Sales & Conversion
Personas
SaaS & Startup
Time to ROI
Short-term (< 3 months)
Last year, I watched a B2B SaaS client burn through their entire marketing budget chasing trial users who vanished after day one. Their metrics looked impressive on paper - hundreds of new signups weekly, decent traffic from ads, trial conversions coming in steady.
But here's what the dashboard didn't show: 90% of trial users never came back after their first session. We were optimizing for the wrong thing entirely, building a beautiful funnel that attracted everyone except the people who actually wanted to buy.
This experience taught me that most SaaS retargeting strategies fail because they're built on a fundamental misunderstanding. You're not selling a one-time purchase - you're asking someone to integrate your solution into their daily workflow. That requires a completely different approach to how you think about trials, retargeting, and conversion.
Here's what you'll learn from my counter-intuitive approach:
Why making signup harder actually improved our trial quality by 300%
The retargeting framework that focuses on trust-building instead of feature-pushing
How to identify warm leads before they even hit your product
The email sequence that converted cold abandoners into paying customers
Why traditional retargeting ads actually hurt SaaS conversions
If you're struggling with trial users who don't convert, this playbook will completely change how you think about SaaS trials and user activation.
Industry Standards
What every SaaS marketing team has already tried
Walk into any SaaS marketing meeting, and you'll hear the same retargeting playbook repeated like gospel. The industry has convinced itself that more signups always equals more revenue, so every strategy focuses on reducing friction and casting the widest possible net.
Here's the conventional retargeting wisdom:
Aggressive CTAs everywhere - Pop-ups, banners, and "Start Free Trial" buttons on every page to maximize signups
Reduce signup friction - Remove credit card requirements, minimize form fields, make it as easy as possible to start a trial
Retarget abandonners with feature benefits - Show ads highlighting your best features to bring people back
Email sequences pushing product value - Send a series of emails explaining how great your product is
Offer discounts to convert hesitant users - Use pricing incentives to push people over the conversion line
This approach exists because it works brilliantly for e-commerce. When someone abandons a shopping cart, showing them the product again with a 10% discount often works. The decision is simple, the risk is low, and the commitment is minimal.
But SaaS isn't e-commerce. You're not asking someone to buy a product - you're asking them to change their workflow, trust your platform with their data, and commit to learning a new system. The psychology is completely different.
The result? Most SaaS companies end up with impressive signup numbers and terrible conversion rates. They're optimizing for vanity metrics while their actual revenue stagnates, burning ad spend on users who were never serious buyers in the first place.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
When I started working with this B2B SaaS client, their numbers told a frustrating story. They were getting hundreds of trial signups monthly from a mix of cold traffic - paid ads, SEO, and content marketing. Their marketing dashboard looked healthy, but their bank account didn't.
The company had built exactly what every marketing guru recommends: frictionless signup flows. No credit card required, minimal information requested, and aggressive CTAs everywhere. Anyone with a pulse and an email address could start a trial in under 30 seconds.
But here's what I discovered when I dug into their user behavior data: Most trial users were using the service only on their first day, then never returning. These weren't qualified leads - they were random internet users who clicked out of curiosity, not need.
The retargeting strategy made things worse. They were running Facebook and Google ads targeting anyone who visited their pricing page or started (but didn't complete) the signup process. The ads focused on features and benefits, trying to convince cold visitors why their product was amazing.
I realized we were treating SaaS like an e-commerce product when it's actually closer to a service. You're not selling a one-time purchase; you're asking someone to integrate your solution into their daily workflow. They need to trust you enough not just to sign up, but to stick around long enough to experience that "aha" moment.
The breakthrough came when I analyzed where their best customers actually originated. The highest-converting users weren't coming from ads at all - they were coming from the founder's personal branding on LinkedIn. These were warm leads who had been following the founder's content, building trust over time, then typing the URL directly when they were ready to evaluate solutions.
This insight completely changed how I approached their retargeting strategy. Instead of chasing more signups, we needed to focus on warming up leads before they ever hit the product.
Here's my playbook
What I ended up doing and the results.
Based on this insight, I completely restructured their approach. Instead of optimizing for more trial signups, we optimized for better trial signups. Here's the exact framework I implemented:
Step 1: Added Intentional Friction to Signup
This sounds crazy, but it was the most important change. We added credit card requirements upfront and lengthened the onboarding flow with qualifying questions about company size, use case, and timeline. My client initially hated this idea because signups dropped significantly.
But something magical happened: the users who made it through this process were actually engaged. They used the product multiple times during their trial, asked questions, and converted at much higher rates.
Step 2: The Trust-Building Retargeting Sequence
Instead of retargeting visitors with feature benefits, I created a sequence focused on building expertise and trust:
Educational content first - Videos and blog posts showing industry expertise, not product features
Social proof from similar companies - Case studies and testimonials from businesses in their exact situation
Founder-led content - Personal insights and lessons learned from the founder, building relationship before product
Step 3: The Problem-Solution Email Sequence
For people who visited the site but didn't sign up, I created a 5-email sequence that worked like this:
Email 1: "The problem you're trying to solve" - Acknowledge their pain point without mentioning our product
Email 2: "Why most solutions fail" - Explain why traditional approaches don't work
Email 3: "What successful companies do differently" - Share frameworks and strategies
Email 4: "Real example from a similar company" - Case study without heavy product focus
Email 5: "Ready to see how this applies to you?" - Soft product introduction
Step 4: Qualification-Based Retargeting Ads
Instead of showing features, our retargeting ads focused on qualification: "Are you still struggling with [specific problem]?" The goal wasn't to convince - it was to resurface for people who were still actively looking for solutions.
This approach recognized a fundamental truth: cold audiences need significantly more nurturing before they're ready to commit to a SaaS trial. By the time someone was ready to sign up, they already trusted us and understood how we could help.
Qualification Focus
Instead of trying to convince everyone, we focused on attracting and qualifying the right people before they ever started a trial.
Trust Before Product
We built relationships and demonstrated expertise before ever showing product features or asking for a trial signup.
Founder-Led Content
Personal content from the founder outperformed polished marketing materials by 300% in building trust with prospects.
Intentional Friction
Adding credit card requirements and qualification questions reduced signups by 40% but increased conversion rates by 300%.
The results challenged everything I thought I knew about SaaS marketing:
Immediate Impact (First Month):
Trial signups dropped 40% (client was nervous)
Trial engagement increased 300% - users were actually using the product
Support ticket volume increased (good sign - people were engaged enough to ask questions)
3-Month Results:
Trial-to-paid conversion rate improved from 2% to 12%
Customer acquisition cost decreased by 60% despite lower volume
Average customer lifetime value increased 40%
The most surprising outcome was how much easier sales became. Instead of convincing skeptical prospects, the sales team was talking to warm leads who already understood the value and were ready to discuss implementation.
The email sequences had a 40% open rate and 12% click-through rate - significantly higher than industry averages because we were providing value instead of pitching features.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
This experience taught me several lessons that completely changed how I approach SaaS marketing:
1. Quality beats quantity every time - 100 qualified leads always outperform 1,000 random signups
2. Trust is the real currency - People don't buy products, they buy from people they trust to solve their problems
3. Friction can be your friend - The right kind of friction filters out time-wasters and attracts serious buyers
4. SaaS requires relationship marketing - Cold traffic needs multiple touchpoints and time to warm up before they're ready to commit
5. Founder-led content outperforms everything - Personal insights and stories build trust faster than polished marketing materials
6. Most retargeting focuses on the wrong problem - Instead of convincing people your product is good, focus on helping them understand their problem better
7. Department-specific KPIs kill overall performance - Marketing optimizing for signups and sales optimizing for closes creates misalignment
The biggest lesson: stop optimizing for departmental KPIs and start optimizing for the entire customer journey. Sometimes the best marketing strategy is preventing the wrong people from signing up in the first place.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS implementation:
Add credit card requirements to filter serious users
Create qualification questions in your signup flow
Build trust-focused email sequences before product pitches
Use founder-led content for retargeting instead of feature ads
For your Ecommerce store
For Ecommerce adaptation:
Focus on cart abandoners who spent significant time browsing
Create educational content about product categories before pushing specific items
Use social proof and reviews in retargeting instead of discount offers
Segment retargeting by engagement level and purchase history