Employment Counsel

Upwork•Chicago, IL

14d•Hybrid

About The Position

As Employment Counsel, you will be the primary legal partner for Upwork’s global People organization, advising on all aspects of employment law, worker classification, and contingent labor practices. You’ll shape scalable policies and programs that support our hybrid workforce and ensure compliance across multiple jurisdictions. This is an exciting opportunity to drive the evolution of Upwork’s employment and contingent workforce strategy in a fast-moving, AI-powered workplace.

Requirements

JD and bar membership in good standing in at least one U.S. jurisdiction.
6+ years of labor and employment counseling experience, including significant hands-on contingent workforce experience and regular advice to or work with staffing companies.
Deep knowledge of employment laws and practices, including Title VII and state/local analogs, ADA, ADEA, FMLA and state leave laws, worker classification, wage/hour, joint-employer and co-employment issues, leaves/accommodations, background checks/FCRA, and related compliance for multi-jurisdictional workforces.
Proven experience drafting and negotiating staffing/vendor agreements and advising on program governance for contingent labor at scale.
Skilled at translating complex legal requirements into crisp, operational guidance with strong writing and communication skills.
Collaborative, practical, and solutions-focused; able to balance risk with business needs and design friction-reducing processes.

Nice To Haves

global counseling experience
familiarity with EOR/PEO models
prior in-house experience supporting contingent labor or HR/People teams

Responsibilities

Serve as the primary legal advisor to HR Business Partners, Employee Experience, Contingent Workforce Program, Talent Acquisition, and HRIS teams on employment law, worker classification, and contingent labor issues in the U.S. and globally.
Design, implement, and continuously improve scalable policies and frameworks for classifying employees, independent contractors, temporary staff, and agency-supplied workers, including guidance on EOR/PEO and other engagement models.
Advise on worker classification and joint-employer risks, boundaries of supervision and control, and compliant day-to-day program practices.
Partner with Employee Experience on compliant processes for onboarding/offboarding, background checks and FCRA compliance, authorization to work, and with the Benefits Team on leaves, accommodations, and benefits eligibility.
Support governance of our contingent workforce program, including development and maintenance of playbooks, operating procedures, and knowledge resources.
Monitor and interpret legislative and regulatory developments impacting classification and workforce practices and drive timely policy and process updates.
Lead or support internal investigations, audits, agency inquiries, and dispute resolution involving employees or contingent workers; develop remediation plans and preventative controls.
Create clear, business-friendly guidance that scales, including templates, checklists, FAQs, and self-service resources for internal stakeholders.