Squarespace
Senior Lead, AI Pricing & Margin Strategy
New York City · Senior
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About the role
- The team works across pricing, packaging & promotions, purchase behavior analysis, and feature monetization - aligning price with customer value and unlocking incremental ARPU and retention.
- Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.
- 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.
Responsibilities
- Lead margin analysis across AI usage - including API costs, token consumption, and inference spend - to build a clear picture of margin across customer-facing features and internal tooling.
- Build and maintain financial models that translate AI usage into credit equivalents, helping the team track unit economics across model providers and feature surfaces.
- Design and evaluate customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics.
- Partner with Finance, Data Science, Product, and Billing teams to gather inputs, align on assumptions, and ensure pricing decisions are grounded in accurate usage and cost data.
- Research how competitors are packaging and monetizing AI capabilities to inform our own positioning and pricing decisions.
- Squarespace is looking for an analytical, curious thinker to help build out the economics of our growing AI product portfolio.
- You will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging for Squarespace's product suite.
- 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.
Requirements
- 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.
- you can synthesize complex information into a clear, decision-ready summary.
Compensation
- 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.
- $125,800 - $170,200 USD
- Hack week twice per year
- Cash Compensation Range: $125,800 - $170,200 USD
Benefits
- A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
- Supplemental Life and Disability Insurance plans
- Fertility and adoption benefits
- Retirement benefits with employer match
- Flexible paid time off
- 12 weeks paid parental leave and family care leave
- Pretax commuter benefit
- Education reimbursement
Company info
- Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees.
- We are proud to be an equal opportunity workplace. #LI-Hybrid Thank you in advance for providing the following details about your work history from your resume!
- This role sits at the intersection of commercial strategy and emerging technology - supporting the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers and manages AI costs internally.
Equal opportunity
- We are proud to be an equal opportunity workplace.
Visa & Work Authorization
- r, 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 app
This listing is sourced directly from Squarespace's careers page and normalized into a canonical job model.