Job Description

Squarespace is seeking an Engineering Manager to lead our Purchase, Access & Subscription Success (PASS) team. The group is responsible for the buyer-facing purchase and subscription experience, including the multi-product cart, secure checkout flows, subscription and billing panel, cross-selling, cancellation surveys, and invoices. This team’s work directly drives revenue by shaping how customers purchase, manage, and retain their Squarespace subscriptions.

As the manager of this team, you’ll lead a group of experienced frontend and backend engineers who build and maintain the cart experience and checkout flows, power the subscription and billing panel UI, drive cross-sell and upsell initiatives, and deliver new product integrations. You’ll work closely with product, design, analytics, and peer engineering teams to deliver seamless, high-converting purchase experiences for Squarespace customers worldwide.

This is a hybrid role working from our Dublin 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 the multi-product cart, secure checkout flows, subscription and billing panel experience, cross-sell services, cancellation surveys, and invoices.
Drive the execution of the Monetization roadmap, including secure checkout migration, new product integrations, and cross-sell optimization.
Coach, mentor, and develop engineers through regular feedback, goal-setting, and technical guidance.
Collaborate with cross-functional partners (Product, Design, Analytics, and peer engineering teams) to align engineering initiatives with 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.
Own operational health: SLOs, on-call, and engineering metrics (cycle time, MTTR, availability targets).

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 e-commerce cart/checkout experiences, subscription management, or SaaS billing UX.
Strong communication and collaboration skills with a focus on cross-team alignment and delivery.
Passion for mentoring engineers and fostering a culture of growth, inclusion, and accountability.
Experience operating in a PagerDuty/on-call culture with production SLO targets.

Benefits & Perks

Health insurance with 100% covered premiums for you, your spouse or partner and your dependent children including medical, dental, and vision
Life and Income Protection
Fertility and adoption benefits
Headspace mindfulness app subscription
Global Employee Assistance Program
Pension benefits with employer match
Flexible paid time off
26 weeks paid maternity leave & 12 weeks paid paternity leave
2 weeks paid family care leave
Education reimbursement
Employee donation match to community organizations
7 Global Employee Resource Groups (ERGs)
Free lunch and snacks
Close proximity to cultural landmarks such as Dublin Castle and St. Patrick’s Cathedral

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/about/careers.

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 customer base, but we also strive for 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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