Design from 0 - 1 to Deepen Social Connections
Stats
NPS
80
In prototype testing
Product Market Fit Survey
40%
Users who answered Very Disappointed, if they could no longer use the app
82%
Conversion
Overview
This is how Thoughtful, a seed stage start-up, proved positive indictors of retention from prototype testing and launched a product to withstand the risk of churn.
Thoughtful is on a mission to disrupt the Wellness category. Our investor calls it Wellness 3.0 where Calm and Headspace meet a soft social network. According to a 80 year old, Harvard study on adult development, the single most important thing you can do for your health is show up for others.
We believe that great relationships are healthy indicators of enduring long-term mental and physical issues.
Coming right out of the COVID19 pandemic in early 2021, we surveyed and interviewed potential consumers on the effects of social distancing on their relationships. This is what we discovered:
The Voice of the Consumer research revealed a strong desire for a supportive community. People realized their true circle of support was smaller than they had originally thought.
When relationships fall by the wayside It feels like an intensive chore than a moment of joy to reach out.
The one obstacle preventing people from initiating communication with their loved ones, particularly during challenging times, is the uncertainty of what to say.
Early on, a cohort of ‘Enthusiasts’ voiced that they were time starved and didn't have the energy to keep up. The distance in their relationships with friends grew both figuratively and literally. It is a gargantuan task to stay on top of all the details that matter for everyone that matters.
Remembering important days for their people, such as birthdays and anniversaries was a high value, low effort way to stay in touch. Dates with emotional weight often didn't make it onto calendars. A calendar was for productivity but reminders to check in with your friends? Where should that go?
Better Social Habits
How might we help users take small steps to improve their network of support?
Empowering Connection
How might we evoke the feelings of ease, safety and joy to set the mood for relationship building?
Expert Guides
How might we provide the knowledge to speak with confidence on the user’s intentions to connect?
Intervention

The above diagrams is an example of how the human centered design process affected the onboarding narrative. We hypothesized that deep architectures would keep the users in a flow state, and make for a satisfying process.
What we learned was the opposite. Intense activities such as preference selection and profile building were easier to complete when broken down into smaller tasks over time, thus creating a longer onboarding process. However users complained that onboarding was too long…
It was the CEOs decision to challenge that perception. In her experience, longer onboarding creates more moments of engagement which is important for the user's first experience with the app. The perception of length needed to be addressed with different tactics. The app launched with a long onboarding, yet still had an 82% conversion rate from download to account creation.
Intervention
Listenng to feedback for more content in relation to your peoples. We needed to gather information on people and we needed to arm them with detaiuls to talk about. Things like natrual distastsd made it as a moment of delight.
What we learned was the opposite. Intense activities such as preference selection and profile building are even more successful when spread out over time as shown in Version 4.
Features
Problem
What to Say guides provide users with comprehensive dos and don'ts to form a response to a given situation. Naturally, after reading the content guides, users wanted to copy and paste the suggestions into their text messages to get their conversation going.
Solution
The initial version of Pre-Drafted Messages existed as a feature within Settings, offering users three response options for events like check-ins, birthdays, or anniversaries. The messages ranged from concise to verbose.
In the second iteration, generative AI was introduced to draft responses based on an event as well as the relationship. This AI feature becomes an option for the user when sending a text message.
Reflection
Figma is a robust collaboration tool, offering versatility and intuitive functionality. I took the initiative to teach others how to leverage its power. Once everyone achieved a level of comfort and basic proficiency, we utilized Figma to visualize the product roadmap on a dedicated board.
Within this Figma board, we organized components such as Epics, Features, Research Insights, and Product Requirements. These boards served as a hub for exchanging feedback and aligning. My efforts were dedicated to visualizing these cross-departmental workflows, resulting in the establishment of consistent written requirements. By the end of the second year, we had successfully streamlined our production processes.
What They Say
Catherine was an exceptional coworker. Her ability to think creatively and on-the-fly helped push our team forward. Her new design and structural initiatives, including developing an internal system for organizing and implementing design elements within the Thoughtful app, helped streamline the creative process and facilitated stronger communication between departments. Catherine's innate ability to recognize problems and implement strong solutions made her a joy to work and collaborate with at Thoughtful.
Recent Case Studies
Reduce Financial Advisor Turnover
Enterprise, B2B, Insurance
Increase Week-Over-Week User Activity
Start Up, B2C, E-Commerce
Optimize for Operational Efficiency
Enterprise, B2B, Financial Services







