In 2014, Stevo co-founded Habitry to make products for health coaches.

It was immediately apparent that the most effective and effecient way to help clients change their health behavior is in groups. However health coaches had no tools to work in groups online that preserved their high-touch, one-on-one approach.

The Approach

Habitry took a Lean UX approach to figuring out potential customer pain points, potential solutions, and how to measure the results. This meant front-loading a lot of hypothesis testing with rapid prototyping, customer interviews, and mock ups.


On the advice of Angel Investor Jesse Robbins, Habitry started a series of Unconferences — The Motivate Summits — as a cheap way to surface customer problems and workshop solutions.

These open, unscripted gatherings proved to be a fertile ground for exploring the non-technical approaches that health coaches were using, and the great lengths to which they were going to scale their businesses into the other 167 hours a week they were not with their clients.

We also conducted interviews with clients working with health coaches and people using health coaching apps in lieu of hiring a coach.


Designing for relationships, emotions, and motives.

Using notes from this process, we developed personas of both coaches and clients to guide us through the ideation process. User stories, however, proved to be short-sighted. With coaches and clients to think about — often working together for years — we needed a less linear and more expansive look at the interlinking webs of stories and values we had encountered in Discovery.

To understand this network, we created a Web of Value Exchanges visualization based on the work of Albert-László Barabási. This focused on empathizing about what the people involved in our context would want to Be,Do,Have, and Feel when working with one another.

The Web of Value Exchanges gave us a rich set of emotional words and motives for the eventual users of our tool and the next Motivate Summits gave us fertile ground to test them out.

Building a Thing

Armed with the words and emotions from the Web of Value Exchanges, the next step was making sure we built something that empowered people to create those stories.


Soon we knew our product would have to:

  • Be mobile first (and on iOS specifically)
  • Allow clients to interact with each other
  • Provide Direct Messaging between coaches and clients
  • Focus on a few key metrics shared by coaches and clients
  • Be flexible enough to let coaches drive the content-creation
  • Come coupled with a rich onboarding and education system for the coaches

From Whiteboards to Sketch

UI iteration started out very LoFi with whiteboards, then pen and paper.

As ideas were validated, Stevo increased fidelity using Keynote which let us show mock up screens to potential customers.

We then brought in Graphic Designer Jenny Ji, to build out the product in Sketch.

Once in Sketch, Stevo used user-testing tools to actually watch potential users engage with sections of the product.

Cute Story Alert

Once we had screens that looked like an real app, Stevo would take the protoype to coffeeshops in Emeryville and ask people for feedback on his competitor's new app. The feedback hurt his soul a little, but it did prevent the team from coding a lot of mistakes.

The Killer Feature:

Push Notifcations

In testing, it became obvious that the make-or-break feature of the mobile app woud be push notifications. Health coaches and their clients had both mentioned them frequently in discovery, and in 2014 people weren't quite sick of them yet.

In order to make sure we got it right, Stevo looked at the research on creating motivating push notifications from Self-Determination Theory. Then he went a step further and recreated one of the study protocols.

Using a Google spreadsheet and the Twilio API, Stevo created an automated testing tool that would send text messages to numbers at times within a range and record their respeonses. Stevo then recruited a dozen volunteers who wanted to receive text messages that mimicked potential push notifications. He asked them to reply with the first thing that popped into their head when they received the message.

Within a few days, the team knew what messages would work and which ones were pissing people off. He and Omar Ganai wrote about the lessons from this experiment in How to Design Motivating Push Notifications.

The Product

The Reaction

At it's peak, Habitry iOS had more than 1,000 users on the platform. Health coaches were making an average of $3,000 per month on the app and clients were checking in with 72% daily adherence and 68% stuck around for a full 365 days.