Senior Lead, AI Pricing & Margin Strategy

Not specified Full-time Senior Operations

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 work streams: 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.

• 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 the cost and quality tradeoffs of model routing configurations to inform routing decisions made with Product & Engineering.
• Design and evaluate customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics.
• Translate pricing strategy into concrete SKU and entitlement definitions, working with Product and Billing to ensure commercial intent is correctly implemented.
• Structure promotional offers and launch incentives for new AI features, modeling expected revenue and margin impact.

• 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.
• Prepare clear, well-structured analyses and presentations that communicate findings to stakeholders across the business.
• Track and report on the commercial performance of AI features, flagging margin risks and opportunities as they emerge.

• Monitor the AI model landscape – tracking pricing changes, capability updates, and new providers across frontier labs – and surface relevant implications for Squarespace’s strategy.
• Research how competitors are packaging and monetizing AI capabilities to inform our own positioning and pricing decisions.
• Private rooftop

Cash Compensation Range: $125,800 – $170,200 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.

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.…