Program Lead, Contingent Vendor & Workforce Planning

We are looking for a strategic operations partner to build our contingent workforce and vendor management practices within the People organization. This newly created role will establish structure, governance, and process discipline for our extended workforce—contractors, consultants, and vendors—while partnering with Legal, Finance, and Procurement to ensure compliance, fiscal accountability, and streamlined operations.

You will bring expertise in contingent workforce strategy, vendor lifecycle management, and collaboration. You excel in environments where you can create clarity and implement sustainable, scalable solutions.

This is a hybrid role working from our NYC office 3 days per week. You will report to the Sr Manager, Talent Acquisition Operations.

Program Design & Implementation

• Design and implement a scalable contingent workforce program, including classification, compliance, onboarding/offboarding, and lifecycle management.
• Establish clear policies, procedures, documentation standards, service level agreements (SLAs), and measurements (KPIs) across the organization to ensure service delivery and risk mitigation.
• Manage tools/systems to track labor usage and spend; develop training and change management resources to support adoption and partner agreement.

Vendor & Contract Management

• Manage end-to-end vendor lifecycle, from onboarding and evaluation to integration and performance tracking.
• Maintain accurate vendor records, including contracts, scopes of service, and renewal timelines.
• Partner with Legal on contract execution, renewals, and data regulations; lead performance reviews to assess quality and identify opportunities for optimization or new partnerships.
• Identify gaps in vendor capabilities and lead strategic sourcing decisions.

Collaboration

• Partner with Finance, Procurement, and Legal to align vendor intake, budgeting, compliance, and sourcing strategies.
• Collaborate on contract negotiations, vendor evaluation, and policy development.
• Advise People Leadership on talent models, market trends, and vendor strategy.
• Work with relevant partners to integrate contingent workforce data into analytics and planning tools.
• Support vendor selection, RFPs, and performance reviews to guide efficiency and cost savings.

Reporting & Insights

• Develop dashboards to track contingent workforce usage, vendor spend, KPIs, and program performance.
• Analyze trends to guide strategic decisions on vendor performance and resource allocation.
• Provide People Partners with data insights to inform workforce planning and budgeting visibility across client groups.
• Deliver executive summaries on program health, risks, and opportunities.
• Conduct regular audits to maintain data accuracy, compliance, and policy integrity.

• 6+ years of experience in vendor management, contingent workforce programs, procurement, or related functions within People, Legal, or Finance teams.
• Experienced success in building and scaling contractor/vendor management processes in high-growth or global environments.
• Experience with employment classifications (W2 vs. 1099), global contractor engagement, and compliance/tax considerations.
• Collaborator with excellent project management and ability to turn data into actionable insights.
• Experience with contract review and working with Legal, Finance, and Procurement partners.
• Familiarity with systems like Workday, Coupa, Zip, or other VMS/procurement tools; HRIS experience is a bonus.
• Certifications such as PMP or CCWP are a bonus.

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

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.

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.

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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