Staff Product Manager, Checkout

At Squarespace, we empower our product teams to solve complex customer and business problems in ways that delight users and drive meaningful results. As a Staff Product Manager, you will operate as a senior-level individual contributor, driving strategy, execution, and cross-functional alignment across high-impact areas of our platform.

The Checkout team is core to the Squarespace Commerce experience. We help sellers across the globe convert more customers, reduce friction, and grow revenue through a modern, performant, and trustworthy checkout experience. Our work spans infrastructure, UX, payments, compliance, and experimentation, making it one of the most critical and interconnected surfaces in the entire product ecosystem.

This is a unique opportunity to lead foundational initiatives in our checkout experience, with high visibility across the company. You'll shape strategy and own end-to-end product delivery while influencing teams across engineering, design, payments, data, and operations.

You will report to the Product Director for Financial Solutions and will be based in our New York City headquarters working on-site (hybrid).

• Define and evolve the long-term product strategy for Checkout, grounded in customer insights, data, and business goals.
• Lead complex initiatives from inception to delivery, influencing multiple teams and domains across Commerce, Payments, and Financial Solutions.
• Drive collaboration across engineering, design, UX research, legal, risk, data science, marketing, and customer operations to deliver holistic solutions.
• Identify new opportunities to accelerate conversion, improve performance, and support global expansion through seamless checkout experiences.
• Anticipate technical and organizational complexity—ensuring the product remains scalable, compliant, and adaptable as the business evolves.
• Champion a data-informed mindset across the team, establishing meaningful success metrics, developing robust A/B test strategies, and driving accountability.
• Serve as a thought leader within the product organization, contributing to the overall Financial Solutions strategy and shaping product culture.
• Mentor and guide other product managers and cross-functional partners, raising the bar for product thinking and execution across the group.

• 7-10+ years of product management experience, with a strong track record of owning and scaling mission-critical platform or transactional experiences.
• Deep experience in e-commerce, fintech, payments, or high-traffic transactional systems—especially in areas involving complex system interactions and global scale.
• Strong understanding of checkout, payments infrastructure, conversion optimization, and/or compliance requirements.
• Knowledge of financial technologies such as digital wallets, payment gateways and alternative payment methods.
• Excellent strategic thinking and structured problem-solving abilities; able to make high-quality decisions with incomplete data.
• Expertise in product discovery and delivery methods, with proven success in launching experiments, validating hypotheses, and iterating quickly.
• Outstanding communication skills, with an ability to align teams and influence senior stakeholders across the company.

• A choice between medical plans with an option for 100% covered premiums
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 20 weeks for parental leave and up to 12 weeks to care for an ill family member
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 8 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

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 on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock.

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 range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

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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