---
title: 'Senior Staff Operations Manager, Applied Data & Insights at Squarespace'
canonical: 'https://feeny.ai/job/senior-staff-operations-manager-applied-data-insights-squarespace-new-york-cgk4tqr3y1x4'
type: 'job'
last_seen: '2026-09-07'
---

# Senior Staff Operations Manager, Applied Data & Insights at Squarespace

- **Company:** Squarespace
- **Location:** New York, NY
- **Posted:** 2026-06-23
- **Last confirmed live:** 2026-09-07
- **Apply:** http://www.squarespace.com/about/careers?gh_jid=8019377

## Job description

Squarespace’s Applied Data & Insights (ADI) organization powers data-driven decision-making across the company with teams spanning Analytics, Data Science & Machine Learning, Analytics Enablement, and Data Platform. As the Senior Staff Operations Manager for ADI, you will drive the way we plan, deliver, and partner inside our organization and across the company.

This role requires a versatile, Chief-of-Staff–like operator who works through prioritization and trade-offs across multiple leaders and cross-functional partners. You are an excellent communicator and well versed in managing stakeholder communications and expectations.You have a track record of translating complexity into clear processes, building credibility with data and analytics leaders, and knowing when to push, when to align, and when to escalate. You are comfortable navigating a changing business environment and thrive in a role where the operating model is still being built.

This is a hybrid role working from our New York City office 3 days per week. You will report to the Senior Director of Operations to ensure alignment with operational standards, consistency across teams, and company-wide best practices, while maintaining a dotted-line relationship to the VP of ADI.

You’ll Get To…

- Set and manage ADI's planning and reporting cadences, both internal (leadership meetings, All Hands, offsites) and company-facing (QBRs, MBRs, WBRs, annual planning), including all associated artifacts.
- Codify the ADI operating model (engagement models, decision rights, and standard operating procedures) across teams and standardize practices where relevant.
- Partner with the ADI Leadership Team to identify, prioritize, and resource critical projects through bi-annual planning cycles; drive alignment on prioritization, support preparation for executive reviews, and ensure communication is clear and consistent throughout.
- Partner with Finance and People on headcount planning, budget management, hiring consistency, org design, onboarding, and review cycles across ADI teams; foster strong relationships and facilitate collaboration across Finance, Marketing, Product, Engineering, and other departments.
- Partner with Data Product Manager and other leaders to support vendor and tooling governance for the organization, including evaluation, contracting, and lifecycle management of data and analytics tools.
- Partner with the ADI Technical Program Manager (TPM) and connect with Operations Managers across the company to share best practices and drive consistency.

Who We’re Looking For

- 10+ years in business operations, strategy, or consulting, ideally at a SaaS or technology company; Chief-of-Staff experience is a plus.
- Experience supporting a data, analytics, data science, or product organization is strongly preferred. Experience supporting growth or growth marketing organizations in a technology company, with an understanding of how those teams use data, measurement, and experimentation to drive business outcomes, is a plus.
- Proven track record of building and improving processes and programs from the ground up, bringing consistency and structure to environments that need it.
- Exceptional communication skills, with the ability to translate between technical and business audiences and build executive-ready presentations.
- Proven track record of stakeholder management, successfully aligning cross-functional teams and senior leadership around core business objectives.
- Proficiency in enterprise AI tools (e.g., ChatGPT, Gemini, Claude, Glean, Cursor) and experience integrating such tools into your daily workflows to automate tasks, optimize processes, and accelerate project delivery.
- Self-driven, hands-on, structured problem solver with bias to action; comfortable navigating ambiguity and operating where processes are still being built.

## Benefits & Perks

- A choice between medical plans with an option for 100% covered premiums
- Fertility and adoption benefits
- Access to supplemental insurance plans for additional coverage
- 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

Cash Compensation Range: $178,500 - $265,000 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-CB1 #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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