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Salary: USD 178,500 - 350,000 / annual
Squarespace is seeking a Chief of Staff–style operator to serve as the President's right hand and architect of the Product, Engineering & Design operating model. This role transforms strategy into a durable execution system by owning the connective tissue across the President's leadership cadence: preparing inputs, creating clarity on decisions and tradeoffs, ensuring follow-through on commitments, surfacing risks early, and continuously evolving the operating model.
Key Responsibilities:
- Run the President's operating cadence, orchestrating staff meetings, WBRs, MBRs, QBRs, finance and portfolio reviews, priority updates, and annual operating-plan inputs. Ensure each ritual has clear purpose, owner, input, output, decision authority, and downstream cascade.
- Drive decision quality by synthesizing diverse inputs into concise narratives that clarify priorities, risks, options, and tradeoffs. Document decisions, assign owners and deadlines, track commitments, and escalate unresolved issues with context and proposed solutions.
- Improve execution velocity by identifying alignment and execution risks before they surface as leadership surprises. Facilitate resolution across Product, Engineering, Design, Commercial, Customer Operations, Finance, People, and Business Operations. Use AI and advanced tooling to accelerate decision-making.
- Evolve the operating model by treating it as a living system. Establish health measures (decision latency, action closure, cascade reach, pre-read quality, participation, recurring issue themes) and recommend changes to cadence, governance, templates, roles, and channels as strategy evolves.
- Lead high-priority strategic initiatives on behalf of the President, from framing through implementation and follow-through. Support annual strategy, goals, headcount, and budget processes.
- Represent the President in meetings, events, and discussions. Navigate difficult conversations and cross-functional tradeoffs without relying on formal authority. Support two-way access through Town Halls, Roundtables, Office Hours, and written follow-up.
- Serve as a trusted thought partner to the President and senior leadership, offering independent perspective and respectfully challenging assumptions.
You will work across Product, Engineering, Design, Commercial, Finance, People, and Business Operations, partnering with senior leaders who do not report to you and influencing through judgment, trust, and clarity. AI fluency is critical: you will use approved enterprise AI tools (ChatGPT, Gemini, Claude, Glean, Cursor, or comparable platforms) to automate repeatable operating work, synthesize information, improve leadership preparation, surface risks and dependencies, and accelerate strategic-initiative delivery.
Success in the first 6–12 months means: implementing a dependable operating rhythm with well-prepared, decision-oriented leadership forums and strong follow-through; improving quality and consistency of pre-reads, decision logs, action tracking, and quarterly communications; establishing AI-enabled workflows that reduce manual effort and improve timeliness of leadership inputs; increasing the organization's ability to reuse knowledge and detect recurring issues; building strong working relationships with the President and leaders across the department and company; and leaving the system more scalable and resilient.
Requirements:
- Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting
- 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 (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: ability to turn large volumes of input into concise, decision-ready narratives tailored to audience
- Strong business and financial acumen, with ability to understand metrics, forecasts, resource tradeoffs, product or portfolio performance, and organizational implications
- Strong executive presence and facilitation skills; ability to 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
- Continuous-improvement mindset: distinguish between process and content, challenge ineffective routines, make change practical and durable
- Bias toward action paired with judgment to know when to decide, seek input, or escalate
