Senior Lead, AI Pricing & Margin Strategy

The role

This role supports the pricing, margin analysis, and packaging work for the AI product portfolio. You will build financial models, analyze usage and cost data, and research the competitive AI landscape.

What you will do

• Lead margin analysis across AI usage including API costs, token consumption, and inference spend
• Build and maintain financial models that translate AI usage into credit equivalents
• Model the cost and quality tradeoffs of model routing configurations
• Design and evaluate customer-facing credit and usage-based pricing models
• Translate pricing strategy into concrete SKU and entitlement definitions
• Structure promotional offers and launch incentives for new AI features
• Partner with Finance, Data Science, Product, and Billing teams
• Prepare analyses and presentations for stakeholders
• Track and report on the commercial performance of AI features
• Monitor the AI model landscape and research competitor packaging

Required qualifications

• 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role
• SQL required
• Financial modeling from scratch
• Comfort stress-testing assumptions
• Ability to query large-scale usage and cost data directly
• Experience working cross-functionally with Product, Engineering, or Finance teams
• Strong written and verbal communication skills

Nice to have

• Working familiarity with the LLM provider landscape (e.g., OpenAI, Anthropic, Google)

Benefits

• 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
• 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
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)

About the company

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. The team of more than 1,700 is headquartered in New York City.