Henry Freel

DoorDash Point of Sale — Multi-Device Platform

Led design for DoorDash’s zero-to-one point of sale platform, shaping a unified ecosystem across in-store operations, customer ordering, and business management. Established core product foundations and a cross-platform design system supporting fast-paced, multi-surface workflows for customers, employees, and business owners—from quick-service environments to complex multi-location operations.

Partnered closely with executive leadership while leading design across a ~75-person team, including 30 engineers and 2 senior designers. Leveraged AI-assisted workflows to scale prototyping and execution, driving product direction from initial concept through launch.

2024 – 2026

Design Lead

DoorDash Point of Sale — product interface overview

Square Cash Flow — Unified Financial Insights

Initiated and drove design for a new cash flow product, aligning with Square’s strategy to become the primary banking partner for SMBs. Developed a unified system across platforms combining multiple financial accounts to give sellers a holistic view of cash flow, business health, and profitability.

Independently advanced the opportunity from concept through validation, building high-fidelity iOS and web prototypes, conducting merchant research, and aligning four cross-functional teams. Secured company-wide buy-in and executive approval, resulting in the product being funded and prioritized as a top company initiative.

2023

Design Lead

Square Banking — Cross-Product Navigation & Dashboard

Collaborated across design, product, and engineering teams to shape a unified dashboard and navigation system for the new fincaical suite, Square Banking, bringing together Savings, Checking, Loans, and the Square Credit Card across platforms. Established a shared foundation for how sellers access and manage all banking products in one place.

Defined core system patterns including account dashboards, activity and detail pages, settings, and transfer flows, enabling multiple teams to build on a consistent framework. Partnered closely with marketing and brand teams on a major cross-company launch, contributing to a cohesive banking experience across a large, multi-team effort.

2021 – 2023

Senior Product Designer

Square Savings — Zero-to-One Banking

Led end-to-end design for Square Savings, a zero-to-one product launched as the first step in building Square Financial Services following approval of an FDIC ILC charter. Designed onboarding, identity verification, account structures, and money movement across savings, checking, and lending, enabling sellers to manage and allocate funds across their business.

Delivered the product under strict regulatory deadlines tied to FDIC charter requirements, exceeding targets with over $130M in balances within the first year. Partnered closely with cross-functional teams to launch a foundational banking product supporting Square’s strategy of becoming a primary financial partner for SMBs.

2021 – 2023

Senior Product Designer

Square Loans — Revenue & Conversion Optimization

Owned design for Square Loans, a core revenue-driving product within Square Banking operating in a highly regulated financial environment. Drove product direction across platforms, partnering closely with product, engineering, and legal teams to support a business-critical lending system.

Delivered new loan types and product features that expanded access to more sellers and increased revenue per loan, while driving higher conversion across high-volume application flows. Supported a product originating over $300M in loans monthly, central to Square’s strategy of serving underserved SMBs.

2020 – 2021

Senior Product Designer

Square Loans — product interface overview

Square Advanced Access — Permissions & Access Control System

Designed core experiences for Square Advanced Access, a centralized permissions and employee management system used across Square’s core products. Defined how businesses manage employee access across roles, locations, and devices, supporting use cases from small businesses to multi-location franchises.

Developed flexible systems for permissions, activity tracking, and reporting, including role-based access, sensitive action logging, and sales tracking for tip pooling and performance insights. Collaborated across product teams—including Retail, Restaurants, Appointments, and Core POS—to deliver a shared platform forming the foundation for employee access across the ecosystem.

2019 – 2020

Product Designer

Square Advanced Access — product interface overview

Square Shifts — Scheduling & Labor Management Tool

Designed core experiences for Square Shifts, an employee scheduling and time tracking product used by sellers to manage labor across their business. Built workflows for clocking in and out, break tracking, wage and overtime management, and scheduling, supporting compliance with local labor regulations across platforms.

Developed systems for tracking labor costs and exporting data to Square Payroll and external providers, integrating with reporting tools to help sellers understand labor versus sales. Collaborated across teams to deliver a cohesive employee management experience supporting critical day-to-day operations.

2017 – 2018

Product Designer