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.
Product
Dewo Meet
Company
Role
Product Owner. Designer
Challenges
Conflicting goals. Overextended MVP
Outcome
User-Centric Pivot. Slack application
Hampus Svallfors
Digital Product Designer
Hampus Svallfors
Digital Product Designer
Background
Dewo Meet was part of Timely’s larger Dewo initiative, designed to protect deep work and boost productivity by tackling key challenges. Dewo Meet specifically focused on solving one of the most disruptive aspects of modern work: meetings. The goal wasn’t just to make meetings more efficient but to schedule them in a way that respected deep work—particularly for "makers" who need uninterrupted time to stay productive.
Development had initially centered on an AI-driven scheduling web app that optimized meeting times by considering participants’ availability, preferences, and focus time. One of its core features was a Doodle-like polling system, where the AI suggested available time slots, and team members voted on which suited them best. When I joined as a designer, the MVP had already been in development for two years, but it had become difficult to communicate and position. Shortly after, I took ownership of Dewo Meet’s direction, with the goal of validating the MVP in the market and hitting key milestones: reaching 10,000 weekly active users, 30% month-over-month growth, and 50% day 2 retention.
Background
Dewo Meet was part of Timely’s larger Dewo initiative, designed to protect deep work and boost productivity by tackling key challenges. Dewo Meet specifically focused on solving one of the most disruptive aspects of modern work: meetings. The goal wasn’t just to make meetings more efficient but to schedule them in a way that respected deep work—particularly for "makers" who need uninterrupted time to stay productive.
Development had initially centered on an AI-driven scheduling web app that optimized meeting times by considering participants’ availability, preferences, and focus time. One of its core features was a Doodle-like polling system, where the AI suggested available time slots, and team members voted on which suited them best. When I joined as a designer, the MVP had already been in development for two years, but it had become difficult to communicate and position. Shortly after, I took ownership of Dewo Meet’s direction, with the goal of validating the MVP in the market and hitting key milestones: reaching 10,000 weekly active users, 30% month-over-month growth, and 50% day 2 retention.
Dewo when I joined the team. Promising but underdelivering, overextended, and little user activity.
Taking Ownership and Identifying the Challenge
As I took on the role of Product Owner, it 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.
Taking Ownership and Identifying the Challenge
As I took on the role of Product Owner, it 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.
Final web-app version before platform pivot, focused solely on scheduling optimal meetings.
Leading the Pivot
In my first few weeks as Product Owner, I took a deep dive into user feedback, product metrics, and the broader context of Dewo Meet’s goals. Interviews with early users revealed that most managers already deeply cared about protecting their teams' focus time and were actively trying to manage it themselves. They loved the idea of speeding up scheduling, but not at the cost of quality. For makers scheduling with other makers, the AI's assistance was appreciated, but for managers, the lack of a human touch in prioritizing meetings was a clear gap.
With these insights in hand, I initiated candid conversations with the team and the steering committee. While Dewo had been championed by Timely's CEO, it was clear to me that the product in its current form wasn’t solving the core problem smoothly. Using first-principles thinking, I challenged assumptions about its direction. Rather than building more features on a foundation that hadn’t proven market fit, we needed to refocus on delivering real value: scheduling with minimal friction while respecting deep work. Once I opened the door to these concerns, the team rallied behind the decision to pivot.
Leading the Pivot
In my first few weeks as Product Owner, I took a deep dive into user feedback, product metrics, and the broader context of Dewo Meet’s goals. Interviews with early users revealed that most managers already deeply cared about protecting their teams' focus time and were actively trying to manage it themselves. They loved the idea of speeding up scheduling, but not at the cost of quality. For makers scheduling with other makers, the AI's assistance was appreciated, but for managers, the lack of a human touch in prioritizing meetings was a clear gap.
With these insights in hand, I initiated candid conversations with the team and the steering committee. While Dewo had been championed by Timely's CEO, it was clear to me that the product in its current form wasn’t solving the core problem smoothly. Using first-principles thinking, I challenged assumptions about its direction. Rather than building more features on a foundation that hadn’t proven market fit, we needed to refocus on delivering real value: scheduling with minimal friction while respecting deep work. Once I opened the door to these concerns, the team rallied behind the decision to pivot.
The new concept and north star
Ditching the Web App for a Slack Integration
The pivot was bold but necessary. We stripped the product down to its essentials by retrofitting the existing web app API to work with Slack as the new client, focusing on seamless integrations rather than building a standalone tool. Slack was already a widely used platform in many workplaces, which allowed us to meet users where they were already working and eliminate the friction of onboarding a separate app.
Working within Slack’s Block Kit framework was a design challenge in itself, but it forced me to innovate creatively within its constraints. The limitations of Slack’s interface meant we had to make careful decisions about how to surface features in a simple, digestible way. This tight framework, however, became an opportunity to rethink the user experience and prioritize what truly mattered: frictionless, fast scheduling. Through this project, I learned that restrictions can often lead to some of the most innovative solutions.
One significant change was the removal of the polling feature, where teams would vote on which meeting time suited them best. Instead, we streamlined the process, empowering the scheduler to complete the action in one go, with minimal delays. This simplification addressed one of the core issues with the original MVP, where the polling process often caused unnecessary delays and confusion.
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 pivot. The rate of successful scheduling attempts—where users picked one of the AI’s suggestions—increased significantly. We also achieved over 1,000 sign-ups from early adopters, with many expressing a willingness to pay to continue using the product. This response confirmed that focusing on users’ core needs—informative, frictionless scheduling—was the right approach.
Although the product was eventually discontinued due to shifting business priorities at Timely, the pivot gave promising indications that Dewo Meet had the potential to solve a real problem that users were willing to pay for.
Ditching the Web App for a Slack Integration
The pivot was bold but necessary. We stripped the product down to its essentials by retrofitting the existing web app API to work with Slack as the new client, focusing on seamless integrations rather than building a standalone tool. Slack was already a widely used platform in many workplaces, which allowed us to meet users where they were already working and eliminate the friction of onboarding a separate app.
Working within Slack’s Block Kit framework was a design challenge in itself, but it forced me to innovate creatively within its constraints. The limitations of Slack’s interface meant we had to make careful decisions about how to surface features in a simple, digestible way. This tight framework, however, became an opportunity to rethink the user experience and prioritize what truly mattered: frictionless, fast scheduling. Through this project, I learned that restrictions can often lead to some of the most innovative solutions.
One significant change was the removal of the polling feature, where teams would vote on which meeting time suited them best. Instead, we streamlined the process, empowering the scheduler to complete the action in one go, with minimal delays. This simplification addressed one of the core issues with the original MVP, where the polling process often caused unnecessary delays and confusion.
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 pivot. The rate of successful scheduling attempts—where users picked one of the AI’s suggestions—increased significantly. We also achieved over 1,000 sign-ups from early adopters, with many expressing a willingness to pay to continue using the product. This response confirmed that focusing on users’ core needs—informative, frictionless scheduling—was the right approach.
Although the product was eventually discontinued due to shifting business priorities at Timely, the pivot gave promising indications that Dewo Meet had the potential to solve a real problem that users were willing to pay for.
Conclusion
Although Dewo Meet was ultimately discontinued due to a shift in business priorities, the user-centric pivot I led remains one of my proudest achievements. The decision to strip the product back and integrate it into Slack resulted in a tool that delivered immediate value and gained strong interest from early adopters. Despite the discontinuation, the pivot succeeded in aligning the product with real user needs, validating the shift to focus on seamless integrations and deep work protection.
Leading a remote, cross-functional team through this process taught me invaluable lessons in leadership and collaboration. Working asynchronously across multiple time zones—using tools like Loom and Slack—showed me the importance of agility, communication, and creative problem-solving. These insights not only helped us achieve the pivot but also shaped how I approach leadership today.
One of the hardest but most valuable lessons came from making the tough decision to pivot, even when the organization—including the CEO—was content with the current direction. Once I opened the door to these concerns, others started to agree, realizing it was okay to challenge the status quo with the right intentions. This experience reaffirmed that it's important to speak up when fully committed to an idea, and that true leadership means making tough decisions in a way that brings people onboard.
In retrospect, this project continues to influence my approach to product design and leadership. It taught me the value of first-principles thinking, the power of collaboration under constraints, and the importance of making decisions with clarity and confidence—even when they challenge the status quo.
Conclusion
Although Dewo Meet was ultimately discontinued due to a shift in business priorities, the user-centric pivot I led remains one of my proudest achievements. The decision to strip the product back and integrate it into Slack resulted in a tool that delivered immediate value and gained strong interest from early adopters. Despite the discontinuation, the pivot succeeded in aligning the product with real user needs, validating the shift to focus on seamless integrations and deep work protection.
Leading a remote, cross-functional team through this process taught me invaluable lessons in leadership and collaboration. Working asynchronously across multiple time zones—using tools like Loom and Slack—showed me the importance of agility, communication, and creative problem-solving. These insights not only helped us achieve the pivot but also shaped how I approach leadership today.
One of the hardest but most valuable lessons came from making the tough decision to pivot, even when the organization—including the CEO—was content with the current direction. Once I opened the door to these concerns, others started to agree, realizing it was okay to challenge the status quo with the right intentions. This experience reaffirmed that it's important to speak up when fully committed to an idea, and that true leadership means making tough decisions in a way that brings people onboard.
In retrospect, this project continues to influence my approach to product design and leadership. It taught me the value of first-principles thinking, the power of collaboration under constraints, and the importance of making decisions with clarity and confidence—even when they challenge the status quo.
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