Senior Lead, AI Pricing & Margin Strategy
About this role
Building financial models, analyzing usage and cost data, researching the competitive AI landscape, and partnering with Product and Billing form the core daily routine in this role. The centralized Commercial Strategy team at Squarespace drives revenue growth across the platform by optimizing monetization models, packaging, and feature monetization. Joining this group means owning the economics of a growing AI product portfolio, leading margin analysis across API costs and token consumption, and designing customer-facing credit and usage-based pricing structures.
An analytical thinker with a background in pricing strategy, commercial analytics, product finance, or management consulting will thrive here. The position requires navigating ambiguity with structure, partnering effectively with Finance, Data Science, and Product departments, and translating complex usage data into clear strategic recommendations. Anyone who combines strong financial modeling skills with a genuine curiosity about LLM provider pricing and market dynamics will find a natural home in this NYC-based team.
What you will do
- Lead margin analysis across AI usage including API costs, token consumption, and inference spend to understand profitability across features and internal tooling.
- Build and maintain financial models from scratch that translate AI usage into credit equivalents to track unit economics.
- Model the cost and quality tradeoffs of model routing configurations to inform technical decisions made alongside Product and Engineering.
- Design and evaluate usage-based pricing models, tier structures, usage limits, and overage mechanics for customers.
- Partner with Finance, Data Science, Product, and Billing teams to ground pricing decisions in accurate data and ensure correct implementation.
- Monitor the AI model landscape by tracking pricing changes, capability updates, and competitor packaging strategies to inform corporate positioning.
What you need
- Bring at least 5 years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.
- Possess a strong analytical toolkit that includes required SQL proficiency, financial modeling from scratch, and the ability to query large-scale usage and cost data directly.
- Demonstrate an interest in AI and a working familiarity with the LLM provider landscape such as OpenAI, Anthropic, and Google.
- Show proven experience working cross-functionally with Product, Engineering, or Finance teams while navigating ambiguity with structure and clarity.
- Exhibit strong written and verbal communication skills to synthesize complex information into decision-ready summaries.
- Maintain a proactive, self-starter mindset with the ability to define scope and drive work forward with limited direction.
Benefits
- A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
- Supplemental Life and Disability Insurance plans
- Retirement benefits with employer match
- Flexible paid time off
- 12 weeks paid parental leave and family care leave
- Education reimbursement
Skills and tech stack
Questions candidates ask
Where is this job located and what is the remote policy?
This role works from the New York City office 2 to 3 days per week as part of a hybrid schedule.
What is the compensation range for the Senior Lead position?
The base cash compensation range is $125,800 to $170,200 USD, which may vary based on job-related criteria such as relevant skills, experience, and location. Employees are also eligible to be granted an option to purchase common stock.
What kind of team will I be working with?
You will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging for the product suite. The team works across pricing, packaging and promotions, purchase behavior analysis, and feature monetization.
What background is required for this role?
Candidates need 5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role. Strong SQL skills, financial modeling from scratch, and familiarity with the LLM provider landscape are required.