Senior Product Manager, Acuity Scheduling at Squarespace

At Squarespace, we empower product teams to solve meaningful customer and business problems. We’re looking for a Senior Product Manager to lead Acuity’s Classes product, the team responsible for enabling group-based businesses to sell, manage, and scale ad hoc and recurring, one-to-many experiences. Classes supports customers who run group sessions, workshops, fitness classes, courses, and events. These sellers have fundamentally different needs than 1:1 appointment businesses, including capacity management, cohort pricing, attendance tracking, flexible enrollment, and scalable checkout. Today, Classes remains an early-stage product with significant untapped potential. This role will define what Classes can become and build the foundation for durable, long-term growth. This role requires a highly rigorous approach to problem definition. You will be expected to deeply understand customer needs, business opportunities, and market dynamics before proposing solutions. Success in this role means consistently anchoring product decisions in validated problems, not inherited workflows or legacy systems. This is a hybrid role, requiring 1–3 days a week in our New York City office. You will report to the Senior Group Product Manager on the Acuity Scheduling team. You'll Get To... • Own the long-term strategy and roadmap for Acuity’s Classes and group-booking products • Lead deep problem discovery to clearly define customer, market, and business opportunities before pursuing major investments • Develop strong, evidence-based problem statements grounded in user research, data, and competitive analysis • Define clear target segments, primary use cases, and expansion opportunities for class-based sellers • Ensure technical and architectural constraints inform implementation choices without narrowing strategic ambition • Resist premature solutioning by validating assumptions and testing hypotheses early • Translate complex, ambiguous spaces into focused, high-leverage product bets • Partner closely with engineering and design to explore multiple solution paths rather than defaulting to the lowest-effort option • Balance near-term improvements with foundational platform investments • Drive improvements in key metrics including active class admins and client checkout conversion • Collaborate with growth, analytics, support, and marketing teams to strengthen acquisition, activation, and retention • Create alignment across stakeholders through clear narratives, documentation, and prioritization frameworks Who We’re Looking For • 6–8+ years of product management experience, ideally in SaaS, marketplaces, education, fitness, events, or subscription businesses • Demonstrated success owning ambiguous, early-stage, or 0→1 products Proven ability to define the “right” problem before designing solutions • Strong business and product instincts, with experience defining segments, sizing opportunities, and validating demand • High technical fluency, comfortable partnering on complex workflows, data models, and platform systems • Track record of leading rigorous discovery in technically constrained environments • Strong judgment in separating legacy limitations from true customer and business needs • Comfortable challenging default approaches when they conflict with user or commercial outcomes • Clear, structured communicator who can align cross-functional partners around strategy • Customer-obsessed, with a history of shipping products that drive outcomes and revenue At Squarespace, we empower product teams to solve meaningful customer and business problems. We’re looking for a Senior Product Manager to lead Acuity’s Classes product, the team responsible for enabling group-based businesses to sell, manage, and scale ad hoc and recurring, one-to-many experiences. Classes supports customers who run group sessions, workshops, fitness classes, courses, and events. These sellers have fundamentally different needs than 1:1 appointment businesses, including capacity management, cohort pricing, attendance tracking, flexible enrollment, and scalable checkout. Today, Classes remains an early-stage product with significant untapped potential. This role will define what Classes can become and build the foundation for durable, long-term growth. This role requires a highly rigorous approach to problem definition. You will be expected to deeply understand customer needs, business opportunities, and market dynamics before proposing solutions. Success in this role means consistently anchoring product decisions in validated problems, not inherited workflows or legacy systems. This is a hybrid role, requiring 1–3 days a week in our New York City office. You will report to the Senior Group Product Manager on the Acuity Scheduling team. Nice to Have • Experience modernizing or rebuilding legacy product areas • Familiarity with scheduling, booking, or operational tools for SMBs Benefits & Perks • A choice between medical plans with an option for 100% covered premiums • Health Savings Account with Squarespace funding • Fertility and adoption benefits • Supplemental Insurance plans • 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 • $100 per month remote Stipend • Access to supplemental insurance plans for additional coverage • Education reimbursement • Employee donation match to community organizations • 7 Global Employee Resource Groups (ERGs) 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 [Upgrade to PRO to see link] 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-Remote 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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