Senior Product Designer, Client Engagement

Squarespace is a design-centric company that empowers anyone to stand out and sell online. We're looking for a Senior Product Designer to join our Client Engagement Group (CEG), where we're building tools that help entrepreneurs scale their businesses through automation. Automations is the engine that lets sellers put repetitive work on autopilot. From sending the right message at the right time to building sophisticated, multi-step workflows, we're making powerful business logic accessible to people who don't think of themselves as technical. The challenge is to make increasingly sophisticated technology feel simple, intuitive, and distinctly Squarespace. You’ll Get To… Simplify the complex. Turn multi-step workflows, branching logic, triggers, conditions, and time-based actions into experiences that feel obvious and approachable. Design for real business logic. Model the complexity behind sophisticated automations while keeping the experience focused on what sellers are trying to accomplish. Design for scale. Create patterns that work equally well for a first-time seller building a simple workflow and an experienced user managing sophisticated automation systems. Shape the future of automation. Help define how automation evolves in an AI-native future—from natural language and prompt-based workflows to intelligent agents that can reason, make decisions, and take action on a seller’s behalf. Prototype motion and state. Use high-fidelity prototyping to explore interactions across dynamic workflows, live data, background processes, and complex UI states. Think end-to-end. Understand how automation fits into the broader seller journey—from capturing a lead and nurturing a relationship to converting and retaining a customer. Partner cross-functionally. Work closely with PMs, Engineers, and Researchers to shape strategy, define constraints, validate ideas, and ship great work. Drive craft and systems. Champion quality design and contribute to scalable frameworks and patterns that raise the bar across the team. Who We’re Looking For 6+ years of product design experience, with a portfolio showing complex systems—workflow tools, automation platforms, or logic-heavy applications—made simple and human-centered. Systems thinker. You can understand how triggers, conditions, actions, timing, and branching logic interact, while still designing for the individual task in front of the user. Strong interaction design instincts. You know how to make sophisticated workflows approachable through clear hierarchy, progressive disclosure, meaningful defaults, and thoughtful interaction patterns. Figma expert & AI prototyping mindset. You build scalable components and high-fidelity prototypes, and use AI-powered tools—or are excited to learn them—to rapidly explore, prototype, and iterate on new concepts and interactions. You can move fluidly from early exploration to refined micro-interactions and production-ready design. Strong communicator. You can articulate design decisions clearly to engineers, PMs, researchers, and leadership, and use design to bring clarity to ambiguous problems. User-first. You talk to users, leverage research, and can put yourself in the shoes of a busy business owner trying to get more done with less effort. Benefits & Perks Health insurance with 100% covered premiums for you, your spouse or partner and your dependent children including medical, dental, and vision Life and Income Protection Fertility and adoption benefits Headspace mindfulness app subscription Global Employee Assistance Program Pension benefits with employer match Flexible paid time off 26 weeks paid maternity leave & 12 weeks paid paternity leave 2 weeks paid family care leave Annual Tax-Free Stipend Education reimbursement Employee donation match to community organizations 7 Global Employee Resource Groups (ERGs) Free lunch and snacks Close proximity to cultural landmarks suc