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Enterprise Transformation, Senior Lead
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Enterprise Transformation, Senior Lead
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About the position
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.
Responsibilities
Serve as the enterprise design authority, defining how transformation initiatives are structured and sequenced across the organization
Influence strategic decisions by engaging directly with cross-functional leaders and translating complex business needs into clear, actionable direction
Resolve cross-functional dependencies, surfacing trade-offs and aligning partners on a path forward
Drive continuous improvement by identifying gaps between current systems and business goals and recommending solutions that scale
Requirements
12+ years of demonstrated experience leading enterprise transformation or financial systems initiatives at scale
Proven ability to take complex, ambiguous problems and develop clear, logical frameworks that drive decisions
Experience presenting strategy and recommendations to executive audiences and earning alignment without direct authority
Demonstrated ability to bridge business requirements and technology solutions, translating between finance, operations, and engineering partners fluently
Nice-to-haves
Experience applying structured problem-solving methodologies in large, matrixed organizations
Familiarity with enterprise financial or ERP platforms (such as NetSuite, SAP, or Oracle)
Benefits
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
Hepace 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