Enterprise Transformation, Senior Lead
Squarespace · New York City
Posted about 3 months ago · $178,500 - $210,000
or apply directly on Squarespace's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 79 days Squarespace's roles stay open a median of 73 days
- Reposted
- No
- Salary listed
- Yes 72% of Squarespace's roles list one
- Ghost-job risk at Squarespace
- high 29 stale, 1 reposted of 29 open
- Hiring momentum
- 37 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-10-24
Measured from postings appearing on and disappearing from Squarespace's own greenhouse board since 2026-08-03. Full hiring picture for Squarespace.
About this role
The Enterprise Transformation Lead at Squarespace will act as the enterprise design authority, overseeing the structure and delivery of transformation initiatives within the organization. This role involves collaborating with cross-functional leaders in Finance, Engineering, and Operations to resolve complex dependencies and align on strategic decisions, driving continuous improvement in financial systems. The position is hybrid, requiring three days a week in the NYC office, and reports to the Senior Manager of Financial Systems.
- benefits
- 5/5
- freshness
- 1/5
- career value
- 4/5
- role clarity
- 4/5
- pay transparency
- 5/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Squarespace as an employer.
What you need
- 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 have
- Experience applying structured problem-solving methodologies in large, matrixed organizations
- Familiarity with enterprise financial or ERP platforms (such as NetSuite, SAP, or Oracle)
What you get
- 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
Worth weighing
- Hybrid role requiring in-office presence three days a week
- No specific mention of technology stack or tools used in financial systems
- Vague description of the transformation initiatives and their impact on the organization
Summarised from Squarespace's posting. Read the full original.
Listed by Squarespace on their greenhouse job board, last confirmed open on 2026-10-24. PitchMeAI is not the employer.
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