Squarespace is looking for a strategic leader responsible for designing, optimizing, & managing the technology & engineering solutions that handle our Checkout, Billing, Payments, Revenue Recognition & Financial Reporting systems. 

You will lead multiple teams that build & manage services & vendor integrations to that end, helping Squarespace reach further, maximize conversion & reduce churn by improving our customer checkout experience, reducing time-to-market for monetization & commercialization features, & efficiently delivering business critical solutions, all while ensuring compliant, reliable & secure backend processing. 

You will partner closely with Squarespaces Executive Leadership, Product Engineering, Product Managers, FP&A, Accounting, & Compliance. This role reports to the VP of Platform Engineering & is based out of Squarespace's NYC Headquarters. Squarespace Engineers work from the office 3 days/week.

You'll Get To

Demonstrate Strategic Leadership:

• Develop & execute the long-term vision & a multi-year roadmap that incorporates Product, Finance & Compliance requirements, aligning with business goals.
• Translate business needs into technical requirements & solutions. 
• Identify & address technical debt & risks. 
• Champion best practices & emerging technologies within the team with a passion for continuous improvement & innovation.

Drive Team Leadership & Development:

• Lead, mentor, & develop a team of engineers & managers, fostering a collaborative & results-oriented environment. 
• Recruit & onboard top engineering talent. 
• Excellent communication, interpersonal, & leadership skills.
• Ability to work in a fast-paced & dynamic environment.
• Experience with Agile methodologies.

Oversee System Design & Implementation:

• Oversee the design, development, & maintenance of robust & scalable revenue systems. 
• Ensure systems meet business requirements & adhere to industry standards. 
• Collaborate with cross-functional teams (e.g., sales, marketing, finance) to integrate systems & processes. 
• Drive automation & optimization of revenue processes. 

Drive Performance & Optimization:

• Monitor system performance & identify areas for improvement. 
• Define, Implement & track metrics to measure success. 
• Conduct root cause analysis & implement solutions to address issues. 

• Stakeholder Management:

• Communicate technical information clearly & concisely to both technical & non-technical audiences. 
• Build & maintain strong relationships with stakeholders across the organization. 
• Represent the engineering team's perspective in cross-functional meetings & at multiple levels of management.

Who We're Looking For

• Proven experience leading & managing engineering teams of 50+ engineers.
• Strong technical background in software development & systems architecture.
• Significant experience with full-stack application development, data integration, & reporting
• Deep understanding of subscription billing, revenue cycle management, GAAP & business processes.
• Experience with relevant technologies & platforms (e.g., billing systems, payment gateways, dunning, revenue recognition).
• Experience developing solutions that meet data security, privacy, & other regulatory compliance burdens
• Experience integrating with 3rd party billing systems

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
• 6 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $255,500 - $365,000 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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