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
• 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