Head of Design, Operating System

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Archive Job Description

It all started with an idea at Square in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic app, bringing a better way to send, spend, invest, and save to our millions of monthly active users. We want to make the world’s relationship with money more relatable, instantly available, and universally accessible. This is our mission, and it’s why working at Cash App means so much more than a job.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward creativity, collaboration and impact. We’ve been a distributed team since day one, and we’ve got offices and remote teammates across the globe. Our offices are great, but many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

Check out our locations, benefits, and more at cash.app/careers to learn more!

Job Description

The Cash App Design team works at the intersection of brand and product to shape and choreograph an exceptional customer experience. The Group Design Lead, Operating System (OS) will lead a team of multifaceted designers, managing and overseeing the design of Cash App’s core product experience across Design Systems, Core App experience, and Customer Lifecycle. The OS team takes a horizontal view of the Cash App product, collaborating with product and engineering partners to build the platforms, primitives and personalization that power our apps and drive our experiences.

You will encourage collaboration across Cash App, enabling us to deliver impactful experiences that guide our mission, business and brand forward. You will amplify design at Cash App by managing and leading, cultivating design disciplines and scaling our team as we take on the next era for the business.

You will be an integral part of the design leadership team and report to the Head of Creative and Design. You will lead and shape the Operating Systems design team and partner with Cash App leadership to innovate and build new solutions that allow us to scale effectively.

You will:

  • Lead and build the Operating System design team, inclusive of Product Designers, Systems Designers, and Design Managers
  • Bring a keen systematic and visual eye to the Cash App product experience and be a leading voice in blueprinting our future
  • Be responsible for mapping the future Cash App product structure and ecosystem, focusing on information architecture and new or changing paradigms around how customers consider and navigate their finances.
  • Bring comfort and expertise in technical environments, with deep knowledge of mobile client-side development process
  • Be responsible for scaling the OS design team, hiring top tier talent and managing a distributed team
  • Guide the careers and development of your team, ensuring the amplification and growth of team members, including established and new managers
  • Collaborate with Design Operations to inform, build, and scale the Operating Systems infrastructure
  • Establish and implement best-in-class design tooling and systems, in partnership with design and creative leadership
  • Be a brand thinker; be passionate about bridging the gap between brand and product, ensuring a more connected, cohesive and expressive Cash App
  • Establish processes to help the team create new solutions or inform principled risk taking
  • Play an integral role in cross-functional strategic planning efforts to understand and bridge business priorities with Design investment and output.
  • Influence design and business decisions at the company and workstream level
  • Collaborate with leadership to establish and elevate design direction and strategy
  • Develop deep partnerships with cross-functional partners to effectively speak to design processes, design goals, and deliver user insights that inform product and go-to-market decisions.


  • 12+ years of design experience
  • 4+ years of experience managing and building multi-disciplinary design teams, preferably within product design or design systems
  • Proven track record of being an influential design leader and delivering impactful, strategic work
  • Proven ability to collaborate with cross-functional leadership to build and implement strategic product roadmaps
  • Ability to accelerate team efficiency by improving processes and workflows
  • Experience translating established brands into new expressions and spaces
  • Experience with product development processes and an understanding of how to solve product challenges across platforms
  • Clear point of view on design direction and an openness to new ideas
  • Understanding of how to leverage creativity to meet business goals
  • Deep understanding of performance marketing and brand marketing strategies
  • Passion for recruiting, motivating, and managing a team of multidisciplinary creatives
  • Composure in the face of ambiguity and an ability to effectively work with multiple leadership styles
  • An action bias and intense desire to solve problems
  • Unmatched attention to detail and due diligence
  • A bias towards transparency and communication
  • A generous dose of humility
  • Extreme empathy for the customer, your teammates, and the company mission

Additional Information

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Square is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

Square, Inc. (NYSE: SQ) builds tools to empower businesses and individuals to participate in the economy. Sellers use Square to reach buyers online and in person, manage their business, and access financing. Individuals use Cash App to spend, send, store, and invest money. And TIDAL is a global music and entertainment platform that expands Square’s purpose of economic empowerment to artists. Square, Inc. has offices in the United States, Canada, Japan, Australia, Ireland, Spain, Norway, and the UK.

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