Role
Product Designer & Chief of Staff
Timeline
2 years
Umbrella Product is a productivity suite designed for talent managers and creative professionals. Working alongside the founder and engineering team, I helped shape the product from early concepts to multiple iterations to launch, over two years.
Coming from the sports management industry, the founder saw the same pattern repeatedly: conversations scattered across text messages, emails, and DMs; schedules lived in calendars; files lived somewhere else; and existing productivity software wasn't designed around the way talent managers actually worked.
Rather than adapting another project management tool, we wanted to rethink how creative work could be organized from the ground up.
Existing tools assumed one way of working.
Most project management tools begin once a project exists. Through interviews and experience, we found that talent managers didn't think about work as isolated projects. Their work revolved around relationships that evolved over time. From conversations and negotiations to signed deals, schedules, deliverables, and ongoing communication.
Rather than asking how to manage projects, we began asking:
How should opportunities, conversations, deals, and projects connect into a single workflow?
How do you design a workflow around relationships rather than tasks?
From conversations and negotiations to signed deals and ongoing projects, how can we create a workflow that mirrors the way talent managers actually work?
The product evolved alongside our understanding of users.
For many talent managers, work begins with a conversation, an opportunity, or a relationship. Our challenge was designing a system that could support that journey. From first contact to signed deal to active work.
Over two years, the product changed significantly as we learned more about how our users thought about their work.
Rather than treating these iterations as redesigns, we viewed each as a step toward a better mental model.
Our initial navigation was built around projects, drawing inspiration from familiar work management tools. This gave users an interface they could understand immediately while allowing us to validate the product quickly.
Through interviews, product testing, and ongoing collaboration with talent managers, we discovered that projects represented only one stage of their workflow. Most work began with a conversation or opportunity, long before a project was ever created. As our understanding of users evolved, so did the structure of the product.
Returning to our original vision, we restructured the product around the idea that conversations were the starting point of work. Every opportunity began with a conversation, making chat the first touchpoint for every project.
Rather than treating conversations as separate from work, we designed them as the place where work naturally unfolded. Files, calendars, task boards, notes, and other tools were all accessible within the conversation, allowing users to move from discussion to execution without switching contexts.
Our most recent iteration emerged while solving a different challenge. One of our clients managed a junior sports league with nearly 50 teams, resulting in more than 100 active projects. Since every project included the same set of built-in tools, the product had to load hundreds of calendars, task boards, file systems, and other resources that were often never used.
This revealed an opportunity to rethink the architecture of the product. Rather than treating every project the same, we introduced a modular toolset that allowed users to add only the tools they needed. The result was a faster, more flexible workspace that could adapt to different types of projects while reducing unnecessary overhead.
The modaular workflow.
This approach reduced unnecessary complexity, improved performance, and allowed the product to support a wider variety of workflows without forcing every team into the same structure.
The modular workspace represented everything that we had learned throughout the project. Rather than prescribing how work should be organized, the product adapted to each team's workflow. By removing unnecessary assumptions, we created a system that was more flexible, more performant, and better aligned with the way our users naturally worked.
Organization should feel organic.
As users created more projects, we looked for ways to make organization feel less administrative and more natural. Rather than asking users to configure folders or navigate complex hierarchies, we explored interactions that mirrored how people physically organize information.
Projects could be grouped through simple drag-and-drop interactions, creating collections as needed instead of requiring users to plan a structure in advance. The result was an experience that felt more flexible and encouraged organization as work evolved.
Conversation shouldn't become dead ends.
The founder's original insight continued to shape the product. Important work often began inside a conversation, yet many productivity tools forced users to recreate that information somewhere else before it could become actionable.
We designed interactions that allowed messages to become tasks and calendar events with a single action. By reducing the distance between discussion and execution, conversations became an active part of the workflow instead of a place where ideas were forgotten.
Where the product landed
After two years of iteration, the product evolved from a traditional project management tool into a flexible workspace centered around conversations, modular tools, and workflows that adapted to users rather than forcing users to adapt to the software.
While the product continued to evolve beyond my time on the team, these explorations established many of the core interaction patterns and organizational principles that shaped its direction.
Reflection
This project taught me that product design is as much about questioning assumptions as it is about designing interfaces. Every iteration challenged our understanding of the problem, and every conversation with users brought us closer to a product that reflected the way they actually worked.
Working in a lean startup reinforced that the best ideas rarely appear fully formed. They emerge through collaboration, iteration, and a willingness to let new evidence reshape the product. I still carry that mindset into every project I work on.