Director, Contingent Workforce Solutions

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.


We are looking for a Director, Contingent Workforce to lead our business-centric, collaborative, and motivated team. We are successfully pioneering a better way to work by enabling businesses and freelancers across the globe to connect, work together, and grow their professional success. You will work across the company to lead strategy, compliance, and education for our internal hybrid workforce programs. 

Are you a  proven leader with the ability to work across organizations to drive a successful and results oriented contingent labor program? Can you thrive in a rapidly changing environment? Do you seek the ability to drive operational compliance excellence and have a talent for problem-solving? If you said yes to any of these, you’ll be able to make a meaningful contribution to this role.

Your Responsibilities:

  • Lead a team of professionals who manage Upwork’s internal contingent workforce program.  
  • Drive business strategy.  Build accountability into the team's orientation.  Translate strategy into actionable initiatives. 
  • Foster an inclusive culture.
  • Serve as a consultative partner to our business disciplines.
  • Utilize deep aptitude of contingent workforce management to refine and evolve policy and team structure for optimized contingent workforce management. 
  • Achieve a deep understanding of the business strategy, goals and objectives and support organizational changes by developing and implementing appropriate change management plans.
  • Define the approach to our contingent workforce management based on external and internal benchmarking of best practices, and collaborate with business leaders to continually reassess program, process, and policies
  • Manage performance expectations of team by ensuring appropriate coaching, alignment with strategy and results orientation.
  • Ability to influence, build collaborative relationships with Upwork managers and key stakeholders to advise and educate on a wide range of contingent workforce issues, both internal and external. 
  • Utilize data driven strategies and techniques to build accountability with stakeholders and team

What it takes to catch our eye:

  • Leadership of a contingent workforce team 
  • Experience with vendor compliance and management, including managing worker relations issues
  • Working knowledge of U.S. employment law requirements and application of international employment law advice 
  • Consulting, coaching and facilitation experience
  • Superior relationship/stakeholder management and consultative skills
  • Strong understanding of independent contractor legal standards to make classification determinations, write compliant project descriptions, ensure proper contracting, and identify risk warranting legal advice
#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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Life at Upwork

We believe in a workplace in which all employees are empowered to see themselves in our One Upwork community. 

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