Time-tracking apps have a trust problem. Sidekick set out to solve it with a privacy-first approach—giving teams the accountability they need without the Big Brother feeling.

Sidekick needed a secure, self-hosted desktop app and web dashboard that balanced complex features with an intuitive interface. The product had to serve two distinct users—managers tracking team capacity and employees protecting their privacy—while integrating seamlessly with ClickUp. The challenge was designing something powerful enough for data-driven managers but lightweight enough that employees wouldn't feel surveilled.

I designed a clean, functional UI system with distinct views for managers and employees, ensuring each user type got exactly what they needed without overwhelming them with irrelevant features. The brand identity communicated security and efficiency in equal measure—professional enough for enterprise clients, approachable enough for small teams.

A standout feature, "Bench Notifications," solved a critical communication gap by alerting managers when team members ran out of tasks, enabling proactive workload distribution. Every interaction was designed to feel lightweight and unobtrusive, reinforcing the privacy-first positioning.

Dual UI workflows for managers and employees

Privacy-first design system balancing transparency with trust

ClickUp integration for seamless task tracking

"Bench Notifications" for proactive team management

Self-hosted architecture for data security

Complete brand identity + developer-ready Figma files

Sidekick launched a successful beta with high user adoption and established a foundation for ongoing iteration. The developer-ready handoff enabled a smooth build process and created a partnership that continues to evolve the product based on real user feedback.