Senior Manager, Data Science and Machine Learning

Senior Manager, Data Science and Machine Learning

New York, NY

Squarespace is hiring a Senior Manager, Data Science and Machine Learning to lead the team behind our predictive models, causal inference frameworks, and AI evaluation systems.  These are the tools that inform how we acquire customers, keep them, and serve them at scale.  Reporting to the VP of Data, you’ll lead a team of 12 data scientists and ML engineers doing work that is directly tied to how Squarespace leverages AI and data-driven capabilities. You will work closely with product, engineering, and analytics partners across the organization to introduce new ways to leverage data in our products and decision systems, for customers and internal use. This is an opportunity to step into a critical senior leadership seat and set the direction for how machine learning and data science are practiced at Squarespace.

This is a hybrid role working from our NYC office 3 days per week. You will report to the VP, Data.

You'll Get To...

• Lead and develop a team of 12, including three direct reports who manage their own teams
• Set the technical and strategic direction for predictive modeling, causal inference, and AI evaluation across Squarespace's product and business priorities
• Apply data science to Squarespace’s biggest growth levers: marketing measurement, sales growth, product optimization, customer support allocation, and risk and credit modeling
• Partner with product, engineering, and business leaders to translate complex statistical and ML work into decisions and systems that drive customer acquisition, retention, engagement, and growth across our global products.
• Build the systems, processes, and team culture that raise the quality and speed of data science delivery across the organization
• Evolve the team's ML infrastructure and tooling as AI capabilities at Squarespace grow

Who We're Looking For

• 12+ years in data science or machine learning, including experience leading technical teams through complex, high-stakes projects
• 5+ years managing managers, with demonstrated ability to develop senior individual contributors and team leads simultaneously
• Hands-on experience building or overseeing production predictive models, causal inference frameworks, or AI evaluation systems
• Skill at aligning product, engineering, and business partners around a shared roadmap and navigating trade-offs clearly, especially in explaining statistical or technical trade-offs to executives without losing the nuance
• Experience scaling a data science or ML function, including team structure, hiring, and technical standards

Nice to Have

• Experience building or overseeing LLM evaluation harnesses, including golden sets and LLM-as-judge methods
• Familiarity with prompt and model lifecycle management in production
• Experience designing human-in-the-loop review for AI-driven features
• Background in marketing science, experimentation, or credit/risk modeling

Benefits & Perks

• 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

Cash Compensation Range: $223,000 - $358,800 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 - from Squarespace and Squarespace Payments, to subsidiaries like Tock, Bio Sites, and Unfold, as well as Acuity Scheduling - works together to help customers stand out and succeed online. By fundamentally changing the way individuals and businesses around the world build an online presence, we empower our customers with a competitive advantage in reaching their audience. The company is headquartered in New York City, with offices in Dublin and Aveiro. For more information about our company, visit https://www.squarespace.com/about-us.

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.

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