Senior Product Manager, Acuity Scheduling, (Classes)

Squarespace; New York (NY); Hybrid; USD 153,500 - 247,250; Full time

Benefits offered by this job

Health benefits with covered premiums

Retirement benefits with employer match

Flexible paid time off

Education reimbursement

Job summary

Squarespace is seeking a Senior Product Manager to lead the strategy for Acuity’s Classes product in New York City. This hybrid role focuses on defining and executing a roadmap for improving group-based selling experiences. The ideal candidate will have extensive product management experience and a customer-centric approach.

With responsibilities that include deep market analysis and collaboration with cross-functional teams, this position plays a critical role in enabling businesses to scale operations effectively while driving product growth.

Qualifications

• 6–8+ years of product management experience, ideally in SaaS or subscription businesses.
• Demonstrated success owning early-stage, ambiguous products.
• High technical fluency comfortable working with complex workflows and data models.

Responsibilities

• Own the long-term strategy for Acuity’s Classes product.
• Lead problem discovery and define business opportunities.
• Partner with engineering and design to explore solution paths.

Skills

Product management experience

Problem definition

User research

Data analysis

Cross-functional communication

Customer obsession

Education

Bachelor's degree or equivalent

Tools

SaaS platforms

Product roadmapping tools

Job description

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

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.

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.