Senior Product Manager, Acuity Scheduling

Squarespace•New York, NY

11h•Hybrid

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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