Time off
Unifying time off requests, balances, and policies into a single, streamlined experience for teams.
Background
I interned on Square Staff, which owns Square's team management and payroll products. During my time on the team, I designed new features for Square's team management experience across Square Dashboard and Square's Team app.
Launched in 2021, Time Off enables employees to request time off and managers to approve or deny those requests. Employees submit requests and track time off directly from the Team app. When an employee submits a request, managers are notified via email and in the Requests blade in Square Dashboard, where they can approve or deny the request. Managers can also review and manage requests from the Team app.
The problem
Owners and managers lacked a single, reliable place to view their team's time off history, past requests, or manually add time off on behalf of employees. Today, only employees can submit requests through the Team app, and managers often rely on email notifications as their primary record—making it difficult to reference or manage time off over time.
Additionally, time off policies defined in Square Payroll are not integrated into employee time off tracking. As a result, employees and managers have little visibility into remaining PTO or sick leave balances, leading to confusion and manual workarounds.
While the initial goal was to design a time off report for owners and managers to track and manage requests, an internal audit revealed broader gaps across the experience. This expanded the scope of the project, prompting a more holistic approach to improving time off management for owners, managers, and employees.
The solution
Time off history
I designed a new Time Off page that serves as a centralized hub for sellers to view time off history, balances, and requests. Managers and owners can see how much time off their team has taken to date, with visibility into unpaid time off, PTO, and sick leave—all in one place.
Requests
The requests tab allows managers to view pending, approved, and denied requests in a single workflow. Requests can be filtered for easier review, and managers can now add time off for themselves or on behalf of their team—removing the dependency on employee-submitted requests.
Settings
I improved the time off settings experience by consolidating settings that previously lived across multiple locations, simplifying navigation and reducing confusion. The experience was migrated to Square's new design system and expanded to include Blocked Days, allowing sellers to prevent time off during critical business periods. I also designed an upgrade pattern as these settings are only available through Team Plus.
Team app
I redesigned the Time Off experience in the Team app, migrating it to the newer design system and extending new functionality to mobile. Employees now have access to a detailed time off summary, helping them understand how much time off they've taken and how much remains. Managers can view team history, add time off, and approve or deny requests quickly from the app.
Outcomes & impact
Shipped August 2024
The dashboard time off requests experience and core Team app flows launched globally, a meaningful step toward giving owners, managers, and employees one coherent place to manage time off. Like most large-scale projects, not everything survived the journey to production — time off history and advanced settings were deprioritized before launch.
Reflection & learnings
This project was my first internship project at Square and the first feature I worked on at the company that shipped. It accelerated my growth as a designer by deepening my experience working within a robust design system, collaborating closely with engineers, and incorporating cross-functional feedback—while also contributing back by proposing new components to our design system. Most importantly, the project reinforced the value of curiosity: asking questions early and often strengthened the work and helped me grow with the support of my team.