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

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

You will partner closely with Squarespace’s Executive Leadership, Product Engineering, Product Managers, FP&A, Accounting, and Compliance. This role reports to the VP of Platform Engineering and 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 and execute the long-term vision and a multi-year roadmap that incorporates Product, Finance and Compliance requirements, aligning with business goals.
• Translate business needs into technical requirements and solutions. 
• Identify and address technical debt and risks. 
• Champion best practices and emerging technologies within the team with a passion for continuous improvement and innovation.

Drive Team Leadership & Development:

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

Oversee System Design & Implementation:

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

Drive Performance & Optimization:

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

• Stakeholder Management:

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

Who We're Looking For

• Proven experience leading and managing engineering teams of 50+ engineers.
• Strong technical background in software development and systems architecture.
• Significant experience with full-stack application development, data integration, and reporting
• Deep understanding of subscription billing, revenue cycle management, GAAP and business processes.
• Experience with relevant technologies and platforms (e.g., billing systems, payment gateways, dunning, revenue recognition).
• Experience developing solutions that meet data security, privacy, and 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 and 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 and 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 and 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, and 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 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 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and 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 and experiences with the world. Not only do we embrace and 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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