Senior Manager, People Technology

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