Senior Manager, People Technology

WebHosting; New York, Northern (NY, KY); Hybrid; USD 179,000 - 250,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Headspace mindfulness app

Private rooftop

Dog-friendly workplace

Free lunch and snacks

Flexible paid time off

12 weeks paid parental leave

Job summary

Squarespace is seeking a Senior People Technology leader to set the strategy and roadmap for the People Technology function in a hybrid New York office. You will lead a team of systems professionals and partner with senior leaders to translate business needs into scalable technology solutions.

You will own the architecture of the People Technology stack (Workday HCM, Greenhouse, learning platforms), drive cross-functional initiatives, and manage vendor relationships to ensure reliability and

Qualifications

• Senior People Technology leader with strategy and delivery experience.
• Experience leading large tech-enabled HR/People stacks (Workday HCM, HRIS, learning platforms).
• Ability to partner with senior leaders across People, Technology, Finance.

Responsibilities

• Lead strategy, roadmap, and delivery of People Technology function.
• Own architecture and optimization of People Tech ecosystem including Workday HCM and integrations.
• Oversee system configuration, releases, and deployments with strong governance.

Job description

Hybrid Full-time Senior People

Job Description

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.
• 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
• 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.

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