case study
Schedule team meetings
in just three seconds
We built a tool protecting deep work by revolutionizing meeting scheduling.
It was game-changing—until we killed it. The experience taught me invaluable lessons in leadership, adaptability, and making tough decisions.
Background
Dewo Meet was part of Timely’s broader Dewo initiative to protect deep work and boost productivity. Its mission: fix one of modern work’s biggest disruptors—meetings. Unlike typical schedulers, Dewo Meet aimed to arrange meetings in ways that respected uninterrupted focus time, especially for “makers.”
The initial MVP was a companion app for web, iOS and Android that used AI to suggest meeting times based on availability, preferences, and focus time. A polling feature let team members vote on options, but after two years in development, the product struggled with positioning and adoption.
Dewo when I joined the team. Promising but underdelivering, overextended, and little user activity.
Taking ownership and identifying the challenge
Dewo tried to do too much for an MVP, especially for our small team.
When I joined as designer, I took ownership of Dewo Meet’s direction, tasked with validating the MVP in market and hitting ambitious targets: 10,000 weekly active users, 30% MoM growth, and 50% day-2 retention.
It quickly became clear that Dewo Meet’s struggles went beyond technical execution. The product had become overextended, caught between conflicting business goals: should it serve as an upsell for existing Timely users or aim to attract new customers as a standalone product? This tension had resulted in bloated features, some of which required integration with Timely, further complicating the user experience.
The AI-driven polling feature, while initially intended to help teams find the best time for most people, often added too much friction. While the AI would suggest the best time slots, the extra step of voting created delays or entire meetings missed entirely, conflicting with our goal of fast, frictionless scheduling. Despite the AI’s sophistication, it couldn’t account for the nuances
of human scheduling, such as differentiating between a quick operational sync and an in-depth strategy session. While a project manager may intuitively prioritize what’s important or what’s inappropriate for certain times, these subtle judgments were much harder to capture in an algorithm. Moreover, the team’s focus on long-term visions had overshadowed the immediate need to validate market fit.
It became clear that a hard break was needed. In order to validate the MVP, the product had to be simplified and refocused—helping teams protect their focus time by scheduling meetings at the best time for everyone. Once I opened the door to these concerns, the team rallied behind the decision to pivot.
Redesigned web-app experience, focused solely on scheduling optimal meetings.
The new concept and north star
Ditching the web app for a Slack integration
We pivoted from a standalone web app to a Slack integration by retrofitting our API, meeting users directly in their workflows and eliminating onboarding friction.
Slack’s Block Kit posed strict design constraints, but these forced us to rethink the experience around what mattered most: fast, frictionless scheduling. We removed the polling feature—which delayed decisions—and streamlined scheduling into a single step.
To better account for the social flexibility and nuances of meetings, we also surfaced more personal information for the scheduler. The AI still generated three suggestions based on participants’ availability and focus time, but now we clearly indicated which suggestion worked best for whom. This allowed schedulers to make informed decisions without having to open individual calendars or send direct messages to team members, saving time and reducing friction.
The results validated the shift: scheduling success rates rose sharply, and over 1,000 early adopters signed up, many expressing willingness to pay. While the product was later discontinued due to shifting priorities, the pivot proved that Dewo Meet solved a real, valuable problem.
