Blog Icon
Upollo Blog
← Back to Blog

How to Have an Awkward Conversation with Your Users About Account Sharing and Repeating Trials

Having uncomfortable conversations with users can be hard or alientating. We provide a tried and tested framework for having uncomfortable conversations with your users.

Peter Photinos
Peter Photinos
Data Scientist
How to Have an Awkward Conversation with Your Users About Account Sharing and Repeating Trials

Sometimes people do things that they shouldn't. They dye their hair an unflattering color. Get an embarrassing tattoo. Sign-up for 10 free trials. Account share with their 15 closest friends.

At Upollo, we think there are two types of bad actors: professional fraudsters and everyday people who see an opportunity to save a bit of money and take it.

The good news is that opportunistic bad actors can often be easily converted into happy, paying customers. The (slightly) bad news is that you need to tell them you know they're account sharing, abusing your free trials, technically defrauding you, or whatever else they might be doing and then ask them to convert. That's not a marketing message anyone wants to get. Or write.

But learning how to write those types of marketing emails, popups, and in-product notifications well can lead to significantly more ARR for your company. So, how do you do it? We walk you through proven strategies for how to structure the conversation that will help you get your users on the right path.

Why it's so Awkward​

No one likes being caught doing the wrong thing. Almost everyone can remember a time when they were exposed for doing something that wasn't terribly flattering. Whether you wanted to hide your head or die from embarrassment, it likely took you a while to feel better about yourself.

You don't want to shame your users - you're trying to make them your customers, after all. So, it's important to communicate carefully. But that can be difficult since it's impossible to avoid the fact that they... did something wrong. Thankfully, there are a lot of ways to make it less awkward to get an email like this.

Upollo's 5 Top Communication Tips​

Don't be Accusatory​

If someone is angry at you, you'll respond emotionally. You might get angry back or focus on defending yourself. Customers are like that, too. Rather than accusing your users of account sharing, using multiple free trials, or whatever else they might be doing, just state the facts.

Accusatory copy: Our systems detected you've been account sharing for the last year.

Stating the facts: It looks like a lot of people might be using this account.

Explain the Scale​

Neutrally showing your customers that you know just how many times they've used free trials, how many people they're account sharing with, or that they've given you the wrong email address helps them understand that they're likely not going to get away with doing so anymore.

Example: It appears at least X number of devices used at X number of locations in the last week.

Show your Value​

They love your product or they wouldn't keep using it. It's important to remind them of the value while you're trying to move them along towards conversion.

Example: Our product helps graphic designers like you do more in less time. We're glad that you've been able to use our product to make your work easier.

Make it a Conversation, Not a Command​

No one likes to be told what to do. If you command your users to subscribe to your product, they might just get angry enough to switch to your competitor. They might be so angry they actually pay your competitor as well. Instead, make it clear that you're interested in hearing from them, too. Ask them for feedback on your product or send them a survey to find out what's stopping them from subscribing.

Example: You've used our product a lot and we would love to hear from you about what you love and what could be better <link to survey or an in situ form>.

Provide a Path Forward​

The last thing you want to do is send the user an email that will end the conversation and make sure they'll never use your product again. You can easily convert these users if you show them the way forward. Tell them HOW they can stop using their friend's account and get their own, invite them to add another user, suggest they upgrade their account, or give them the opportunity to refer the friends using their account for a subscription. You can also offer them an email to contact you at if they think they wrongly got the message.

Example: [Invite] If you would like to continue using this account as you have been you can add an extra user <CTA: Direct to payment screen to increase the number of users who can access account.>

Sample template: Multi-accounting and repeat trials

Clear as mud? We find it's easier to explain with templates. While you can plug any awkward thing you're trying to communicate into these templates, we'll show you how to communicate with someone who is using multiple accounts to access free trials. For this example, the person is trying to sign-up for another trial of a music app.

Content Template

Present the facts:

  • It looks like you may have made an account with us before

Explain the scale:

  • You’ve used X (free) trials with us so far. We get it. We love music, too.
  • Your first trial with us was dd/mm/yyyy. We’re glad you’ve listened to a lot of great music.

Show your value:

  • We pride ourselves on having the best selection of music, podcasts, and more. Did you know that by upgrading to a paid account you will get rid of ads and give you access to additional podcasts like X and Y?

Have a conversation:

  • We’re always trying to make our product better. We would love to hear from you about what you love and we could improve <link to survey or email address etc>

Provide a path forward:

  • [Long tenure users] You’ve been with us for a while and, although we can’t offer you a free trial again, we’ve got a plan just for you. <CTA: Signup for premium with 10% off first month>
  • [Short tenure users] Unfortunately, we can only offer one free trial per user, but we’d love it if you stuck around. <CTA: Signup for premium>

Sample Template: Account sharing

Here's a template for how to communicate with someone who is account sharing. For this example, the person is account sharing their seat for your video editing software.

Content Template

Present the facts:

  • It looks like more than one person is using this account.

Explain the scale:

  • We have seen logins from more than 5 devices in the last 2 days.
  • This account has been used in 3 cities in the last 24 hours.

Show your value:

  • We love that your team is getting a lot of value from our tool. Did you know that by creating separate accounts, you can access X and Y functionality that will make your work easier?

Have a conversation:

  • As your colleagues seem to be getting a lot use out product, we would love to know what’s stopping your company from purchasing multiple seats so everyone can have their own account. <link to survey or email address etc>

Provide a path forward:

  • [Invite] If you would like to continue using this account as you have been, you can add an extra user <CTA: Direct to payment screen to increase the number of users who can access account.>
  • [Upgrade] We’re glad you all love our product and suggest you upgrade to a team plan here. <CTA: Direct to payment screen to upgrade plan>
  • [Stop] If you are using an account that is not yours you can switch to your own here. <CTA: Log out now, direct to account creation flow/sign in>
  • [Secure] If you think someone may be using your account without your permission, secure it now. <CTA: Log your account out everywhere and change your password>

You can do it. We'll help you.​

See, it's not that hard! By applying our framework, you can easily swap in messaging and customise it for the situation, your product, and your users. You can then start sending non-awkward messaging to all those opportunistic users you'd like to convert via emails, in-product nudges, pop-ups, and other strategies. Then, just sit back and watch your company convert more happy (and shame-free) customers.

At Upollo, we help you identify which of your users are abusing free trials, account sharing, and more. Then, we help you come up with strategies that improve your conversion rate, up your ARR, and increase your user base. Our goal is to help your company maximize its revenue. Curious? Sign up for a free trial today to see how many of your users could easily be converted — and how much extra ARR you could be earning.

Read the Report: Upollo SOC 2 Type 1
PDF • 2.4mb

Join the Wave

Ready to revolutionize how you recognize opportunities? Sign up for the waitlist below and be among the first to experience its transformative power when it launches.

Thanks! We'll let you know when you're off the waitlist.
Oops! Something went wrong while submitting the form.
About the Author
Peter Photinos
Peter Photinos
Data Scientist

You Might Like:

All Posts
How to Convert Account Sharers without Alienating your Users
Effective strategies to convert account sharers into paying customers without pushing away the people who love your app the most
The Power Duo: Product Led Growth and Customer Success
Maximize user acquisition and expansion by aligning Product-Led Growth with Customer Success strategies
B2B Businesses are Applying Netflix and Disney’s Tactics and it is Paying Off
How B2B companies are harnessing the account sharing challenge to fuel revenue and user base growth

Get Started for Free

Start understanding and upselling your customers today.