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.

Cost & Margin Analysis

• Analyze AI usage data — 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.
• Support the development of model routing frameworks by modeling the cost and quality tradeoffs of different routing configurations.

Pricing & Packaging Support

• Support the design and evaluation of customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics.
• Help translate pricing strategy into concrete SKU and entitlement definitions, working with Product and Billing to ensure commercial intent is correctly implemented.
• Assist in structuring 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.

• 2–4 years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.
• Strong quantitative and financial modeling skills — you're comfortable building models from scratch, stress-testing assumptions, 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 take a complex dataset and turn it 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.

• 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

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. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers. 

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

#LI-Hybrid