Senior Product Manager Acuity Scheduling

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.

• 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

• 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.

• Experience modernizing or rebuilding legacy product areas
• Familiarity with scheduling booking or operational tools for SMBs

• 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)

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.

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 1700 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.

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.

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What We Do

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. At Squarespace we celebrate creative possibility. With a culture rooted in curiosity Squarespace aims to provide its employees with the support to turn possibility into reality – learning from challenges and celebrating progress. At Squarespace we root for customer and employee success uplifting them with the tools needed to achieve their goals while also applauding what makes them unique and fulfilled. Our customers and employees alike are imaginative with the confidence to put their ideas out into the world and welcoming input and iteration. And our people run towards the next frontier to create our success motivated by the unknown and inspired by “first-ever” opportunities truly embracing a sense of possibility.

Why Work With Us

Squarespace employees are ownership-minded builders tenacious resourceful hands-on humble self-motivated experimental curious resilient inclusive and empathetic.

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