At Squarespace, we empower our product teams to solve complex customer & business problems in ways that delight users & drive meaningful results. As a Staff Product Manager, you will operate as a senior-level individual contributor, driving strategy, execution, & 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, & grow revenue through a modern, performant, & trustworthy checkout experience. Our work spans infrastructure, UX, payments, compliance, & experimentation, making it one of the most critical & 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 & own end-to-end product delivery while influencing teams across engineering, design, payments, data, & operations.

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

You'll Get To...

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

Who We're Looking For

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

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums
• Fertility & 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 & 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 & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $185,500 - $299,000 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, & 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.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & 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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