Spotted: SaaS Free Trial Conversion Strategies

Every SaaS team with a free trial shares the same problem - their sales & marketing does not join up with their product and trial experience.

And so their sales & marketing efforts aren't able to leverage all the momentum that comes with a free trial model.

Yes, free trials can create a more seamless, simpler, better buying experience for users.

Yes, free trials enables you to grow quickly with reasonable CAC and without having to hire & equip an enormous sales team.

And yes, product-led growth can be stickier and create a more natural retention loop (vs. traditional tactics that rent or otherwise draw attention from platforms like Google & Facebook).

In a new reality where Google and Facebook are the only two platforms that offer opportunities for user acquisition at scale. Because it’s scalable and cheaper, product driven growth is how the biggest products have grown so large so quickly. It’s also how new products will win in the future.

Kieran FlanaganVP Growth at HubSpot

Free trials are not a silver bullet that works in isolation. Sales & marketing tools & teams are being left behind.

Without being connected to the new buying experience, they have to lean on old tactics (like cold impersonal outreach to their trial users) which don't convert easily and create a disjointed user experience.

The challenge most SaaS sales and marketing teams have is connecting their content, campaigns & activities with the new way of buying. They need to "join the dots".

How to "join the dots" between your free trial experience & your sales and marketing

In this Spotted post, we're going to share the trends, tactics & techniques used by data-driven marketing and sales teams with a free trial model like Appcues, Mention, Gorgias, and more.

For all of these teams, the buying experience is not led by traditional "gated" content from marketing and sales-directed demos and bookings - the lead having to fit the sales & marketing process.

Instead, it's about sales & marketing activities understanding the context of a lead, and engaging them in a personal, relevant, helpful way. And to do track & engage them in real-time.

Here are five tactical takeaways you can implement to optimize your free trial conversion strategies.

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In our Spotted series, we break down and share the trends, tactics & techniques we see scaling SaaS teams do (not just what they say) on Hull and beyond. Subscribe below for the next article in the series.

Tactical Takeaway #1: Connect your SaaS product to your sales & marketing tools

Unless you connect your product to your sales & marketing tools, your sales and marketing team will be blind to everything that happens in your free trial. This means they have no context to reach out.

Most ops teams will setup a custom sync to update the lifecycle stage of a trial lead, but few teams have more detail than that.

To recap our previous Spotted posts, data-driven lead nurturing depends on:

And data-driven sales outreach is about:

  • WHO to talk to
  • WHAT to say
  • WHEN to reach out

With a free trial, all the answers for this lie in your product. Your sales and marketing team need a constant stream of how trial users are engaging with your product.

There are two methods for extracting product data in real-time

  1. Analytics tracking tools - Capture Events from within your product using tracking libraries like Segment analytics.js, tools with tracking libraries within them like Intercom or full Analytics tools like Amplitude and Mixpanel.
  2. Backend database - Fetch everything in your product's backend, including consumption & usage data.

SQL queries (usually batched based on last updates) and events (as a stream) don't always natively "fit" into your sales & marketing tools. Often, you need to be able to transform your lead & customer data in-between to map updates into a "digestible" form for tools like HubSpot and Salesforce.

You also need to be able to sync your product data to your sales and marketing tools in real-time. We'll explore the tactics this enables later, but if you're stuck with slow or manual data your sales & marketing team will never be able to keep up with your leads. Outdated data is almost as bad as no data.

There are several real-time customer data integration methods to explore. When you're evaluating methods to sync product usage data to sales & marketing tools, look for how you can:

  • Capture a stream of product usage data
  • Transform it into a standard form
  • Sync & update your sales & marketing tools
  • Sync data in real-time (so your teams & automation can react)
  • Be able to backfill your sales & marketing tools

Voila! Your sales & marketing team now have full visibility into your free trial

Tactical Takeaway #2: Define your key "activation events"

Now you have your product data in your sales & marketing tools, you need them to able to "make sense" of the new buying journey.

Traditional sales & marketing tools would work off a flow like this:

  1. Website visitor
  2. Lead captured
  3. Meeting set
  4. Opportunity created
  5. Closed Won

With a free trial, your sales & marketing tools need to adapt to the new buying journey.

  1. Website visitor
  2. Trial sign up
  3. User successfully sets up the product
  4. User starts subscription (or sets up a meeting with a sales rep)

The key part is the third part - what constitutes success for a user? What do your trial users absolutely have to use and what tasks do they have to complete in order to successfully use your product?

This data should be captured via your product tracking plan. You need to outline the key features in your product (often called "objects" for data modelling) and the actions that can be taken.

For example, at Hull, users install Connectors to integrate with different tools. To use Hull, you have to connect to your tools, tracking & databases to bring data into Hull to unify, enrich, segment & sync. Therefore, a one of our key activation events is the first Connector Installed.

You also want to setup triggers for when sales & marketing can reach out. For example, at Appcues they trigger outreach around inviting users ("Invite your designer!"), installing their software, and setting up your first few flows.


Pro Tip: Advanced** data-driven teams also look at the detail of each event. At Digital Ocean, they look at the consumption levels and naming conventions of how their users are working with their product - "Test" vs "Production". To do this, you need to have a segmentation tool that can query event properties.

With a list of your key activation events, you need to understand which are most likely to lead to free trial conversion - what are the "aha!" moments?

One simple method to do this is to evaluate the actions taken by your converted customers. For instance, 100% installed your connector, 80% invited another user, 60% customized their design.

You can also try using regression ("line of best fit") analysis to identify the thresholds of events or activity that trigger "activation".

With your activation events spotted, you can now put them in a logical order. How should users work through their trial experience (according to the actions that increase the likelihood to buy)?

Now, you can now use your activation events to create a new set of lifecycle stages into your sales & marketing tools so they can make sense of how trial users move through the buying journey.

Organize your deal stages by your leads actions, not your reps actions.

John ShererDirector of Sales, Appcues

Voila! Your sales & marketing tools have context on the new buyer's journey

Tactical Takeaway #3: Build a segmentation plan over your free trial experience

Now you have your activation steps mapped, you can start to build a segmentation plan to command how your sales & marketing tools can engage your trial sign ups.

Segmentation enables you to group alike leads at different stages of your customer journey.

This is the first rule in building your personalization strategy - WHO to talk to comes before WHAT you say.

Segmenting your trial experience should with your activation events - creating a sequence for trial users to be nurtured through.

Pro Tip: The best teams break this up further by the different type of trial user. For instance, segmenting by:

  • Job seniority and roles - "Marketers, invite your developers". "Developers, here's our API documentation"
  • Industry - finance, education, health
  • Company size - Startups, Mid-Market, Enterprise

Be careful. Segmenting by different buyer journey paths can quickly lead to many different combinations of segments and content you need to create & maintain. Best practice is to extend your logic brick-by-brick (avoid BIG BANG releases). Pick one to start with.

If you're unsure how to prioritize, compare different dimensions of data (e.g. job roles, industry, company size) and evaluate which has the widest spread in conversion rates to becoming a customer. For example, industry might have a small spread (Finance converts at 10% and Health at 12%) whereas job roles might have a large spread (Marketers at 15% and Engineers at 5%). This indicates a more personalized, relevant message is more likely to work since you have a bigger difference in response to your current messaging.

To tie this all together, you need a segmentation engine that can query all this data & update segments in real-time.

Since a trial user may move quickly through the process (or not), your segments need to update in real-time when new events are tracked to stop the wrong message being sent (like a "install your first connector!" right after they've installed their fifth).

One way to test event-triggered segmentation tools and see if they work as expected (before setting up sales & marketing automation that depends on it) is to setup notifications via email or tools like Slack. Slack is also good for democratizing data and exciting your team - "Look! {BigName} just signed up!

Together with your buyer journey paths, you need to be able to create queries similar to this.

Once you have a defined segment of trial users to nurture towards their next activation event, you can now begin to design their experience.

Voila! You've mapped the buying journey (and variations) in your free trial

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Tactical Takeaway #4: Map content over your segmentation plan

Now you can identify how your trial users are moving through the buying experience, you need to design the best content experience.

For many data-driven sales & marketing teams, this is where they trip up. They use intelligent event-driven segments to perfect timing of sales outreach, marketing email, updating ad audiences and so on - but they don't use the context they have on each trial user to tailor what they say.

Personalizing content based on product usage data not only makes you far more relevant and cut through the noise, but it also positions your brand and your sales reps as helpful experts. It's your best opportunity to surprise, delight, and differentiate from competitors.

Once you have all this rich, contextual data, your outreach is really only as good as your content. It’s not okay just to say, ‘We noticed X, let’s have a call.

Emmanuelle SkalaPrev-VP Sales at Digital Ocean

The best way to think about personalizing content is to imagine them right in front of you - given what you know about them (they signed up, they've taken X actions, they're on Y buyer's journey path), what would you say to them?

From your ordered sequence of activation events, what are the steps the user needs to take? And what content and support do they need to get there?

Grab existing support tickets, live chat conversations, phone transcripts and more. Pair this with your existing documentation and help content. Build a picture of what your trial users want most at each stage, and find the matching content & assets your team has that you can leverage.

This becomes the outline and briefs for the templates and content you need to create.

Voila! Now you can maximize your trial users chance of success through your platform

Tactical Takeaway #5: Setup segments, templates & workflows across all your sales & marketing tools

Finally, you need to tie all your tools, teams & data together to optimize your free trial experience.

  • Capture your product data as events
  • Use your key activation events to create segments
  • Use segments to map the free trial buying process
  • Map those segments to your sales and marketing tools

To build this into your sales & marketing tools and automate it (so you can reach out in a timely way, you need control three rules:

  • Segments (WHO to talk to)
  • Templates (WHAT to say)
  • Workflows (WHEN to reach out)

We've discussed earlier how to build event-based segments to group together trial users by the next step in their activation.

For templates, you can create messages for each of these groups within your sales & marketing tools to address the exact.

These messages will already feel personal since the context of who they're sent to (let the segmentation do the work) but it can be helpful to add a first name, sign off from the sales rep they're talking to, and personalize content within based on their persona or customer fit (using either separate templates or a more powerful templating engine).

With your segmentation plan built around activation events, it becomes very simple to create highly-focused messaging around moving your trial users towards conversion.

The final piece is WHEN to trigger your messages. These messages need to be timely and powered by events, and they need to stop being sent when the activation event you're nurturing towards is tracked. Even if you can add a "goal" to the automation tools you use, this is why having event-powered segments is so powerful.

By controlling the logic across your product and sales & marketing tools from one place, you can reliably unify & sync data to control your message across all your team's tools.

Voila! You can now target and trigger sales & marketing automation based on your product data

Best-fit criteria for free trial conversion

Post product-market fit

For scaling sales & marketing automation, it's important to know you're heading in the right direction before investing in aligning the resource you need (tools, teams & data) in that direction.

Clear ideal customer profile

You can still waste time talking to the wrong teams or the wrong sorts of people. Activated users might not be ideal customers.

Your team needs to know how to separate out ideal customers from your trial signups. You need a clear, common, objective ideal customer profile.

Clear tracking plan implemented

Your tracking plan will set the definition you see your trial users in. If your tracking plan is missing elements or is poorly structured, you won't be able to "see" how trial users are behaving in your product and so your sales & marketing tools & teams will miss out.

You can make do with other elements (like querying your backend database) but a clean & consistent tracking plan over your key activation events is core to making free trial conversion strategies work.

You have a trial conversion "owner"

Combining product data to automate sales & marketing flows can cover many disciplines. Best practice we've seen is to have one person own this who works under your sales or marketing department.

They'll lead the sourcing of data, finding your key activation events, building segments, templates & workflows, and bringing this product-led growth system to life.

Jack Moberger owns low-touch sales conversions at Appcues. He wrote about their implementation on Sales Hacker.

Low-touch sales conversion rate increased 70%, ASP [average sale price] increased 25%, and ARR [annual recurring revenue] closed in the quarter increased 60% over our 4Q’17 levels. We’re talking hundreds of thousands of dollars converted to ARR.

Jack MobergerAppcues

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What you should do now

  1. Request a custom demo - and see how to unify & sync all your tools, teams & data (like we did for all these companies), or book a demo with a product expert.

  2. If you'd like to learn our best practice for customer data integration, read our free Guide to Getting Started with Customer Data Integration.

  3. If you enjoyed this article, perhaps your team will too? Why not share it with the links below.

Ed Fry

Prev 'Ed of Growth at Hull, working on all things content, acquisition & conversion. Conference speaker, flight hacker, prev. employee #1 at (acq. HubSpot). Now at Behind The Growth

If you've questions or ideas, I'd love to geek out together on Twitter or LinkedIn. 👇