by Zack Andresen

Anyone who’s ever been set-up on a blind date before knows the pressures of a successful user onboarding experience.

You’re sitting at a restaurant you can’t afford across from a complete stranger – could be the love of your life, could be a serial killer (that’s why they’re single!) – trying to make the best possible impression and not chew with your mouth open.

This is it. They are here; this is yours to lose. How are you going to make an immediate connection, demonstrate your value and entice them to come back again, all while getting some information about them for yourself?

This is the same question startups face everyday. There are 2.2 million apps in the app store and an estimated 100 million new businesses started every year around the world. The competition for your attention is at an all-time high and with that, there’s never been more of a need for sites to be giving thoughtful consideration to how they create stickiness with users from the get-go.

Like the dating world, everyone has their own unique approach – I once had a woman tell me she didn’t “believe in dinosaurs” – but also like dating, it often takes only one bad experience to make you acutely aware of what makes a good one (I met my wife shortly thereafter – she fully believes in dinosaurs).

Here’s everything you need to consider while building out your startup’s user onboarding experience (along with examples of sites who are already at the top of the game):

Make your purpose known.

You know what it is you do and your value proposition, but as a new prospective user, what am I doing here and what problem is your platform going to solve?

Bringing your value prop to the forefront of the onboarding experience sets expectations for delivery, but also creates opportunity for you to delight your new user by exceeding those expectations with the true depth of your platform.

Take the golden child of the SaaS start-up world, Slack, for example. Slack’s mission is to “make your working life simpler, more pleasant, and more productive.” An ambitious, albeit slightly ambiguous aspiration. Slack is aware of that ambiguity though and for new users, simplifies it’s purpose to it’s core function: “Slack is a messaging app for teams.”


It’s a succinct, well-defined expectation for Slack’s most recognizable purpose: easier, streamlined chat communication amongst colleagues. What’s behind the curtain, however, is a platform capable of much more than just replacing your email (we detailed 7 ways Slack can help optimize your startup back in December).

The lesson to be learned here is K.I.S.S.: keep it simple, startup. Shed the complexity of what you aspire for your platform to deliver (“…make your working life more pleasant…”) and focus in on what likely drove the user to you in the first place (Slack’s disruptive new approach to workplace communication). Validate your user’s expectations immediately and then surprise them with what you’re truly capable of doing once they’ve bought into that initial value prop.

Deliver a small win, quickly.

The secret to that new user buy-in lies in minimizing the time between your value prop and your new user’s first “win.”

There’s plenty of research backing the idea of quick wins as critical to the psychology of success, but the focus of user onboarding is often selfishly misaligned toward information gathering rather than making your new user feel successful.

It’s a simple role reversal: rather than forcing members to create a login or profile in order to experience the benefits of your platform, deliver small, quick wins on your platform as a way to incentivize profile creation.

Duolingo, a language-learning site that offers “everyone access to a private tutor experience through technology,” understands the importance of smalls wins. A new user to Duolingo is visiting with the goal of acquiring a new language – obviously not something that they’ll be able to complete in one visit. So, Duolingo sets about establishing small wins on the path toward the larger goal.

After selecting your language of choice and committing to one of four daily time commitments (a strategy which is itself pretty crafty – the highest level, which they’ve labeled “Insane” is still only a 20-minute daily time commitment so it’s not too hard to feel like an overachiever from the outset), you’re launched into a basic vocabulary lesson.

Within minutes, you’ve completed your first lesson, learned a simple phrase in your new language, gotten a feel for the way Duolingo educates, and earned your first 10 XP points – Duolingo’s measurement of language fluency – all without creating a profile (an onboarding tactic we’ll discuss in more detail below).


Headspace implements small wins and progress measurement in another field – meditation – where even those with the best of intentions won’t find success overnight. The “Headspace Journey” as it is so aptly labeled by the company’s co-founder and lead instructor, Andy Puddicombe, launches new users into their free, introductory “Take10” course: a basic, low-commitment and consistently reassuring hand-holding through the foundations of a successful meditation practice. Each of the 10-minute sessions ends with Puddicombe’s velvety voice signing off with: “We’ll see you back here tomorrow for Day X of Take 10,” a big checkmark overlaying the just-completed course, and the “Next Session” arrow jumping forward.


There’s psychology behind what Headspace is doing here. We mostly all know that a daily meditation practice is good for the mind, but few make the time. Most would likely blame a busy schedule, but the real reason resides in a new meditator’s progression: are you making headway (no pun intended) in your pursuit for mindfulness? Headspace highlights that progress visually and celebrates it with follow-up emails like the one below.


Both Duolingo and Headspace are taking advantage of something called the goal gradient effect: as people come closer to achieving a set goal, they work harder to make it happen. It’s the same effect that made Seinfeld’s Elaine Benes obsessed with retrieving her Atomic Sub punch card and it’s what will help ensure your new users return to your platform again.

Show and tell.

A good product tour doesn’t feel like a product tour. Like a pair of top-notch salsa dancers (not me), each step should feel natural, intuitive even. Walking users through the platform feature-by-feature doesn’t stick; giving them a task, helping them achieve that small win and then introducing features in a natural flow along the way is the best way to ensure when they come back, they know exactly where to go and what to do.

Slack does this well with the introduction of Slackbot early on in the new user experience, but I’d to highlight Evernote, the popular notebook tool/idea hive. Evernote introduces new users to the platform through a checklist of to-do’s that guide you, step-by-step, through all of the core features.

After downloading the application and setting up your account, a checklist appears in the top left corner of the platform with a series of tasks starting with the simple “Create Notes” and ending five steps later with “Set Reminders.” The five functions introduced build off one another, creating a workflow that’s intuitive and easy to replicate.

Notice that there’s no mention of “Work Chat” or tags or audio notes and certainly no prompt to upgrade from Evernote Basic to Premium. The goal of the first visit is to clearly highlight the features and quickly create that first win.

Be careful what you ask for.

The days of registration forms the length of most government background checks are behind us. As a startup evaluating what information to require in a user’s first visit, ask yourself one simple question: what do I absolutely need this first time around?

Social logins – those nifty “Login with Facebook” or “Connect with Google” buttons that are prevalent now in most onboarding processes – have dramatically simplified the information collecting process. Users don’t need to enter their name, email, date of birth and a flurry of other information into different fields to gain access to your site or app (a relief for mobile users in particular, for whom this was a particularly arduous process); instead, they can link directly to another site that’s already done the legwork of getting to know you.

And while the process is certainly easier and undoubtedly has a positive effect on your conversion rate of first-time visitors, it’s not foolproof.

There’s a range of permissions that social logins are able to request and while it may be tempting to request access to things like my friend list or “likes,” remember: the guiding question is “what do I absolutely need?” not “what do I want?”

Pinterest is an example of a site that likely needs most of what they request access to when you login with Facebook.


By gaining access to my Facebook likes and interests, not only am I up and running on Pinterest – a site I’ve never used before – in less time than it takes a dog to eat a hamburger, but I am coming in with an already well-curated feed of content mapped directly to me and my interests (screenshot not included because it was mostly pictures of barbeque and a checklist for building a home bar – yikes).

Recently, more and more sites are pushing the registration request to the end of the onboarding process in an attempt to minimize disruptions between the value prop and that first small win that creates user buy-in.

Our friend from earlier, Duolingo, does this by planting the opportunity to create an account and “save progress” directly following that first small win, right when that dopamine is kicking in and you’re feeling proud of yourself.


The real expert in backending the registration process, however, is Eventbrite.

Eventbrite is a “a global marketplace for live experiences;” a platform for figuring out what to do – and where your friends are going to be – on a Friday night. There’s plenty of competition in the event space, so how does Eventbrite differentiate? By removing all barriers between you and that first small win.

As a new user, you’re greeted with a simple but exciting value proposition (“Find your next experience”) and then given direct, immediate access to Eventbrite’s entire database of upcoming events in your area – no registration required.


Once you’ve found one you’re interested in attending, your registration with Eventbrite is built directly into the ticket-buying process. It’s so ingrained in the natural flow of using the platform that you don’t even realize it’s happening until it’s over.


All in all, your goal in registering new users should be to minimize the friction between them and finding value. The best way to do that is to think carefully about what information you need in the first visit to create the best experience possible.


This is just the tip of the iceberg. Just as your startup is constantly evolving, so should the process with which you bring on new users. And while there will always be new tools and methods to help you increase your conversion rate, remain true to creating the best possible experience for them. They’ll thank you for it by coming back for more.

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