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About the Role
Squarespace is looking for an analytical, curious thinker to help build out the economics of our growing AI product portfolio. Sitting at the intersection of commercial strategy and emerging technology, this role supports the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers while managing internal AI costs.
As part of a centralized Commercial Strategy team, you will drive revenue growth across the platform by optimizing monetization models and packaging for Squarespace's comprehensive product suite. Reporting to the Commercial Lead from our New York City office (2–3 days per week), you will build financial models, analyze usage and cost data, research the competitive AI landscape, and partner closely with Product and Billing to bring pricing decisions to life.
Key Technical Responsibilities
- check_circle 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.
- check_circle Build and maintain financial models that translate AI usage into credit equivalents, helping the team track unit economics across model providers and feature surfaces.
- check_circle Model the cost and quality tradeoffs of model routing configurations to inform routing decisions made with Product & Engineering.
- check_circle Design and evaluate customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics.
- check_circle Translate pricing strategy into concrete SKU and entitlement definitions, working with Product and Billing to ensure commercial intent is correctly implemented.
- check_circle Structure promotional offers and launch incentives for new AI features, modeling expected revenue and margin impact.
- check_circle 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.
- check_circle Prepare clear, well-structured analyses and presentations that communicate findings to stakeholders across the business.
- check_circle Track and report on the commercial performance of AI features, flagging margin risks and opportunities as they emerge.
- check_circle Monitor the AI model landscape — tracking pricing changes, capability updates, and new providers across frontier labs — and surface relevant implications for Squarespace's strategy.
- check_circle Research how competitors are packaging and monetizing AI capabilities to inform our own positioning and pricing decisions.
Prerequisites & Qualifications
- check 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.
- check 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.
- check An interest in AI and a working familiarity with the LLM provider landscape (e.g., OpenAI, Anthropic, Google).
- check Experience working cross-functionally with Product, Engineering, or Finance teams, and an ability to navigate ambiguity with structure and clarity.
- check Strong written and verbal communication skills with the ability to synthesize complex information into a clear, decision-ready summary.
- check A proactive, self-starter mindset — comfortable asking the right questions, defining scope, and driving work forward with limited direction.
About Squarespace Greenhouse Board
Verified hiring organization details.
Squarespace Greenhouse Board refers to the centralized recruitment and talent acquisition infrastructure utilized by Squarespace, a New York City-based technology company specializing in website building and hosting platforms. The board serves as the primary interface for managing the company's global hiring pipeline, candidate tracking, and talent operations, facilitating the recruitment of engineering, product, and design talent to support the company's integrated suite of web publishing tools and e-commerce solutions.