The Squarespace Growth team is looking for a Senior Product Manager II, Help Experience to drive the strategy and execution of all user-facing Customer Support surfaces and select agent-facing Customer Support internal tools.  

Our Help Center is a critical resource for our users, providing centralized help content through knowledge base articles, help videos, AI-powered chat, and contact with our CustOps agents. We are a team committed to building products that unblock our users and leveraging 1st- and 3rd-party tools to ensure their ongoing success. You will work closely with Engineering, Design, and stakeholders across CustOps to transform the Help Site into a critical asset for both in-trial users and existing subscribers across our product lines, as well as for leads in our nascent B2B funnel.

This is an opportunity for you to lead a massive fundamental redesign of this platform, transforming it from a set of siloed knowledge bases into a singular discovery-led Product that drives quantifiable metrics.

In addition to the Help Center, our CustOps employees rely on a suite of agent-facing tools to better support our users. As the primary Product-side point of contact for CustOps, this product manager role will also help shape the roadmap for these internal tools whenever critical product thinking is required. 

As the primary product leader over a vast and critical territory, this role offers ready opportunities for visible impact and scope expansion for the ambitious PM. 

This is a hybrid role working from our NYC office strongly preferred. You will report to the Product Director of Growth. 

You’ll Get To…

• Define and own the Help Site strategy, specifically leading the "Multi-Brand Help Center" initiative to create a cohesive personalized experience across Squarespace properties.
• Drive blue-sky Product thinking for the Help Site and new B2B support initiatives, identifying user-centric features that move the needle on deflection rates, trial conversion, and retention.
• Lead a dedicated team of engineers and designers, managing shared rituals and providing an actionable strategic framework to avoid delivery bottlenecks and ensure high-velocity execution.
• Lead the discovery-delivery cycle, forming and validating hypotheses, iterating on features, and presenting your impact and learnings to Squarespace leadership. 
• Act as the primary Product point of contact for CustOps, supporting a vast network of stakeholders (Cust Ops leaders, agents, KB writers, and solutions specialists) to contextualize their needs within a larger strategic framework.
• Be the Product voice of record for Agent Experience, supporting our internal agent tooling with product thinking, prioritization frameworks, and roadmapping support when needed. 
• Partner with Growth leadership to ensure the Help Site is a key surface in the setup journey for trialers and a viable sales-supporting workstream for B2B.
• Contribute to the brand and vision, ensuring the product experience is beautiful, cohesive, and aligned with Squarespace’s broader brand.

Who We’re Looking For

• 5+ years of experience in product management, with a focus on user-facing products, support enablement, growth initiatives, and/or complex site redesigns.
• A nuanced understanding of modern product discovery, with the ability to lead an empowered team from loosely-defined objectives to rigorous iterative development, including rapid AI-enabled prototyping. 
• Ability to thrive in a high-volume environment, managing roadmap complexity across diverse simultaneous contexts to make clear prioritization calls under tight timelines.
• Strong stakeholder management skills, with the ability to align diverse groups—from technical engineering teams to customer operations leadership—around a strategic vision and roadmap. 
• Experience with AI applications, specifically in leveraging AI tools to support, personalize, and scale user self-service.
• Excellent communication skills, with a track record of delivering well-reasoned presentations that influence team and group strategy.
• Experience in a "Growth" context, understanding how support surfaces impact the end-to-end user lifecycle.
• Specific experience in operations, support enablement, and/or program management is a plus, due the complex cross-org real-time nature of many of this role’s responsibilities.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• 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
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $153,500 - $247,250 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

#LI-Hybrid #LI-JP1

Squarespace is a design-centric product company at heart, 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.

We’re looking for a Staff+ Product Designer to join our 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.

This is a hybrid role based in our New York City headquarters.

You’ll Get To...

• 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.

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 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.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• 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
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $223,000 - $358,800 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

#LI-Hybrid #LI-JP1

Squarespace is a design-centric product company built on the belief that beautiful design should be accessible to everyone. We help millions of people and businesses build an online presence, from stunning websites to full commerce and service experiences. We are looking for a Product Design Manager to own a significant portion of the website creation experience, focused on the editing and refining experience of how Squarespace users build their sites.

This role sits at the heart of how users create and refine their websites. You will lead a portion of the Websites design organization focused on the moment-to-moment experience of building on Squarespace. That includes the precision of every editing interaction, the quality of what is published, and the systems that make both possible at scale.

The teams in your area are pushing into new territory, including creative tooling and AI-assisted workflows that expand what users can build and express. Your teams shape core parts of the Squarespace editing experience used by millions of people building their online presence.

You are a people and systems operator first, but you carry a strong craft bar yourself. The designers on these teams are seasoned, including a Staff Designer, and they need a manager who earns their trust through taste and judgment, not just process. You know how to set direction, step back, and let strong ICs do their best work, while still being the person who raises the bar when it matters. You build the kind of team culture where high-quality craft is not negotiable.

You will report to a Product Design Director on the Websites team in NYC.

You’ll Get To...

Team Leadership & Development

• Build and develop a high-performing team of senior and staff-level designers, setting clear goals, delivering direct feedback, and creating the conditions for each person to do their best work.
• Own hiring, performance, and compensation decisions for your teams, and proactively invest in the growth of the people around you.
• Translate broad product goals into a clear design roadmap for your teams, maintaining the focus and prioritization needed to execute with quality.
• Foster a team culture where craft is expected, ownership is real, and collaboration is genuine.

Design Quality & Direction

• Insist on the highest standards across visual design, interaction design, and systems thinking for everything your teams ship.
• Engage actively with the work as a sharp, opinionated reviewer. You know what great looks like, you can articulate why something is not there yet, and your designers trust your judgment.
• Guide your teams through complex, systems-level problems where design decisions have long-lasting consequences for the quality and coherence of the product.
• Ensure the work your teams ship raises the overall quality bar of the Squarespace editing experience.
• Stay current on the evolving landscape of creative tools, website builders, and AI-powered experiences, and bring that perspective into how your teams approach their work.

Cross-Functional Partnership

• Partner with product management and engineering to shape roadmap direction, push on product strategy, and advocate for the user experience.
• Build strong relationships across design, research, and brand, and drive alignment on the things that cut across teams.
• Present your teams' work and strategic rationale with clarity and conviction to leadership.

Who We’re Looking For 

• 8+ years of product design experience.
• 3+ years of management experience leading seasoned designers, with direct ownership of hiring, performance, and career development.
• Actively uses AI tools in their design practice and is curious about how AI is reshaping the creative process.
• Strong portfolio demonstrating systems-level thinking alongside craft-level execution that demonstrates how you solved business problems while delighting users, including how you have guided teams through complex work.
• Discerning taste in visual and interaction design, with the confidence to hold a point of view and the judgment to know when to evolve it.
• Superior presentation and stakeholder management skills.
• Ability to focus and adjust in an ever-shifting internal and external landscap

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• 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
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $185,500 - $299,000 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

#LI-Hybrid #LI-JP1

The Squarespace Technical Program Management (TPM) team is looking for a Senior TPM to support our mission of helping teams to deliver top company priorities with efficiency and predictability. You will work within the Commerce organization, collaborating across Product Management, Engineering, and Design teams. Your responsibilities will include ensuring clear program planning, transparent progress tracking, risk mitigation, team process improvement, and efficient delivery.

This is a Dublin-based role working from our office 2 days per week. You will report to the Senior Manager of Technical Program Management.

TPMs oversee the product development lifecycle end-to-end:

• Create clear & helpful plans throughout product discovery and delivery (scope, milestones, tasks, roles and responsibilities, risk mitigation, etc.)
• Break down silos and bridging communication gaps across teams and disciplines (Product, Engineering, Design, etc.)
• Drive discovery momentum from ideation to defined scope and requirements
• Track goal and project statuses and reporting updates to project stakeholders

Who we're looking for…

• 6+ years of experience in a technical program manager (or similar) position, working on product and engineering-driven projects through all phases of the software development lifecycle
• Experience working collaboratively across organizations, influencing without direct authority
• Ability to partner with leadership to build and maintain roadmaps, lead planning meetings, and implement efficient communication and practices
• Agile background, with experience implementing scrum/kanban best practices and facilitating team level process improvement
• Ability to thoroughly follow through, chase down and close out open questions and tasks; while creating a collaborative and healthy culture
• Prior experience working on high-priority strategic business initiatives in a fast-paced product development environment
• Working knowledge of the Atlassian suite and Google Workspace

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
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Free lunch and snacks
• Close proximity to cultural landmarks such as Dublin Castle and St. Patrick's Cathedral

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

At Squarespace we empower our product teams to solve hard problems – customer and business problems – in ways that our customers love, yet work for our business. As a Product Manager, you will contribute to your product team with knowledge of business constraints, a deep understanding of our users, and awareness of product trends.

The Online Stores team develops and scales the services, products, and frameworks essential for delivering the best selling experience to all Squarespace customers. The team supports key components of our sales functionality, including storefront setup, inventory, checkout, and post-purchase experiences. We design user experiences that guide users through the process of setting up their store, listing products and services, and making their first and repeat sales.

As a Senior Product Manager, Online Stores Activation, you will own the end-to-end activation journey for commerce sellers—from first touchpoint through first value and beyond. You’ll create a vision and tactical roadmap that reduces the effort customers need to launch a high-quality store, reach their first sale, and build healthy selling habits that grow their business.

This is a hybrid role working from our New York City office 2–3 days per week. You will report to a Product Director.

You’ll Get To…

• Own the activation strategy for Online Stores, defining what successful activation looks like for different seller segments (e.g., physical goods, services, digital products) and mapping journeys from signup to first sale.
• Create and prioritize a roadmap rooted in data, informed by multiple sources (quantitative funnels, customer research, market insights, and go-to-market feedback) and justified by return on investment.
• Improve core onboarding flows including store setup, product/service creation, payments configuration, and launch checklists so that sellers can successfully launch faster with less friction.
• Define and monitor activation metrics such as time-to-first-publish, time-to-first-sale, key setup completion rates, and early retention, and use these to guide prioritization and measure impact.
• Guide product development end-to-end—from problem discovery and solution definition through launch and iteration—with consideration for your specific team, adjacent teams, and the broader Squarespace ecosystem.
• Partner closely with design, engineering, UX research, and analytics as a single, mutually supporting force to deliver cohesive experiences that feel simple even when the underlying systems are complex.
• Run structured experiments (A/B tests, feature flags, and staged rollouts) to learn which interventions drive meaningful improvements in activation and early cohort health.
• Collaborate cross-functionally with:
  • Marketing and Growth to align product and lifecycle campaigns that nudge sellers through setup and launch.
  • Customer Operations to ensure we have excellent support and education for new merchants.
  • Data teams to build and refine dashboards that surface activation performance and seller behavior.
• Set outcomes based goals for your team with your engineering and design counterparts and contribute to group-level goal setting for Online Stores.
• Influence broader commerce strategy by championing the needs of new sellers, sharing insights from activation funnels, and advocating for investments that improve long-term customer value.

Who We’re Looking For

• 6+ years of product management experience, managing software products from creation through launch and iteration.
• Experience owning activation, onboarding, or growth funnels for a consumer or SMB-facing product, ideally with measurable improvements to conversion and retention.
• A nuanced understanding of modern product discovery and delivery, including experimentation, hypothesis-driven development, and user segmentation.
• Demonstrated ability to use data and research to define problems, size opportunities, and make tradeoffs, including experience with funnel analysis and core product analytics tools.
• Excellent communication and interpersonal skills, with the ability to align designers, engineers, marketers, and operations partners around shared goals and customer outcomes.
• Comfort working with complex systems (e.g., editors, payments, checkout, or inventory) and simplifying them into intuitive experiences for users.
• Proven track record of setting clear goals and metrics, and driving teams to deliver meaningful business and customer impact.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• 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
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $153,500 - $247,250 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

#LI-Hybrid #LI-JP1