Squarespace is seeking an Engineering Manager to lead our Checkout & Payments team - the group that enables customers around the world to seamlessly complete their purchases using their preferred payment methods. This team is responsible for the checkout experience & operates the services that power both real-time & recurring payment processing across Squarespace.

As the manager for this team, you'll guide a group of experienced frontend & backend engineers who integrate with global payment gateways, maintain our payment infrastructure, & ensure the reliability & scalability of systems that drive all payments for Squarespace's customers. You'll work closely with product, design, & finance partners to deliver seamless, secure, & performant checkout & payment experiences for our customers.

This is a hybrid role working from our NYC office 3 days per week. You will report to the Senior Engineering Manager of Revenue Systems.

You'll Get To

• Lead a full-stack engineering team responsible for billing address collection, payment information, & payment processing (on-session & asynchronous).
• Drive the evolution of our payment gateway integrations (e.g., Stripe, PayPal) & internal payment services.
• Coach, mentor, & develop engineers through regular feedback, goal-setting, & technical guidance.
• Collaborate with cross-functional partners to align engineering initiatives with product & business priorities.
• Foster a culture of technical excellence, reliability, & continuous improvement in critical revenue systems.
• Participate in incident command rotations & guide the team's response to high-impact production events.

Who We're Looking For

• 3+ years experience managing software engineering teams building production systems.
• Experience leading or partnering across both frontend (React/TypeScript) & backend (Java, PostgreSQL, distributed systems) domains.
• Familiarity with payment processing, gateway integrations, or transactional system design.
• Strong communication & collaboration skills with a focus on alignment & delivery.
• Passion for mentoring engineers & fostering a culture of growth, inclusion, & accountability.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums including medical, dental, & vision
• Supplemental Life & Disability Insurance plans
• Fertility & adoption benefits
• 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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