---
title: 'Senior Staff Operations Manager, Office of the President (PED) at Squarespace'
canonical: 'https://feeny.ai/job/senior-staff-operations-manager-office-of-the-president-ped-squarespace-t22y9a1mpfby'
type: 'job'
last_seen: '2026-10-12'
---

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

- **Company:** Squarespace
- **Location:** California
- **Work type:** remote
- **Posted:** 2026-09-17
- **Last confirmed live:** 2026-10-12
- **Apply:** http://www.squarespace.com/about/careers?gh_jid=8205269

## Job description

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.

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).

## About Squarespace

## Company Overview
- **One-liner**: Squarespace is a website building and hosting platform that provides tools for entrepreneurs and creators to build, manage, and grow their online presence, including websites, ecommerce stores, domains, and marketing.
- **Entity Type**: Public (NYSE: SQSP)
- **Headquarters**: New York City, USA (with offices in Dublin, Ireland, and Aveiro, Portugal)
- **Founded**: 2003
- **Founders**: Anthony Casalena

## Core Business
- **Primary industry/industries**: Website building & hosting, ecommerce, content management, marketing technology
- **Target customers**: B2B and B2C – small businesses, entrepreneurs, creators, freelancers, and enterprises building online brands
- **Mission or purpose statement**: “A future where everyone can be an entrepreneur.” Design is the ultimate competitive advantage, making professional online tools accessible to all.

## Products & Services
- **Squarespace Websites**: Drag-and-drop website builder with customizable templates, hosting, and built-in SEO; SaaS.
- **Squarespace Commerce**: Ecommerce platform with inventory management, checkout, payments, and shipping; integrated into websites.
- **Squarespace Scheduling**: Online booking and appointment scheduling tool (formerly Acuity Scheduling); SaaS.
- **Squarespace Domains**: Domain name registration and management.
- **Squarespace Marketing**: Email campaigns, social media integration, and analytics tools to grow customer reach.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (public company; market cap available via stock market data)
- **Key Metric**: Annual Revenue ~$1.0B (LinkedIn)
- **Notable Investors/Partners**: Public company; no recent funding rounds. Partners include payment processors (Stripe), and the company owns the Unfold brand.
- **Growth Signals**: Headcount grew 11.7% year-over-year to 1,523 employees (LinkedIn, about page reports “more than 1,760”). Continues to expand offices in Dublin and Portugal; recognized as Great Place to Work and Best Large Places to Work multiple years.

## Competitive Advantages
- **Design-first philosophy** – every product is built with a focus on aesthetics and usability, differentiating from more utilitarian competitors.
- **All-in-one platform** – customers can get websites, domains, ecommerce, scheduling, and marketing under one roof, reducing the need for third-party integrations.
- **Strong brand and community** – millions of websites created; consistently ranked among top workplace awards, attracting top talent.
- **Flexible work policy** – offers both office-space and home-space classifications, enabling a hybrid model that balances collaboration and remote autonomy.

## Strategic Focus
- **Betting on big ideas** – investing in game-changing products like improved ecommerce features, AI-powered design tools, and deeper integrations.
- **International expansion** – growing engineering and support teams in Dublin and Portugal to serve a global customer base.
- **Inclusion & Impact** – driving diversity through employee resource groups, inclusive policies (20 weeks paid family leave, fertility benefits), and matching charitable donations up to $600 per employee.

## Why Work Here
- **Culture**: Highly collaborative, design-driven, and fast-paced. Emphasis on “protect creativity,” “be the customer,” and “learn fast, act fast.” Strong focus on inclusion with 7 ERGs and an Inclusion Advisory Council.
- **Work flexibility**: Hybrid and remote options are core to the model. Employees can be “Officespace” (in-office at least part of the week) or “Homespace” (fully remote). Previously 13% were fully remote pre-pandemic; now many roles have flexible arrangements.
- **Perks & benefits**:
  - Competitive salary, equity grants, and 401(k) with company match.
  - Up to 20 weeks paid family leave and 12 weeks personal care leave.
  - Fertility and adoption benefits (up to $10k/year, $20k lifetime).
  - Mental health support via Headspace, Talkspace, and EAP.
  - Charitable donation matching ($600/yr).
  - Free Squarespace and Unfold subscriptions for employees.
- **Recognition**: Great Place to Work (US, Ireland); Built In Best Places to Work; Comparably Best Work-Life Balance; Healthiest Employers of NYC; Best Companies for Diversity, Women, and Career Growth.
- **Engineering culture**: Teams work on backend (Java, Go), frontend (React, JavaScript), infrastructure, and product analytics. Open roles include Staff Engineer, Senior Software Engineer, and DevOps roles.

## Sources
1. [squarespace.com/about/careers](https://www.squarespace.com/about/careers)
2. [squarespace.com/about/company](https://www.squarespace.com/about/company)
3. [squarespace.com/about/inclusion-and-impact](https://www.squarespace.com/about/inclusion-and-impact)
4. [linkedin.com/company/squarespace](https://www.linkedin.com/company/squarespace)
5. [squarespace.com/careers/jobs](https://www.squarespace.com/careers/jobs)

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