Enterprise Transformation, Senior Lead

location_on New York City · Posted Oct 15, 2026
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Squarespace Greenhouse Board
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About the Role

Squarespace is looking for an Enterprise Transformation Lead to serve as the enterprise design authority, shaping how transformation initiatives are structured and delivered across the organization. Our Financial Systems team drives the systems and processes that keep Squarespace's financial operations running with precision and scale. We are a focused, cross-functional team based in NYC, partnering closely with finance, technology, and operational leaders to move critical work forward. You will work closely with cross-functional leaders across Finance, Engineering, and Operations to resolve complex dependencies and align on strategic decisions. This is an opportunity for you to own enterprise-level design decisions at a company scaling across hundreds of countries and multiple products.

This is a hybrid role working from our NYC office 3 days per week. You will report to the Senior Manager Financial Systems.

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Key Technical Responsibilities

  • check_circle Serve as the enterprise design authority, defining how transformation initiatives are structured and sequenced across the organization
  • check_circle Influence strategic decisions by engaging directly with cross-functional leaders and translating complex business needs into clear, actionable direction
  • check_circle Resolve cross-functional dependencies, surfacing trade-offs and aligning partners on a path forward
  • check_circle Drive continuous improvement by identifying gaps between current systems and business goals and recommending solutions that scale
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Prerequisites & Qualifications

  • check 12+ years of demonstrated experience leading enterprise transformation or financial systems initiatives at scale
  • check Proven ability to take complex, ambiguous problems and develop clear, logical frameworks that drive decisions
  • check Experience presenting strategy and recommendations to executive audiences and earning alignment without direct authority
  • check Demonstrated ability to bridge business requirements and technology solutions, translating between finance, operations, and engineering partners fluently
  • check Experience applying structured problem-solving methodologies in large, matrixed organizations (Nice to Have)
  • check Familiarity with enterprise financial or ERP platforms such as NetSuite, SAP, or Oracle (Nice to Have)
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About Squarespace Greenhouse Board

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Squarespace Greenhouse Board refers to the centralized recruitment and talent acquisition infrastructure utilized by Squarespace, a New York City-based technology company specializing in website building and hosting platforms. The board serves as the primary interface for managing the company's global hiring pipeline, candidate tracking, and talent operations, facilitating the recruitment of engineering, product, and design talent to support the company's integrated suite of web publishing tools and e-commerce solutions.

Engineering Culture: Squarespace maintains an engineering-centric culture focused on design-led product development and high-performance web infrastructure. Their recruitment philosophy emphasizes the acquisition of talent capable of balancing aesthetic precision with scalable software architecture. The company prioritizes a collaborative, cross-functional environment where engineers are expected to contribute to the end-to-end user experience, adhering to rigorous standards for code quality, reliability, and intuitive interface design.
Enterprise Transformation, Senior Lead
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