Employment Law Paralegal

Chicago | Illinois | United States

Upwork ($UPWK) is the leading tech solution for companies looking to hire the best talent, maintain flexibility, and get more done. We’re passionate about our mission to create economic opportunities so people have better lives. Every year, more than $2 billion of work is done through Upwork by skilled professionals who want the freedom of working anytime, anywhere. Top companies connecting with extraordinary talent around the globe? Upwork is how.


You'll join the award-winning Upwork Legal Team. We are a collaborative, trusting and high-performing team that loves to work on state-of-the art legal issues and generate practical solutions. The team has a passion for what we do that has been recognized in the industry. 

This rare in-house opportunity is ideal for a person seeking to make a direct business impact. You will focus on 50-state and global worker classification and employment law compliance support for our Upwork Enterprise solution, which is used by nearly 20% of the Fortune 500 and growing. You will monitor legal developments and partner with employment lawyers on your team to provide high-caliber contingent workforce solutions for large companies.

Your Responsibilities:

Under the supervision of a licensed attorney: 

  • Partner with the Enterprise Sales and Success teams to meet Enterprise client needs in a diverse range of legal areas, including worker classification. 
  • Assist with advising  the Enterprise Compliance Team on worker classification and track relevant legal developments.
  • In addition to members of the legal team, collaborate with various cross functional business partners
  • Create templates and process documents that will assist with operational support.
  • Conduct preliminary fact gathering on certain company initiatives and create summaries.
  • Manage FAQs and assist with responses to internal and external information requests.
  • Support the Upwork Payroll Team and research U.S. and global staffing agencies. 
  • Help Marketing craft informative content on legal and industry topics.
  • Provide training on new developments. 
  • Occasional support on litigation matters as needed.

What it takes to catch our eye:

  • 4+ years' experience as a paralegal.
  • Experience supporting employment law matters. 
  • Project management skills, including the ability to define the project scope, establish a timeline and manage resources. 
  • Extreme attention to detail, strong organizational skills, and timely follow up.

How to really knock our socks off:

  • Am Law 100, staffing experience, or other relevant in-house experience.
  • Strong analytical skills, including ability to collect, organize and analyze information with accuracy.
  • Experience in any of these areas is a plus: international employment law, contingent workforce issues,  and staffing industry. 
  • Strong oral and written communication skills to explain complex concepts for a variety of audiences.
  • Ability to balance workload under short deadlines and pivot to changing priorities in a fast-paced environment.
  #LI-BH1

Come change how the world works.

At Upwork, you’ll shape talent solutions for how the world works today. We’re a remote-first organization supported by offices in Santa Clara and Chicago, working together to create exciting remote work opportunities for a global community of professionals. 

Our vibrant culture is built on shared values and our mission to create economic opportunities so that people have better lives. We build amazing teams, put our community first, and have a bias toward action. We encourage everyone to bring their whole selves to work and grow together through development opportunities, mentorship, and employee resource groups. Oh yeah, we’ve also got amazing benefits.

Check out our Life at Upwork page to learn more about the employee experience.

Upwork is proudly committed to recruiting and retaining a diverse and inclusive workforce. As an Equal Opportunity Employer, we never discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical condition), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. 

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