Strategic AI Pricing & Margin Leader

Squarespace; New York (NY); Hybrid; USD 126,000 - 170,000; Full time

Benefits offered by this job

Medical plans (100% premiums)

Fertility and adoption benefits

Headspace app

Retirement match

Flexible PTO

12 weeks parental leave

Pre-tax commuter benefits

Education reimbursement

Dog-friendly workplace

Free lunch

Hack week twice per year

Job summary

Squarespace is seeking an analytical thinker to help build the economics of our growing AI product portfolio. The role sits at the intersection of commercial strategy and emerging tech — supporting the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers and manages AI costs internally.

You will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging

Qualifications

• 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or related analytical role.
• Strong analytical toolkit: SQL, financial modeling from scratch, stress-testing assumptions.

Responsibilities

• Lead margin analysis across AI usage, including API costs and inference spend.
• Design and evaluate customer-facing pricing models, including tier structures and usage limits.
• Structure promotional offers and launch incentives for new AI features with revenue impact.
• Collaborate with Finance, Data Science, Product and Billing to align assumptions and data.

Skills

SQL

Financial modeling

Pricing strategy

Commercial analytics

Cross-functional

Stakeholder communication

Tools

Excel

Job description

Squarespace is seeking an analytical thinker to help build the economics of our growing AI product portfolio. The role sits at the intersection of commercial strategy and emerging tech — supporting the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers and manages AI costs internally.

You will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging