How to Win an Enterprise Client to Transform Your Small Business

9 Min Read

Signing an enterprise client is the holy grail for many small businesses. And for many good reasons.

Landing a corporate customer offers a ton of revenue security. Large enterprises are more financially stable than small or midsize businesses. They’re also likely to buy your most elite product or subscribe to your most expensive pricing tier. At the same time, cross-selling to other silos within their organization also becomes a possibility.

Make no mistake, all of these will transform your business. It will benefit your cash flow, your growth prospects, and your ability to attract other high-value customers.

In this article, we’ll take a look at ways you can remove common obstacles many businesses face as they pursue their first enterprise client.

1. To Win an Enterprise Client…Know Their Business

First thing’s first. You must understand your prospect’s business or your pitch has no chance of success. And I’m not talking about just being familiar with their history, their marketing material, and their roadmap.

If you want to show how you’re going to be valuable to an enterprise, you need to have remarkable insight into their operations and strategy. You need to know the objectives that drive them. You need to demonstrate that you understand the mechanisms required to get them there.

Fortunately, publicly traded companies always have highly detailed information available via their investor relations (IR) departments.

Another approach would be to Google the company’s name and look at their News results. Big business makes big news, so there’s likely going to be a wealth of up-to-date information on your prospect.

2. Understand and Articulate How You Can Add Value

Once talks with your prospect start picking up momentum and you get face time with decision-makers, the conversation should not be about you and what your company offers. This is not the time to go through a rehearsed sales pitch where you quote figures and cite case studies.

Yes, there’s a time for this spiel, but once you’re sitting in front of someone working in procurement, that time has gone.

The deeper you get into discussions, the more you need to steer the topic of the conversation toward the specifics of how your product or service will benefit them. At this point, they don’t care that you reduced administrative overhead costs by 15% for one of your other clients.

What they want to know, whether they’ll say this to you or not, is: 

  • How can you make our lives easier?
  • What will you do to you make us more profitable?
  • How will you protect us from the risks that are unique to our industry?

In short, you have to speak their company’s language. To do this, you need to have insight into their world. You’ll also need remarkable knowledge of your product’s capacity to make it better.

Practice these conversations. Meet with your colleagues and other industry specialists. Be ready to preempt every single question they may throw at you. Have smart, insightful, non-generic answers prepared for them.

3. Fine-Tune Your Company Image

Involve a branding specialist to ensure that your company’s public-facing presence is up to standard. This process typically involves a thorough audit of everything “out there” that could shape the public’s perception of your company and its reputation.

There’s a lot to this. There are websites, social media accounts, news mentions, press releases, the tone and content of your blog, even the online profiles of your management team.

In some cases, it might be worth the effort to start positioning your CEO as a thought-leader in your industry. 

Yes, this could take a while. However, the positive reputational impact of speaking at a conference or taking part in a round-table discussion with other experts can be huge.

Even simply building a solid, thought-provoking presence on Twitter will sometimes be enough to make your prospects take your brand a little more seriously. Make no mistake, your company’s leadership will be Googled.

4. Be Prepared for Serious Scrutiny from an Enterprise Client

Large organizations are extremely cautious when integrating their systems with an external party. Corporate governance often dictates that an absurd amount of auditing has to happen before a deal with a vendor is finalized.

This is most keenly visible in the digital security arena. If your company offers a solution that needs to be integrated with your prospect’s technical environment, be prepared to be placed under a very powerful, very intimidating microscope. Onboarding a new technology vendor is a lengthy process that typically kicks off with something called an Enterprise Security Questionnaire.

Don’t be fooled by the term. This is no one-pager with Yes/No answers. Your commitment to cybersecurity will face a level of scrutiny you may not be ready for.

Experts in cybersecurity cite this as the number one reason new customers contact them. Any potential enterprise client will assess your technical environment and, often, a small business is simply not ready for this.

It’s often a good idea to involve a consultant even before the questionnaire hits your CTO’s desk. As negotiations start heading into the closing phases, be proactive. Hop on the phone with a company that knows the questions enterprise clients are going to ask.

5. Understand the Impact a Long Sales Cycle Will Have

This is a biggie. Be prepared for many of your resources to be tied up in negotiations that can go on longer than expected. Much, much longer.

A long sales cycle will affect every company differently. It’s not always possible to preempt how this will impact other areas of your operations. The best approach is to stay aware of the risk and to never base any predictions on having the deal finalized by a specific date.

Also, tread carefully if your company somehow becomes dependent on closing the deal with an enterprise prospect. It’s understandable that this could happen. If it does, do whatever you can to avoid letting your prospect finding out. Desperation is not a good look in the business world. What this scenario says about your company’s ability to plan (amongst other things) isn’t great.

Signing Your First Enterprise-Level Client Will Require Patience

The sales cycle for landing a big fish is lengthy. Things move slowly at big corporations for a variety of reasons that can be both understandable and infuriating.

The truth is that large organizations are immensely risk-averse. They take new partnerships incredibly seriously as accountability is a big deal for them. As a result, the tactics we talk about in this article represent a lot of effort on your part. Get comfortable with this.

To create the optics you need to be taken seriously could take months, if not a year. You might have to make some challenging internal changes to align your operations with your prospect’s regulatory needs.

This is the price smaller businesses have to pay as they start wading toward the deep end of the corporate swimming pool. Know what the sacrifices are and be prepared to make them.

Fortunately, the benefits of succeeding in your pursuit of an enterprise client are immense. There’s no doubt about that.

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