Enterprise Selling Tips - HuffPost