Senior Lead, AI Pricing & Margin Strategy

Squarespace is looking for an analytical, curious thinker to help build out the economics of its 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.

Responsibilities

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 the cost and quality tradeoffs of model routing configurations to inform routing decisions made with Product & Engineering.

Pricing & Packaging Support

• 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.

Cross-functional Collaboration

• 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.

AI Market Research

• 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.

Requirements

• 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.
• Strong analytical toolkit: SQL required, financial modeling from scratch, and comfort stress-testing assumptions , you're comfortable querying large-scale usage and cost data directly and presenting findings clearly.
• An interest in AI and a working familiarity with the LLM provider landscape (e.g., OpenAI, Anthropic, Google); you don't need to be a practitioner, but you should be genuinely curious about how these systems work and how they're priced.
• Experience working cross-functionally with Product, Engineering, or Finance teams, and an ability to navigate ambiguity with structure and clarity.
• Strong written and verbal communication skills; you can synthesize complex information into a clear, decision-ready summary.
• A proactive, self-starter mindset , you're comfortable asking the right questions, defining scope, and driving work forward with limited direction.

Benefits & Perks

• 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
• 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)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year