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 Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process. 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