Reexamining the Revered Superhuman Onboarding, and Other Product-First Lessons in Scaling SaaS with Sunsama’s Founder, Ashutosh Priyadarshy

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From the moment it was first documented, Superhuman’s concierge onboarding practice has received unreserved admiration.

The many vetted promises — the 1:1 access to a firehose of contextual customer feedback, the ready knob for guiding different segments, and the impact of tailoring first experiences on activation and retention — made it so. That it seemed markedly at odds with the ascendant PLG-is-everything narrative, helped as well.

As far as good friction goes, this has been exquisite, storied, gold standard.

And it mostly continues to be so. Invaluable for all the merits stated above, reasserts Sunsama’s founder, Ashutosh Priyadarshy (@priyadarshy). Yet, as Ashutosh and his co-founder realized just a few weeks into implementing it, not something to be embraced blindly.

What follows is an object lesson in adopting new approaches, discerning what they might mean for one’s own aspirations and constraints, and the elemental virtue of software:

Why Sunsama decided on concierge onboarding in the first place
Why they paused despite the crazy amount of learning it had enabled, switched (primarily) to self-serve, and how that change immediately impacted key metrics
How and why they emphasize the philosophy of a daily planning habit over the typical, prescriptive how-tos on using the product
Pricing that conveys a differentiated approach and attracts customers with hair-on-fire problems
The enduring importance of not building for everyone (even with horizontal SaaS products)


The philosophical and practical reasons behind Sunsama’s choice

Let me start with the reasons why we chose to do concierge onboarding in the first place:

  1. It was a great way to talk to customers directly, learn about what they needed, what they wanted, and where they were getting stuck in their first product experiences. In that sense, it was one of the most fruitful ways to quickly iterate on an early product.

  2. The other thing is that in our space (productivity tools), the hardest question you face is, how do you activate people and get them to turn your product into a daily habit? Because one thing you see with productivity products is that there’s probably a new app launching on Product Hunt, almost every day, and people want to try that.

Because everybody has this desire of wanting to work better. But going from ‘hey, this looks cool, I’d like to try this’ to ‘this is a tool that is essential to my daily workflow’ is a very difficult transition. A guided 1-1 conversation definitely helps.

Those are the two philosophical reasons behind that choice.

The third (a more practical one) for us at the time was a recommendation from Michael Siebel, our partner at YC. He had been working closely with Superhuman and said, ‘hey, this thing they’ve been doing works, you should try it.’

And when we joined YC, we were in that phase where we were just like, ‘well, whatever we’ve been doing so far isn’t working, let’s listen to these people who have a lot more wisdom and sort of, blindly, try different things and see what happens.’

Turns out, this ended up being really good for us.

We learned a tonne in the process.

“You really do want software to be scalable”

There were a couple of factors that sort of coalesced that moved us from concierge to self-service onboarding. Initially, it was just my co founder, Travis, and I, who were doing all the onboarding. A two-person team.

And very quickly, within a few weeks that is, we got to a point where our calendars had literally nothing else but onboarding calls, perhaps 12 a day, each.

We were learning a lot. Sure.

But in order to build what customers were asking for, we had to start paring these down urgently from at least Travis’ schedule.

Then we decided to hire someone who would do nothing but customer onboarding. Soon enough, even this person had their calendar booked wall-to-wall.

Thus the question was, ‘okay, if we want to keep growing this way, we’ll need to:’

  • hire another customer onboarding person,
  • train them,
  • make them an expert in the product,
  • and continue this process over and over.

Going through the training routines, a part of us felt that we were almost building this meta product which was our customer onboarding.

And that made us ask: Did we really want to go down this path where we’re going to need to hire a small army of people to onboard customers? Wouldn’t it be better if we were pouring our efforts into making our product more intuitive for the end user, instead?

Once you start thinking about the unit economics of this method, it’s hard to say that this will ever make sense. Unlike Superhuman, we weren’t rolling in 10s or hundreds of millions of dollars in venture capital. We had raised a fairly modest, $2.4m round, after YC.

We wanted to be a lot more careful about how we were spending our money and we felt that it would be better spent on product development.

Plus, you really do want software to be scalable.

What we did to transition was to take all the things that we were aiming to teach customers in the onboarding process and productize them. Chiefly, what that ended up looking like was a daily planning ritual that guides you step-by-step through the process of planning your day.

This feature (a core Sunsama feature) didn’t even exist until we did concierge onboarding. In fact, it came about because of concierge onboarding. And once we rolled it out, the conversion rates were better overall, and, surprisingly, churn was down.

Let me explain.

So an interesting thing with the onboarding calls was that you had to become a paid user to talk to us and use the product for the first time. And a lot of people would pay, do the call, and then just cancel immediately. As they were willing to risk a $20 charge on the credit card to find out what’s behind the gate.

Not just churn, all our metrics improved when we went the self-service route. But we were only able to do that because we learned so much in the concierge mode.

And then, at the very top of the funnel, there was a particular user behavior that clashed with the concierge way of doing things. A lot of our customers were and are people who tend to be fairly autodidactic.

They’ve built their own processes for how they manage their day, how they plan their work. So, to be told, ‘hey, before you can use this product, you need to, like book a call, wait a week, and talk to some guy,’ just doesn’t tally with their expectations. And instead makes people feel as if their hands were tied in some way.

If you’re able to generate the right kind of excitement around that process, like Superhuman has done a really great job of highlighting invite-only exclusivity. For them that works really well. Probably making the product more special. But we weren’t deeply committed to that kind of exclusive approach.

Our biggest hesitation with getting rid of the concierge onboarding was that we wouldn’t have that face time with customers to learn how they thought about their day, their pain points, which they’re kind of expressing to you as they’re going through the onboarding.

So as we went self service, we switched to a 14-day free trial. And then after people upgraded, we gave them the option to do a 1-1 chat with either myself or my co-founder, Travis.

Not as many people take that option. But we still fill out our calendars one day a week with customer calls. All of our best product insights and improvements have come from just talking to customers.

You still need to find a balance.

From time to time, we stop doing these calls when we feel ‘okay, last month we talked to a bunch of customers, and there are these big points of feedback in the product that we’re hearing again and again, and need to address.’

At that point, it’s actually more important to spend the day actually building the things that the customers need as opposed to just hearing the same thing over and over and not being able to act on it.

“Tooltips are frustrating”

This is another thing we can thank Superhuman for. They are famous for their onboarding email sequence. We certainly took a page from that.

Sunsama is, effectively, a tool for helping you plan out your workday. So as you go through your first two weeks of using the product, we send out a daily email at the time (exactly within five minutes of whatever time you’ve mentioned) that you intend to do your planning.

Aside from these targeted deliveries, we tried not to talk about the product at all in these emails. Especially in terms of tasks, ‘here’s how you can do X, or here’s how you can set a repeating step or anything like that,’ and really emphasized some core planning principles.

Sharing snippets on how to work well, how to prioritize better, and so on. Hoping to imbue their first moments with feelings along the lines of: ‘hey, if I take five minutes to plan out my day, I’m going to feel better, more focussed, and calmer.’

Which meant, even if you decided not to use Sunsama and use, say, good old pen and paper, we’d hope that the daily planning ritual and ideas surrounding focussed work was helping our users build a useful habit. Whether you’re doing it in Sunsama, or somewhere else.

I mean, we did care. We wanted you to use Sunsama. But our goals were really about building that motivation. Because we’ve learned that when a user is sufficiently motivated to solve their problem, they’ll find how to use the UI, they’ll find how to use the settings.

So teaching people that is kind of like a pointless activity, if you haven’t gotten them motivated and inspired to use the product.

Similarly, we’ve been pretty intentional about having very minimal notifications, or alerts or nudges on how to use the product within the product.

As I said, if a customer is motivated, let’s say, they want to have a task that repeats every day, people are smart enough to Google, ‘how do I make a task repeat every day in Sunsama, or click around in your settings,’ or click around in the app and figure those things out.

And for the most part, having those tooltips is frustrating.

What we’ve tried to do, in terms of nudges and encouragement, is not nudge people to use certain things, but to use the product as part of their daily ritual.

And that just goes back to the email. So you get the daily emails at the time that you say you want to plan your day, there’s the same thing for weekly planning. And there’s also a notification from the app itself, a push notification that goes, ‘hey, it’s time to plan your day.’

That’s it. That’s the extent of it.

The other thing that we’ve done differently is that our first-time user experience is basically the core workflow that you do in Sunsama every day, which is going through this four-step, daily planning ritual.

Except we basically redid the UI for it and the UX of those four, five steps to be very specifically catered for what it’s like as a first time user, as opposed to a user who’s on their second, third, or 300th day.

The way we did that is, instead of adding a lot of tooltips, what we really did is we took the core UI, and we just simplified it down, we broke it into a few more steps.

So that learning the principles of the product, its philosophy, how the UI works, is a little bit more digestible. What people tried to do with tooltips, oftentimes, it’s like, ‘hey, we have this fairly sophisticated, possibly complex UI. And in order to make it digestible, we’re going to point things out to you.’

And our approach was, basically, we have this UI, let’s build a whole other custom workflow that’s very similar to that, but helps you digest that.

It’s a lot more work, obviously. Because it’s like, instead of putting pointers, you’re doing something that already exists, but making it different for very particular use cases.

But in the case of a product such as ours, it’s the most important thing. If you can’t get people to plan their first day, and since they’re never gonna plan their second, third, fourth day, so for us,

Thus quite a bit of the product development energy goes into getting people to plan their first and second day and if we can do that, we’re off to the races.

The many sustainable gains of charging what your product is worth from the outset

Very early on at YC, one of the things Michael Seibel really pushed us to do was to charge an uncomfortable amount for our product, and really embrace building a premium product with a premium price point.

That’s what we’ve done. Sunsama is almost $20 a month, which in the productivity space is more than many other products. But we also think that our product is a lot smoother, better, and worth every dollar.

But the idea behind charging a premium price point, it’s not really about, ‘Oh, you’re gonna make more money this way.’

The reason you do that is, well, there’s a bunch.

First of all, it helps you select customers who really need your product, somebody who’s happy to pay $20 a month, probably needs your product a lot more than somebody who kind of wants to pay $5 a month. Put another way, it helps you attract the kind of customer who has a hair-on-fire problem.

Then as you interview, build and iterate for these folks with a hair-on-fire problem, a virtuous cycle ensues, where you start to ship really valuable things and make the product more and more valuable. As opposed to having a large set of free/low-tier customers who’d offer volumes of diluted feedback that never really points anywhere useful.

Fundamentally, that’s the biggest reason. When you have an early product, that isn’t great, yet, starting with a high price point sets a high level of expectation, and then you as a product team have no option, but to meet it or fail.

This has certainly helped us create a high quality product experience. There’s still more to do. But I think if we had chosen a different price point, we wouldn’t be where we are today.

The other thing that was part of the calculus was the simple fact that the polish, the breadth, the quality of the product that customers expect is extremely high in this category.

Our customers are expecting our product to be at the same level as tools such as Asana, Superhuman, and Linear. These are products that have literally hundreds of millions of dollars in product development. That’s not an exaggeration.

And we’re just a small team.

Thinking: ‘Hey, how can we do that without spending a ton of money? And, of course, the easiest way is to just extend the runway. And we do that by building a somewhat sustainable business and charging for what we’re worth.

So instead of deferring and saying, ‘one day we’ll monetize,’ we’re choosing to monetize now, extend our runway, as that buys us time to keep building the best-in-class daily planner.

That’s been the plan.

Being honest that you can’t help everyone allows you to solve way better for those you can

Accept the fact that your product is not for everyone.

Avoid pursuing everybody on the planet as a user. While it’s a great ambition in the long run, you have to start very specific.

For instance, my product is only going to serve people who use Asana and Google Calendar. That’s a good starting point. You build that. Make that specific product work for a cohort of users. Then get to that Ajira integration. And further down the line, add the Outlook integration.

But before you have that, when users ask, ‘hey, I wish you had an Outlook integration,’ you just say sorry. It’s painful because you feel as if you’ve lost an opportunity.

Just know that in time, you will have an opportunity to add new integrations. New features that will expand your market horizontally.

But you don’t want to get carried away with that, and then miss out on providing the level of depth and quality that your existing customer base wants.

To that end, one of the things that was very helpful for us as part of the signup flow is having this qualification survey where we ask you ‘hey, what tools do you use?’ What are you looking for in the product? What are your issues with your current workflow and productivity?

And then just being very upfront with users who said, ‘hey, I use whatever Monday.com and responding with: ‘Hey, sorry, we don’t support that. You probably don’t want to use Sunsama.’ Just being honest that you can’t help someone.


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This is such an important read, @priyadarshy. Products that belong to a similar space, are built for similar high-frequency usage patterns, and lead with premium price points, can still have starkly different experiences with different playbooks.

Thanks for sharing these first-hand lessons!

I recall reading Sunsama’s super earnest HN launch post, where you had mentioned how you and Travis had built many (6?) different products prior to Sunsama, so I have to ask as a fellow founder, what keeps you going? :slight_smile:

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We’ve always been interested in the question of how we can be intentional and focused with our time each day. That question remained important even when our product iterations failed.

And then, with each iteration, we learned something new that we were eager to try and validate.

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