Senior Staff Operations Manager, Applied Data & Insights

Squarespace's Applied Data & Insights (ADI) organization powers data-driven decision-making across the company. As the Senior Staff Operations Manager for ADI, you will drive planning, delivery, and partnership across the organization. This role requires a versatile, Chief-of-Staff–like operator who works through prioritization and trade-offs across multiple leaders and cross-functional partners.

• Set and manage ADI's planning and reporting cadences (leadership meetings, All Hands, offsites, QBRs, MBRs, WBRs, annual planning).
• Codify the ADI operating model (engagement models, decision rights, SOPs) and standardize practices.
• Partner with ADI Leadership to prioritize and resource projects through bi-annual planning cycles.
• Partner with Finance and People on headcount planning, budget management, org design, onboarding, and review cycles.
• Support vendor and tooling governance for data and analytics tools.
• Partner with the ADI Technical Program Manager and other Operations Managers to share best practices.

• 10+ years in business operations, strategy, or consulting, ideally at a SaaS or technology company; Chief-of-Staff experience is a plus.
• Experience supporting data, analytics, data science, or product organizations strongly preferred.
• Proven track record of building and improving processes and programs from the ground up.
• Exceptional communication skills, able to translate between technical and business audiences.
• Proven stakeholder management, aligning cross-functional teams and senior leadership.
• Proficiency in enterprise AI tools (e.g., ChatGPT, Gemini, Claude, Glean, Cursor) and integrating them into workflows.
• Self-driven, structured problem solver comfortable with ambiguity.

Cash Compensation Range: $178,500 - $265,000 USD. Eligible for stock option grant.

Benefits include medical plans with 100% premium option, fertility and adoption benefits, supplemental insurance, Headspace subscription, Employee Assistance Program, retirement benefits with employer match, flexible PTO, 12 weeks paid parental and family care leave, pretax commuter benefit, education reimbursement, employee donation match, ERGs, dog-friendly office, free lunch and snacks, private rooftop, hack week.

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online, serving millions of customers in over 200 countries. Headquartered in New York City with offices in Dublin and Aveiro.