# Senior Lead, AI Pricing & Margin Strategy

**Company**: Squarespace
**Location**: New York City
**Work arrangement**: hybrid
**Experience**: senior
**Job type**: full-time
**Salary**: $125,800 - $170,200 USD
**Category**: Finance
**Industry**: Technology

**Apply**: https://job-boards.greenhouse.io/squarespace/jobs/8205265?utm_source=yubhub.co&utm_medium=jobs_feed&utm_campaign=apply
**Canonical**: https://yubhub.co/jobs/job_570c6be3-274

## Description

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

## Skills

### Required
- SQL
- financial modeling
- analytical thinking
- AI
- LLM provider landscape
- communication skills

---

Source: [Apply at job-boards.greenhouse.io](https://job-boards.greenhouse.io/squarespace/jobs/8205265?utm_source=yubhub.co&utm_medium=jobs_feed&utm_campaign=apply)