Create a website and grow your business with a free Squarespace trial. Start with customizable website templates, AI website builder tools, or a domain name. Backed by Accel and Index.
About the role
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.
What they're looking for
- 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
- 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
More about this role
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.
- Lead margin analysis across AI usage — including API costs, token consumption, and inference spend — to build a...
Browse similar: AI jobs · AI startup jobs · Startup jobs