Senior Staff Product Designer

Squarespace•New York, NY

3h•$223,000 - $358,800•Hybrid

About The Position

Squarespace is a design-centric product company with a mission to be the all-in-one platform for anyone who wants to stand out and grow their business online. Product designers at Squarespace are embedded in deeply collaborative product teams, where every member plays a critical role in the team’s success. This role is for a Staff+ Product Designer to join the Client Engagement & CRM team, with a focus on Contacts, CRM, and Automations. This team is responsible for the core tools sellers use to understand, communicate with, and retain their customers — from contact records and automations to campaigns and service communications. This is a Player–Coach individual contributor role at the Staff+ level. You’ll combine deep systems thinking and exceptional craft with the ability to drive alignment and execution across teams. You will own some of the most complex, logic-driven surfaces in our CRM and automations ecosystem and act as a force multiplier for the team — shaping vision, creating momentum in ambiguous spaces, and mentoring designers across CRM and CEG.

Requirements

10+ years of experience in product design at a digital product company, including time operating at a Staff or equivalent level.
A portfolio that demonstrates complex, systems-level work (e.g., CRM, marketing automation, communication tools, or other data-rich, logic-heavy platforms) 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.
You navigate ambiguous, loosely defined problems by imposing structure — framing the problem, surfacing constraints, and clarifying goals for others.
You are a high-agency operator who can create momentum without fully defined requirements or perfect inputs.
You lead structured collaboration — workshops, audits, whiteboard sessions — that help partners see the system, make tradeoffs, and “disagree and commit” when needed.
You are a strong storyteller, using vision decks, North Star narratives, and clear artifacts to align PM, Engineering, and stakeholders around a shared direction.
You know when to sweat the details (e.g., how we distinguish transactional vs. marketing communications, how contact health is visualized, how automation status is surfaced) because those details carry meaning and trust.
You lead by example, setting a craft and systems bar that other designers actively look to emulate.
You enjoy coaching designers at different levels, helping them break down complexity, refine their process, and strengthen both their product thinking and craft.
You are an exceptional communicator, able to zoom from high-level strategy and systems to concrete UX decisions and rationale with clarity.
You are comfortable representing design decisions to leadership and cross-functional stakeholders, and you can connect your work directly to business and user outcomes.

Responsibilities

Design end-to-end experiences that bring together campaigns, SMS, transactional emails, and automations into a cohesive, intuitive communication system.
Lead design for complex areas such as Automations, rich customer profiles and full-page contact views, custom fields, analytics & insights, and future communications entry points beyond automations.
Architect complex systems that feel simple by mapping data models, flows, and dependencies across multiple product areas.
Drive strategy through facilitation and storytelling by leading workshops, audits, and whiteboarding sessions with Product, Engineering, Data, and other partners to frame the problem space, align on principles, and break down large, ambiguous bodies of work into clear milestones and decisions.
Leverage AI and rapid prototyping to de-risk decisions with interactive prototypes, and AI/agentic workflows to quickly explore possibilities, expose assumptions, and validate approaches early — from vision decks and North Star flows to detailed interaction prototypes.
Deliver high-quality, execution-ready design by owning the journey from discovery to delivery, producing refined end-to-end workflows and UX specs.
Mentor and elevate the team’s craft by serving as a craft mentor across CRM and related communication surfaces — giving sharp, actionable feedback, pairing with other designers on complex systems problems, and raising the quality bar for both systems thinking and visual/interaction design.