Squarespace

Senior Product Manager, Acuity Scheduling, (Classes)

Squarespace$153K — $247K *
Consumer Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6-8+ years of product management experience in SaaS, marketplaces, education, fitness, events, or subscription businesses
  • Proven track record defining ambiguous or early-stage products
  • Strong business instincts with experience in market segmentation and demand validation
  • High technical fluency for complex workflows and data models
  • Experience leading significant discovery efforts in constrained environments
  • Ability to discern legacy system limits from actual customer needs
  • Strong communication skills for cross-functional alignment and strategy
  • Customer-focused with experience delivering impactful products

Responsibilities

  • Own the strategy and roadmap for Acuity's Classes and group-booking products
  • Lead problem discovery to clarify market and business opportunities
  • Develop evidence-based problem statements grounded in user research
  • Define target segments and use cases for class-based sellers
  • Manage technical constraints without limiting strategic goals
  • Validate assumptions and test hypotheses early in the process
  • Translate complex scenarios into actionable product strategies
  • Collaborate with teams to enhance acquisition and retention metrics

Benefits

  • Choice of medical plans with 100% premium coverage option
  • Health Savings Account funded by the company
  • Fertility and adoption support
  • Supplemental insurance options
  • Subscription to Headspace mindfulness app
  • Global Employee Assistance Program
  • Retirement plan with employer matching
  • Flexible paid time off
  • 12 weeks of paid parental leave
  • Remote work stipend of $100 per month
  • Education reimbursement program
  • Employee donation matching for community contributions
  • Access to diverse Global Employee Resource Groups (ERGs)
Full Job Description
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 01 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

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 website building and hosting company headquartered in New York City. The company provides a platform that allows users to create and manage websites, blogs, and online stores. Squarespace was founded in 2003 by Anthony Casalena and has since grown to become one of the leading website building and hosting platforms in the world. The company has over 1,200 employees and serves millions of customers worldwide. Squarespace is known for its user-friendly interface, customizable templates, and powerful e-commerce tools.
Learn more about Squarespace
Size
1,200 employees
Market Cap
$2.9 billion
Industry
Founded
2003
NASDAQ

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