Head of Corporate Finance and FP&A

Finance ManagerThe 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.You'll Get To…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 planningBuild 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 servicesDevelop ROI methodologies and scorecards for AI initiatives, helping leadership evaluate where investments are generating value and where to reallocateMonitor AI spend efficiency metrics such as cost-per-output and cost as a percentage of revenue, and surface trends and anomalies proactivelyPartner with Engineering, Product, and Data Science teams to create visibility into how AI costs scale with product usage, helping the company plan for growth scenariosPartner 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 businessTrack and forecast all R&D investments including headcount, software, contracted services, and other operating expenses across products globallyPerform variance analysis and deliver actionable recommendations on spend across organizational teamsPresent financial results and strategic insights independently to executive stakeholders and corporate finance leadershipIdentify and drive process improvements that enhance reporting efficiency and the quality of business metricsWho We're Looking For8+ years of experience in FP&A or related finance roles, with experience supporting technical or R&D organizations strongly preferredBachelor's degree in Finance, Economics, AccountingDeep expertise in financial modeling and FP&A systems (e.g., Workday, NetSuite); mastery of Excel requiredDemonstrated ability to operate with a high degree of autonomy — making sound decisions on budget, forecasting, and investment analysis without constant oversightStrong strategic thinking skills with the ability to develop long-term financial plans and assess risk across a large, multifaceted portfolioIntellectually curious about emerging technology, with a willingness to develop fluency in AI cost structures and how they differ from traditional software spendProven ability to communicate complex financial topics clearly to non-financial stakeholders at the executive levelA self-starter who thrives in dynamic environments and takes ownership of workstreams end-to-endStrong ethical foundation with a commitment to presenting unbiased, accurate information to all stakeholdersBenefits & PerksA choice between medical plans with an option for 100% covered premiumsFertility and adoption benefitsAccess to supplemental insurance plans for additional coverageHeadspace mindfulness app subscriptionGlobal Employee Assistance ProgramRetirement benefits with employer matchFlexible paid time off12 weeks paid parental leave and family care leavePretax commuter benefitEducation reimbursementEmployee donation match to community organizations7 Global Employee Resource Groups (ERGs)Dog-friendly workplaceFree lunch and snacksPrivate rooftopHack week twice per yearCash Compensation Range: $148,500 - $208,000 USDThe base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.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.About SquarespaceSquarespace 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. This helps us ensure that your candidate information is accurate and consistent during the hiring process.Squarespace will never solicit your personal banking information or ask you to transfer money in connection with a job offer or interview. We also will not reach out to you via phone or SMS without your permission or knowledge. If you plan to use AI in any capacity during your candidate journey, please review our Candidate AI Policy.