"How do I measure if my onboarding is actually working?"

Measuring (consistently) how your onboarding is doing is, I believe, one of the best time investments you can make for your biz to succeed.

“The faster you help customers understand and extract value from your product, the stickier and more successful they’ll be.”
— Jeff Gardner (CEO and founder)

Successful SaaS founders and their teams keep monitoring how well onboarding does. Because they know how critical onboarding is in driving activation, early adoption, conversion and habit formation, all driving to long-term retention and what i call "true growth".

True growth?

By "true growth", I mean growth that stems from unit economics that work. Users stick long-term (enough for to payback CAC per user + increasing CLTV), revenue grows steadily. That's the only kind of business I'd invest in (if i had the money).

I often hear/read people talk about growth when they are attracting users and converting them. But if people churn after just a few months, before the revenue they've generated covers the cost of acquiring them (CAC payback), then all we have done is pay for them to come, use our product, and leave. It may have felt like growth, but at best it was only short-term growth.

If you’re losing 60% of your new users after the first session, it doesn’t make sense to spend a ton on acquiring signups or your CAC will be high. The unit economics will not work out.
— Francois Bondiguel, Head of Growth of B2B Marketing and Growth at Canva

So our goal is clear: make sure users make it from signup to retaining (and paying for) our product long-term. And that's onboarding's job.

How to measure whether your onboarding is actually working

If you want to know whether onboarding is actually working, i recommend you track:

• signup completion rate
• return rate after session 1
• retention by week 1, week 4, week 12...
• free-to-paid conversion
• churn (especially after first billing cycle)
• CAC payback
• MRR and NRR trends

These metrics, from top to bottom, follow the AARRR funnel:

acquisition -> activation -> retention -> revenue -> referral

And the first stage where you lose the most users is usually your biggest onboarding bottleneck.

What you can do to improve each stage of onboarding

Now let's what questions you can ask to improve each of these stage and associated metric.

1/ how to improve signup completion rate

If you observe people starting your signup flow but dropping before the end, here are a few questions to help reduce friction:

• is your signup flow on-brand?
  (meaning, users don't feel they're on another website after they clicked "Sign up" and are potentially suspicious)?
• are you asking too much info?
  (every bit of info you ask the user to provide should add value to both you and them. if you're only asking for marketing purposes, maybe consider removing it or asking later.)
• are you asking questions users struggle to answer, or that take too much cognitive load?
• are you offering too many choices/options, making them potentially freeze?
• are you asking things in a way that's unclear (jargon?) to your ideal users?
• if there is a paywall, are you providing enough reassurance & motivation so users don't freeze, as well as enough payment options?
  (if you're asking for a credit card, are you mentioning transactions are secured, data won't be shared? for an opt-out trial, are you mentioning they'll be noticed X days before it ends so they're not billed if they don't want to?)
• if you have to ask multiple information, are you making it low-cognitive load by breaking the process down to a series of small, easy steps?
• for every info you ask, are you explaining clearly why users need to input it, and how it'll benefit them later?
  (personalize the onboarding/product, avoid asking critical info later on)

2/ how to improve return after session 1 rate

Hopefully, users ended their first session by reaching a first moment of value — a first meaningful win — that proved them your product actually delivers on the value it promises, and let's them on a high emotional peak.

But that doesn't mean they'll necessary come back. Here are a few questions to help get them back in:

• if they haven't achieved a first meaningful outcome within session #1, are you prompting them off-platform (emails?) to get back in until they experience that first meaningful win?
• is your core flow seamless enough for users to go through and win "fingers in the nose"?
  (if they experienced meaningful value but your product is difficult to use, or confusing or whatever, they may not be that motivated to come back)
• if they reached a first meaningful win during session #1 but don't come back, are you prompting them (still off-platform) to remind them the win they just achieved and come back to repeat the core action or progress with next steps?
  (and are those next steps clearly explained, with the value users will get?)
• if after 2-3 nudges and still nothing, are you reaching out personally to ask if they're stuck and could us some help?
  (sounding needy here is not a good idea. i'd rather recommend you remind them you're here for them, and provide value if you can)

3/ how to improve retention

To earn retention, we must first make sure users experience meaningful value right from the start. And then, we must make sure they keep winning with our product, and to encourage habit formation. Questions you can ask:

• are you measuring how many of specific behaviors happen before we see retention happen?
• if so, are you reminding users to come back to your product until they reach that threshold?
  (this is known as the activation threshold. the team at Slack observed users who sent 2,000 messages within the app had 93% likelihood of staying long-term. that became their onboarding north-star)
• are the users who signed up right-fit users for your product? is the value they experience aligned with the value you promise in marketing?
• do you have effective engagement loops in place that help users create a "pace of usage" and realize the more they use your product, the more value they get out of it?
  (or put differently, are you remind them why they came in the first place and what they already have achieved with you?)
• are you providing all the guidance users need to keep winning with your product?
• and are you actively working on understanding where unnecessary/frustrating/confusing friction could be removed?
• is your product constantly adapting to your users' needs as they progress?
  (here i mean, not building features they request, but features that help them achieve their goals, which is very different. people are good at saying what they want, but very bad at knowing what they need. that's actually our job.)

4/ how to improve free-to-paid conversions

Long-term retention is the result of your users believing:

• your product is truly valuable to them right now (aka, it's helping them achieve their goals, and it's the best option they've tried so far)
• they'll keep winning and reaching their goals if they keep using it

But to convert from free to paid (whether coming from a free trial or a freemium plan), they must believe the value they'll get is worth (meaning, exceeds) the investment. Here are a few questions you can ask:

• for free trial to paid conversion:
  • are users experiencing meaningful value (and enough of it) to believe your product is worth paying for, before the end of the trial?
    (if your free trial is only about setup or vague product discovery, but doesn't lead to a first meaningful outcome where they realize your product works for them — before they hit the paywall — you'll much likely lose them. That's why defining a clear first meaningful to drive users during the free trial is so important)
  • are you actively guiding users to achieve that first meaningful win asap?
    (this means in-app guidance, email nudges to keep them on track, easy access to support and relevant content like tutorials, guides...)
  • are you prompting them to upgrade during the free trial (without disrupting them, that's super annoying) and by explaining the value they'll get by upgrading (and maybe what they'll lose/miss on if they don't)?
    (upgrading shouldn't benefit only your business. it should also benefit the user. users should think something like "okay i have experienced enough to believe this product is working and is helping me achieve my goals. now it's fair to start paying to keep winning/get more.")
  • this one might feel obvious, but are you making the upgrading flow simple and easy?
• for freemium to paid conversion:
  • do users have a valid/compelling enough incentive to upgrade?
    (for instance, if all they need to keep winning is comprised in the free plan, there's no chance they'll ever upgrade. why would they?! as a Notion user, i spent years on the free plan, until i needed advanced features and upgraded. but of Notion had reasonably capped my usage enough for me to experience meaningful value and adopt the product, but just not enough so i feel compelled to pay for more usage, i'd have been happy to.)

It's always about giving before asking

I think many times we're overcomplicating things.

If you’re crystal clear on who your ideal users are, what they’re trying to achieve, and what first meaningful win proves your product can help them, then the rest becomes much easier.

Because that’s really what onboarding is: not a checklist, a tour, a clever sequence of screens or whatever, but a system that helps users get to meaningful value fast enough that they want to come back.

And once they come back, these things follow as consequences:

• users stick
• users upgrade
• users stay long enough for CAC to be paid back
• retention and revenue grow
• unit economics start working and create true growth

So if I had to reduce all of this to one test, it would be this:

Does your onboarding help the right users reach value quickly enough to believe your product is worth coming back to?

If the answer is yes, you’re on the right track.
If not, you don’t have a growth problem yet.
You have an onboarding problem.

Hope this was useful.

If you'd like to discuss how to diagnose your onboarding or apply these concepts to your unique situation, feel free to get in touch and we can have a quick, no-strings-attached chat.

PS_

Want me to review your onboarding for $0? Apply here.

I'll record a short Loom walking through what I'd work on first, and why. I'll look at it through both a strategic, user psychology and UX lens, based on the same system I use with clients.

(No commitment, no following harassment with a drip email campaign)