As an experienced People Technology leader, you will lead the strategy, roadmap, and delivery of Squarespace’s People Technology function. You will ensure our systems, processes, data, and technology infrastructure support the organization’s current and future needs. You will lead and develop a team of systems professionals, establish clear operating standards and priorities, and deliver a multi-year roadmap that supports the People and company strategy. You will partner closely with senior leaders across People, Technology, Finance, and the wider business to solve complex challenges and translate business needs into scalable technology solutions. You will report to our Head of People Operations & Technology and be based in our New York office (hybrid). You'll Get To… - Own and deliver the People Technology strategy and 1- to 2-year roadmap, aligning priorities and investments with the broader People and company strategy. - Lead the People Technology function, setting clear priorities, operating standards, resource plans, and measures of success. - Build and develop an inclusive and effective team, expanding its capabilities and supporting the growth of future leaders. - Own the architecture and ongoing optimization of the People Technology ecosystem, including Workday HCM, Greenhouse, learning and development platforms, and integrations, and reporting. - Lead complex, cross-functional technology initiatives from discovery and requirements through design, implementation, and adoption. - Partner with People Operations, Benefits, Talent Acquisition, IT, Finance, and other stakeholders to understand business needs and establish clear technology priorities. - Provide senior technical and functional leadership, guiding solution design and resolving complex systems, data, and integration issues. - Identify technical and organizational debt, evaluate trade-offs, and establish plans to improve scalability, reliability, and efficiency. - Oversee system configuration, integrations, testing, releases, and deployments, ensuring changes are well controlled and successfully adopted. - Lead Workday’s semiannual release process, assessing new functionality and coordinating impact reviews, testing, communications, and deployment. - Own vendor and resource management, balancing business priorities, cost, capacity and long-term requirements. - Partner with the Internal Controls team and People process owners to maintain strong controls, data integrity, and audit readiness. - Evaluate emerging People Technology and AI capabilities and identify practical opportunities to improve employee experience, self-service, and operational effectiveness. - Act as a trusted adviser and escalation point for complex People Technology decisions, influencing senior stakeholders and navigating competing priorities. Who We're Looking For - 8+ years of experience leading a People Technology, HRIS, or enterprise HR Systems function in a complex organization. - Strong people leadership experience, with a track record of building inclusive and effective teams, setting clear expectations, and developing others. - Deep knowledge of Workday HCM, including configuration, business processes, security, reporting, and integrations. - Experience overseeing a broader People Technology ecosystem, ideally including applicant tracking, payroll, benefits, learning, and reporting platforms. - Strong understanding of systems architecture, integrations, data governance and technology controls. - Experience leading complex, cross-functional programs and translating business requirements into scalable solutions. - Sound commercial judgment, including experience managing vendors, contracts, and external resources. - The ability to influence, offer constructive challenge, and make clear recommendations. - The ability to balance strategic planning with operational delivery and make effective decisions when priorities compete. - Experience working within SOX or a similarly controlled environment and supporting internal and external audits. - Curiosity about emerging technology and a practical understanding of how AI and automation can improve People processes and experiences. - The ability to communicate complex technical matters clearly to a range of audiences. 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 US Cash Compensation Range Cash Compensation Range: $178,500 - $250,000 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/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. #LI-Hybrid Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process. 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