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

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, Cursor, or comparable platforms, to automate repeatable operating work, synthesize information across functions, improve leadership preparation, surface risks and dependencies, and accelerate strategic-initiative delivery.

This role reports to the VP of Operations at Squarespace and is based remotely in California or locally at our New York City headquarters. You’ll Get To… Run the President's operating cadence .

Own end-to-end orchestration of the leadership rhythm: staff meetings, WBRs, MBRs, and QBRs, finance and portfolio reviews, priority updates, and annual operating-plan inputs. Ensure each ritual has a clear purpose, owner, input, output, decision authority, and downstream cascade. Drive decision quality.

Synthesize diverse inputs into concise narratives that ma