14 Days To Fail—Where Trial Periods Go Wrong And How To Fix It

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The cost of acquiring new customers in the technology industry is relatively inexpensive when compared to selling physical products. This is particularly true in the software as a service (SaaS) space. That is why free trial offers are one of the most common ways technology companies, like Pipedrive, find and nurture new customers. Across the board, SaaS companies that use free trials say they can account for up to 10 percent of new sales, with the top 27 percent getting more than a quarter of their new business by converting free trials into paying subscribers—but free trials can also hinder your closing rates when your salespeople keep making the same mistakes.


Common reasons free trials don’t work

There are several different free trial models, from freemium versions to those requiring credit cards that get charged automatically if not canceled. Each one can be successful when used properly, but in general, conversion rates on free trials are between 1 percent and 10 percent.

There are many reasons why more than 9 out of 10 of free trial offers fail to convert. The trial is too long/short; the pricing is too high; or too many key features are locked during the trial period. These decisions are often made at the corporate level and are out of the frontline salespersons’ control. Today, we want to focus on a few common mistakes that salespeople make during the trial period and what they can personally do to improve their closing rates over those 14 days. Here’s what we’ll cover:


Mistake No. 1: The customer doesn’t know enough about the product to see it’s full potential

This is one of the most common problems with free trials. Without proper guidance, prospects will register for the trial and immediately gravitate to the one or two features that they are most familiar with. Unless regularly prompted to explore new features, they emerge 14 days later underwhelmed, let the trial expire, and move onto another option.

Fortunately, it is also one of the easiest mistakes to fix. During that 14-day trial, you need to be the prospect’s guide through the landscape of your product and point out the best features and benefits that meet their needs. It all starts with your onboarding process: This is the prospect’s first interaction with your company, and a simple and seamless onboarding process can set the tone for the rest of the trial period.

Once properly onboarded, it is critical to combine education with your sales pitch to close the deal. You can send emails to tutorials, invitations to webinars, schedule personalized demos, or explainer videos. Whatever method you choose, all of these tools should be designed with one goal in mind: ensuring that your prospect has the opportunity to experience the key features and benefits of your product during the trial period.

Ultimately, you will be the prospect’s best source for information during the trial, and it is critical that you know how to use your product. But it is also important that you have a working knowledge of competitors’ products to point out areas where you have advantages. One note of caution is to make sure that you sell only what you can deliver today, not what is in development. Too often, salespeople get excited and talk up the next big thing, and the customer is left feeling disappointed once they realize those features are not in the product they are using.

The more you can help your prospect experience the true value of your product during the trial period, the better off you will be when the time comes to convert them into paying customers.


Mistake No. 2: Lack of follow-up and sales cadence

Folks who sign up for free trials are obviously interested in your product, so why not show them that you’re interested in them as well? Not in a way that is intrusive and pushy, but in a way that shows you are trying to help them get the most out of their trial period. 

Your sales cadence is the predefined series of touchpoints where you check in with your prospects during the trial period. It can be via email, phone calls, or social media. The current pandemic environment limits the opportunity for face-to-face meetings, but Zoom or Microsoft Teams calls are doing what they can to fill that void, while being cheaper and less time-consuming than travel.

The right sales cadence is different for everyone based on your industry, the complexity of your product or service, and your customer profile. It may take some trial and error before you get it right. Too little contact and you risk missing the opportunity to answer questions and provide guidance; too much, and you’ll annoy your customer. 

Over the 14-day trial period, you will likely reach out to make contact with your prospect via different channels from 10 to 20 times. From your initial welcome email until the final expiration of the trial, you have a built-in reason to communicate with prospects who actually want to hear from you–as long as you’re helpful. Manually keeping track of all of these touches can be daunting if you have multiple prospects on trials. That’s where automation comes in.

Customer relationship management (CRM) systems are constantly evolving to help you better maintain regular and consistent contact with your prospects. A CRM can be useful in many ways, including:

  • Automating your email and social touches: Yes, it would be ideal to personalize every email or social media outreach, but good sales professionals will develop a sense of what customers need to hear at various stages of their trial, and having automated templates is a significant time-saver. 
  • Tracking your sales cadence outreach: Keeping track of what step each trial is at in your sales candace manually is a daunting task. A CRM shows you where the customer is in your cadence and how they have responded to your outreach so far. 
  • Keeping you focused on a one-step-at-time approach: Yes, it’s good to keep your eye on the prize, but too often salespeople miss important little steps along the way. A CRM keeps you on track as you walk your prospect through every step of their customer journey; right up to the close.

Automating your sales cadence works. Our data indicate that customers who use CRMs close 28 percent more deals on average after one year.


Mistake #3: Your demo is “show and tell” rather than hands-on

You may have the best product, your sales cadence might be on point, and your educational products may be engaging and informative—but nothing can beat a good one-on-one demo with the prospect. Unfortunately, too many salespeople consider a demo the time for them to shine, and they do more talking than listening. 

In order to make the most out of the short time you have for a demo, you should personalize any required setup beforehand and be ready to let them “drive” as much as possible. This allows them to make a visceral connection between what you are showing them and how they will use the product later on their own.

A good demo will focus on the product. A great demo will focus on the prospect. Understand ahead of time what specific challenges your prospect is facing and tailor your demo time toward showing them how to solve it. Propose the demo in a way that shows you have been listening. “Can I walk you through how you would use our product to manage your inventory better? This will save you a ton of time compared to the way you have been doing it.” 

Another important opportunity that is often overlooked is to pay close attention to what gets the customer excited during your demo. Your engineering team may have spent 5,000 hours building features that make your product the fastest in the industry, so it’s natural to lead with those features. However, if your prospect keeps talking about how important it is to have a simple user interface, put your time and energy into showing them your navigation and talk about your efforts to improve user experience.

You likely wouldn’t buy a car if you had to sit in the passenger seat during the test drive. The same is true of your demo. Make it personal, show them how to solve a specific problem they are having, and let them drive the process as much as you possibly can.


14 days to glory

A proactive sales team can dramatically help improve conversion rates during the 14 days of a free trial by helping the prospect understand your product, using automation to stay in close and consistent contact with them, and tailoring their demo and trial period toward solving specific problems the prospect may have. When managed properly, the two-week free trial period will remain a productive tool for any SaaS company looking to grow its customer base efficiently and profitably.

Diogo Silva, Global Sales Expert and Senior Account Executive, Pipedrive headshot

Diogo Silva is a senior account executive at Pipedrive and a global sales expert.

  • Originally published August 26, 2021, updated April 26, 2023