Senior Lead, AI Pricing & Margin Strategy

Squarespace is looking for an analytical, curious thinker to help build out the economics of our growing AI product portfolio. 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.

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. The team works across pricing, packaging & promotions, purchase behavior analysis, and feature monetization — aligning price with customer value and unlocking incremental ARPU and retention.

In this role, you will support the team's AI pricing and margin workstreams: building financial models, analyzing usage and cost data, researching the competitive AI landscape, and partnering with Product and Billing to bring pricing decisions to life. You will report to Commercial Lead and work from our NYC office 2–3 days per week.

What You'll Do…

Cost & Margin Analysis

• 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.

• Model

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