47 Top Sales Experts Share their Best Enterprise Selling Tips

47 Top Sales Experts Share their Best Enterprise Selling Tips
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This article was originally published on the Knowlarity blog.

It’s tempting isn’t 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 don’t 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 World’s Leading Authorities on Sales

To find out, we asked 47 of the world’s 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 world’s leading authorities in sales.

Many are bestselling authors in the field of sales

Some of them are in executive roles in Training Industry’s 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 company’s needs, even if they don’t 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

10. And a lot more…

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

Enterprise Sales Tips from 47 Top Sales Experts

Steve Andersen

President and Founder, Performance Methods, Inc.

“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 customer’s organization before the sale (these sponsors and supporters understand the seller’s 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. It’s 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 there’s a need and a budget.

2. Understand the process and track your time goals.

3. Don’t waste time building relationships with anyone who’s 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 I’ve found is while you may think every one of your competitors is calling on the “Big Fish” or the major players in your category that’s not always the case. I’ve seen many times where competitors either were intimidated, didn’t want to go through the extra work a large account required or simply thought there was no way they could earn the business. It’s like the old story about the prettiest girl in school. Every guy thinks she has a date Friday night–and 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 organization’s 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 it’s 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 company’s 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. It’s 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. Let’s 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 today’s 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. It’s 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, it’s harder for salespeople to share relevant information with prospective customers.

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

Oh! And that’s 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 today’s 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. That’s because LinkedIn does all the sleuthing for you. You put in the name of a company and title you’re 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. You’re looking for a common connection that will help you build an authentic connection. You don’t start with the hard sale — that turns everyone off. Instead, look for common ground such as you’re 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 you’re trying to attract. Instead, look for authentic ways you can be helpful and just do it. That’s the best way to connect and being a real relationship. Large Enterprise sales take time. If you think you’re 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 you’re not prepared to do that, stick to smaller companies until you have enough income to support an investment in a larger enterprise."

Jim Cathcart

Founder, Cathcart.com

“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 person’s 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

President & Founder, TopLine Leadership Inc.

"When responding to a lead of some kind, you don’t 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 you’re the first, you have a chance to influence the buying criteria in your favor. If you’re 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 don’t currently recognize they have. That’s 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. Here’s 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."

John D. Elsey

President & CEO, Richardson

“At Richardson, we’ve spent almost 40 years helping sales organizations unlock revenue by selling to large, complex organizations. What we know is that, to be successful, there are some things you need to do well here that are unique, and others that frankly apply to almost any sale you try to make, irrespective of how large your buying organization might be.

To be successful, sellers always need to build trust, demonstrate credibility, and create differentiated value in the moments that matter most — the time in front of buyers. Trust ranks as the most important factor in influencing buying decisions and the seller can earn or erode this essential element by the way he interacts with a prospective buyer.

What makes selling to large, complex organizations uniquely challenging is that you must deal with multiple stakeholders, often championing competing or misaligned business goals and then navigate frustratingly opaque procurement practices. Sometimes it is a miracle that buying decisions ever get made.

The opportunity is to recognize that this complexity exists both for the buyer as well as the seller. Sellers that see their role as educators throughout the buying cycle, who ask thoughtful questions and share insights from their experiences along the way, help shape unanticipated solutions that create real lasting value and ultimately win the deal. Best practices to keep in mind:

o Remember, your job is not to sell something (not initially anyway), but to understand and align stakeholders around a solution that solves real problems

o Recognize that not all stakeholders are equal, expect the same outcome or are equally invested in the purchasing decision – use Relationship Maps to chart the organizational landscape

o Large complex companies rely on teams to buy – make sure your team is ready (right people, correctly organized, practiced and ready to execute)

o Have a dynamic sales process that clearly articulates critical stages in the process, rooted in buyer behaviors (not sellers)

Selling to large, complex organizations is the pinnacle of any seller’s career. Never easy, most often challenging but uniquely rewarding when done right.”

Jon Ferrara

“I truly believe in what Zig Ziglar said which is that “you can have everything in life, if you will just help other people to get what they want.” It essentially brings us down to the basics of what sales is which is a service. I think that the number one key to selling to large enterprises is not to sell but rather find ways how you can help other people grow and solve their problems. Your goal is to be seen as a trusted advisor and you become one by building your personal brand and your network in the areas of the promise of your product and services.

The hardest part of selling to large enterprises is the prospecting part and identifying which person to connect with. You need to take the time to do your research and figure out who the real decision maker or decision makers are. In large enterprises it will most likely be multiple people making the decision so you need to use your own personal connections to get introductions or find ways to add value to the decision makers’ journey by using skills like social selling.”

Peter Fillmore

CEO & Founder, Momenta Systems Inc.

“First tip – in Enterprise B2B situations, don’t rush to prepare a Product proposal, even if they ask for it. The final decision will be made by multiple people’s input, and the senior decision maker will need a brief internal proposal stating the pain points (or Enterprise goals), the payback (for this year’s business plan) and the time drivers (reasons to act in concert with other Enterprise activities). So ask questions that show a definite concern for their business – then make a proposal to:

o Collaborate in preparing a Project Outline – (this will end up serving as their definitive internal proposal)

o Pre-set a series of 3 dated meetings to write up the 3 key components – Pain (Goals), Payback, Time drivers (usually over the next 3 weeks) – Later, your Product offer can be added as section 4 …. Now framed as the best and most relevant solution, fully in context.”

Patricia Fripp

“Selling to large enterprises can be complex, but your sales presentation does not have to be.

You are often speaking to the audience of your audience. In other words, your presentation will be repeated and discussed for months with individuals you may not have met.

When your message is clear, concise, and focused on the prospect’s needs or opportunities, you have their attention. Everyone on the presentation team must deliver a consistent message and be well rehearsed.

Your presentation should feature shorter sentences, with only one idea in each, and all language must be specific. A question I often ask my clients is, “What do you mean by ‘thing’”? Record your rehearsals, and watch them. How often do you hear “kind of” and “stuff” or “tons” (when the speaker is not talking about weight). Specificity builds credibility.”

Joe Hart

“Selling big deals to big companies is complex, but once the essential requirements of the deal are met, what drives the purchase decision is the same as in any buyer-seller relationship: Emotions. Having said that, the dynamics of emotion in a large company sale are different.

In smaller and mid-market companies, with individuals or small teams making the buying decision, there may be a wider range of dominant buying motives that are emotionally based. For larger enterprises, the driving emotion is more often expressed as fear. Fear of making the wrong decision, fear of the product or service failing to deliver as promised and the cascade of negative consequences that could result: lost reputations and/or promotions, missed deadlines, lost productivity, falling profits – or worse.

So what’s the solution?

Success in complex sales happens when the buyer feels confident that the sales person has fully understood and evaluated the risks from the buyer’s point of view or simply put when they validate and address their fears. The central work of any sales individual or sales team selling to a large corporation is to understand and address risks across the buying team. Uncover the fears of each member of the decision-making team and demonstrate how their risks will be mitigated. Doing it effectively requires highly-sophisticated interpersonal skills and the genuine intention of understanding potential risks from the buyers’ perspective.”

Alice Heiman

Founder and Chief Sales Officer, Alice Heiman LLC.

“Biggest mistake I see is cold calling large companies and getting one interested person and thinking you’ve got a deal moving. This person may end up blocking you or giving you a false sense of security.

If you get an appointment with one buyer, ask who else should be invited to the meeting. Buyers will block you for different reasons. Sometimes it is because they are tasked with something and want to be sure they get the job done without interference. They have to talk to other vendors and get everything organized for the other decision makers.

Usually if someone is blocking you and telling you they are the only one you need to talk to, it is because they are worried or insecure. They want to feel important and be the one to make things happen at their company so they can be the hero. They want to be in control.

In almost all cases when someone tells you they are the only one you need to talk to, you are in trouble. It’s rare that one person at a company makes a decision on a complex, high dollar stakes deal. You have to build rapport and ask good questions. Win them over. First understand what they need and want and help them understand how to get that. Ask questions like, who else besides yourself will be involved in making the decision and what is the best way to involve them? It’s best to stay out of this position by making multiple contacts in the organization.

You need to get to know the people. Today this is easier than ever but sales reps fail to do an adequate job. Look them up on every social media channel you can and when appropriate, interact with them and at the right time ask to connect with a personalized message about something they posted or that you have in common. You need to determine who will be involved in making the decision and know that you may not get to have any contact with some of those involved.

Always plan your sales call. Don’t wing it. There are many nuances to a complex sale with a large enterprise. The better prepared you are the more wins you will have.”

Leanne Hoagland Smith

Chief Results Officer, Advanced Systems

“In sales these are 3 truisms:

#1-People buy from people they know and trust.

#2-People buy you first.

#3-People buy on value unique to them.

To be successful selling within a large and complex enterprise suggests having as many people know, trust and buy you because you have connected to their value drivers. The more people that know you and trust you within that enterprise the greater opportunity for them to experience how you connect to their value drivers and ultimately add value.”

Jonathan M. Hodge

President and CEO, Advantage Performance Group

“Larger companies move at a different pace in comparison to smaller enterprises. Therefore, it is critical that you understand where they are in their own unique buying cycle and align your sales efforts to their timeline rather than follow a rote set of steps outlined in an internal sales process.

An example of misalignment would be a salesperson providing a proposal when a client is much earlier in their buying cycle and maybe still assessing needs. Just because you think you have the answers and are ready to present a solution, it doesn’t mean the client is anywhere near the point in their process to be considering options let alone decisions. In fact, they haven’t even completely framed the issue they are trying to address! By aligning yourself with your client’s buying cycle it keeps you from getting ahead (or worse, behind) your client’s decision making process.”

Mark Hunter

Sales Speaker / Author, The Sales Hunter

“Being seen as a peer is essential. Large enterprises have their own cultures and their own eco-systems, and the last thing they have time for is helping a small company or someone who simply thinks small. To be seen as a peer you need to not just dress and act like you’re with a large enterprise company but you have to think at their level tool. What does this mean? It means understanding their industry and their competitors. It means being able to relate to the key issues they’re dealing with and not being fixated on your own world. When you present yourself as a peer, you’re able to ask different questions and have different meetings, because you’ll be seen as one of them. This becomes especially important due to the number of people who likely will be involved in making a decision, including the purchasing department. Your ability to be seen as a peer who has strategic value will allow you to minimize the negative impact the purchasing department might have on the decision.”

Keith Johnstone

Marketing Manager, Peak Sales Recruiting

“Sellers need to identify and qualify prospects as “mobilizers”. Mobilizers are individuals within business units who acknowledge that current business practices, approaches, or model is not sustainable or is somewhat flawed. These are people who are not only receptive to the sellers solution but is willing to explore their business need further by committing resources to the purchase exploration. They actively bring stakeholders together to achieve consensus that your solution is best positioned to support their needs. However, the seller needs to provide the mobilizer the tools to forge stakeholder consensus.”

Connie Kadansky

“Make sure that the salespeople who will be representing your company are emotionally comfortable in complex sales dynamics.

There are three types of Sales Call Reluctance that can affect a salesperson selling to large enterprises.

Social Self-Consciousness is defined as the degree of energy lost to emotional discomfort and hesitation to contact up-market prospective buyers. Research reveals that veteran salespeople can be ultra-sensitive to the hierarchy which can limit their success in high-stake selling environments. Some salespeople are habitually intimidated by persons of wealth, prestige, power and/or education. This reluctance can show up in being over-reliant on supportive influencers to sell them into the company rather than going straight to the high-level decision makers. When you detect that a salesperson is intimidated by his/her prospects, immediately invest in coaching to help them realign their self-image so can deal confidently with their high-level prospects.

Complex Sales Reluctance is the emotional discomfort and hesitation to initiate and engage in complex selling activities required to close large accounts. These activities can include, but are not limited to, contacting and selling to senior level executives and multiple decision-makers, making boardroom or formal group presentations to key decision-makers, preparation of professionally written proposals, and patiently and methodically managing complex, long-term negotiations. Require an organic, written strategic plan from initiating contact with the large enterprise to signed contract. When you feel emotional hesitation, address it immediately.

Stage Fright is the anxiety or fear which can be aroused by the requirements to present in front of an audience. Salespeople must be exceptional presenters. Research has proven that veteran salespeople perceive themselves to be better presenters than they are, resulting in over-confidence and awkward moments. Sales leaders across the global benefit from participating in a local Toastmasters Club. Their fellow members will not placate them. This is where they can get honest feedback to master presentation skills.”

Nick Kane

Managing Partner, Janek Performance Group

“Top sales professionals know complex and lengthy sales processes for large enterprises require them to be on their toes and have a plan. These engagements can include numerous presentations, multiple meetings with key stakeholders from different departments, passing the procurement department’s screening process, negotiating with the legal team and more. With all the moving pieces, it is easy to get lost and therefore, critical that sales professionals have a strategic plan to navigate the process effectively.

It is also important to remember large companies employ these complex processes to ensure that major purchases are viable to them and unbiased. That being said, one of the most important elements for any sales professional is to ensure they understand the end-to-end buying process.

They will need to know who is involved, at what point and most importantly what level of influence that person or department will have on the decision. This also means being prepared to explain the unique benefits of their solution to the various stakeholders and departments. The reason someone will buy will vary greatly from person to person or department to department. Sales professionals must have comprehensive understanding of their challenges and needs so they can tailor what they offer to what matters most to each person/department uniquely.”

Ron Karr

Author/Consultant, Karr Associates Inc.

“To begin with, you must have a clear objective and detailed strategy. To create the strategy, you must have a planning session that includes executives from all disciplines in your company that will have to support your strategy. They must be involved because if they are actively helping to create the plan, they will most likely support it.

By disciplines I mean manufacturing, customer service, engineering, project management, etc. You must also include the customer in your strategy session.

Too often vendors make the mistake of creating key account plans without having the customer participate. Invite the highest level executive you can get to come in and present the customer’s strategic plan as to what their goals, objectives and obstacles are. This way you can take that into account as you create your plan. As part of the plan, you must identify all of the players in the customer’s org chart you need to address.

Bottom line: Selling to large enterprises requires a detailed plan that is properly executed with measurable results.”

Alice Kemper

“I’ve always find it interesting when businesses want to go after the FedX’s of the world and I ask two questions: “Who’s assigned to the team going after this big enterprise?” and “What’s the framework and proven strategy you plan to use?”

More often than not, they planned on assigning it to one rep, often the top producer, and figure they can ‘just do it’. That’s a set-up for failure.

Today the average enterprise deal has 5.4 decision makers attached to it. Which means you need to sell with a team approach. You don’t want to rely on 5.4 people not connecting with your one sales person. Plus, the longer sales cycle, which selling to large enterprises is, requires a proven strategy and framework to close. One sales person does not have the time or expertise to manage every aspect of the proper preparation and execution of a well thought out plan.

One other key tip: Include in your strategy ways to distinctively differentiate your team as well as your solution. You want to be extraordinary to stand out in as many ways as possible from the competition.”

Craig Klein

Founder and CEO, SalesNexus

“The larger the organization, the more structured and bureaucratic the decision making tends to be. This means that the sales process will be more complex and take more time than with smaller organizations, while also hopefully leading to much larger orders.

It’s crucial to choose your battles strategically before investing the resources in developing relationships. What large organizations seem to have strategies and goals that align with the services you provide? Which organizations seem to be making changes and making new purchases aggressively? Pick the most strategically aligned targets and then map out a unique plan for each account. Who do you know in the organization? What competitors are they working with? Who are the likely influencers in a decision? How can you establish relationships with each of them?”

Mike Kunkle

Sales Transformation Strategist, Transforming Sales Results, LLC

“Small or large, enterprises don’t buy anything. People do. Selling to people is complex, and the more of them that are involved in the purchase decision, the more difficult it can be. There are other factors that make selling to large enterprises challenging, but if you address this one well, some of the others are easier to manage.

Among other things, I advise clients to focus on understanding their buyers’ roles, decision process, and decision criteria, especially “buying process exit criteria” (BPEC).

BPEC are whatever the decision-makers or influencers need to see, hear, feel, understand, and/or believe in each stage of their buying journey to feel comfortable moving forward to the next stage of the process with you. You uncover these criteria through great discovery and check-ins, that are ongoing throughout the process.

This removes what I refer to as the “superstition of selling” and allows sales reps to focus on what really matters to each buyer. If you remember that decisions are made with both logic and emotion, you will include emotional and personal factors/pressures in the mix.”

Dave Kurlan

Founder & CEO, Kurlan & Associates

“The most important things to remember are that the process must not change just because the size of the opportunity has more zeros. The three things that differ with large companies are the number of decision makers, the difficulty reaching decision makers, and the amount of competition you will face. This usually results in a longer sales cycle.

The key skill you’ll need to navigate this more complex process is the ability to manage the balance of patience. Be patient with the additional layers of decision making and length of the sales cycle, but not so patient that you allow stalls, put-offs, and smoke screens.”

Michael Nick

“I think the key to selling into a large enterprise is two-fold. First, you must look at larger enterprises as a group of small companies that have their own agendas. Find a trigger event within a small subset and work through selling to them. This technique will establish you as a trusted source for whatever it is you sell. I am of course glossing over all the effort it takes to sell into a small group. You must still research the prospect, identify issues, pains, and goals, determine status quo, and propose how you are going to resolve their issues.

Second, I will call it “land and expand”. Once you are seated into a subset of the enterprise you can then ask for referrals and introductions. Again, I would suggest you find a trigger event and then ask your advocates to make an introduction. There is no substitute for a referral.”

Erik Peterson

Chief Customer Officer, Corporate Visions Inc.

In a complex sales cycle, you have two things fighting against you. One, you need to engage multiple decision-makers to get the deal done. And two, the complexity of the deal increases the likelihood that the deal will stall out and lose momentum before it comes to a close, ultimately ending in the wastebin of no decision.There are two tools you can use to fight through these challenges.The first tool is to avoid the trap of creating different messages for each decision-maker. In psychology, this is called the “fundamental attribution error.” The fundamental attribution error is the mistake of putting too much emphasis on a person’s personality and not enough emphasis on their context or situational influences. Trying to create individual messages for each decision maker misses the context in which they’ll need to make their decisions, which is the needs of the business overall, not just their department. Build your message around the organizational needs, and you’ll have a message that helps all your decision makers reach consensus faster.The second tool is Pivotal Agreements. Pivotal agreements are value-based exchanges that you can use to advance your deals while protecting your value. In a complex sales cycle there are many things you might want or need: access to decision makers, access to information, proof opportunities, certain deal structures, and other expansion opportunities like quarterly business reviews. Instead of giving stuff away for free just to stay in a deal, use Pivotal Agreements to exchange value by getting something you value. This purposeful exchange of value creates momentum in deals and gives you the chance to expand the deal and protect your margins. Learning to use Pivotal Agreements is like gaining a superpower in terms of how it improves your deal velocity and its overall profitability.

Daniel Pink

Author of ‘To Sell is Human’

Think of yourself less as a salesperson and more as a management consultant. Understand the prospect’s business inside and out. Then identify hidden problems — and provide insights and solutions to address them.

Steve Richard

Founder & CRO, Execvision

“When selling to large enterprises never underestimate the number of decision makers. It feels more like a political campaign than a sales process. Be sure to shake every hand and kiss every baby. Treat everyone as if he or she is THE most influential decision maker in the buying group. When you are on a call or a meeting with a buying group be sure to address every member individually. Know their names. Follow up with each individually after. Understand what each person is trying to accomplish and how thy will define success.

And don’t get out-relationshipped by your competitors. I once lost a deal because the SVP of Sales was a golfing buddy of my competitor. Doh! Be sure to look at LinkedIn to figure out the relationship web.”

Linda Richardson

Founder of Richardson, Consultant, Author

“Large enterprise companies have internal resources at their finger tips. Research and creativity are essential to sell to them. These customers have done their homework. Do yours! The rarely need you for product knowledge. But they do need you for the insights you can bring to add to what they know and help them solve their problems and achieve their outcomes.

Identify and sell to multiple clients in the organization and build relationships with all of them not just the key decision maker. Develop a coach, or multiple coaches, who are invested in your winning the business.”

Steven A. Rosen

Founder, STAR Results

“Since enterprise sales is highly complex, it’s important for your sales managers to support the sales people in the process. Here are two ways in which the sales leadership can help:

1. Sales managers should play a more active role in each deal by coaching their sales teams as opposed to trying to be the closer of super rep. Great coaches facilitate the selling process by asking effective questioning to ensure their salespeople understand the issues, challenges and objections of each of the key stakeholders. Highly effective coaches will use though provoking questions to help their salespeople find solutions to move the sales forward.

A few coaching questions that work well are:

o Who else is involved in the buying decision?

o What objections do they have and how are you resolving each objection?

o Who else is being considered?

o What are the next steps?

o What resources do you need from me?

Training your sales managers to become effective sales coaches is an investment. However, if you want to convert more enterprise deals, it makes absolute sense to invest in it. That’s because winning just one additional deal can add millions of dollars to your revenue.

2. Another way sales managers can support their sales people is to conduct joint meetings so they get to know key stakeholders. However, the sales manager should use these meetings as opportunities to coach. By observing their salespeople making a sales call the sales manager can provide precious feedback and see potential areas for improvement. All sales reps can elevate their skills through effective coaching and close more sales.”

Aaron Ross

Bestselling Author, Predictable Revenue

“Many companies get off the ground with the product passion and vision of the founder team. If it’s a first-time team, they hold on too long to ideas like ‘we don’t want to have to sell’ and ‘sales is a necessary evil and expensive’. The sooner they realize that sales is a high-ROI investment and enterprise companies need help from salespeople in order to buy, because it’s so damn complicated there… the sooner the founders can get as excited about investing in building a sales machine as they are about their product.”

Jill Rowley

“One of the biggest keys to success in enterprise sales is doing extensive research the companies that fit your Ideal Customer Profile “ICP”. You need to learn and understand several facets about the company before you can expect to initiate a conversation. Most people who try to sell to enterprises do not conduct enough research, but by going the extra mile, they can radically increase their chances of winning the business.

Here are two key areas where doing extensive research can make a big difference to the sale.

The Business Environment

Begin your research by developing an understanding of their business model and strategy. The more you know, the better you will be able to position your offering in a way that resonates with their current circumstances. Ask several questions that give you an in-depth understanding of the challenges they face and the goals they want to achieve. For instance:

o What goals are important to them and how can your offer help them to fulfill those business goals? Who are their investors and what goals do they want the company to achieve over the next few quarters?

o Understand the nature of the industry and their products. Do they sell a commodity and face a lot of competition, or do they have an innovative offering?

o Understand their vendor ecosystem – who else do they buy from? What can you learn about the type of vendors they like to work with? How can you position yourself as a vendor they would be comfortable working with?

The Decision Makers

Create and influence map of the multiple stakeholders who would be involved in the purchase decision. To do this accurately, do not limit yourself to checking out the LinkedIn profiles of their employees. If you have connections in any of their vendor companies, get in touch with them and ask them about the company. How does the decision-making process work in their company? Who are the key decision makers and who are the influencers?

Once you have identified the decision makers, look at the deal from the perspective of the roles of these different stakeholders. How does your offering help them to fulfill their individual goals and targets? Look for video interviews, podcasts, blog posts or social media mentions of the different stakeholders where they are talking about what’s important to them. Use these insights to position what you can do for them.

Try to find out ways to build rapport with the decision makers. What do the CEO and other stakeholders care about? Look at who they follow on Twitter to know more about their interests and what they might be passionate about. Bringing up these topics in your conversations can go a long way in forging a stronger bond with your prospects.

The more you find out about the company, its decision makers and what matters to them, the more relevant and impactful your conversations will be, thereby increasing your chances of getting the deal.”

Neal Schaffer

Social Media Keynote Speaker, Maximize Your Social

“Social media can play a valuable role in navigating the complexities of enterprise sales.

There can be multiple decision makers across the organization spread across several locations or even across different companies which are under the umbrella of one parent company. An increasing number of people are becoming involved in the decision making process in large enterprises. The key thing to do is to map out the decision makers and that’s what social media can help you with. Social media can also help you confirm who fits where within the decision making hierarchy. There might have been people who you might not have come across, but nevertheless who are part of the decision making process. You should try to identify them to anticipate roadblocks in advance before they happen.

A tip related to the above, is to create an advocate within the organization who will be your coach and provide you with all the information that you need to sell. They will help you map out the decision making process. You can bounce off ideas with this person.

You can use social media to learn about the competition you might be up against. Are the decision makers communicating with your competitors over social media or following them? You should accordingly be ready to demonstrate how you can offer something better than your competitors.

Social media also allows you to engage with the decision makers whenever they post content and add value to discussions, although without trying to sell. This is a great way to build relationships as well as demonstrate your credibility.”

Tom Searcy

Founder and CEO, Hunt Big Sales

“Many of the exciting benefits, financial gains and technology advantages are what creates interest in a new purchase by a large enterprise. However, because the group of people involved in the buying process by the large enterprise is large, doubts and concerns develop. Fear overtakes advantage as the driving force in the final purchasing choice. There is often a temptation by the selling company to re-state the value of their proposal. In fact, the decision to purchase will be made as much if not more by the removal of fear in the secondary players in the buying company. You have to win the fear to win the deal.”

Kurt Shaver

“The number of people on the buying committee for enterprise sales decisions has increased year after year. In order to gain consensus, a seller must know who’s on the buying committee and what their priorities are. Linked in is a great way to discover your prospect’s colleagues on the organizational chart and see what types of information they’re posting and commenting on to gain insights. For example, imagine that a marketing software salesperson is working with the marketing director at a prospective customer. Chances are good that the VP of Marketing, the CMO, a financial executive (i.e. CFO), and an IT executive (i.e. CIO) may also be involved in the decision. Now imagine that the CMO comments on a LinkedIn post about “Sales and Marketing Alignment”. That could give the seller insights to include sales considerations into future discussions and add the VP of Sales to the Watch/Connect list, too.”

Amar Sheth

Social Selling Evangelist, SalesForLife

“Enterprise/larger accounts typically have buying committees that can take time to uncover. Using social platforms as a part of your sales strategy is critical here. For example: use LinkedIn advanced search and determine who the key players are, who they’re connected to and determine their spheres of influence.

Knowing buyers is one thing; but knowing who they’re connected to can accelerate sales cycles.

Next, do your research: it’s amazing how much information is online. This is about knowing what specific people are saying, their positions and how power-players are helping to shape the market. For example: consider analysts. Are you following what the key analysts are predicting for a prospect’s industry? How about your prospect’s competitors: what can you learn about them?

The beauty of generating insights online is that it’s free and powerful – it also need not take a lot of your time. Sales professionals that prepare can significantly improve their chances of creating value for prospects and capturing it for themselves.

In short, conquer enterprise/larger accounts with knowing your buying committee, understanding their spheres of influence, and do research to bring greater contextualization to your offering.”

Colleen Stanley

President and Chief Selling Officer, SalesLeadership, Inc.

“It’s important to remember that there are people behind the titles in a complex sale. Take time to customize your approach with customized value propositions. Value propositions can be customized by industry, buying influence or line of business you are discussing. Eliminate one size fits all conversations.

How you start a conversation will determine if you are treated as a vendor or advisor. Generic, one size fits all value props lead to generic, no action conversations.”

Brian Sullivan

Vice-President, Sandler Training

Competitive Knowledge is Competitive Advantage

Enterprise pursuits pose many daunting challenges for selling organizations, not the least of which is that these huge, game-changing opportunities attract the very best of the competition.

In selling into small and medium-sized accounts, you do run up against tough competitors now and then, no doubt. But in complex enterprise opportunities, you can count on the competitors being sophisticated and well-prepared. Prepared to sell against you. And to win, to prevail over these formidable adversaries, you need to know everything about them. Your strategy, simply put, must account for them.

You need to comprehensively understand their business models, their people, their offerings and any partners they might potentially bring to the table in a deal. And you must be able to effectively predict, understand and strategize against the customized value propositions they’ll be focusing on in each specific opportunity.

Successfully executing in these areas and others will increase your likelihood of success and help ensure that you make educated business decisions to pursue the deals you’re most likely to win and to forego the others.”

Babette Ten Haken

Founder & President, Sales Aerobics for Engineers

“When selling to the enterprise, understanding the context of the decision you are targeting becomes critical not only to new customer acquisition but to customer retention, as well. Unlike selling to startups or small to midsize companies, enterprise selling environments are complex. Root causes create very large contexts involving multiple layers of decision makers, influencers and end users. Do you know who they are? Do you understand their respective voices? Can you connect the dots?

Often the solution to be placed impacts more than meets the eye. It is your role, as an enterprise sales leader of worth, to fully discover not only today’s implications of placing your solution, but the future of your solution within that enterprise. Decision makers want to understand how your solution, and future solutions, impact line of business value creation for the enterprise. To anticipate and address their questions, work cross-functionally and non-linearly with your team.”

Andrea Waltz

Author of ‘GoforNo’

“The challenge with enterprise deals is that the complexity requires a deeper level of persistence. You may watch decision makers change and have other challenges arise during the process. It may feel like you have to start from the beginning of the deal sometimes. We like to say, ‘easy yeses produce little successes.’

So, when you are going for big deals, with complexities, stay the course and don’t give up because in the end it will be worth it. In addition, the more you go through such sales, the better skilled you become at handling similar challenges in the future.”

Craig Wortmann

Founder and CEO, Sales Engine Inc.

“My biggest recommendation for selling into large enterprises is ‘don’t take yes for an answer.’ What this is means is that we often think that the one contact who responds to us is the person who’s going to bring us to the dance. Nope. So often, we let ourselves be seduced in our own sales process by that one buyer who is sending the right signals. But the reality in a large (vs. small) enterprise is that there are likely 3-5 more people who must be on board, and it’s our job gather them into our sales process and bring them aboard, one by one. This is the biggest failure I see in selling to large companies.”

Rene Zamora

“With start-ups and mid market selling a top sales person can leverage their charisma and assertiveness to open doors to people involved in the buying process. With an enterprise deal too much of an assertive approach can kill the deal. You can still have success, but the risk might not be worth it.

Instead of being direct and assertive, earn the trust of each contact so they’ll be willing to introduce you to the others involved in the decision process.

Secondly, make it non-negotiable to move forward without being introduced and meeting with all of those involved, including the highest level contact. I realize this can also be a risky move as the deal can shut down if they say no.

To minimize this risk, be committed to your requests, let your sponsor know what questions you will ask and allow for flexible interviewing duration and methods.

Interviewing doesn’t have to be face-to-face, or by phone, and they don’t have to be thirty plus minutes long. Five minutes with one or more quality questions can build favor and trust in a CEO’s eyes. Interviewing through email or web cam can work just fine. By sharing your questions with your sponsor you are removing an unknown to them and they might help you with your questions.

If it’s important to you, more people will work to accommodate you. Never move forward without being introduced so each contact is prepared to give you the time you deserve to do your job well.”


Enterprise sales might be complex, but if you follow these tips, you will find it far easier to crack win these high-ticket deals.

To get more tips from top experts and successful entrepreneurs on how to grow your business faster, check out the Knowlarity Blog.

By Peter Banerjea

Peter is a Co-Founder at SuccessIsWhat. He is also a content marketing advisor at Knowlarity, Asia's biggest cloud communications company with more than 15,000 customers.

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