Onboarding 101 with OthersideAI

Gaby Goldberg
7 min readOct 22, 2020

You never get a second chance to make a first impression

Over the past few months, I’ve been lucky to meet and work with Matt, Miles, and Jason at OthersideAI. They’re building productivity and communication tools using GPT-3: in one summer, they’ve generated over 3,000 followers on Twitter, along with a waitlist of nearly 8,000 people who want to get their hands on Otherside’s early access alpha product.

But perhaps one of the most intriguing parts of OthersideAI’s story is their approach to onboarding: every single user who gains access to the coveted alpha is personally onboarded through a one-on-one call. On this front, Jason is Otherside’s onboarding guru: he’s onboarded nearly 100 early users, crafting an intentional community of excited alpha testers and maintaining constant dialogue with users as the Otherside team makes product iterations. “User centricity is at the center of every single thing we do, and I want to establish a close relationship with each individual testing our product,” Jason states. “I want them to feel like they’re part of our team, like they can reach me whenever they have issues or feedback.”

“User centricity is at the center of every single thing we do.” —Jason of OthersideAI

In this piece, I’m digging into the consumer onboarding experience — what it is, why it matters, and how you can create a successful onboarding for your own product.

What is onboarding? And why should I care?

At the highest level, onboarding is the experience between “signing up and becoming an engaged user.” To put it simply, if users don’t understand your product, they won’t use it.

“Onboarding can be the most welcoming part of your product. It can turn people who are curious about your app into your most committed users. It can turn doubters into superfans. Great onboarding is a superpower of your app.” — Josh Elman

Onboarding matters because it touches just about everyone: every single user goes through the flow. As I’ve written about previously, customers have more choice and less patience than ever before: last year, 25% of apps were only accessed once after their initial download. With consumer products, time and attention are often inversely proportional: as time goes on, users become busy, distracted, or simply uninterested, and they might be less inclined to spend active time with your product. But when someone is trying your product for the first time, they’re all yours. And that first impression will stick with the user long beyond the initial onboarding flow.

When onboarding is designed correctly, it increases the likelihood of successful adoption, and can drive major growth and retention for your product. (Note: If you needed any additional conviction, even Facebook attributes its onboarding to be a major factor in its rise to 1 billion users.)

Onboarding can be both active and passive.

I’ve broken down the term onboarding into two parts: active onboarding, like the white-glove experiences we’re seeing more and more with subscription-based consumer productivity tools, and passive onboarding, which describes the actual design features that affect a user’s experience.

Active onboarding is hands-on. As discussed earlier, we see this clearly through Jason’s personal onboardings to OthersideAI; further examples of active onboardings are Yac, Superhuman, and Command Dot.

Specifically, Superhuman and Command Dot follow a similar white-glove concierge flow to that of OthersideAI: users have a one-on-one call guiding them through the product and answering any questions.

Although Yac doesn’t utilize a white-glove process like the aforementioned products, they still succeed in creating an effective onboarding experience for users. Upon downloading Yac, each user gets a personalized voice message from one of the co-founders. Users are encouraged to respond directly — through Yac — to learn how to further use the product. Additionally, users receive the following email (thanks Jason for the screenshot):

Active onboardings are memorable to users and can be valuable when seeding early product evangelists. However, these active, white-glove onboardings aren’t always sustainable, especially for companies that want to grow quickly without charging their users exorbitant amounts of money. Fortunately, it’s not the only aspect of a successful onboarding.

Passive onboarding, on the other hand, doesn’t require a one-on-one call or structured introduction. Instead, the onboarding is largely embedded in the product’s design. I break down some of my favorite strategies (with examples & case studies) in the following section:

Onboarding Best Practices

A successful consumer product onboarding:

Emphasizes the product’s value proposition.

It’s less about the features, and more about what your users can do with those features. Jason Fried of Basecamp said it best:

A great example of this is Cameo, which crystallizes its value proposition from the very first screen. Upon opening the Cameo app to sign up or log in, users are presented with a real video of a customer experiencing their very own Cameo gift. If your product has a magic moment like this, capitalize on it — it adds a level of emotional response to the onboarding flow and creates a memorable experience that stays with the user.

Has a clear activation metric.

An activation metric is a measure of how many actions it takes a user to receive value out of a product. With clearly defined activation metrics, you can turn your onboarding into an educational experience and guide users to activation more quickly, setting yourself up for increased retention in the long run. “The truth is that if a user doesn’t know how to use a product, optimizing for activation is useless.”

A great example here is Duolingo, which, in this case, gets the user to pick a language and complete a lesson before the onboarding is even completed.

Duolingo’s onboarding screens

Keeps it simple.

In consumer, a great onboarding flow gets you to the core value of the product in the minimum number of steps required. As such, successful onboardings avoid text-heavy explanations. Instead, opt for screenshots and illustrations to get the point across. It can also be helpful to include progress indicators if your onboarding process is multi-step, so your users can see how far along they are in the introduction to the product.

A simple progress indicator during an onboarding flow

Is personalized to the user.

Headspace is a great example of utilizing in-app personalization, promising the user a personalized experience based on answers given during the onboarding process. The more relevant information the new user gives, the more they’ll get out of the app as a whole.

(Related: Designing with Intuition — Vicki Tan from Headspace)

Another great example of incorporating personalization into the onboarding flow is Zenly. For a deeper look, check out Josh Nelson’s The Zenly Experience — a product case study.

Note: These are only a few case studies! For additional crowdsourced thoughts and insights, check out this Twitter thread I shared recently. A few standout examples:

  • Public: incentivizes completion with a free stock in the middle of the flow
  • Pitch: includes a mini tutorial upon signing up to get the user started
  • Lemonade: makes the process fun and personalized to the user
  • Apple Card: “the flow was so easy it felt like an accident”
  • Wild card: “If Quibi had anything going for it, it was the onboarding. 10/10” — Bryce Natale

Other examples shared in this thread include TikTok, Rippling, Spotify, and more:

Onboarding doesn’t end after the user’s first interaction with the product. On the contrary, onboarding is ongoing: as users continue to engage with your product, they’ll discover more features and learn about new updates. Identifying early on what value to provide the user upon first engagement is incredibly important — and it’s a funnel point you should revisit as you grow.

At the end of the day, there’s no one-size-fits-all approach to onboarding. Depending on the type of product or service you offer, your users might want — or need — a different experience. But regardless of what your onboarding looks like in the end, first impressions rule. A great onboarding should be emotive, personalized, and scalable. Make it easy to engage from the moment your users land on your product, and engagement from that point on will be an easier win in the future.



Gaby Goldberg

Investor at TCG Crypto. Alum @Stanford. Follow me @gaby_goldberg.