Advancing social connection via a mobile app that addresses the epidemic of loneliness and isolation
As the VP and Head of Design at Thoughtful, I led the design efforts (collaborating closely with the CEO) in shaping and executing the company's strategic vision, ensuring a cohesive and user-centric approach. I initiated the implementation of a comprehensive design system fostering consistency and promoting efficiency across all interfaces. I facilitated collaboration by systematizing our cross-functional workflows, which led to improved communication in a distributed team. By ensuring that our design solutions aligned with business objectives and customer needs, I prepared the team for launch.
The Vision
The COVID-19 pandemic has brought to the forefront that isolation and loneliness significantly affect mental health and well-being. Years of social distancing and lockdown guidelines left disruption to our day-to-day lives that had, for better or worse, changed our social circles, relationships, and appetites for connection.
Thoughtful makes it easier to fulfill our intentions to be considerate to our family and friends. The platform allows us to set aside time as we do for mindfulness, diet, and exercise. This app is a space dedicated to considering our relationships where we can note down thoughts, create reminders of important dates, and deepen our social connections.
Applications such as Calm and Headspace are excellent answers to mindfulness, as proven by their number of subscribers and valuation. Our user experience borrows the daily ritual as a habit-forming convention. Thoughful’s concept centers around strengthening social ties. It is grounded in wellness. However, it is what we would like to call Wellness 2.0, an ‘other-centric’ form of self-improvement.
Designing & Evaluating Solutions for Product Market Fit
We sought answers to questions on product-market fit by evolving a prototype of the onboarding flow. We analyzed each test's moments of interest, dislike/confusion, and delight. By identifying ideas that worked well and what didn't, we pieced together new narratives that increased the likelihood of achieving success by measuring NPS and a Disappointed KPI. With a few basic concepts in place, Prototype 1.0 scored 20 by NPS standards. By prototype 1.6, we saw world-class results with a score of 80 for men and women (25-40).
Through qualitative research and the Voice of the Consumer program, I learned much about people’s experiences during the COVID-19 pandemic. I observed aggravated social patterns in our respondents, and feelings of uncertainty arose, especially with no end in sight. There was a desire to strengthen social ties to remedy isolation and maintain a supportive community. Hearing their stories firsthand allowed me to further ideate on features that could be of most help.

Figure 1. A few screens of the onboarding flow branded by Red Antler

Figure 2.1. An early sketch of the user journey featuring the habit-forming Daily Guided tour that eventually became known as Daily Actions.

Figure 2.5. Shown above is prototype 1.6, where we met our NPS KPI for product market fit. The onboarding sequence above illustrates how we visualize user testing results to evaluate designs against user needs.

Figure 2.6. The above flow charts are a few examples of how our iterative design process affected the onboarding narrative. We hypothesized that deep architected flows would keep the users in a flow state, resulting in a satisfying onboarding process. We learned that intense activities such as preference selection and profile building are even more successful when spread out over time.
Figure 3.1. What to Say guides: When we developed Thoughtful 1.0, guidance on how to help friends through difficult life situations was the most popular feature we proposed. Pairing content with reminders of important dates gave depth to the Thoughtful experience. It transformed us from a mere reminder system into a well-rounded tool for deepening relationships.
Figure 3.2. Pre-Drafted Messages: While doing Daily Actions, we make sending an SMS easy. In settings, you can select responses for everyday events, such as a birthday or an anniversary of a loss. Three choices per event provide variation in what to send. Shown above is a verbose option for a kid’s birthday.
Figure 3.3. Intention to Connect is a favorite feature of building a profile for testers and live app users in Thoughtful 2.0. Enthusiasts loved the idea of a reminder to connect with an individual.
Figure 3.4. Full Person View
Figure 4.1 Typography, Icons, & App Bars were the first design elements to be formalized into components.
Figure 4.2. The ten app view templates that all views within the app are derived from.

Figure 4.3. The eight libraries of Thoughtful.

Figure 5.1. Shown here is a Figma board displaying features within an epic.

Figure 5.2. Requirements writing was simplified through the use of components.
Nurturing Design
It is challenging to keep up with the speed of an early-stage start-up. My junior product designer wanted to articulate her design decisions better. She aspired to speak with confidence and defend her design thinking. I challenged her to describe the process using a Problem/Solution framework. By reframing the problem statement (in her own words), she rationalized the outcome by connecting it to research insights. Preparing presentations for the quarterly reviews gave her the space to think critically about her impact on the business objectives.
I enjoyed my time at Thoughtful and was fortunate to be on a team of incredibly talented individuals.
For more information visit www.thoughtful.com