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Strategy & Planning Updated on: May 15, 2023

Top 5 challenges of marketing SaaS to enterprise companies

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Sales and marketing teams face a number of unique challenges in the world of enterprise B2B SaaS, where buyers are sophisticated, sales cycles are long, and the product is invisible. Here are five of the most common challenges that SaaS companies face when marketing their software to enterprise companies, as well as how to overcome them.

1. Complex products

Enterprises are complex, and enterprise SaaS is no exception. 

Your software must be complex enough to handle the enterprise's workload while also supporting many users across the enterprise and the company's goals.

Whatever software you are attempting to sell must be able to integrate with a wide range of existing enterprise applications and software. Enterprise software typically requires extensive customization and configuration, which is expensive, time-consuming, and difficult to create. 

This presents a unique challenge to the marketing and sales teams tasked with selling these products, as their features, benefits, and differentiators are often difficult to quickly and concisely communicate. 

How do you describe what makes your solution special when a social media ad gives you just 100 characters to work with?

Complex products require more time and effort on behalf of the sales team to nurture leads, educate prospects, answer questions, perform product demonstrations, converse with decision-makers, develop support packages, and negotiate customization. The more work you put into your go-to-market (GTM) strategy, however, the easier this task will become.

A strong GTM strategy will lay out the precise pains, claims, gains, and value propositions you should be speaking about, allowing you to capture your audience’s interest without the extra characters.

2. Qualifying leads and nurturing prospects

The complexity of enterprise SaaS also means that product-led marketing approaches like freemium offerings and self-service demos are often not a good fit. A more hands-on, sales-led approach will be necessary. 

With the huge data sets, teams, and variety of needs, enterprise companies are working with a barrier to entry, and the amount of onboarding needed with a new SaaS offering is frequently too high to take on without support. This can make scaling your sales and marketing operation even more difficult as the need for sales and customer success rises with demand.

Not only is lead generation a problem but there is often a follow-up problem as well

Unfortunately, some sales representatives tend to disregard leads that aren't ready. According to InsideSales.com, 50% of sales occur after the fifth touch; however, in far too many enterprise SaaS sales cycles, sales reps give up before the fifth touch, and their closing rates suffer as a result. 

Following up with leads who aren't ready after 30 days, and then following up again if they're still not ready, is crucial nurturing to get them to the next stage in their buyer journey. The nurturing process will help you move them along the sales pipeline toward sales conversion.

Following up with prospective clients and providing compelling content at each stage of the buyer's journey can help you keep them interested and engaged. Buyers are hungry for content that answers questions at each stage of the buying process. 

Buyers want to

  • Read white papers
  • Watch product demonstration videos
  • Download case studies
  • Read blog posts
  • Review original research. 

Because your sales team is probably used to selling and pitching rather than writing and creating content, they may lack the content their prospects want to see before making a decision. 

According to Forrester, delivering the right content to the right prospects at the right time results in 50% more sales-ready leads at 33% less cost. 

Content leads to contracts, and your marketing team can assist sales by providing content throughout the awareness-to-consideration stages that inform the buyer along their journey.

So, getting qualified leads is more difficult, but why?

3. Buyers want to help themselves  

According to a Miller Heiman Group study, more than 70% of B2B buyers fully define their needs before engaging with a sales representative—nearly half of them identify specific solutions before reaching out. 

As a result, the majority of buyers think that sellers are not necessary for the majority of the sales cycle. 

Only 23% of B2B buyers believe that salespeople are their best resource for resolving business problems, according to the Miller Heiman survey. This indicates that most buyers don't contact sellers until late in the sales process. 

Consumers nowadays are more resourceful and independent than ever before. Many customers will go down the online rabbit hole and look for solutions themselves rather than hiring salespeople for their knowledge. 

This presents a challenge for sales teams attempting to pitch software solutions to enterprise businesses. 

Customers and potential customers who look for solutions on their own are avoiding the personal sales cycle that allows you to guide them toward your offering or product. It can be difficult for you and your solution to change a customer's mind once they have discovered something online and convinced themselves that it’s a guaranteed solution. 

To combat this, marketing must be extremely diligent in providing the appropriate educational materials for buyers conducting their own research. 

Consider how you can provide educational content for your audience at each funnel stage. 

  • What do they need to know? 
  • What channels will they use to get that information?

4. Multiple buyer personas 

As discussed in T2D3, written by Stijn Hendrikse and Mike Northfield, the enterprise SaaS buying committee is generally composed of several stakeholders from various organizational divisions. So, selling software to enterprises isn't as simple as marketing to one persona.

Enterprises typically take longer to make decisions because deals and contracts frequently pass through multiple hands for review before making a final decision. Sales teams and marketers face the unique challenge of marketing the value of their product or solution to multiple personas at various levels of the company. 

With multiple stakeholders and different buyer personas, it's difficult to focus on one key area or know which buyer persona to approach when prospecting.

Each buyer persona has a unique problem that the software you're trying to sell must solve. Because each stakeholder has their own set of challenges, needs, requirements, and goals, communication with different departments and levels within the organization will be key. You can increase the credibility and value of your selling process by learning about the company you want to sell to and preparing yourself with industry-specific perspectives, insights, and content.

A strong GTM strategy will once again be crucial here. Defining these buyer personas, identifying the messaging that will speak most effectively to each, and ensuring that your sales and marketing teams are aligned on this will allow them to easily reference how they should communicate with each persona they encounter.

Okay, the product is complicated, as are the leads and prospects. What else is there?

5. Longer sales cycles

Larger deals lead to longer sales cycles; the sales cycle length increases as the product, service, or solution becomes more complex or prices rise.

According to SaaStr founder Jason Lemkin:

  • SaaS solutions with an annual contract value (ACV) of $2,000 close within 14 days. 
  • Deals with an ACV of around $25,000 close in 90 days. 
  • Depending on the number of stakeholders who must approve the purchase, deals worth $100,000 or more in ACV close in 90 to 180 days.  

One of the most difficult challenges is that your deal sizes will be large when working with enterprises, so you will need a lot more time to build trust with clients. 

Simple "spray and pray” outbound and ad campaigns will not suffice. Prospects will have done their homework, spent a significant amount of time shopping options, and only select the one they believe is a true thought leader and an ideal fit for their solution. 

All of this adds up to a longer sales cycle, more sales resources, more time, and more attention to detail. As trust is among the top qualities buyers seek when engaging with sellers, there will be increased pressure to develop and nurture trusting relationships with prospective clients over time. 

A longer sales cycle also gives the client more time to scrutinize the process or reconsider your solution. Sales teams must work hard to keep prospects engaged and positive throughout the lengthy sales cycle. Researching strategies that will help you nurture prospective clients and connect with them based on their core values will be crucial for honing your GTM strategy.  

Marketing software to enterprises can be challenging, but it doesn't have to be

When you use creative marketing to get enterprise attention with a warm introduction rather than cold calling, you open the door to developing a trusting relationship with your potential clients. 

Because great marketing supports your customers' dreams and goals, strive to understand their objectives, priorities, and strategic initiatives and tailor your sales strategy accordingly. Workshops with industry leaders can enhance your learning experience while also providing expertise and advice on how to begin connecting with your target audience. 

Develop a trusting relationship to understand better the enterprise's needs and business model and where you fit into the equation. Identify pain points to break through resistance, and connect their pain to how you can alleviate it. Be an advocate for your buyer and support them along the way; focus on cultivating a long-term relationship rather than just selling. To attract top enterprises looking for a simple solution—use clear, compelling, and concise messaging that stands out among the jargon.

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