Running Successful Free Trials For Subscriptions

One of the fastest-growing Substack creators (100k+ subs) asked me to review their funnel to help them monetize faster. Here’s what I found: This creator is absolutely crushing it. They’re getting thousands of free subscribers both from Substack and LinkedIn every month. Their problem? Most of those free subs aren’t upgrading to paid. And after looking at their welcome flow, I could see why. They are not leveraging their welcome email—the single most important touchpoint in their entire funnel—to drive paid conversions. So with that in mind, I came up with 2 potential strategies to help them fix this bottleneck: Strategy 1: Free Trial (Lowest Effort, Lower Potential Upside) Since they only offer yearly subscriptions, I suggested offering a 30-day trial - but adding some urgency to the mix: “Start your free trial by end of day and reply to this email—I’ll send you [bonus 1, bonus 2, and bonus 3] as a thank you for upgrading today.” The key: Only mention the price of the yearly membership *after* breaking down everything they’d unlock as a paid member. Ideally, too, you want to find a wat to “quantify” the value they’d be getting from each thing included in the subscription and compare it to the actual price they’d pay for it. Strategy 2: Personalized Onboarding Funnel (Highest Effort, Highest Potential Upside) When you have a huge resource library, you can run into an unexpected problem: People don’t know where to start and feel overwhelmed as a result. (This is definitely the case for this creator.) But this can also be an opportunity to turn free users into paid readers. How? By adding a simple survey to your welcome email you can identify where subscribers are in their journey as well as their biggest challenges. Then, you can use this data to send personalized drip sequences with specific resource recommendations based on their individual responses. So instead of just saying “Here’s my paid newsletter, go subscribe!” you create a personalized roadmap for each subscriber to get the most out of your paid newsletter resources. The key takeaway for you (whether you run a free or a paid newsletter): Your welcome email gets the highest open rates—make it count. Hope this is helpful!

5 mistakes to avoid to convert more free trial users into paying customers (and what to do instead): ❌ Offer only a one-week trial period 7 days likely isn’t enough time for people to really test-drive your product and see if the value they get is worth the price. ✅ Give people 14-30 days to try your app and design an email journey that helps them reach their "aha" moment ASAP. ❌ Send an onboarding email that squeezes all of your features into one message This is overwhelming, leaving users unsure of the first step they should take. ✅ Focus each email on a single feature or action you want people to take so they can explore your app step-by-step. ❌ Send the same messages to people regardless of whether or not they’ve been using your app This signals that you’re not tracking user behavior, delivers a general email experience, and fails to nudge people along the user journey. ✅ Use time and behavior triggers in your sequence to meet people where they are. ❌ Focus your messaging entirely on introducing your brand and what makes your features so great Brand and feature-focused copy alienates your customer and doesn’t showcase the real value they can get. ✅ Ensure that every email puts the user and their needs front and center. ❌ End the email sequence without a limited-time offer to subscribe. If you don’t give people a reason to buy now, chances are they never will. ✅ Create a welcome offer to nudge any fence-sitters over the edge. Any other common mistakes you see brands making with free trials? Let me know in the comments. #emailmarketing #saas #healthtech --------------------------------------------------------------------------- 👋 In case we don’t know each other, hey! I’m Kayla, a certified conversion copywriter. I write data-driven copy that gets people to say “yes” to healthtech brands. 🖥️ Need help with your website? Check out my new guide to turn visitors into buyers (linked in the comments).

My #1 learning from launching a free trial over the last year: Marketing, product, and sales teams should all be aligned on what success looks like for a free trial. Seems obvious, right? Just as any other GTM strategy, your free trial should align to company-wide goals. So, if the ultimate goal is to drive customer growth using a free trial as a tactic, then your teams will work together to: 👉 Define goals for your free trial Measure conversion rates for visitor to FT; FT to active; and active to paid 👉Acquire more free trialers What channels will you use? Paid? Organic only? 👉 Show your value Segment users and make it easy for them to see how to use your product for their use case. Consider emails, product tours, in-app notifications, etc. 👉 Provide a frictionless way to purchase Do they need to talk to sales to buy? That's not frictionless. 👉 Provide a frictionless way to upgrade What features are "locked" and is it obvious what value they will get with upgrading? Can they purchase on their own? If teams are not aligned on these goals, your free trial won't be as successful and may be abandoned altogether. #b2bsaas #productmarketing #freetrial

Most product trials fail but it’s not your product’s fault. Here’s what really breaks the deals for us I used to think that if I built a great product and launched a free trial, users would naturally convert themselves. What shifted my mindset was realizing that success in trials comes from how well we guide users, not just what we build. Here are three key moves that changed our trial metrics: 1️⃣ Personalized onboarding journeys Generic walkthroughs don’t cut it anymore. Exclusive onboarding based on user persona and behavior helps users see value fast before they get overwhelmed or lost. 2️⃣ Proactive, timely nudges Waiting for users to figure it out is a trap. Sending contextual tips, feature highlights, and reminders at the right moments keeps engagement alive and prevents drop-offs. 3️⃣ Leveraging user feedback loops In-app surveys, quick feedback buttons, and real-time support reveal where users struggle enabling us to fix friction points faster and prioritize product improvements that matter. Trial success is about crafting an experience that feels human not robotic. It’s the ongoing conversation, the timely support, and the empathy that win users over. What’s one strategy that changed the game for your product trials? Share your story below as I’m eager to learn and explore #ProductTrials #UserOnboarding #SaaS #CustomerSuccess #ProductLedGrowth