How to Onboard Free Users with Email Sequences

I analyzed 100+ SaaS onboarding email sequences. Here's what actually works: 📊 After reviewing over a hundred onboarding email sequences across various B2B SaaS products, clear patterns emerged distinguishing what drives user activation from what gets ignored. ⏱️ Timing is as crucial as content ▪️ First email: Sent within 3 minutes of signup to capitalize on user engagement. ▪️ Key information: Delivered promptly, ideally within the first day, to guide users effectively. ▪️ Follow-up emails: Aligned with typical user behavior patterns, not arbitrary schedules. 🧠 Subject line psychology ▪️ Specific value propositions: Outperform generic welcomes. ▪️ Personalization: Including the user's name or specific goals can increase open rates. ▪️ Concise phrasing: Subject lines under 7 words tend to perform better. 📱 Content structure that converts ▪️ Single, clear CTA: Avoid multiple calls to action to reduce decision fatigue. ▪️ Bulleted action steps: Enhance readability and user engagement. ▪️ Mobile-first design: Essential, as a significant portion of users access emails on mobile devices. ▪️ Strategic placement of social proof: Position testimonials or success stories before key actions to build trust. 🔄 Effective sequence logic ▪️ Optimal sequence: 7–10 emails over 14 days. ▪️ Day 0: Immediate value and quick win. ▪️ Days 1–2: Core feature education. ▪️ Days 3–7: Use cases and success stories. ▪️ Days 8–14: Advanced features and potential upsells. 💡 Key insight: Emails that help users visualize outcomes ("Here's what you'll achieve") tend to drive more engagement than those focusing solely on product features. What strategies have you found effective in your onboarding email sequences?

Here are 3 things that improved activation rates in my onboarding email flows, and 3 things I tested and didn’t see statistical significance… Improved: 1) Onboarding Audit: When I audit most onboarding flows, I find that in the first 2 weeks of onboarding for a SaaS product, most teams send 4-5 onboarding emails PLUS 2-3 triggered automated emails PLUS often a personal touch or two from a sales or implementation rep. When you send 10 emails to a new trial in a week or two, they are going to tune out. I have done a ton of audits where we line up all the touchpoints, and then refine to get it to 3-4 TOTAL touchpoints in those first two weeks, with emails that are focused on one specific activation behavior at a time, and conversions always go up. 2) Have it come from a person. Whether it’s your newsletter or your onboarding flow, having it come from a person (your send-from name can be “name @ company” if you want) gets improved responses and engagement. But beyond just the send-from, use relatable, human language, share perspectives and personal experiences etc. 3) Customer/referral intros are magic. If you have a trial that does a number of activation behaviors but doesn’t add a CC by the end of the trial, send out an email like “Want to talk to a [their industry] customer?”. Let them know in the copy that you understand it can be helpful to talk to customers like them and learn the good and the bad. Most teams start with a dozen or so requests a month, and you can find a few steady users and offer a year free on their account in exchange for say 10 customer meets a month. If you get huge inbound volume, you can always pay a customer on retainer, say $3-5k/m to take X # of calls. The conversion of this customer/referral email is bonkers Didn’t provide lift: 4) Personalization works, but you have to be careful. Personalization can absolutely provide a lift, but here is where folks typically screw up. In an effort to include relevant case studies or niche specific insights, they REPLACE core activation emails. If a customer needs to set up a template and connect their XYZ system, you need to make sure you don’t eliminate those emails. 5) Got too clever with the subject lines. I had a client a while back and open rates were abysmal for their onboarding flow so we tried to pique interest by getting clever with subject lines. It didn’t work. I think when it comes to SaaS it’s all about expectation to reality. Just be crystal clear about the value they are receiving and focus on the benefit (not the feature). For example: “Reduce inbound tickets by 20% with [company] AI chat assist” is better than “Set up your AI chat assist bot” 6) We tested having all plain text emails. The thought was that less designed emails might appear more human and thus get better engagement, but we didn’t see that in the data. Actually, the majority of times I have tested plain text vs. designed templates for onboarding, plain text performs 10-15% worse.

Building a successful PLG motion is hard enough. Too many companies make it even harder by ignoring one of the most important elements of a successful PLG motion - the onboarding email flow. - User #1 signs up and immediately abandons > gets sent onboarding flow A. - User #2 signs up and does 20 things > gets sent onboarding flow A. - User #3 signs up and stops logging back in after their initial sessions > gets sent onboarding flow A. See a problem with any of this? These users couldn't be on more different journeys with the product. So why are companies treating them the same? It isn't a technology issue. Just about any email provider in the world can do personalization. The most common blocker I see is companies struggle with is making sense of the unlimited ways and things people are doing. Here are 2 simple strategies for segmenting users into distinct buckets: 1) Engagement Level: Track how often and how long a user interacts with the product. Are they a heavy user, a moderate one, or a ghost? Each of these requires a different communication approach. 2) Feature Usage: Identify which features are being used and which are ignored. A user only touching one specific feature might need a different nudge compared to someone who's trying a bit of everything. While there are a million other ways to personalize the flows, crawl before you walk and just start with something simple. You can continue to add complexity as you go. Remember, the goal is not just to send the emails. The goal is try and guide each user through your product. You can only do that if you meet them where they are.