[All remote jobs](https://jobicy.com/jobs.md)[![Squarespace logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/02/WRILS-210217203348-525354.jpg)](https://jobicy.com/company/squarespace.md)[Squarespace](https://jobicy.com/company/squarespace.md) # Senior Staff Operations Manager, Office of the President (PED) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/squarespace.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 178,500–350k / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished7 Oct 2026Apply before6 Nov 2026Listing views257Application actions7Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. This is a senior Chief of Staff–style operations role supporting Squarespace's President of Product, Engineering, and Design. The role owns leadership operating rhythms, including staff meetings, business and quarterly reviews, portfolio and finance reviews, decision logs, and follow-through. It requires influencing senior cross-functional leaders without formal authority while identifying execution risks and driving ambiguous strategic initiatives. The successful candidate will pair strong business, financial, and product-development acumen with executive communication and facilitation skills. Enterprise AI tools are expected to be used to automate repeatable operational work, synthesize information, and improve decision quality and execution velocity. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe role operates at executive level across Product, Engineering, Design, Finance, People, and Commercial functions, with substantial ambiguity and sensitive decisions. Success depends on independently creating alignment, resolving tradeoffs, and maintaining execution discipline without direct authority. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianHighly competitive$264,250US market range$190k–$330k0$363k AI insightThe disclosed U.S. cash compensation range is $178,500 to $350,000 USD yearly, producing a job median of $264,250. This is a competitive range for a senior staff-level Chief of Staff or Product/Business Operations leader supporting an executive in a major U.S. technology company; the estimated U.S. market range is $190,000 to $330,000 yearly, excluding equity and other benefits. ## Core skills Skills and capabilities most closely associated with this opportunity. [Executive operations](https://jobicy.com/jobs?search_keywords=Executive%20operations.md)[Chief of Staff](https://jobicy.com/jobs?search_keywords=Chief%20of%20Staff.md)[Operating model design](https://jobicy.com/jobs?search_keywords=Operating%20model%20design.md)[Strategic planning](https://jobicy.com/jobs?search_keywords=Strategic%20planning.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md)[Program management](https://jobicy.com/jobs?search_keywords=Program%20management.md)[Executive communication](https://jobicy.com/jobs?search_keywords=Executive%20communication.md)[Financial acumen](https://jobicy.com/jobs?search_keywords=Financial%20acumen.md)[Stakeholder influence](https://jobicy.com/jobs?search_keywords=Stakeholder%20influence.md)[Enterprise AI tools](https://jobicy.com/jobs?search_keywords=Enterprise%20AI%20tools.md) Sample interview questionsHow have you designed or improved an executive operating cadence across multiple functions?I begin by clarifying each forum's purpose, decision rights, required inputs, accountable owner, expected output, and downstream communication path. I then standardize pre-reads, decision logs, action tracking, and escalation mechanisms, measuring effectiveness through indicators such as decision latency, action closure, and recurring issue themes. I refine the cadence based on leader feedback and outcomes rather than adding process for its own sake. Describe a time you influenced senior stakeholders to make a difficult decision without formal authority. I created a concise decision narrative that made the objective, options, tradeoffs, financial and organizational implications, and recommendation explicit. Before the meeting, I gathered perspectives individually to surface objections and align on facts. In the discussion, I facilitated around the decision needed, documented the outcome and owners, and followed through on unresolved dependencies. How would you use enterprise AI tools in this role while maintaining appropriate judgment and confidentiality? I would use approved tools for repeatable work such as synthesizing meeting inputs, drafting pre-read structures, identifying dependencies across updates, and creating action-tracking summaries. I would validate outputs against source material, apply human judgment to recommendations, and follow company policies for sensitive people, financial, and strategic information. AI should reduce manual effort and improve signal quality, not replace accountability or executive judgment. How do you identify execution risk before it becomes a leadership surprise? I maintain a structured view of priorities, decisions, dependencies, owners, milestones, metrics, and unresolved issues across functions. I look for leading signals such as repeated deferrals, unclear ownership, conflicting assumptions, deteriorating delivery confidence, and missing decision inputs. When risk emerges, I frame the issue with context, impact, options, and a recommended escalation path. How would you balance strategic work for the President with the detailed mechanics of meeting preparation and follow-up? I treat preparation and follow-through as strategic leverage rather than administrative tasks. A disciplined operating system creates reliable information flow, which frees leadership capacity for the highest-value decisions. I would prioritize work by business impact, establish reusable templates and AI-supported workflows for routine tasks, and reserve focused time for ambiguous initiatives and emerging issues. Opportunity details ## 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, 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 to decide, when to seek input, and when to escalate. ### What Success Looks Like In the first 6–12 months, you will: * Implement a dependable operating rhythm in which leadership forums are well-prepared, decision-oriented, and followed through. * Improve the quality and consistency of pre-reads, decision logs, action tracking, portfolio updates, and quarterly communications. * Make it easy to see what changed, what matters now, what decisions are needed, who owns the next step, and where risk is accumulating. * Establish a small number of reliable AI-enabled workflows that reduce manual preparation and reporting effort, improve the timeliness and quality of leadership inputs, and make follow-through more visible. * Increase the organization’s ability to reuse knowledge, detect recurring issues, and move from raw information to clear decisions without adding unnecessary process. * Build strong working relationships and trust with the President and his leaders across the department and company, leading with tact, discretion and respect. * Help the President and leadership team make faster, clearer, better-informed decisions without adding unnecessary processes or meetings. * Leave the system more scalable and more resilient than you found it. ### Benefits & Perks * A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision * Supplemental Life and Disability Insurance plans * Fertility and adoption benefits * Headspace mindfulness app subscription * Global Employee Assistance Program * Retirement benefits with employer match * Flexible paid time off * 12 weeks paid parental leave and family care leave * Pretax commuter benefit * Education reimbursement * Employee donation match to community organizations * 7 Global Employee Resource Groups (ERGs) * Dog-friendly workplace * Free lunch and snacks * Private rooftop * Hack week twice per year ### US Cash Compensation Range: $178,500 – $350,000 USD The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors. In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary. ### About Squarespace Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit [https://www.squarespace.com/about/careers](https://www.squarespace.com/about/careers). ### Our Commitment Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace. #LI-Remote #LI-Hybrid Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process. Squarespace will never solicit your personal banking information or ask you to transfer money in connection with a job offer or interview. We also will not reach out to you via phone or SMS without your permission or knowledge. If you plan to use AI in any capacity during your candidate journey, please review our [Candidate AI Policy](https://sqsp.link/Sxow3s). 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