Every SaaS founder I talk to thinks they’ve handled activation.
They’ve got an onboarding checklist. Maybe a welcome email sequence. A tooltip or two on the complicated screens. They’ve “done activation” and moved on to what feels more important: marketing, features, sales.
But most of them haven’t done activation. They’ve done the checkbox version of activation. And the proof is in their free trial to paid conversion rates.
For bootstrapped founders under $1M ARR, the average free trial to paid conversion rate is around 15%. For bootstrapped founders between $1M and $5M ARR, it ticks up to about 19%. VC-funded companies at the same stage? They’re often seeing 30, 35, even 40%.
Same product categories, similar ICPs, but wildly different conversion rates. And I don’t think the gap is marketing budgets. VC-funded companies typically have the resources to hire experienced product and growth talent who know how to invest in activation. Most bootstrapped founders haven’t been exposed to the process. They don’t know there’s a repeatable way to improve it, so they guess, or they skip it entirely.
That’s what we talked about on this episode. And if you’ve been ignoring activation, or if you think you’ve handled it because you added some tooltips, this one is for you.
Activation is the middle child
I love activation projects. I think it’s because activation is the middle child of growth. It sits between acquisition and retention, it doesn’t get nearly enough attention, and yet it impacts both sides.
If your activation experience is great, your marketing becomes more efficient. The right people sign up, they experience value quickly, they stick around, they refer others. Everything compounds.
If your activation experience is not great, it works in reverse. You pour money into acquisition, people show up, they struggle, they leave. You never know why. Your retention suffers. And you’re constantly refilling a leaky bucket.
Activation is also, I would argue, the most underinvested area for bootstrapped SaaS founders specifically. And I think I know why: most founders have never been taught that there’s a process for improving activation. They think it’s guessing, or intuition, or trial and error. It’s not. It’s a highly repeatable process, and the more you build that muscle, the better you get at it.
So let’s talk about what activation actually is, and then how to actually do it.
What is activation?
Activation is the journey through which a new user understands or experiences the value of the product. And the goal is for that to happen as fast as humanly possible.
I want to be specific about why “as fast as possible” matters. We are an impatient, forgetful species. You do not have someone’s attention for very long. And in the PLG world, data suggests you have less than 10 minutes with the average new sign-up. Less than 10 minutes before they get distracted, close the tab, and move on with their day.
And here’s the number that should make your stomach drop: about 70% of people who sign up for a PLG product will drop off within the first 24 hours and never come back.
If your product experience doesn’t create a clear path to value in that window, most people won’t find it.
Activation also starts earlier than most people think. It’s not just the sign-up flow. It’s every touch point that shapes a new user’s experience, including the marketing site. The expectations you set on your homepage are part of the activation experience. By the time someone hits your sign-up button, they’ve already formed an opinion. That opinion shapes how they engage with everything that follows.
And activation doesn’t end when someone converts to paid. New customers are still going through activation. They’re still learning your product, building habits, figuring out whether this is actually going to work for their business. That process (what I’d call later-stage activation) is where a lot of churn happens that teams incorrectly attribute to retention.
The misconceptions
Before we get into process, let’s clear up what activation is not.
Activation is not:
- Just your onboarding emails
- Just your sign-up flow
- Just the payment screen
- Just tooltips and walkthroughs
I see the same pattern constantly: a team adds an onboarding checklist, configures a few popups, and calls it done. And then they’re confused when their conversion rates don’t move.
Here’s my honest take on popups, tooltips, and visual walkthroughs: they are only helpful on top of an already-great product experience. They are not a substitute for great design. And in 2026, most users don’t even acknowledge popups anymore. Pop-up blindness is real.
We do a lot of UX interviews (we’ll get to that in a minute) and I can tell you that most people don’t even register overlays and walkthrough prompts anymore. They’ve tuned them out.
What this means is that teams who rely on these tools to explain their product are gambling. They’re depending on something that a large percentage of their users will simply ignore. And instead of fixing the underlying experience, they’re papering over it.
I don’t say this to be harsh. I say this because the better path, actually improving the product experience, is more achievable than most teams realize.
The process
Here’s how you improve activation.
Step 1: See your product through someone else’s eyes
The first and most important step is UX interviews. Not session replays or heat maps. Actual conversations with real humans navigating your product for the first time.
I know what you might be thinking: session replays are easier, cheaper, faster. That’s true. And they have their place (maybe 10% of the value). But here’s the problem with session replays: they don’t have context. You don’t know if that person is qualified. You don’t know what they were trying to accomplish. You can’t ask them when they’re confused. You’re just making assumptions based on where a cursor moved.
UX interviews give you 80% of the value because they let you understand what’s happening inside someone’s head while they’re in your product.
Find 3-5 participants who are not your customers. This is crucial. Not customers. Not people who’ve heard of you. Strangers, ideally within your ICP.
Why strangers? Because your customers are survivors. The people who became customers are the ones who made it through whatever friction exists in your product. They navigated the broken flows, figured out the confusing UI, and stuck with it long enough to convert. They’re not representative of everyone who tried and left.
If you ask customers to evaluate your onboarding experience, they’ll tell you it’s fine. Because for them, it was fine enough. You’ll develop a false sense of security. The people you want to talk to are the ones who would have left.
For B2B audiences, finding qualified participants is faster than you might think. We can typically source participants in 24-48 hours using platforms like userinterviews.com or respondent.io. It runs about $200 per participant ($100 for the platform and $100 for the incentive). Five interviews runs roughly $1,000.
They don’t have to be perfectly qualified either. A good proxy (someone who’s close to your ICP even if not exact) will give you useful signal. Great product experiences are universal. If a proxy gets confused, your core audience probably will too.
Give them prompts tied to your value moment. Start by having them share their screen and navigate the marketing site as if they were evaluating it for their own business. Then give them prompts designed to get them to your product’s aha moment, the one or two or three things they have to accomplish to actually experience the value.
For a time-tracking platform we recently worked with, that was: add employees, configure time tracking, and actually track time. Watching strangers struggle for their lives to add employees was illuminating. And painful. But mostly illuminating.
Don’t help them. This is the hardest part, especially if you built the product. You are going to watch someone struggle. Maybe badly. You’re going to want to point at the screen and say “it’s right there, just click that.” Don’t.
Users will often blame themselves before they blame the product. You’ll hear things like “I’m so dumb, I didn’t get that” or “that’s probably just me.” It’s not them. It’s the UX. But if you jump in, you’ll never know where the actual friction is.
By the third interview, you’ll have a clear picture of where people get stuck. The fourth and fifth are where you can start testing slightly different scenarios.
Step 2: Map and annotate
After the interviews, sign up for your own product on a normal screen. Not your giant developer monitor. Something closer to what your users actually use. A 13 or 15-inch laptop. Maybe even your phone if the product is primarily mobile.
Take a screenshot of every single screen. Put everything in Miro and annotate. Mark where people got confused. Where they got stuck. Where they clicked something that did something unexpected. You’re building a map of the friction points.
Step 3: Fix the right things
As you look at your annotated map, you’re looking for three specific problems:
Cognitive overload. The screen has too much happening, and it’s not clear what to do next. Maybe there are four blue buttons competing for attention and none of them are obviously the right one. Maybe there’s a lot of information and it’s hard to parse what matters.
Uncertainty. The user doesn’t know what to do next. Not because the page is overwhelming, but because it’s not guiding them anywhere. They hover. They move the mouse around. They’re looking for a signal that isn’t there.
Limited attention. You’re asking too much. Sign-up flows are the most common offender here. I signed up for a product recently that had ten steps. Even as someone who uses a lot of SaaS, I was thinking “when is this going to be over?” Limited attention means: are you respecting how little time and patience someone actually has?
For each friction point you identify, you’re solving for one of these three things. That’s your design brief.
Step 4: Iterate
Implement changes, then do another round of five interviews. Different participants, same prompts (or adjusted prompts if you’ve made significant changes). See what moved.
This is where it gets interesting. On a recent project, we finished the first batch of interviews, identified a major barrier in the employee-adding flow, the team fixed it quickly, and we ran a second batch. People were now making it past that step, which meant they were exploring parts of the product nobody had seen in an interview before. New friction points emerged. We fixed those too.
Activation is iterative. It’s not a one-time sprint. The muscle you’re building is the ability to see your product through your customers’ eyes, over and over, as the product evolves.
Only after you’ve done this work (the interviews, the annotations, the real UX changes) should you think about adding tooltips or onboarding checklists. They can be helpful on top of a great experience. They cannot replace one.
The survivor bias problem
There’s a concept I come back to a lot when I think about activation: survivor bias.
Your customers are survivors. They made it through whatever friction exists in your product. And because they made it, they don’t represent the full picture of who showed up. Every person who got confused and left, who blamed themselves and never came back, who decided the product probably wasn’t for them. Those are the people whose perspective you’re missing if you only talk to customers.
Most people who struggle with your product won’t tell you it’s the product’s fault. They’ll tell themselves it wasn’t for them. And then they leave. And you never hear from them.
This is why UX interviews with strangers are so powerful. They let you observe the behavior of the people who don’t survive. The ones who get confused, get frustrated, and leave. And once you see it, you can’t unsee it.
Later-stage activation
Everything I’ve described so far is about new user activation: getting someone from sign-up to value moment as fast as possible.
But activation doesn’t end when someone converts to a paid customer. When I was on the board of Moz, we had a concept called qualified vs. unqualified churn. Unqualified churn was people who churned within a certain period of time after becoming a customer, even if they’d paid, they hadn’t really activated. The trial worked well enough to get a credit card. But then things fell apart.
Just because someone becomes a customer doesn’t mean it’s solely retention’s problem. For new customers especially, they’re still learning the product, still building habits, still deciding if this is actually going to work for their business. That’s still activation.
You can apply the same UX interview process to newer customers. Observe them completing the jobs they’re trying to do. Watch where they get stuck. You’ll find friction you didn’t expect. Friction that’s costing you retention.
What this looks like in practice
A typical activation project with DemandMaven runs 6-10 weeks, depending on the pace of implementation between rounds of interviews. In that time, teams usually go through:
- First round of UX interviews (3-5 sessions)
- Screenshot and annotation mapping
- Design changes and implementation
- Second round of UX interviews (3-5 sessions)
- Iteration
The progress teams make in those 6-10 weeks is often more than they’ve made on activation in years. Not because the process is magic, but because they’ve finally stopped guessing. They’ve actually watched their users.
The moment a founder watches a stranger try to use their product and sees exactly where the confusion is, there’s nothing like it. It’s humbling. It’s a little painful. But it’s clarifying in a way that no analytics tool can replicate.
The benchmark is the floor, not the ceiling
One last thing.
When bootstrapped founders hit that 20% free trial to paid conversion rate, a lot of them feel like they’ve arrived. They’re at or above the benchmark. Time to focus elsewhere.
I’d push back on that. The benchmark is the floor, not the ceiling.
I’ve seen products (no credit card required) convert at 60% with incredible retention to match. Getting from 20% to 25% might not sound dramatic, but that 5-point improvement compounds. Every month, you’re converting more of the people who show up. That delta builds. And as your marketing improves, as your product gets better, as your acquisition sharpens, all of it speaks to each other.
Activation is the lever that makes everything else more efficient. If you’ve been treating it like a box to check, it might be the highest-leverage investment you’re not making.
What do you think? Have you run UX interviews on your product before, and if so, what surprised you most?
Or if this is something you want help with: activation research is something we do at DemandMaven. Book a discovery call with Asia.