Neil Patel

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Sell to Large and Enterprise Businesses Using This 16 Point Checklist

Selling your service or software to large and enterprise-sized businesses requires a different approach than selling to small and medium-sized businesses.

As a founder and CEO, I’ve spent my career selling to medium, large, and enterprise banks, credit unions, and lenders nationwide. The average deal size was $500,000 annually, the smallest was $25,000 annually, and the largest was $7,000,000 annually.

I’ve spent time on the ground as the only salesperson at a startup. I’ve hired and managed senior salespeople. And I’ve overseen sales through monthly reporting only. My goal is to humbly share with you my perspectives on what I’ve seen work and how I think you can apply it to your business.

Let’s jump right in.

What’s the difference?

There are approximately 6,064,000 businesses (firms with payroll) in the U.S. according to the United States Census Bureau, and of that only 0.32% qualify as large or enterprise sized businesses. Here are estimates derived from that data:

tims table

Relationships are everything

Covet relationships.

Let’s be clear. You never actually sell anything to a business. You sell to people who work inside a business. The relationship you hold with your potential customer is what tips the scale, either in your favor or against.

Assuming you offer a product of value, people buy from those they trust, have confidence in, and like. There’s no shortcut to this; it just takes time. That’s why average sales cycles can range from 6 to 24 months, and that’s why there are some deals you will never close.

Selling to a business is a very rewarding experience. Over time, you’ll develop personal relationships with your customers, many of whom you will consider good friends.

Know how decisions are made

In order to close a deal, you need to understand how decisions are made. If you don’t understand the process, your sale will be delayed — or worse, you won’t have a sale to delay at all!

Every organization is different, but there are three common structures you should be aware of:

  1. The first is the sole 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.
  2. 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.
  3. 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.

As you can see, it’s not always about the CEO or president. In a large company, there could be many people who have the scope of authority to influence and get your deal inked. You just need to identify that person or persons.

This naturally begs the question, “How do you get to the right decision maker in the first place?”

That, my friend, is literally the million dollar question we’ll cover in the next 16 sections.

1. Start with the people you know

When selling to a business, start with the relationships you already have with people you know personally.

If you’re new and have never sold anything to anyone, your #1 goal is to find a warm referral to the organization you’re trying to get into. Your contact could be a college friend who works as an account manager who in turn services that potential client, or it could be another vendor who doesn’t directly compete against you.

Exhaust your relationships.

Your goal is to get an appointment with your contact, share your business with them, and get a warm referral to others. What you’re trying to do is meet champions for your business. People who believe in what you’re selling and who can help you get inside your target businesses.

Of course, if you already have experience and contacts, start with those you’ve sold to in the past or have tried to sell to. Tap your industry contacts. Everyone should know what your new venture is.

2. Get your first customer

Your very first paying customer will likely be a small or medium-sized business that will help you step up to the larger and enterprise-sized businesses. Once you get your first customer, and assuming they’re actually a happy customer, you’ll have an advocate for your business who will be your customer testimonial for your second client and maybe even your two-hundredth client.

Particularly for startups, it’s critical to get this first customer under your belt because it proves you are a real business to future customers, helps slow the cash burn, and attracts investors.

The good news is your first customer probably knows they are your first. Anyone who picks your brand new company wants to help you grow.

3. Be a connector

“You can have everything in life you want, if you will just help enough other people get what they want.” – Zig Ziglar

In business, people do business with other people. Your goal is to make meaningful and mutually beneficial connections between your contacts. Be open in making introductions to people you know, and help your contacts develop new relationships with each another.

Of course, when you make a referral, you’re putting your own name on the line. Be sure to make quality connections, not just any connection for the sake of just making a connection. A bad introduction is much worse than no introduction at all.

Don’t forget to look beyond your customers. Look to connect with vendors, partners, and even competitors as well.

4. Solve problems

Don’t be a salesperson; be a consultant and resource.

You never sell a product; you sell a solution to a problem. This means that your product itself is never the primary focal point. The focal point is what value your product actually provides. What real-world pain point do you make unpainful?

For example, you don’t sell CRM software. You sell a way to never lose opportunities.

If you focus on your customers’ issues, you can help them solve their problems. But you’ll need to be an expert in your space. Your aim is to become a valuable addition to the company, not just a vendor. You want to be the person they call when issues relating to your expertise unfold. And if you really want to be a valuable resource, be the one who helps them identify issues they don’t even know they have yet.

You can’t fake expertise. You’ll have to actually deeply embed yourself in their world. Understand industry cycles, pain points, opportunities, and the shifting landscape.

But offering solutions does not imply talking and talking and talking. Listen and understand so you can help offer a better solution. Ask more questions than you answer.

5. Participate in industry events

If you serve a particular industry, participating in industry functions such as associations and trade organizations is a great way to learn and meet people within the industry. Consistency is everything. Your aim is to become an active participant, become a regular contributor, and essentially become a fixture at industry events.

There are many different organizations throughout the country. Some are regional in scope while others focus on national concerns. You don’t need to go to all of them. Pick a few to start with and plan on attending for years to come.

Your first few shows can be lonely since you may not know many people. However, there are endless opportunities everywhere, such as the trade show floor, booths, lobby, parties/mixers, and educational seminars.

6. Join a committee

Take your participation with industry trade organizations a step beyond the semiannual events and get involved with their committees. Business associations are always looking for assistance in organizing membership drives, planning for events, bringing on sponsors, or all of the above.

Being a part of a committee that is well respected in your industry goes a long way in developing your credibility, contacts, and industry knowledge. It also shows that you’re not just there trying to make a buck, but that you’re there trying to further your customer’s industry and success.

7. Partner with non-competing vendors

The easiest place to find a warm introduction into a company is via those who already sell to that company! Seek out these relationships and share your solution with them.

Vendors who are already inside a company, especially if they are consultative (see Section 4, above), have a keen perspective on the company’s needs. If they can identify a need you can solve, many are willing to make referrals without compensation.

For example, let’s say you sell employment screening technology. Team up with a payroll provider and share with them what makes your product unique. As they come across current clients who express this very pain point, they’ll make a direct introduction.

You can even take this one step further and do joint sales calls and marketing campaigns.

At a company I advised years ago that sold a business networking platform, my business was able to distribute our offering through various partners’ email lists. Of course, we did the same and exposed them to our customers, too.

8. Write for industry publications and press

Industry specific publications are one of the best ways to deliver a message to your potential customers. Because the channel is specific and trusted, your brand will develop, and opportunities will emerge.

Pitch the appropriate editorial staff to be featured and to be called on when the reporters need quotes or content contributions. If you don’t have the time and can afford the cost, use a PR firm that specializes in your particular space.

9. Use email campaigns

For businesses, email is still very much alive and remains one of the best ways to reach your target audience. If you don’t have your own list, you can rent lists from industry associations and industry publications. You’ll have to pay a fee, but your emails will be targeted and will reach the eyes of the decision makers you need to speak with.

We won’t go into how to craft an email campaign, but we’ll cover a few approaches I’ve seen work well. Click here for a great article about B2B email campaigns.

Refrain from speaking about your product and features. Instead, use a direct approach where you identify the company’s problem and offer a solution. Ask them to take action, and make it easy for them to get in touch with you. Offer a phone number or suggest that they simply “reply back” to engage.

Another approach is to offer industry updates that help convince them you’re an expert and one who can help them solve problems and generate results. If your potential customers learn from you, they’ll naturally identify you and your company as a solution.

10. Reach out through cold calls and emails

I’m betting I’ll get some arguments about this claim, but let me tell you, it still works! If you’re selling a $100 per month widget, don’t bother. But if your sales can be tens of thousands to millions annually, cold calling is a strategy you simply cannot ignore.

Don’t get me wrong, I strongly believe in inbound marketing. All I’m saying is cold calls still work and deserve your consideration.

As the world and your competitors are focused on inbound marketing, you’ll be one of the few doing outbound calls. The first person who builds a relationship with a business has a much higher chance of winning the deal. Combine this with a consultative sales approach, and you’ll be ahead of the curve.

Be sure to do research first. Understand the customer’s problem, how they currently solve it, how your platform will help them reach their goals, and how they’ll implement your solution. For example, before I cold call or email someone, I already understand how they currently do what they do. Therefore, when I craft my pitch, I focus on how our company can solve their problem and what it’ll take to implement our solution within their infrastructure.

Click here for an excellent article on cold emails and calls.

11. Publish white papers

White papers are a solid way to showcase your solution, industry knowledge, and case studies of how you have already helped customers. It builds credibility and deal flow.

Think of a white paper as a blog post on steroids. White papers are usually authoritative, technical in nature, and contain supported research and real-world customer use cases. They should not be sales pitches. You want to make sure your white paper helps the reader identify their own problem and helps them visualize a solution.

Who will read your white paper? At many companies, management will designate a person to perform research, seek out new solutions, do product demos, and kick recommendations up to a team or manager. Expect your white papers to be read by an entry-level employee, but anticipate that they may get kicked up throughout an organization as well.

Here are some great examples of white papers.

12. Advertise on LinkedIn

LinkedIn advertising is a natural channel for a B2B company. One of the easy things about selling to businesses is that you know your target demographic very well. Use LinkedIn to target specific regions, companies, titles, and groups.

When you consider the cost of acquisition for a 6- to 24-month sales cycle, LinkedIn is cheap. Spending hundreds and even thousands of dollars on a prospect that may generate hundreds of thousands of dollars in revenue is a good ROI.

LinkedIn has great resources and analytics to test your campaigns and ensure your message and call-to-action is effective. In fact, LinkedIn won’t let you proceed if it isn’t. LinkedIn will shut down your campaign if it doesn’t receive a minimum conversion. Makes sense, right? For LinkedIn, there’s no point in displaying your brand for free if it doesn’t convert into dollars.

13. Hire sales reps

Hiring sales reps is a must. You’re able to capitalize on the relationships they’ve spent years developing and open up doors quicker than you can on your own.

Be sure to differentiate between finders and miners.

A finder is someone who can find business. They’re the ones who shake hands and kiss babies. They’re already part of the good ole boy network. Finders are usually high priced and difficult to manage. Attention to detail isn’t always their strong point, so be sure you know how to support finders properly.

A miner, on the other hand, is someone who knows how to mine for business from existing customers and marketing campaigns. These are usually the people who make great internal sales people and account managers. They develop deep relationships through day-to-day interaction with customers. Unlike finders, miners are usually more technical and detailed oriented.

Develop a good strategy for finders and miners to work together, and you’ll have an amazing one-two combination.

14. Recruit rainmakers

The best rainmakers usually aren’t looking for a job at the moment, but those are precisely the ones you want. Hire a headhunter, and offer your prospect a better package selling a better product.

Remember that top salespeople already make a ton of money, so offering more money isn’t good enough. You’ll need to help support their growth. You need to identify their professional and personal goals and be the one to make them come to life. It could be anything from the need for ownership through stock options or equity buy-in to new responsibilities to a work-life balance.

15. Acquire or partner with competitors

Remember Section 3, “Be a connector,” above? You must network with competitors as well.

There are two things you’re looking for: a partnership or an acquisition.

For example, let’s say you sell a stand-alone functional software system that services smaller volume customers better, while your competitor, who you’re friendly with, concentrates on mid-tier larger volume clients where integration is required. Bingo! This is a great opportunity to serve one another.

In regard to acquisitions, the question is how do you acquire if you don’t have a large amount of cash or credit? Easy! Be creative.

In my last company, we acquired two companies with no upfront cash through the creative use of salary, sales incentives, bonuses, and an employment agreement with a golden parachute. I’ve also advised a company that would pay out a small amount of cash in addition to stock with dividend payouts. They did this a total of 8 times, growing to a point where they paid out $1 million per month in dividends.

These opportunities don’t just pop out of the blue. They require that you build relationships with competitors. When the opportunity presents itself, such as when a competitor is struggling financially, they’ll reach out to you for help.

16. Prepare a response to requests for proposal

A request for proposal (RFP) is a document that an organization posts to solicit bids from potential vendors. It’s essentially an advertisement to come sell to them. You, as the vendor, will usually put together a formal package (and it’s a big one) based on the issuer’s preferred format.

I highly recommend putting together a standard RFP package, which you update quarterly, so when RFPs come up, you can easily reformat it to fit the entity’s requirements.

The RFP process is meant to create structure and provide transparency to a vendor provider decision. RFPs are almost always issued by governments. Large and enterprise-sized companies do the same under varying degrees, with the biggest difference being that they are not required to post publicly.

Your relationships and industry contacts will be the ones to open doors and inform you when RFP opportunities arise.


As you can see, there are many different ways to approach B2B sales, but they ultimately all boil down to just a few key takeaways.

Relationships are everything. Be trustworthy, be confident, and hope they like you!

What do you think? What other strategies have worked for you?

About the Author: Tim Nguyen is co-founder and CEO at BeSmartee, a new way of getting a home loan that’s as easy as booking a plane ticket online. Visit their website to sign up for their exclusive private launch.

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