Thursday, July 18, 2024

Hurdling the Unique Challenges of Selling SaaS to Enterprise Clients

For B2B SaaS brands, selling to solopreneurs and small firms is fairly straightforward, and can even be automated with a good marketing stack. But you may be missing out on some huge potential by ignoring the bigger fish – potential customers on the enterprise level.

Focusing on enterprise leads may seem counter-intuitive. After all, they represent just a tiny market share, and are definitely not low-hanging fruit. According to the U.S. Census Bureau, there are just over 6 million businesses (firms with active payrolls), in the U.S. Of those, less than one out of every 300 companies qualifies as a large or enterprise sized business by employing 500 or more team members. That’s about 9,000 large businesses, and 11,000 enterprise sized businesses.


Source: Kissmetrics


So why invest time and effort in landing one of these whales? Here are two huge reasons:

  1. Enterprise account purchases tend to be more significant and more consistent.

A typical enterprise deal is worth at least five times the amount of the smallest plan offered. The more resources that an enterprise business requires, the more money you can make. You can sell far fewer and still earn higher recurring monthly revenue.

  1. The brand equity gained from a big name client is massive.

The brand equity associated with having those big name clients makes it easier to sell more to the smaller business because of the trust it builds. You’ll rack up valuable social proof, being able to use their logo, testimonials, case studies, and more in your own marketing.  If a small business sees that you supply a service to such a widely recognized brand, then they’re more likely to believe you will provide stellar value to them.


The Big Fat Challenges of Enterprise Sales

Clearly enterprise sales are important for your SaaS brand. But they come with some fairly significant challenges to overcome.

  1. More opportunities for friction

With enterprise level sales, there are more tiers and layers of management to get through before closing the deal. The process can be long and cumbersome. Deals are known to die at any number of points along the process, due to the friction. For many businesses, this is reason enough to make enterprise sales a low priority.

  1. Lack of clarity

Gallup’s State of the American Workplace report revealed a somewhat startling fact: Only 50% of U.S. workers have a clear and definite idea of what’s expected of them in their jobs. This means that when dealing with enterprise leads, it’s often extra hard to find someone who believes they have the power to make decisions, and is motivated to wield this power.

  1. It just plain takes more work

Moving through these additional tiers means there’s more follow-up, additional information and non-standard work. It draws out the process, sometimes taking months, or even years, to close the deal. As the time passes, the uncertainty, risks, doubt, and costs add up.


Three Ways to Overcome the Challenges

Just because it can be hard to land a deal with a large client doesn’t mean it can’t (or shouldn’t) be done.

Keep these challenges in perspective, though. “You must follow an effective territory, account and opportunity planning process that maximizes the likelihood that the deals you pursue are the ones you’re most likely to win,” says Brian W. Sullivan, co-author of Sandler Enterprise Selling: Winning, Growing, and Retaining Major Accounts. “And having such an intuitive process that maps what you do best to the opportunities you’re considering pursuing also acts as your guide to insure that you don’t embark on the deals that don’t match your profile.”

Start by developing solid business relationships throughout your target organization, and giving them the information they really need.

Terrence O’Toole, Director of Brokerage and Enterprise Sales at FreightCenter explains that all sales processes need to “include discovery techniques for asking questions that uncover needs and create a demand for your services. Take the information you learn,” he continues, “and tell the story of how the value of your services will support the needs of your client and their customers. When you discover how to make your customers’ customers happy, you will win and grow more enterprise client accounts.”

Here’s how to accomplish exactly that.

  1. Start with people you know.

Think of people you’ve sold to in the past, or have tried to sell to. Tap into your industry contacts. Use your existing network to get a warm referral to the organization or department you’re trying to break into. It could be an old college buddy who works as an account manager that provides services to your potential client, or maybe another vendor who isn’t in direct competition with you. The point is, you should be working to exhaust all your existing relationships. Instead of selling, give information.

  1. Use lead generation technology to track site visitors.

Data shows us that only about 2% of site visitors leave any contact details. The rest visit, then vanish.  Leverage a good lead generation tool to mine the data you get from your anonymous site visitors. The right tech will work with your existing analytics and CRM solutions to figure out what companies have visited your website, and what they did while there, smoothing the way for the next contact.



  1. Focus on ROI

To smooth the friction in the sales process, make ROI the focus of all your discussions, regardless of what tier you’re on. Keep things simple – avoid the fluff. Whatever proposal you send needs to include materials that will support your point that your product or service will impact the enterprise’s bottom line. Period. Describe the problem they need to solve, and how your product/service can do it. Clearly spell out the costs, and then highlight the savings.


Land a Big One

Enterprise sales do present some unique and fairly complex challenges, but the payoffs can be well worth the investment. Be consistent, be persistent, and use the tools available to build relationships with the people who can move the sale forward.


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Joe Liebkind
Joe Liebkind
Joe Liebkind is a Berlin-based tech writer, originally from NYC. He has worked with tech startups in sales and marketing with a specialty in ecommerce and SaaS platforms.