The Complete Guide to Selling SaaS to Enterprise

Selling SaaS to enterprise customers is not easy, but it can pay off big time. Can you imagine closing just one deal a month to meet your target revenue? While this sounds great in theory, closing enterprise level deals does take a unique sales approach. In this guide we’ll explore the challenges and benefits of SaaS enterprise sales, SaaS enterprise pricing tactics, and sales strategies to close enterprise-level deals.

The Benefits of SaaS Enterprise Sales

Landing enterprise-level deals can bring many benefits to your company including:

  • More revenue with less deals: because the value of enterprise deals is so high, you could close a fraction of the deals and still hit target revenue for the year.
  • Greater revenue predictability: because enterprise deals are often one or two year contracts, it’s revenue you know you can count on. Also, provided that your customer is satisfied with the product and service support, there’s a good chance they’ll renew the contract when it expires.
  • Build your company’s reputation: enterprise-level customers make great candidates for case studies or testimonials on your website.

The Challenges of SaaS Enterprise Sales

While enterprise deals are lucrative, they’re much harder to land. Here are just some of the challenges you’ll face when selling to enterprise:

  • Much longer sales cycle: because enterprise level deals are so complex, the sales cycle is typically much longer. These deals may take 6-18 months to close.
  • More demanding sales process: enterprise level deals will require a great deal of time and attention from your sales and support teams.
  • Technological demands: enterprise customers may require increased security measures, customized interfaces, or other technological considerations.
  • Chicken and egg dilemma: many enterprise level customers want to know that you’re already working with and able to support other enterprise-level clients. This makes it extra tough to land your very first enterprise deal without any social proof to rely on.
  • Ongoing support: even after you close an enterprise sale you’ll still have work to do. Ensuring a smooth onboarding process and ongoing customer support is essential to the success of your enterprise sale.

Preparing to Sell SaaS to Enterprise

Before attempting to sell SaaS to an enterprise-level account, you should first consider if your team and product are ready to sell at an enterprise level. Many factors come into play including size of your customer success and developer teams, flexibility of your product, ability to handle a large influx of data, and more. Here are some key criteria to consider:

  • Security: security is one of the major concerns for most enterprise clients. Oftentimes an IT department will have to inspect and approve a solution before it can even be considered by purchase decision makers. If you can’t answer all of a potential enterprise account’s questions about security, chances are you won’t land the deal.
  • Customization: most enterprise clients will require some degree of customization. This may mean maintaining multiple versions of your product, one for traditional customers and another for each of your enterprise customers. You should consider if you will able to accommodate this.
  • Control: enterprise customers will require a greater level of control over data and users. Consider if you have the technological capacity to offer this.
  • Support: onboarding, training, and providing ongoing support to an enterprise client will be a huge undertaking for any customer success team. Consider if your team is prepared to handle this.
  • Legal: enterprise deals come with increased legal concerns. Often they will include lengthy contracts which you’ll need to hire legal representation to review.

SaaS Enterprise Pricing

Because enterprise deals are much larger scale, they won’t fall neatly into your existing pricing structure. Here are some things to consider when it comes to pricing SaaS for enterprise sales:

  • Consider discounts in your pricing structure: go into an enterprise deal understanding you’ll have to offer discounts. In fact, it’s not uncommon to agree on a discounted price with one decision maker and then have another decision maker ask for an additional discount. Always factor discounts into your pricing.
  • Factor in the costs: while landing an enterprise deal can be lucrative, there are many costs associated with pursuing one. Costs include your sales team’s time, additional support staff, technology customization, and more. Make sure you factor in all these costs when determining cost of acquisition.
  • Consider LTV: to ensure customer acquisition costs are reasonable you should project potential LTV for enterprise clients.
  • You might take a loss: consider that you might take a loss on your first enterprise client. This would be due to misestimating the costs associated with landing the deal. However, it might still be in your best interest to close the deal at a loss. This is because once you land your first enterprise client it becomes must easier to close more enterprise deals.

Selling SaaS to Enterprise

Selling SaaS to enterprise requires a much more time-intensive, personalized sales approach than a traditional SaaS sales model. Here are some things to keep in mind when selling SaaS to enterprise:

  • While a traditional SaaS sales model is low-touch, enterprise clients expect a personalized sales approach and dedicated attention from sales reps.
  • Rather than selling on features, a more effective approach is to focus on value. Enterprise buyers are most concerned about how the purchase is going to affect their bottomline. Focus sales conversations around return on investment (ROI).
  • Case studies are particularly impactful when dealing with enterprise-level deals. Make sure case studies focus on ROI and include specific, quantifiable claims.
  • Oftentimes enterprise deals will require sales touch points with many different prospects. In fact, six people are involved in a decision purchase, on average. Remember that each prospect may need a personalized sales approach, including a unique value proposition.
  • It’s important to discover and map the target organization’s purchase evaluation process as soon as possible. The last thing you want to do is waste three months selling to someone who doesn’t have the power to buy.
  • Along with mapping the decision-making process, it’s also important to identify and get in contact with the key decision makers who will ultimately be involved in the purchase decision.
  • Mockups, proof-of-concepts, and other sales tools can be helpful in demonstrating value and ROI to potential enterprise clients.
  • Because many touch-points with multiple prospects will occur during an enterprise sale, it’s crucial to keep detailed notes in a CRM tool.

After the Sale

Even after a contract is signed, an enterprise deal is still far from done. The responsibility now falls on you to ensure a smooth and painless onboarding process. This is also the crucial point where you hope the product’s value comes to fruition for the customer. Here are some tips on perfecting the post-sale process:

  • It’s crucial that your tool gets widely and successfully adopted by your new enterprise client’s team. Then and only then with the value prop of the product be realized.
  • Providing high-quality product training and support can help in the adoption process. It also helps to provide personalized training which demonstrates how the new product fits into the company’s existing tech stack.
  • Dedicated customer success staff can help with a smooth onboarding process.
  • Ensure your customer success and software developer teams are prepared to migrate a client over from their existing product.

Selling SaaS to enterprise clients is challenging but rewarding. With a strategic multipoint sales process and outstanding customer support, it’s quite possible you can land your first enterprise deal.


  1. I particularly like the two points in Selling SaaS to Enterprise; focusing on value (1) via case studies (2). The ROI numbers are important and when combined with the story, you now have attached the emotion necessary to sway the people involved in the decision. Numbers and emotional connection. I’ve been on both sides of the sale of SaaS and decision support systems. On the buying side, inevitably after all the discussion of features/benefits and ROI are finished, the last question is “How does everyone feel about the product and working with these people?” Your stories and your demeanor carry a lot of weight in the mind of the prospect.


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