Headquarters: Remote, California

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 make priorities, risks, options, tradeoffs, and recommended decisions clear to the President and leadership team. Document decisions in the room, assign owners and deadlines, track commitments, and escalate unresolved issues with context and a proposed path forward.

• Improve execution velocity. Identify alignment and execution risks before they surface as leadership surprises, and facilitate resolution across Product, Engineering, Design, Commercial, Customer Operations, Finance, People, and Business Operations, connecting planning, performance, financial, organizational, and roadmap inputs. Use AI and advanced tooling to make decisions faster and better-informed.

• Evolve the operating model. Treat the operating system as a living thing. Establish health measures such as decision latency, action closure, cascade reach, pre-read quality, participation, recurring issue themes, and use them to assess whether rituals, artifacts, and escalation paths are producing the right outcomes. Recommend and implement changes to cadence, governance, templates, roles, and channels as strategy and priorities evolve, codifying what works so the model is easy for leaders to understand and operate.

• Lead high-priority strategic initiatives. Drive complex, ambiguous, cross-functional work on behalf of the President, from framing and workplan through decision, implementation, and follow-through, including emerging problems that don't yet have a clear owner. Support annual strategy, goals, headcount, and budget processes by connecting them to the department's operating rhythm.

• Represent the President and build transparency. Stand in for the President in meetings, events, and discussions, exercising the remit of the position. Navigate difficult conversations and cross-functional tradeoffs without relying on formal authority. Support two-way access to the President through Town Halls, Roundtables, Office Hours, and written follow-up, using sound judgment about what should be broadly communicated, selectively shared, or handled privately.

• Serve as a trusted thought partner to the President and senior leadership team, offering an independent perspective and respectfully challenging assumptions when needed.

Who We’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

• Demonstrated proficiency with enterprise AI tools, such as ChatGPT, Gemini, Claude, Glean, Cursor, or comparable approved tools, and experience integrating them into daily workflows to automate repeatable tasks, optimize processes, improve synthesis, and accelerate project delivery.

• 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.

• Demonstrated ability to influence senior stakeholders, build consensus, resolve conflict, and push for decisions without formal authority.

• High judgment and discretion when handling sensitive organizational, people, financial, and strategic information.

• Comfort operating in ambiguity, switching between strategic altitude and detailed execution, and taking ownership of problems that cross organizational boundaries.

• A continuous-improvement mindset: you distinguish between process and content, challenge ineffective routines, and make change practical and durable.

• A bias toward action, paired with the judgment to know when t