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About the Role
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.
Key Technical Responsibilities
- check_circle 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
- check_circle 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
- check_circle Develop ROI methodologies and scorecards for AI initiatives, helping leadership evaluate where investments are generating value and where to reallocate
- check_circle Monitor AI spend efficiency metrics such as cost-per-output and cost as a percentage of revenue, and surface trends and anomalies proactively
- check_circle 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
- check_circle 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
- check_circle Track and forecast all R&D investments including headcount, software, contracted services, and other operating expenses across products globally
- check_circle Perform variance analysis and deliver actionable recommendations on spend across organizational teams
- check_circle Financial results and strategic insights presented independently to executive stakeholders and corporate finance leadership
- check_circle Identify and drive process improvements that enhance reporting efficiency and the quality of business metrics
Prerequisites & Qualifications
- check 8+ years of experience in FP&A or related finance roles, with experience supporting technical or R&D organizations strongly preferred
- check Bachelor's degree in Finance, Economics, Accounting
- check Deep expertise in financial modeling and FP&A systems (e.g., Workday, NetSuite); mastery of Excel required
- check Demonstrated ability to operate with a high degree of autonomy — making sound decisions on budget, forecasting, and investment analysis without constant oversight
- check Strong strategic thinking skills with the ability to develop long-term financial plans and assess risk across a large, multifaceted portfolio
- check Intellectually curious about emerging technology, with a willingness to develop fluency in AI cost structures and how they differ from traditional software spend
- check Proven ability to communicate complex financial topics clearly to non-financial stakeholders at the executive level
- check A self-starter who thrives in dynamic environments and takes ownership of workstreams end-to-end
- check Strong ethical foundation with a commitment to presenting unbiased, accurate information to all stakeholders
About Squarespace Greenhouse Board
Verified hiring organization details.
Squarespace Greenhouse Board refers to the centralized recruitment and talent acquisition infrastructure utilized by Squarespace, a New York City-based technology company specializing in website building and hosting platforms. The board serves as the primary interface for managing the company's global hiring pipeline, candidate tracking, and talent operations, facilitating the recruitment of engineering, product, and design talent to support the company's integrated suite of web publishing tools and e-commerce solutions.