Chief of Staff, Strategic Product Analyst

As a Senior Strategic Product Analyst, you will serve as the analytical backbone of Acuity Scheduling, translating complex financial and product data into a coherent performance narrative that drives actionable insights for senior executives. You'll partner closely with the Acuity Leadership team to enable data-informed decision making and identify opportunities for business growth and optimization.

You will establish and maintain a robust performance monitoring system, including daily metric tracking and alerts, comprehensive weekly business reviews, and monthly deep-dive analyses for executive stakeholders. These regular touchpoints ensure early detection of business anomalies, enable data-driven course corrections, and provide strategic recommendations that inform long-term business planning. Additionally, you will be a key contributor to long-term strategic planning, helping shape growth initiatives through scenario modeling, pricing, market analysis, and forecasting.

You will report to the VP, Product of Acuity Scheduling and can work on-site at our New York City headquarters or remotely in an approved US state.

• Lead end-to-end analysis of performance metrics for our Acuity business across product, finance, and operations, synthesizing findings into comprehensive business narratives for executive stakeholders
• Design and maintain scalable reporting systems and dashboards that provide real-time visibility into key business drivers
• Synthesize data across product analytics, marketing efficiency, and platform health to evaluate business impact of key initiatives
• Partner with cross-functional teams to develop analytical frameworks for measuring business health and forecasting future performance
• Conduct deep-dive analyses to identify growth opportunities, operational inefficiencies, and areas for strategic investment
• Partner with Analytics and Data Engineering to build infrastructure that supports analytical rigor and to develop models and tools that improve business impact
• Provide data-driven recommendations to the leadership team to influence strategic planning and resource allocation
• Monitor industry dynamics by analyzing market trends and competitor movements

• 8+ years of experience in strategy, business analytics, data analysis, or similar roles with increasing scope of responsibility
• Advanced proficiency in SQL and experience with business intelligence tools (e.g., Tableau, Looker, Power BI)
• Expert-level Excel/Google Sheets skills including complex modeling, pivots, and advanced formulas
• Knowledge of statistical analysis and experimental design
• Familiarity with product analytics tools (e.g., Amplitude)
• Experience in designing and implementing metrics frameworks to measure business performance
• Proven track record of translating complex analyses into clear, actionable recommendations for senior audiences

• A choice between medical plans with an option for 100% covered premiums
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• 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
• 8 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

The 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.

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. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. 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. We are proud to be an equal opportunity workplace.