Software Engineering Manager, Checkout & Payments

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 and operates the services that power both real-time and recurring payment processing across Squarespace.

As the manager for this team, you'll guide a group of experienced frontend and backend engineers who integrate with global payment gateways, maintain our payment infrastructure, and ensure the reliability and scalability of systems that drive all payments for Squarespace's customers. You'll work closely with product, design, and finance partners to deliver seamless, secure, and performant checkout and 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, and payment processing (on-session and asynchronous).
• Drive the evolution of our payment gateway integrations (e.g., Stripe, PayPal) and internal payment services.
• Coach, mentor, and develop engineers through regular feedback, goal-setting, and technical guidance.
• Collaborate with cross-functional partners to align engineering initiatives with product and business priorities.
• Foster a culture of technical excellence, reliability, and continuous improvement in critical revenue systems.
• Participate in incident command rotations and 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) and backend (Java, PostgreSQL, distributed systems) domains.
• Familiarity with payment processing, gateway integrations, or transactional system design.
• Strong communication and collaboration skills with a focus on alignment and delivery.
• Passion for mentoring engineers and fostering a culture of growth, inclusion, and accountability.

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: $185,500 - $299,000 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 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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/