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Senior Staff Operations Manager, Office of the President (PED)

Squarespace · Remote, California · Remote

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About Squarespace

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About the role

This role will turn strategy into a durable execution system. You will own the connective tissue across the President’s leadership cadence: preparing the right inputs, creating clarity on decisions and tradeoffs, ensuring commitments are followed through, surfacing risks early, and improving the operating model as the organization changes.

What they're looking for

  • Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting
  • A track record of owning an operating model, leadership cadence, or portfolio of complex cross-functional initiatives, preferably in tech companies
  • Knowledge of the product / software development lifecycle
  • Exceptional written communication: you can turn a large volume of input into a concise, decision-ready narrative tailored to the audience
  • Strong business and financial acumen, with the ability to understand metrics, forecasts, resource tradeoffs, product or portfolio performance, and organizational implications
  • Strong executive presence and facilitation skills, you can create clarity and momentum in high-stakes or ambiguous settings
More about this role

We are looking for a Chief of Staff–style operator to serve as the President’s right hand and help run, maintain, and continuously evolve the Product, Engineering & Design operating model and cadence.

This role will turn strategy into a durable execution system. You will own the connective tissue across the President’s leadership cadence: preparing the right inputs, creating clarity on decisions and tradeoffs, ensuring commitments are followed through, surfacing risks early, and improving the operating model as the organization changes. You will work across Product, Engineering, Design, Commercial, Finance, People, and your peers in Business Operations, partnering with senior leaders who do not report to you and influencing through judgment, trust, and clarity.

The successful candidate will combine executive judgment, operational rigor, business acumen, comfort with ambiguity, strong written and verbal communication, and the ability to move fluidly between strategic questions and the execution details required to make the system work.

AI fluency is an important part of this role. You will use approved enterprise AI tools, including tools such as ChatGPT, Gemini, Claude, Glean,...

Read the full posting on Squarespace's site ↗

Operations

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