Senior Staff Operations Manager, Applied Data & Insights

Squarespace’s Applied Data & Insights (ADI) organization powers data-driven decision-making across the company with teams spanning Analytics, Data Science & Machine Learning, Analytics Enablement, and Data Platform. As the Senior Staff Operations Manager for ADI, you will drive the way we plan, deliver, and partner inside our organization and across the company. This role requires a versatile, Chief-of-Staff–like operator who works through prioritization and trade-offs across multiple leaders and cross-functional partners. You are an excellent communicator and well versed in managing stakeholder communications and expectations.You have a track record of translating complexity into clear processes, building credibility with data and analytics leaders, and knowing when to push, when to align, and when to escalate. You are comfortable navigating a changing business environment and thrive in a role where the operating model is still being built. This is a hybrid role working from our New York City office 3 days per week. You will report to the Senior Director of Operations to ensure alignment with operational standards, consistency across teams, and company-wide best practices, while maintaining a dotted-line relationship to the VP of ADI. You’ll Get To… Set and manage ADI's planning and reporting cadences, both internal (leadership meetings, All Hands, offsites) and company-facing (QBRs, MBRs, WBRs, annual planning), including all associated artifacts. Codify the ADI operating model (engagement models, decision rights, and standard operating procedures) across teams and standardize practices where relevant. Partner with the ADI Leadership Team to identify, prioritize, and resource critical projects through bi-annual planning cycles; drive alignment on prioritization, support preparation for executive reviews, and ensure communication is clear and consistent throughout. Partner with Finance and People on headcount planning, budget management, hiring consistency, org design, onboarding, and review cycles across ADI teams; foster strong relationships and facilitate collaboration across Finance, Marketing, Product, Engineering, and other departments. Partner with Data Product Manager and other leaders to support vendor and tooling governance for the organization, including evaluation, contracting, and lifecycle management of data and analytics tools. Partner with the ADI Technical Program Manager (TPM) and connect with Operations Managers across the company to share best practices and drive consistency. Who We’re Looking For 10+ years in business operations, strategy, or consulting, ideally at a SaaS or technology company; Chief-of-Staff experience is a plus. Experience supporting a data, analytics, data science, or product organization is strongly preferred. Experience supporting growth or growth marketing organizations in a technology company, with an understanding of how those teams use data, measurement, and experimentation to drive business outcomes, is a plus. Proven track record of building and improving processes and programs from the ground up, bringing consistency and structure to environments that need it. Exceptional communication skills, with the ability to translate between technical and business audiences and build executive-ready presentations. Proven track record of stakeholder management, successfully aligning cross-functional teams and senior leadership around core business objectives. Proficiency in enterprise AI tools (e.g., ChatGPT, Gemini, Claude, Glean, Cursor) and experience integrating such tools into your daily workflows to automate tasks, optimize processes, and accelerate project delivery. Self-driven, hands-on, structured problem solver with bias to action; comfortable navigating ambiguity and operating where processes are still being built. Benefits & Perks A choice between medical plans with an option for 100% covered premiums Fertility and adoption benefits Access to supplemental insurance plans for…