Senior Staff Operations Manager, Office of the President

About the role

This role serves as a Chief of Staff-style operator to the President, responsible for running and evolving the Product, Engineering, and Design operating model. The position focuses on turning strategy into a durable execution system by managing leadership cadences, facilitating decision-making, and driving cross-functional alignment. The successful candidate will leverage AI tools to automate workflows and synthesize information to improve leadership efficiency.

Responsibilities

• Run the President's operating cadence including staff meetings, WBRs, MBRs, and QBRs.
• Synthesize diverse inputs into concise narratives to drive decision quality.
• Identify and facilitate the resolution of execution risks across multiple departments.
• Evolve the operating model by establishing health measures and refining governance.
• Lead high-priority strategic initiatives on behalf of the President.
• Represent the President in meetings and build transparency across the organization.

Required skills

• Operating model design
• Leadership cadence management
• Cross-functional leadership
• Executive communication
• Enterprise AI tools
• Strategic planning
• Financial acumen
• Project management

Qualifications

• Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting
• Track record of owning an operating model or portfolio of complex cross-functional initiatives
• Knowledge of the product / software development lifecycle

Benefits

• Medical, dental, and vision insurance
• Supplemental Life and Disability Insurance
• Fertility and adoption benefits
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• Paid parental leave
• Pretax commuter benefit
• Education reimbursement

About the Company

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. The company empowers millions of customers in more than 200 countries with tools to create an online presence, monetize, and scale their business.