Staff Product Designer, Commercial Growth

Staff Product Designer, Commercial Growth Squarespace's Commercial Growth organization brings together the product, engineering, and strategy teams responsible for how Squarespace builds, prices, and grows its business across every product line. Within that org, the Commercial Product team owns the customer-facing experiences that drive purchase, adoption, and expansion — from the moment a prospective customer discovers Squarespace to the point they convert, upgrade, and grow. We're looking for a Staff Product Designer to own the end-to-end commercial experience across cart, checkout, cross-sell, and pricing pages. This is a high-leverage, high-visibility role at the intersection of monetization strategy and product craft — translating pricing, packaging, and bundling goals into scalable, intuitive user experiences that work across Squarespace's full product portfolio. This is a Player–Coach individual contributor role at the Staff level. You'll bring deep systems thinking and exceptional craft to some of the most commercially consequential surfaces in the product, while also serving as a force multiplier for the broader Commercial Growth design community. This role reports to the Director of GTM Product Design. This is the right role for a senior designer who understands that commercial UX is not just a conversion problem — it's a systems problem. If you can hold the full arc from Frontsite discovery through post-purchase expansion, think in merchandising patterns and interaction models rather than one-off flows, and partner credibly with product, engineering, and revenue systems counterparts, this role is built for you. You’ll Get To… Own the Commercial Product Design Surface: Lead design across plan selection, cart merchandising, and cross-sell — creating cohesive, intentional experiences across the full commercial ecosystem rather than isolated flows. Translate Monetization Strategy into Scalable UX: Work closely with Commercial Strategy to translate pricing, packaging, bundling, discounting, and messaging requirements into flexible, reusable design patterns that hold up across products and offers. Design Cross-Sell and Merchandising Systems: Develop cross-sell placements, supporting assets, and interaction models tied to targeting strategy — designing for flexibility so that what works for one product line can scale across others. Partner Across Product, Engineering, and RevSys: Collaborate closely with product and engineering leaders on customer-facing purchase and conversion flows, and work with RevSys counterparts where commercial product experiences depend on shared systems or implementation constraints. Connect Frontsite to Downstream Conversion: Extend design thinking across Frontsite-connected journeys so that discovery and downstream conversion feel intentional and connected — not like separate experiences owned by separate teams. Partner with Platform and Data Science on Targeting and Experimentation: Work alongside Platform and Data Science teams when targeting logic or experimentation affects the user experience, ensuring that personalization and testing are designed with the customer journey in mind. Establish Design Consistency Across Commercial Growth: Help raise the design bar across the newly unified Commercial Growth organization — establishing patterns, principles, and standards that create coherence across a complex, multi-surface ecosystem. Mentor and Elevate Craft: Serve as a craft mentor across Commercial Growth design as we expand — giving sharp, actionable feedback, pairing with designers on complex systems problems, and raising the quality bar for both systems thinking and visual and interaction design. Who We’re Looking For 10+ years of experience in product design at a digital product company, including time operating at a Staff or equivalent level. A portfolio demonstrating complex, systems-level work — ideally across commerce, checkout, pricing, or monetization surfaces — with clear impact on user and business outcomes. Experience leading cross-functional workstreams from ambiguity to shipped product, including setting direction, defining milestones, and aligning stakeholders across product, engineering, and data teams. A track record of translating business and monetization requirements — pricing, packaging, discounting, merchandising — into scalable, intuitive UX patterns that work across a broad product portfolio. Strong systems thinking: you architect experiences that feel simple by mapping data models, flows, and dependencies across multiple product areas. High-agency operator who can create momentum without fully defined requirements — you impose structure on ambiguous problems by framing the space, surfacing constraints, and clarifying goals for others. Experience designing for or alongside experimentation and targeting systems, with an understanding of how personalization and A/B logic affect the user experience. Exceptional communication and storytelling skills — you can zoom from high-level strategy to concrete UX decisions with clarity, and you're comfortable representing design rationale to senior leadership and cross-functional stakeholders. You lead by example, setting a craft and systems bar that other designers actively look to emulate, and you enjoy coaching designers at different levels. Experience working on Frontsite or marketing-site-connected journeys, with an understanding of how discovery and conversion relate across the funnel, is a strong plus. Benefits & Perks A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision Supplemental Life and Disability Insurance plans Fertility and adoption benefits Headspace mindfulness app subscription Global Employee Assistance Program Retirement benefits with employer match Flexible paid time off 12 weeks paid parental leave and family care leave Pretax commuter benefit E