Head of Finance (Full-Time)

Not specified Full-time Not specified Finance

The Squarespace Finance team is seeking a Finance Manager to serve as a dedicated FP&A business partner to our R&D organization. This is a high-impact, high-autonomy role responsible for overseeing the financial health of a large, complex technology portfolio spanning Engineering, Product, and Squarespace’s expanding AI initiatives.

As Squarespace scales its investment in artificial intelligence, this role will be instrumental in building the financial infrastructure to track AI costs, evaluate ROI, and translate complex technology spend into strategic insights for senior leadership. The ideal candidate brings deep financial expertise, strong cross-functional instincts, and the judgment to operate independently in a fast-moving environment.

You will report to the FP&A Director and be based in our New York City office.

Serve as the primary finance business partner for the R&D organization, including Engineering and Product, owning the full planning cycle: monthly close, forecasting, and annual planning

Build and own financial frameworks to track AI-related costs end-to-end including model API usage and inference costs, GPU/cloud compute infrastructure, AI tooling and software licenses, and AI-related headcount and contracted services

Develop ROI methodologies and scorecards for AI initiatives, helping leadership evaluate where investments are generating value and where to reallocate

Partner with Engineering, Product, and Data Science teams to create visibility into how AI costs scale with product usage, helping the company plan for growth scenarios

Partner with the FinOps team to track and optimize cloud infrastructure costs, including compute, storage, and data transfer spend across cloud providers and data center environments; collaborate on cloud cost allocation, commitment-based savings strategies, and ongoing efficiency initiatives to ensure infrastructure investment scales responsibly with the business

Track and forecast all R&D investments including headcount, software, contracted services, and other operating expenses across products globally

Present financial results and strategic insights independently to executive stakeholders and corporate finance leadership

Identify and drive process improvements that enhance reporting efficiency and the quality of business metrics

A choice between medical plans with an option for 100% covered premiums

Headspace mindfulness app subscription

Global Employee Assistance Program

Retirement benefits with employer match

Flexible paid time off

Employee donation match to community organizations

Dog-friendly workplace

Private rooftop

Cash Compensation Range: $148,500 – $208,000 USD

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. 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.